CN102127420A - Spiro-iridium organic electrophosphorescent material and preparation method thereof - Google Patents
Spiro-iridium organic electrophosphorescent material and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a spiro-iridium organic electrophosphorescent material which belongs to the technical field of organic photoelectric materials, and particularly discloses a spirofluorene xanthene pyridine iridium (III) coordination compound material which can be applied to organic electronic fields of organic luminescence display, organic laser and the like. The material has a structure shown in the specifications, and has the advantages of high luminous efficiency and capabilities of improving thermal stability and raising glass transition temperature by using a loop ring, reducing concentration quenching and the like. The material has commercial application potential in the aspect of phosphorescent materials.
Description
Technical field
The present invention is specifically related to based on the functional organic ligand of fluorenes and has metal iridium (III) intermediate of phosphorescent characteristics and the preparation method of title complex, and relates to step and the raw material that these materials adopt in preparation process.
Technical background
21 century is the epoch of information, also is the epoch of Information technology and industry high speed development thereof.Information material is the basis of realizing the required element of advanced IT application.Therefore, information material and device with the response speed of being exceedingly fast, very big information content and high information efficiency transformation efficiency enjoy people to pay close attention to, and this also is one of the most active field of current research in the world.Organic Light Emitting Diode causes people's very big concern because of the main product that its special advantages very likely becomes novel flat-plate technique of display of future generation.From the Tang of U.S. Kodak company in 1987 and Vanslyke with oxine aluminium (tris (8-hydroxyqu-inolinato) aluminum, Alq
3) as luminescent layer, obtained high brightness organic electroluminescence device (the organic light-emittingdiodes that DC low-voltage drives, OLEDs) since, cause great repercussion, worldwide started the electroluminescent organic material research boom rapidly.Compare with other display devices, organic elctroluminescent device has unrivaled advantage: volume is little, response speed is fast, the visual angle is wide, material source is wide, manufacturing process is simple, driving voltage is low, luminous efficiency is high, energy consumption is little and in light weight, can make flexible large-area flat-plate by technology cheaply shows, so it is the gordian technique that the following ultrathin type of realization can be rolled up wall-hanging color TV, now be acknowledged as the graphic image display device of new generation after liquid-crystal display LCD, plasma show PDP.Therefore, the OLEDs technology is thought the flat panel display of future generation of the most desirable and tool development prospect by industry.
The organic molecule electromechanical phosphorescent material is owing to its preparation succinctly efficiently receives much concern.In the past few decades, owing to do not make full use of its triplet excitons energy, there is 25% theoretical limit in the device internal quantum efficiency always.The 3rd transition metal makes singlet and triplet excitons participate in the electroluminescent process with after the organic molecule part combines owing to heavy atoms effect exists intensive to revolve the rail coupling.Thereby make the organic molecule phosphor material break through the one theory of internal quantum efficiency 25% and reach 100%.Calendar year 2001 Baldo etc. are (ppy)
2Ir (acac) is entrained among the TAZ, has prepared the high efficiency phosphorescent device, and the internal quantum efficiency of this device almost reaches 100%, and its external quantum efficiency reaches 19%.Make the efficient of electroluminescent device obtain unprecedented raising and caused great sensation.The 3rd transition metal title complex, particularly Ir (III), Pt (II) title complex, compare its unique characteristics with other heavy metal compound: intensive revolves rail coupling and electro phosphorescent device efficiently.In addition, the title complex of metal Ir (III) at room temperature demonstrates high brightness phosphorescence because of short fluorescence lifetime and high-quantum efficiency are arranged.Glow color and luminous efficiency can be regulated by part.Yet, many electroluminescent devices can not show high color purity, luminous efficiency height, good stability and organic small molecule material and also have evaporation conditional request harshness, simultaneously the high density triplet state bury in oblivion and high purity and efficiently blue light material be its fast-developing bottleneck of obstruction always.For this reason, exploration is closed advanced luminescent material and is inquired into various influence factors and mechanism of action thereof that its purity of color, luminous efficiency, thermostability, prevention triplet excitons are buried in oblivion and seems particularly important.Theoretically still in the practical application for synthesizing stable, efficient, optimised devices structure and simplify manufacture craft important significance for theories and huge actual reference are all arranged.
Organic electromechanical phosphorescent material is owing to it exists the integrated demonstration of big area in light weight, low-cost, flexible to cause the extensive interest of academia and the great attention of industry member aspect photoelectric device.Phosphor material can mix singlet owing to it in numerous luminescent materials and triplet excitons makes theoretical quantum yield reach 100%.Complex of iridium is shown one's talent owing to its efficient height and controllable color.Yet its luminous efficiency has much room for improvement, and because of crystallization reduces the stability of luminous efficiency and infringement device, high-concentration dopant makes problem such as fluorescent quenching be badly in need of separating.And xanthene spiral shell fluorenes is owing to have 3-D solid structure and can effectively suppress molecular interaction under the solid film state, raises the efficiency and the stability of device thereby reach.Organic compound of fluorene class is the luminescent material of a class excellent performance simultaneously.Therefore, the spiral shell fluorenes is introduced complex of iridium not only can realize effective phosphor material preparation with synthetic, simultaneously also can implementation efficiency and the raising of device stability.
In a word, the present invention is under the prerequisite to current electroluminescent organic material overall understanding, and tracking organic electronic devices forward position is dynamic, launches around the preparation and the dependent interaction mechanism thereof synthetic, El element of electroluminescent organic material.With the molecular designing is guidance, introduces fluorenyl xanthene volution part in the title complex, inhibition concentration cancellation, design synthesizing new high efficiency phosphorescent material.
Summary of the invention
Technical problem: purpose of the present invention provides a kind of volution iridium organic electromechanical phosphorescent material and preparation method thereof, the synthetic functional ligand of design based on the fluorenyl spirane structure, prepare phosphor material efficiently, there is widespread use in it aspect electroluminescent, bio-sensing, the memory device.
Technical scheme: the present invention is a kind of material based on volution iridium organic electrophosphorescenpolymer, and this material is the on-plane surface organic semiconductor of nuclear with the complex whorl aryl fluorene, has following structure:
Ar is nitrogenous aromatic ring structure, its array structure specific as follows:
In the formula, L
1, L
2Identical or different, for
Perhaps following ligand structure;
Wherein the Ar of part is the aromatic ring system of nitrogen atom, the ortho position carbon and 9 of its nitrogen-atoms, and 2 carbon atoms of 9-xanthene spiral shell fluorenes are connected.
The preparation method of volution iridium organic electromechanical phosphorescent material is: a. is that the catalysis that is included in methanesulfonic reaches down under 150 ℃ of conditions that refluxed 24 hours, after 2-bromine Fluorenone, methanesulfonic and the cooling in 24 hours of phenol hybrid reaction, be neutralized to alkalescence with aqueous sodium hydroxide solution, suction filtration obtains highly purified 2-bromo-9,9 '-(2-oxa-anthryl) fluorenes.B. get 2-bromo-9,9 '-(2-oxa-anthryl) fluorenes is put into two mouthfuls of flasks, vacuum nitrogen filling gas, with reaction unit in-78 ℃ of low temperature that dry ice and acetone produce, get the new THF dissolving of steaming of anhydrous and oxygen-free, n-Butyl Lithium is added drop-wise in two mouthfuls of flasks, and at-78 ℃ of reaction 1h, then to room temperature reaction 1 hour, under-78 ℃, be added to the positive butyl ester of boric acid in the reactor rapidly, low temperature 1h slowly gets back to temperature, and reaction is spent the night; The dilute hydrochloric acid hydrolysis 3-5h of triplication, ice-water bath cancellation reaction, the NaCl washing, dichloromethane extraction, drying, underpressure distillation obtains thick product; It is transferred in the single port flask add 1, ammediol and reflux in toluene are spent the night, the cooling after washing, and dichloromethane extraction, anhydrous magnesium sulfate drying concentrates, and column chromatography gets product.C. with 2-9; 9 '-(2-oxa-anthryl) spiral shell fluorenes-1; 3; the aqueous solution of 2-dioxy boric acid purport and nitrogenous heteroatomic halogenated aryl hydrocarbon (halogenated compound of aryl Ar as claimed in claim 1) palladium catalyst, Tetrabutyl amonium bromide, halogenated compound, salt of wormwood is in the mixing solutions of toluene and tetrahydrofuran (THF), and 90 ℃ were refluxed 48 hours under lucifuge and nitrogen protection.After the cooling, through obtaining highly purified product behind the column extractor chromatography.D. will have the organic ligand of C^N chelating function and hydration iridous chloride by two-to-one equivalent in the ethylene glycol ethyl ethers ether solvents, nitrogen protection refluxed 24 hours down, cooling washing suction filtration obtains highly purified dimer.E. highly purified dimer and organic ligand prepared in reaction being obtained corresponding phosphor material, below is the structure of optimizing back design dimer synthon:
The preparation method of volution iridium organic electromechanical phosphorescent material can be by the functional ligand of synthetic three teeth of two kinds of diverse ways or bidentate C^N chelate structure feature; the title complex of bidentate C^N chelating is to be solvent with the ethylene glycol ethyl ether; add yellow soda ash; under nitrogen protection, refluxed 24 hours; and three tooth C^N chelant complexes are to be solvent with the glycerol; add salt of wormwood, 200 ℃ were reacted 24 hours under nitrogen protection, and its general feature structure is as follows:
Synthetic and the preparation of step 1. xanthene spiral shell fluorenes organic ligand: earlier by friedel-crafts reaction through aqueous sodium hydroxide washes wash, suction filtration obtains highly purified bromine xanthene volution, then it is prepared into boric acid ester and 2-bromopyridine and obtains crude product by the Suzuki reaction, column chromatography gets high purity product;
The dimeric synthetic and preparation of step 2.: xanthene spiral shell fluorenes part and hydration iridous chloride react in ethylene glycol ethyl ether, prepare dimer through the washing suction filtration;
Synthetic and the preparation of step 3-1. three tooth C^N chelating ligands: dimer and pyridine xanthene spiral shell fluorenes part are solvent with the glycerol, at high temperature react thick product, obtain highly purified complex of iridium through column chromatography, perhaps refluxing in cellosolvo obtains the metal complexes of bidentate C^N cyclization;
Synthetic and the preparation of step 3-2. bidentate C^N chelating ligand: dimer is solvent with the ethylene glycol ethyl ether with corresponding organic ligand, adds yellow soda ash and refluxes 24 hours, washes suction filtration after the cooling with water and gets crude product, and column chromatography gets product.
The present invention has effectively inhibition concentration cancellation of 3-D solid structure in conjunction with spirane structure, simultaneously in conjunction with second part timely adjustment phosphorescence spectrum and the luminous efficiency thereof, thereby reaches synthetic simple and high-efficient phosphor material.
Beneficial effect: characterized the complex whorl aryl fluorene material structure by ultimate analysis, infrared spectra (FTIR), nucleus magnetic resonance (NMR), chromaticness online (GCMS), gel chromatography (GPC), by the thermostability that thermogravimetric analysis and differential thermal analysis have been tested material, characterized their light, electrochemical properties by Ultraluminescence spectrum and cyclic voltammetric method.This class material shows good thermostability in thermogravimetric analysis and differential thermal analysis, ultraviolet, fluorescence and electrochemical analysis show that it has excellent photoelectric performance.Therefore, this class material can be widely used in Organic Light Emitting Diode, organic laser, electromechanical memory devices is arranged, organic field-effect tube etc.
On this basis, design preliminary electroluminescent device and estimated volution complex of iridium luminescent properties.Wherein the structure of device is transparent anode/luminescent layer/electron injecting layer/negative electrode, wherein the volution complex of iridium by the vacuum evaporation mode prepare, negative electrode prepares by vacuum coating technology.Experimental result shows: these volution complex of iridium have shown phosphorescent emissions performance efficiently, can realize white light with PFO through the secondary spin coating technique.
Major advantage of the present invention is:
1. simple, the mild condition of synthesis step;
2. high thermal stability and second-order transition temperature have been kept.
Description of drawings:
Fig. 1 .2-pyridyl-9, the GCMS figure of 9 '-(2-oxa-anthryl) fluorenes;
Fig. 2 .2-pyridyl-9,9 '-(2-oxa-anthryl) fluorenes
1HNMR figure;
Fig. 3. three (the 2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III)
1HNMR figure;
Fig. 4. (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) is the spectrogram of luminescent layer device with three.
Embodiment
Further describe technical scheme of the present invention below in conjunction with embodiment, but these embodiment and unrestricted embodiments of the present invention.The present invention has multiple different embodiment, has more than to be limited to content described in this specification sheets.Those skilled in the art is under the situation of the present application spirit, and the scheme of being finished should be within the scope of the invention.
Embodiment 1:2-9,9 '-(2-oxa-anthryl) spiral shell fluorenes-1,3,2-dioxy boric acid purport synthetic
Get 2-bromo-9,9 '-(2-oxa-anthryl) fluorenes (14.64mmol, 6.0211g) put into two mouthfuls of flasks of 500ml, vacuum nitrogen filling gas, with reaction unit in-78 ℃ of low temperature that dry ice and acetone produce, get the new THF dissolving of steaming of anhydrous and oxygen-free, (17.57mmol 10.97mL) is added drop-wise in two mouthfuls of flasks, and reacts 1h at-78 ℃ with n-Butyl Lithium, then to room temperature reaction 1 hour, (73.2mmol 19.79mL) is added in the reactor low temperature 1h rapidly with the positive butyl ester of boric acid under-78 ℃, slowly get back to temperature, reaction is spent the night; The dilute hydrochloric acid hydrolysis 3-5h of triplication, ice-water bath cancellation reaction, the NaCl washing, dichloromethane extraction, drying, underpressure distillation obtains thick product.It transferred in the single port flask of 500mL add 1, ammediol (73.2mmol, 5.84mL) and the 150mL reflux in toluene spend the night, the cooling after washing, dichloromethane extraction, anhydrous magnesium sulfate drying concentrates, column chromatography gets product 1.8270g, productive rate is 30%.
Embodiment 2:2-pyridyl-9,9 '-(2-oxa-anthryl) fluorenes synthetic
Get 2-9,9 '-(2-oxa-anthryl) spiral shell fluorenes-1,3,2-dioxy boric acid purport (0.5mmol; 0.208g), the 2-bromopyridine (0.5mmol, 0.05mL), TBAB a little add in two mouthfuls of round-bottomed flasks of 100ml, vacuumize; add tetraphenyl base phosphorus palladium, vacuumize nitrogen protection.The solution of potassium carbonate 1mL that adds 2mol/L, the mixing solutions of adding 5mL tetrahydrofuran (THF) and toluene, under the lucifuge condition, heating 90 degree reaction 48h.After reaction finishes, use chloroform extraction, anhydrous magnesium sulfate drying, concentrated crude product, column chromatography gets product 0.1820g, and productive rate is 89%.Embodiment 3:2-pyridyl-9, the dimeric synthetic 2-pyridyl-9 of getting of 9 '-(2-oxa-anthryl) fluorenes and hydration iridous chloride, 9 '-(2-oxa-anthryl) fluorenes (1mmol, 0.4090g), (0.5mmol 0.17632g) joins in the reaction flask hydration iridous chloride, vacuumizes nitrogen and protects, injection cellosolvo and water (volume ratio is 3: 1) also refluxed 24 hours under 120 ℃, solution is changed into by black: red, Huang is green.Difference suction filtration after reacting completely, washing, washing with alcohol vacuum-drying gets yellow solid and is product 0.5019, and productive rate is 96%.
Embodiment 4: three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) synthetic
2-pyridyl-[9; dimer (the 0.1mmol of 9 '-(2-xanthene) spiral shell fluorenes iridium (III); 0.2089g), salt of wormwood (1mmol; 0.1380g), part 2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes (and 0.25mmol, 0.1023g) and 5mL glycerine join in the 100mL round-bottomed flask; under nitrogen protection; be heated to 190 ℃ gradually, reaction 24h, yellow solid gradually becomes the red-brown solid.After the cooling, add 20mL water, the red-brown solid of suction filtration, column chromatography gets product 0.1699g, and productive rate is 60%.
5: two (2-pyridyl-[9 of embodiment; 9 '-(2-xanthene) spiral shell fluorenes) Synthetic 2-pyridyl-[9 of methyl ethyl diketone iridium (III); dimer (the 0.1mmol of 9 '-(2-xanthene) spiral shell fluorenes iridium (III); 0.2089g), yellow soda ash (1mmol; 0.1060g), part methyl ethyl diketone (0.25mmol; 0.026mL) and the 10mL ethylene glycol ethyl ether join in the 100mL round-bottomed flask; under nitrogen protection, reflux; reaction 15h; wash with water after the cooling, suction filtration; column chromatography gets product 0.1197g, and productive rate is 54%.
Embodiment 5: the invention provides a kind of with three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) is the electro phosphorescent device of luminescent layer, device architecture be ITO/PEDOT:PSS/PVK+ three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) (8%)+PBD (30%) (100nm)/poly-fluorenes/Ba/Al.This device comprises: anode, hole injection and transport layer, emission layer, electronics inject buffer layer and negative electrode.Wherein anode is selected ITO for use, hole injection layer is the PEDOT:PSS of 40nm, emission layer PVK+ three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) thickness of iridium (III) (8%)+PBD (30%) is 100nm, blue-light emitting layer is poly-dioctyl fluorene, through the secondary spin coating technique, negative electrode is selected Ba/Al for use.Its emmission spectrum such as Fig. 4.
Embodiment 6: the invention provides a kind of with three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) is the electro phosphorescent device of luminescent layer, device architecture be ITO/PEDOT:PSS/PVK+ three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) iridium (III) (8%)+PBD (30%) (100nm)/poly-fluorenes/Ba/Al.This device comprises: anode, hole injection and transport layer, Huang and blue emission layer, electronics inject buffer layer and negative electrode.Wherein anode is selected ITO for use, hole injection layer is the PEDOT:PSS of 40nm, yellow emission layer PVK+ three (2-pyridyl-[9,9 '-(2-xanthene) spiral shell fluorenes) thickness of iridium (III) (8%)+PBD (30%) is 80nm, blue-light emitting layer is poly-dioctyl fluorene, through the secondary spin coating technique, negative electrode is selected Ba/Al for use.Obtain maximum current efficient 6.4cd/A under 5V, chromaticity coordinates is (0.31,0.32), its emmission spectrum such as Fig. 5.
Claims (5)
1. a volution iridium organic electromechanical phosphorescent material is characterized in that this material is a spiral shell fluorenes xanthene title complex, and it has following structure:
Ar is nitrogenous aromatic ring structure, its array structure specific as follows:
In the formula, L
1, L
2Identical or different, for
Perhaps following ligand structure;
2. volution iridium organic electromechanical phosphorescent material according to claim 1, the Ar that it is characterized in that described part is the aromatic ring system of nitrogen atom, the ortho position carbon and 9 of its nitrogen-atoms, 2 carbon atoms of 9-xanthene spiral shell fluorenes are connected.
3. the preparation method of a volution iridium organic electromechanical phosphorescent material as claimed in claim 1 is characterized in that the general method for preparing is:
A. be that the catalysis that is included in methanesulfonic reaches down under 150 ℃ of conditions that refluxed 24 hours, after 2-bromine Fluorenone, methanesulfonic and the cooling in 24 hours of phenol hybrid reaction, be neutralized to alkalescence with aqueous sodium hydroxide solution, suction filtration obtains highly purified 2-bromo-9,9 '-(2-oxa-anthryl) fluorenes;
B. get 2-bromo-9,9 '-(2-oxa-anthryl) fluorenes is put into two mouthfuls of flasks, vacuum nitrogen filling gas, with reaction unit in-78 ℃ of low temperature that dry ice and acetone produce, get the new THF dissolving of steaming of anhydrous and oxygen-free, n-Butyl Lithium is added drop-wise in two mouthfuls of flasks, and at-78 ℃ of reaction 1h, then to room temperature reaction 1 hour, under-78 ℃, be added to the positive butyl ester of boric acid in the reactor rapidly, low temperature 1h slowly gets back to temperature, and reaction is spent the night; The dilute hydrochloric acid hydrolysis of triplication 3-5 hour, ice-water bath cancellation reaction, the NaCl washing, dichloromethane extraction, drying, underpressure distillation obtains thick product; It is transferred in the single port flask add 1, ammediol and reflux in toluene are spent the night, the cooling after washing, and dichloromethane extraction, anhydrous magnesium sulfate drying concentrates, and column chromatography gets product.
C. with 2-9; 9 '-(2-oxa-anthryl) spiral shell fluorenes-1; 3; the aqueous solution of 2-dioxy boric acid purport and nitrogenous heteroatomic halogenated aryl hydrocarbon (halogenated compound of aryl Ar as claimed in claim 1) palladium catalyst, Tetrabutyl amonium bromide, halogenated compound, salt of wormwood is in the mixing solutions of toluene and tetrahydrofuran (THF), and 90 ℃ were refluxed 48 hours under lucifuge and nitrogen protection.After the cooling, through obtaining highly purified product behind the column extractor chromatography.
D. will have the organic ligand of C^N chelating function and hydration iridous chloride by two-to-one equivalent in the ethylene glycol ethyl ethers ether solvents, nitrogen protection refluxed 24 hours down, cooling washing suction filtration obtains highly purified dimer.
E. highly purified dimer and organic ligand prepared in reaction being obtained corresponding phosphor material, below is the structure of optimizing back design dimer synthon:
4. the preparation method of a volution iridium organic electromechanical phosphorescent material as claimed in claim 3; it is characterized in that functional ligand by synthetic three teeth of two kinds of diverse ways or bidentate C^N chelate structure feature; the title complex of bidentate C^N chelating is to be solvent with the ethylene glycol ethyl ether; add yellow soda ash; under nitrogen protection, refluxed 24 hours, and three tooth C^N chelant complexes are to be solvent with the glycerol, add salt of wormwood; 200 ℃ were reacted 24 hours under nitrogen protection, and its general feature structure is as follows:
Synthetic and the preparation of step 1. xanthene spiral shell fluorenes organic ligand: earlier by friedel-crafts reaction through aqueous sodium hydroxide washes wash, suction filtration obtains highly purified bromine xanthene volution, then it is prepared into boric acid ester and 2-bromopyridine and obtains crude product by the Suzuki reaction, column chromatography gets high purity product;
The dimeric synthetic and preparation of step 2.: xanthene spiral shell fluorenes part and hydration iridous chloride react in ethylene glycol ethyl ether, prepare dimer through the washing suction filtration;
Synthetic and the preparation of step 3-1. three tooth C^N chelating ligands: dimer and pyridine xanthene spiral shell fluorenes part are solvent with the glycerol, at high temperature react thick product, obtain highly purified complex of iridium through column chromatography, perhaps refluxing in cellosolvo obtains the metal complexes of bidentate C^N cyclization;
Synthetic and the preparation of step 3-2. bidentate C^N chelating ligand: dimer is solvent with the ethylene glycol ethyl ether with corresponding organic ligand, adds yellow soda ash and refluxes 24 hours, washes suction filtration after the cooling with water and gets crude product, and column chromatography gets product.
5. the preparation method of a volution iridium organic electromechanical phosphorescent material as claimed in claim 1, it is characterized in that arriving organic electroluminescence device, wherein the structure of LED device is transparent anode/luminescent layer/electron injecting layer/negative electrode, wherein, luminescent layer is the Subjective and Objective system, and spiral shell fluorenes xanthene title complex is as the guest materials of luminescent layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911145A (en) * | 2012-09-20 | 2013-02-06 | 苏州大学 | Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device |
| CN103833790A (en) * | 2013-12-25 | 2014-06-04 | 石家庄诚志永华显示材料有限公司 | Organic phosphorescent OLED materials |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1671819A (en) * | 2002-06-04 | 2005-09-21 | H·C·施塔克股份有限公司 | Phosphorescent and luminescent conjugated polymers and their use in electroluminescent assemblies |
| CN101146814A (en) * | 2005-03-01 | 2008-03-19 | 新加坡科技研究局 | Solution processed organometallic complexes and their use in electroluminescent devices |
| CN101440082A (en) * | 2008-12-12 | 2009-05-27 | 南京邮电大学 | Spirofluorene xanthene material, and preparation and use thereof |
| JP2009191232A (en) * | 2008-02-18 | 2009-08-27 | Toppan Printing Co Ltd | Fluorescent compound, light-emitting ink composition and organic el device |
-
2010
- 2010-12-13 CN CN2010105902598A patent/CN102127420A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1671819A (en) * | 2002-06-04 | 2005-09-21 | H·C·施塔克股份有限公司 | Phosphorescent and luminescent conjugated polymers and their use in electroluminescent assemblies |
| CN101146814A (en) * | 2005-03-01 | 2008-03-19 | 新加坡科技研究局 | Solution processed organometallic complexes and their use in electroluminescent devices |
| JP2009191232A (en) * | 2008-02-18 | 2009-08-27 | Toppan Printing Co Ltd | Fluorescent compound, light-emitting ink composition and organic el device |
| CN101440082A (en) * | 2008-12-12 | 2009-05-27 | 南京邮电大学 | Spirofluorene xanthene material, and preparation and use thereof |
Non-Patent Citations (1)
| Title |
|---|
| ELISABETH HOLDER等: "new trends in the use of transition metal-ligand complexes for applications in electroluminescent devices", 《ADV. MATER.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911145A (en) * | 2012-09-20 | 2013-02-06 | 苏州大学 | Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device |
| CN103833790A (en) * | 2013-12-25 | 2014-06-04 | 石家庄诚志永华显示材料有限公司 | Organic phosphorescent OLED materials |
| CN103833790B (en) * | 2013-12-25 | 2016-07-13 | 石家庄诚志永华显示材料有限公司 | A series of Phosphorescent OLED material |
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Application publication date: 20110720 |