CN104725410A - Tetraphenyl-silicane-unit-containing blue-light phosphorescence host material, and preparation method and organic electroluminescent device thereof - Google Patents
Tetraphenyl-silicane-unit-containing blue-light phosphorescence host material, and preparation method and organic electroluminescent device thereof Download PDFInfo
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- CN104725410A CN104725410A CN201310726994.0A CN201310726994A CN104725410A CN 104725410 A CN104725410 A CN 104725410A CN 201310726994 A CN201310726994 A CN 201310726994A CN 104725410 A CN104725410 A CN 104725410A
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Abstract
The invention belongs to the field of organic electroluminescent materials, and discloses a tetraphenyl-silicane-unit-containing blue-light phosphorescence host material, and a preparation method and an organic electroluminescent device thereof. The structural formula of the material is disclosed in the specification. In the tetraphenyl-silicane-unit-containing blue-light phosphorescence host material, the tetraphenyl silicane is a superhigh-energy-gap material with higher triplet-state energy level, can effectively prevent the energy from being fed back to the host material in the luminescence process. The tetraphenyl ethylene is a large-plane rigid structure, and has favorable fluorescence quantum yield and heat stability, thereby greatly enhancing the luminescence efficiency.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of containing tetraphenyl-silicon unit blue emitting phosphor material of main part and preparation method thereof.The invention still further relates to and a kind ofly use this to contain the organic electroluminescence device of tetraphenyl-silicon unit blue emitting phosphor material of main part as emitting layer material.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide and changes luminescent properties by chemical structure fine setting makes rich color, easily realize the advantages such as resolving power is high, lightweight, large-area flat-plate display, 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 singlet and triplet excitons can all be caught by they, thus realize the internal quantum efficiency of 100%.But, because the excited state exciton lifetime 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, triplet emission thing is often doped in organic host material by investigators.
In recent years, green and red phosphorescent OLED shows gratifying electroluminescent efficiency.And blue phosphorescent device is little efficiently, simultaneously major cause lacks to have good carrier transmission performance and higher triplet (E
t) material of main part.
Summary of the invention
Problem to be solved by this invention be to provide a kind of carrier transmission performance and triplet higher containing tetraphenyl-silicon unit blue emitting phosphor material of main part.
For achieving the above object, provided by the invention containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it obtains as follows:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be dissolve during 1:2 ~ 2.4 ratio is added into containing catalyzer and alkaline solution organic solvent according to mol ratio, the mixing solutions obtained carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtaining structural formula is
described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.
In a preferred embodiment, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or,
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and the mol ratio of described organic palladium and organophosphorus ligand is 1:4 ~ 8; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums, and described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; Preferably, described mixture is the mixture of palladium and three (o-methyl-phenyl-) phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In a preferred embodiment, 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 mol ratio of alkali solute and described compd A is 20:1.
In a preferred embodiment, organic solvent is selected from solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
Described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.
In a preferred embodiment, oxygen-free environment is made up of at least one gas in argon gas, nitrogen.
Another object of the present invention is to provide the preparation method containing tetraphenyl-silicon unit blue emitting phosphor material of main part that a kind of synthetic route is simple, material is cheap and easy to get, described preparation method comprises the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, compd A and B are added in the organic solvent containing catalyzer and alkaline solution and dissolve, compd A and B mol ratio are 1:2 ~ 2.4, the mixing solutions obtained after dissolving carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains containing tetraphenyl-silicon unit blue emitting phosphor material of main part described in following structural formula:
Above-mentioned preparation method's principle is simple, easy and simple to handle, low for equipment requirements, can wide popularization and application.
Another object of the present invention is to provide a kind of organic electroluminescence device, its emitting layer material is above-mentioned containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 '; 4 "-(2,2-toluylene-1,1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes).
The structure of this organic electroluminescence device comprises conductive substrates and is sequentially laminated on the hole injection layer of conductive substrates, hole transmission layer, luminescent layer, electron transfer layer, electron injection buffer layer, cathode layer; Wherein:
Conductive substrates comprises substrate of glass and is deposited on the anode layer of glass basic surface, and the material of this anode layer is indium tin oxide (ITO); Therefore, this conductive substrates is also called ito glass;
The material of hole injection layer is PEDOT:PSS;
The material of hole transmission layer is N, N '-two [(1-naphthyl)-N, N '-phenylbenzene]-1,1 '-xenyl-4,4 '-diamines (NPD);
The material of luminescent layer is that material of main part adulterates the mixing material of guest materials composition of 11% mass percent, described material of main part is described above containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 '; 4 "-(2,2-toluylene-1,1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes); Described guest materials is two (4,6-difluorophenyl pyridinato-N, C
2) pyridinecarboxylic conjunction iridium (FIrpic);
The material of electron transfer layer is oxine aluminium (Alq3);
The material of electron injection buffer layer is LiF;
The material of cathode layer is Al.
Provided by the invention containing tetraphenyl-silicon unit blue emitting phosphor material of main part, tetraphenyl-silicon is extrahigh energy gap material, there is higher triplet, effectively prevent energy in luminescence process from returning to material of main part, tetraphenyl ethylene is large plane rigid structure, there is good fluorescence quantum yield and thermal stability, thus greatly improve luminous efficiency; In addition, this material has good thermostability.
The above-mentioned preparation method containing tetraphenyl-silicon unit blue emitting phosphor material of main part, have employed better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure containing tetraphenyl-silicon unit blue emitting phosphor material of main part that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 5 obtains.
Embodiment
In order to understand the content of patent of the present invention better, 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 purchased from scientific and technological in lark prestige.
Embodiment 1: the present embodiment containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 ', 4 "-(2; 2-toluylene-1; 1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes), structural formula is as follows:
The preparation technology of this compound is as follows:
Under argon shield, 4,4'-(2,2-toluylene-1,1-bis-base) two (bromobenzene) (90mg, 0.2mmol), (4-tetramethyl ethylene ketone boric acid ester phenyl) tri-phenyl-silane (185mg, 0.4mmol) add in the flask filling 10ml toluene solvant, by salt of wormwood (2mL after abundant dissolving, 2mol/L) solution joins in flask, vacuumize deoxygenation and be filled with argon gas, then adding bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol); Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.Productive rate is 75%.Mass spectrum: m/z1001.4(M
++ 1); Ultimate analysis (%) C
74h
56si
2: theoretical value: C88.75, H5.64, Si5.61; Measured value: C88.67, H5.60, Si5.73.
Fig. 1 is the thermogravimetic analysis (TGA) figure containing tetraphenyl-silicon unit blue emitting phosphor material of main part that embodiment 1 obtains; Thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, containing the thermal weight loss temperature (T of tetraphenyl-silicon unit blue emitting phosphor material of main part 5%
d) be 397 DEG C.
Embodiment 2: the present embodiment containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 ', 4 "-(2; 2-toluylene-1; 1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes), preparation process is as follows:
Structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen and argon gas gas mixture are protected; by 4; 4'-(2; 2-toluylene-1; 1-bis-base) two (bromobenzene) (135mg; 0.3mmol), (4-tetramethyl ethylene ketone boric acid ester phenyl) tri-phenyl-silane (305mg; 0.66mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein, after fully dissolving, add sodium bicarbonate (3mL, 2mol/L) solution again.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 70 DEG C and carry out Suzuki coupling reaction 48h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.Productive rate is 72%.
Embodiment 3: the present embodiment containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 ', 4 "-(2; 2-toluylene-1; 1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes), structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 4,4'-(2,2-toluylene-1,1-bis-base) two (bromobenzene) (135mg, 0.3mmol), (4-tetramethyl ethylene ketone boric acid ester phenyl) tri-phenyl-silane (333mg, 0.72mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join in the flask of the DMF filling 12mL, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution, after in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.Productive rate is 78%.
Embodiment 4: the present embodiment containing tetraphenyl-silicon unit blue emitting phosphor material of main part, namely 4 ', 4 "-(2; 2-toluylene-1; 1-bis-base) two (biphenyl-4 ', 4-bis-base)) two (tri-phenyl-silanes), structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection; by 4; 4'-(2; 2-toluylene-1; 1-bis-base) two (bromobenzene) (135mg; 0.3mmol), (4-tetramethyl ethylene ketone boric acid ester phenyl) tri-phenyl-silane (319mg; 0.69mmol), 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 filling 12mL; sodium carbonate (3mL, 2mol/L) solution is added after abundant dissolving.After in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 90 DEG C and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.Productive rate is 84%.
Embodiment 5:
The present embodiment is organic electroluminescence device 300, and as shown in Figure 1, it comprises substrate 301, anode layer 302, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308.
The material of substrate 301 in the present embodiment is glass, vacuum plating anode 302 successively in substrate 301, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308, anode 302 adopts square resistance to be the tin indium oxide of 10 ~ 20 Ω/mouth, thickness is 150nm, hole injection layer 303 adopts poly-(3, 4-ethene dioxythiophene)-polystyrolsulfon acid, thickness is 30nm, hole transmission layer 304 adopts N, N '-phenylbenzene-N, N '-(1-naphthyl)-1, 1 '-biphenyl-4, 4 '-diamines, thickness is 20nm, (the 4' that luminescent layer 305 main body luminescent material adopts the present invention to prepare, 4''-(2, 2-toluylene-1, 1-bis-base) two (biphenyl-4', 4-bis-base)) two (tri-phenyl-silanes), and to take material of main part as benchmark doping mass percent be 11% guest emitting material two (4, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (III), luminescent layer 305 thickness is 20nm, electron transfer layer 306 adopts three (oxine) aluminium (Alq
3), thickness is 30nm, and electron injection buffer layer 307 adopts lithium fluoride, and thickness is 1.5nm, and negative electrode 308 adopts metallic aluminium, and thickness is 150nm.
ITO adopts magnetron sputtering film preparation, and other functional layers all adopt thermal evaporation process to deposit, and vacuum tightness is 10
-3~ 10
-5pa, the thickness of film adopts film thickness monitoring instrument to monitor, except guest materials, the vaporator rate of all organic materialss is
/ second, the vaporator rate of lithium fluoride is
/ second, the vaporator rate of metallic aluminium is
/ second.
This electroluminescent device has higher luminous efficiency, can be widely used in the illumination field such as blueness or white.The I-E characteristic of device is completed by Keithley source measuring system (Keithley2400Sourcemeter) with corrected silicon photoelectric diode, brightness is tested by the CS-100A colourimeter of Konica Minolta company, and all measurements all complete in atmosphere at room temperature.Result shows: the trigger voltage of device is 4.8V, at 1000cd/m
2brightness under, luminous efficiency is 7.0lm/W.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not 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., containing a tetraphenyl-silicon unit blue emitting phosphor material of main part, it is characterized in that, it obtains as follows:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be dissolve during 1:2 ~ 2.4 ratio is added into containing catalyzer and alkaline solution organic solvent according to mol ratio, the mixing solutions obtained carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtaining structural formula is
described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.
2. according to claim 1 containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
3. according to claim 1 containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it is characterized in that, described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the composition mixture of organophosphorus ligand; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. according to claim 3 containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
5. according to claim 4 containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it is characterized in that, described mixture is the mixture of palladium and three (o-methyl-phenyl-) phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
6. according to claim 1 containing tetraphenyl-silicon unit blue emitting phosphor material of main part, it 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 mol ratio of alkali solute and described compd A is 20:1.
7. the preparation method containing tetraphenyl-silicon unit blue emitting phosphor material of main part according to claim 1, it is characterized in that, described organic solvent is selected from as at least one in toluene, DMF, tetrahydrofuran (THF).
8. arbitrary described containing tetraphenyl-silicon unit blue emitting phosphor material of main part according to claim 1 to 7, it is characterized in that, described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, with dichloromethane extraction reaction solution repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described containing tetraphenyl-silicon unit blue emitting phosphor material of main part.
9. the preparation method containing tetraphenyl-silicon unit blue emitting phosphor material of main part as claimed in claim 1, it is characterized in that, its step is as follows:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:2 ~ 2.4 and B are added into containing catalyzer and alkaline solution organic solvent, the mixing solutions obtained carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, what obtain described in following structural formula is described containing tetraphenyl-silicon unit blue emitting phosphor material of main part:
10. an organic electroluminescence device, it is characterized in that, the material of its luminescent layer is that material of main part adulterates the mixing material of guest materials composition of 11% mass percent, described material of main part is for containing tetraphenyl-silicon unit blue emitting phosphor material of main part described in claim 1, described guest materials is two (4,6-difluorophenyl pyridinato-N, C
2) pyridinecarboxylic conjunction iridium.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114957313A (en) * | 2022-04-29 | 2022-08-30 | 山东大学 | Siloxane-bridged tetraphenylethylene derivatives, process for their preparation and their use |
-
2013
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114957313A (en) * | 2022-04-29 | 2022-08-30 | 山东大学 | Siloxane-bridged tetraphenylethylene derivatives, process for their preparation and their use |
| CN114957313B (en) * | 2022-04-29 | 2024-04-30 | 山东大学 | Siloxane-bridged tetraphenyl ethylene derivatives, process for their preparation and their use |
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