CN104419402A - Carbazolyl blue phosphorescent host material as well as preparation method and application thereof - Google Patents
Carbazolyl blue phosphorescent host material as well as preparation method and application thereof Download PDFInfo
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- CN104419402A CN104419402A CN201310386213.8A CN201310386213A CN104419402A CN 104419402 A CN104419402 A CN 104419402A CN 201310386213 A CN201310386213 A CN 201310386213A CN 104419402 A CN104419402 A CN 104419402A
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- carbazyl
- emitting phosphor
- phosphor material
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- IHAGUHVDXDPWCN-UHFFFAOYSA-N BrC(CCC1)CC1Br Chemical compound BrC(CCC1)CC1Br IHAGUHVDXDPWCN-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N CC(C)(C)c1ccc2[nH]c(ccc(C(C)(C)C)c3)c3c2c1 Chemical compound CC(C)(C)c1ccc2[nH]c(ccc(C(C)(C)C)c3)c3c2c1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- KVLYKJFQUYSVRK-HQMCVCOQSA-N CC/C=C\C(N(/C(/CC)=C/C=C)c1cccc(B2OC(C)(C)C(C)(C)O2)c1)=C Chemical compound CC/C=C\C(N(/C(/CC)=C/C=C)c1cccc(B2OC(C)(C)C(C)(C)O2)c1)=C KVLYKJFQUYSVRK-HQMCVCOQSA-N 0.000 description 1
- 0 CCC=CC([*@]1OC(C)(C)C1(C)C)=CC*(C(C=CC(C1)C(C)(C)C)=C1C1=CC2)C1=CC=*2C(C)(C)C Chemical compound CCC=CC([*@]1OC(C)(C)C1(C)C)=CC*(C(C=CC(C1)C(C)(C)C)=C1C1=CC2)C1=CC=*2C(C)(C)C 0.000 description 1
- ZYGAJFFTEMFUHW-UHFFFAOYSA-N CCCCCC[N](C)(C)C Chemical compound CCCCCC[N](C)(C)C ZYGAJFFTEMFUHW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the field of organic semiconductor materials and discloses a carbazolyl blue phosphorescent host material as well as a preparation method and application thereof. A structural formula of the material is shown in the specification. The carbazolyl blue phosphorescent host material provided by the invention has the advantages that the host material has hole transport property and electron transport property at the same time, so that holes and electrons in a luminescent layer are balanced in transport; the host material also has a higher triplet energy level, so that energy is effectively prevented from being transferred back to the host material in the luminescence process, thus greatly improving the luminescence efficiency.
Description
Technical field
The present invention relates to organic semiconductor material field, particularly relate to a kind of carbazyl blue emitting phosphor material of main part and its preparation method and application.
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 is to provide a kind of carbazyl blue emitting phosphor material of main part with good carrier transmission performance and higher triplet.
Technical scheme of the present invention is as follows:
Carbazyl blue emitting phosphor material of main part provided by the invention, its structure is such as formula shown:
i.e. 1,3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene.
The present invention also provides a kind of preparation method of carbazyl blue emitting phosphor material of main part described above, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
i.e. 1,3-dibromo-cyclohexane;
i.e. 3,6-di-t-butyl-9-(3-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole;
In oxygen-free environment (preferred nitrogen, the oxygen-free environment of one or both compositions in argon gas) under, be after the organic solvent dissolution that is added into containing catalyzer and alkaline solution of the compd A of 1:2 ~ 2.4 and B by mol ratio, Suzuki coupling reaction is carried out 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance is under vacuo after 50 DEG C of dry 24h, obtain the described carbazyl blue emitting phosphor material of main part that following structural formula represents:
In the preparation method of described carbazyl blue emitting phosphor material of main part, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is tri-o-tolyl phosphine mixture or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In the preparation method of described carbazyl blue emitting phosphor material of main part, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and in alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
In the preparation method of described carbazyl blue emitting phosphor material of main part, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
In the preparation method of described carbazyl blue emitting phosphor material of main part, Suzuki coupling reaction, preferable reaction temperature is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
The present invention also provides the application of above-mentioned carbazyl blue emitting phosphor material of main part in organic electroluminescence device luminescent layer.
(1) in carbazyl blue emitting phosphor material of main part of the present invention, carbazole is plane biphenyl structural, there is higher triplet and hole mobility, electric charge local accumulation and region enrichment can be avoided, the injection of further raising current carrier, effectively prevent energy in luminescence process from returning to material of main part, thus improve the luminous efficiency of this material in luminescent device;
(2) better heat stability of carbazyl blue emitting phosphor material of main part of the present invention;
(3) preparation method of above-mentioned carbazyl 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 of the carbazyl blue emitting phosphor material of main part that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation of embodiment 5.
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 and compd B are all purchased from scientific and technological in lark prestige.
Embodiment 1: the carbazyl blue emitting phosphor material of main part of the present embodiment, i.e. 1,3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene, structural formula is as follows:
The preparation technology of this compound is as follows:
Under argon shield, 1,3-dibromo-cyclohexane (48mg, 0.2mmol), 3,6-di-t-butyl-9-(3-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (192mg, 0.4mmol) add in the flask filling 10ml toluene solvant, after abundant dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol) is added; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described carbazyl blue emitting phosphor material of main part.Productive rate is 83%.Mass spectrum: m/z790.5(M
++ 1); Ultimate analysis (%) C
58h
66n
2: theoretical value: C 88.05, H 8.41, N 3.54; Measured value: C 88.12, H 8.35, N 3.49.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the carbazyl blue emitting phosphor material of main part that embodiment 1 obtains; Wherein, thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series 7 Thermo System, and measurement completes in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of carbazyl blue emitting phosphor material of main part 5%
d) be 387 DEG C.
Embodiment 2: the carbazyl blue emitting phosphor material of main part of the present embodiment, i.e. 1,3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen and argon gas gas mixture are protected; by 1; 3-dibromo-cyclohexane (73mg; 0.3mmol), 3; 6-di-t-butyl-9-(3-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (317mg; 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; sodium bicarbonate (3mL, 2mol/L) solution is added again after abundant dissolving.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, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described carbazyl blue emitting phosphor material of main part.Productive rate is 81%.
Embodiment 3: the carbazyl blue emitting phosphor material of main part of the present embodiment, i.e. 1,3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 1,3-dibromo-cyclohexane (73mg, 0.3mmol), 3,6-di-t-butyl-9-(3-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (346mg, 0.72mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL, 2mol/L) solution is added, after logical nitrogen purge gas is about 30min in flask subsequently after abundant dissolving; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described carbazyl blue emitting phosphor material of main part.Productive rate is 76%.
Embodiment 4: the carbazyl blue emitting phosphor material of main part of the present embodiment, i.e. 1,3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection; by 1; 3-dibromo-cyclohexane (73mg; 0.3mmol), 3; 6-di-t-butyl-9-(3-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (332mg; 0.69mmol), three or two argon benzyl acetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N filling 12mL; in the flask of dinethylformamide, after fully dissolving, add sodium carbonate (3mL, 2mol/L) solution.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, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described carbazyl blue emitting phosphor material of main part.Productive rate is 84%.
Embodiment 5:
Originally be embodied as organic electroluminescence device, as shown in Figure 2, this organic electroluminescence device 300 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, by magnetron sputtering plating anode layer 302 in substrate 301, then evaporation process is passed through, evaporation hole injection layer 303 is stacked gradually on anode layer 302 surface, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308.
In this organic electroluminescence device, the material employing square resistance of anode layer 302 is the tin indium oxide (ITO) of 10 ~ 20 Ω/mouth, and thickness is 150nm; Hole injection layer 303 adopts poly-(3,4-rthylene dioxythiophene)-polystyrolsulfon acid, and thickness is 30nm; Hole transmission layer 304 adopts N, N '-phenylbenzene-N, N '-(1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines, and thickness is 20nm; The compound 1 that luminescent layer 305 main body luminescent material adopts the invention process 1 to prepare, 3-bis-(3-(3,6-di-t-butyl-9H-carbazole-9-base) phenyl) hexanaphthene, 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), and luminescent layer 305 thickness is 20nm; Electron transfer layer 306 adopts three (oxine) aluminium (Alq
3), thickness is 30nm; Electron injection buffer layer 307 adopts lithium fluoride, and thickness is 1.5nm; Negative electrode 308 adopts metallic aluminium, and thickness is 150nm; The material of main part of luminescent layer 305, also can adopt the carbazyl blue emitting phosphor material of main part that embodiment 2 ~ 4 is obtained.
On ito anode layer 302, adopt thermal evaporation process to stack gradually deposition and complete hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308, 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.
By the current versus brightness to this organic electroluminescence device-voltage characteristic test, the trigger voltage of this organic electroluminescence device is 4.4V, at 1000cd/m
2brightness under, luminous efficiency is 7.6lm/W; Wherein, the test of current versus brightness-voltage characteristic is by with under the Keithley source measuring system (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter) of corrected silicon photoelectric diode, complete in atmosphere at room temperature.
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 (9)
1. a carbazyl blue emitting phosphor material of main part, is characterized in that, the structural formula of this material of main part is as follows:
2. a preparation method for carbazyl blue emitting phosphor material of main part as claimed in claim 1, is characterized in that, comprise the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be after the organic solvent dissolution that is added into containing catalyzer and alkaline solution of the compd A of 1:2 ~ 2.4 and B by mol ratio, Suzuki coupling reaction is carried out 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, repeatedly organic phase is merged afterwards with dichloromethane extraction, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain thick product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, this crystalline substance is under vacuo after 50 DEG C of dry 24h, obtain the described carbazyl blue emitting phosphor material of main part that following structural formula represents:
3. the preparation method of carbazyl blue emitting phosphor material of main part according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of carbazyl blue emitting phosphor material of main part according to claim 2, it is characterized in that, described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of carbazyl 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; Described organophosphorus ligand is tri-o-tolyl phosphine mixture or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of carbazyl blue emitting phosphor material of main part according to claim 2, 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, and in alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
7., according to the preparation method of the arbitrary described carbazyl blue emitting phosphor material of main part of claim 2 to 6, it is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
8., according to the preparation method of the arbitrary described carbazyl blue emitting phosphor material of main part of claim 2 to 6, it is characterized in that, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
9. the application of a carbazyl blue emitting phosphor material of main part according to claim 1 in organic electroluminescence device luminescent layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511212A (en) * | 2019-09-12 | 2019-11-29 | 南京邮电大学 | A kind of bipolarity D-A type material of main part and organic electroluminescence device |
| CN115093363A (en) * | 2022-04-26 | 2022-09-23 | 南京邮电大学 | Organic blue light micromolecules and preparation and application thereof |
-
2013
- 2013-08-29 CN CN201310386213.8A patent/CN104419402A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511212A (en) * | 2019-09-12 | 2019-11-29 | 南京邮电大学 | A kind of bipolarity D-A type material of main part and organic electroluminescence device |
| CN115093363A (en) * | 2022-04-26 | 2022-09-23 | 南京邮电大学 | Organic blue light micromolecules and preparation and application thereof |
| CN115093363B (en) * | 2022-04-26 | 2023-09-22 | 南京邮电大学 | Organic blue light small molecule and preparation and application thereof |
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