CN104628706A - Bipolar blue-ray phosphor compound, as well as preparation method and organic electroluminescent device thereof - Google Patents

Bipolar blue-ray phosphor compound, as well as preparation method and organic electroluminescent device thereof Download PDF

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CN104628706A
CN104628706A CN201310568035.0A CN201310568035A CN104628706A CN 104628706 A CN104628706 A CN 104628706A CN 201310568035 A CN201310568035 A CN 201310568035A CN 104628706 A CN104628706 A CN 104628706A
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phosphor compound
emitting phosphor
blue emitting
preparation
bipolarity blue
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周明杰
张振华
王平
黄辉
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a bipolar blue-ray phosphor compound, as well as a preparation method and an organic electroluminescent device thereof. The compound has a structural formula as shown in the specification. In the bipolar blue-ray phosphor compound, carbazole is an electron-enriched nitrogenous heterocyclic aromatic hydrocarbon, and has an excellent hole transmission performance; and triazole and imidazole are relatively good electron transmission units. The material has hole transmission property and electron transmission property at the same time to balance the transmission of hole and electrons in a luminescent layer, and has relatively high triplet state level, energy is effectively prevented from transmitting back to the blue-ray phosphor compound, and the luminescence efficiency is greatly improved.

Description

Bipolarity blue emitting phosphor compound and preparation method thereof and organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of bipolarity blue emitting phosphor compound and preparation method thereof.The invention still further relates to a kind of this compound that uses as the organic electroluminescence device of luminescent layer material of main part.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide and 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 carrier transmission performance and the higher bipolarity blue emitting phosphor compound of triplet.
For achieving the above object, bipolarity blue emitting phosphor compound provided by the invention, its structure is such as formula as follows: i.e. 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole.
Another object of the present invention is to provide the preparation method of the bipolarity blue emitting phosphor compound 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 bipolarity blue emitting phosphor compound described in following structural formula:
Wherein, 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 tri-o-tolyl 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 described preparation method, 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.
In a preferred embodiment, 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 bipolarity blue emitting phosphor compound.
In described preparation method, oxygen-free environment is made up of at least one gas in argon gas, nitrogen.
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, the material of main part of its luminescent layer adulterates the mixing material of guest materials composition of 7% mass percent, described material of main part is bipolarity blue emitting phosphor compound according to claim 1, described guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic conjunction iridium.
The structure of this organic electroluminescence device comprises conductive anode substrate and is sequentially laminated on hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, the cathode layer of conductive anode substrate; Wherein:
Conductive anode substrate comprises with substrate of glass, and is deposited on the conductive anode layer of glass basic surface, and the material changing conductive anode layer is indium tin oxide (ITO); Therefore, this conductive anode substrate 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 bipolarity blue emitting phosphor compound described above, i.e. 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole adulterates two (4 of 7% mass percent, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (FIrpic) dopant mixture that forms;
The material of electron transfer layer is oxine aluminium (Alq 3);
The material of electron injecting layer is LiF;
The material of cathode layer is Al.
In bipolarity blue emitting phosphor compound provided by the invention, carbazole is a kind of nitrogen heterocyclic ring aromatic compound of electron rich, has excellent hole transport performance; Triazole and imidazoles are good electric transmission unit.Therefore this material has hole transport character and electronic transport property simultaneously, and the transmission of hole and electronics in luminescent layer is balanced; This material also has higher triplet, effectively prevents energy in luminescence process from returning to blue emitting phosphor compound, greatly improves luminous efficiency.
The preparation method of above-mentioned bipolarity blue emitting phosphor compound, 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 bipolarity blue emitting phosphor compound 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 bipolarity blue emitting phosphor compound of the present embodiment, i.e. 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under argon shield, 9-(4-(3,5-bis-4-bromophenyl)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole (124mg, 0.2mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (158mg, 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 bipolarity blue emitting phosphor compound.Productive rate is 79%.Mass spectrum: m/z998.4(M ++ 1); Ultimate analysis (%) C 70h 46n 8: theoretical value: C84.14, H4.64, N11.21; Measured value: C84.14, H4.64, N11.21.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity blue emitting phosphor compound 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, the thermal weight loss temperature (T of bipolarity blue emitting phosphor compound 10% d) be 388 DEG C.
Embodiment 2: the bipolarity blue emitting phosphor compound of the present embodiment, its structure is 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen and argon gas gas mixture are protected, by 9-(4-(3, 5-bis-4-bromophenyl)-4H-1, 2, 4-triazole-4-yl) phenyl)-9H-carbazole (186mg, 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (261mg, 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 is added again after abundant dissolving, 2mol/L) solution.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 bipolarity blue emitting phosphor compound.Productive rate is 82%.
Embodiment 3: the bipolarity blue emitting phosphor compound of the present embodiment, its structure is 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 9-(4-(3, 5-bis-4-bromophenyl)-4H-1, 2, 4-triazole-4-yl) phenyl)-9H-carbazole (186mg, 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (285mg, 0.72mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL is added after abundant dissolving, 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 bipolarity blue emitting phosphor compound.Productive rate is 76%.
Embodiment 4: the bipolarity blue emitting phosphor compound of the present embodiment, its structure is 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 9-(4-(3, 5-bis-4-bromophenyl)-4H-1, 2, 4-triazole-4-yl) phenyl)-9H-carbazole (186mg, 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (273mg, 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, sodium carbonate (3mL is added after abundant dissolving, 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, 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 bipolarity blue emitting phosphor compound.Productive rate is 80%.
Embodiment 5:
The present embodiment is organic electroluminescence device, the material of main part of its luminescent layer is the bipolarity blue emitting phosphor compound that the present invention obtains, i.e. 9-(4-(3,5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1,2,4-triazole-4-yl) phenyl)-9H-carbazole.
As shown in Figure 2, this organic electroluminescence device 300, its structure comprises substrate 301, anode 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 conductive anode layer successively 302 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, wherein, 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, 9-(the 4-(3 that luminescent layer 305 main body luminescent material adopts the present invention to obtain, 5-bis-(3 '-(1-phenyl-1H-benzo [d] imidazoles-2-base) xenyl-4-base)-4H-1, 2, 4-triazole-4-yl) phenyl)-9H-carbazole, and to take material of main part as benchmark doping mass percent be 7% 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 Alq 3, three (oxine) aluminium, 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.
Organic layer and metal level 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.Current versus brightness-the voltage characteristic of device is all completed in atmosphere at room temperature by all measurements completed with Keithley source measuring system (Keithley2400Sourcemeter) correcting silicon photoelectric diode.Result shows: the trigger voltage of device is 4.6V, at 1000cd/m 2brightness under, luminous efficiency is 8.2lm/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. a bipolarity blue emitting phosphor compound, is characterized in that, its structure is such as formula as follows:
2. a preparation method for bipolarity blue emitting phosphor compound 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, obtains the described bipolarity blue emitting phosphor compound described in following structural formula:
3. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, 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.
4. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, 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.
5. the preparation method of bipolarity blue emitting phosphor compound according to claim 4, 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.
6. the preparation method of bipolarity blue emitting phosphor compound according to claim 5, it is characterized in that, described mixture is the mixture of palladium and tri-o-tolyl phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
7. the preparation method of bipolarity blue emitting phosphor compound 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; In described alkaline solution, the mol ratio of alkali solute and described compd A is 20:1.
8. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, described organic solvent is selected from as at least one in toluene, DMF, tetrahydrofuran (THF).
9. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, 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 bipolarity blue emitting phosphor compound.
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 7% mass percent, described material of main part is bipolarity blue emitting phosphor compound according to claim 1, described guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic conjunction iridium.
CN201310568035.0A 2013-11-14 2013-11-14 Bipolar blue-ray phosphor compound, as well as preparation method and organic electroluminescent device thereof Pending CN104628706A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106590632A (en) * 2016-12-20 2017-04-26 盐城工学院 Organic electroluminescent material and device and preparation method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106590632A (en) * 2016-12-20 2017-04-26 盐城工学院 Organic electroluminescent material and device and preparation method

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