WO2004026870A1 - Phenanthroline compound and organic light emitting device using same - Google Patents
Phenanthroline compound and organic light emitting device using same Download PDFInfo
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- WO2004026870A1 WO2004026870A1 PCT/JP2003/011485 JP0311485W WO2004026870A1 WO 2004026870 A1 WO2004026870 A1 WO 2004026870A1 JP 0311485 W JP0311485 W JP 0311485W WO 2004026870 A1 WO2004026870 A1 WO 2004026870A1
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- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2c1cccc2 Chemical compound C[n]1c2ccccc2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Definitions
- the present invention relates to a novel organic compound and an organic light emitting device using the same.
- An organic light emitting device is a device in which a thin film containing a fluorescent organic compound or a phosphorescent organic compound is interposed between an anode and a cathode; excitons of the fluorescent compound or the phosphorescent compound are generated by injection of electrons and holes from the electrodes and a light radiated when the excitons return to the ground state is utilized.
- non-patent document 1 In a research by Eastman Kodak Company in 1987 (non-patent document 1) , there is reported a light emission of about 1,000 cd/m 2 at an applied voltage of about 10 V for a device of functionally separated two-layer structure using ITO for an anode and a magnesium/silver alloy for a cathode, respectively, an aluminium-quinolinol complex as an electron- transporting material and a light emitting material and a triphenylamine derivative as a hole transporting material.
- Related patents include patent documents 1 to 3.
- Non-patent document 3 an organic light emitting device using a conjugated polymer other than the organic light emitting device using the low- molecular materials as described above.
- light emission in a onolayer is confirmed by forming a film of polyphenylenevinylene (PPV) in a coating system.
- PPV polyphenylenevinylene
- phenanthroline compounds are used as an electron transporting material or a light emitting material by the excellent electron transporting property thereof.
- Examples of documents in which the phenanthroline compounds are reported to be used for an organic light emitting device include patent references 17 to 21, but their properties when they are used as a light emitting material or an electron transporting material are not sufficient. [Patent document 1]
- Patent document 10 Japanese Patent Application Laid-Open No. H5- 202356 (no corresponding foreign document)
- Patent document 11 Japanese Patent Application Laid-Open No. H9- 202878 (no corresponding foreign document) [Patent document 11]
- Patent document 12 Japanese Patent Application Laid-Open No. H9- 227576 (no corresponding foreign document) [Patent document 12]
- Patent document 17 Japanese Patent Application Laid-Open No. H5- 247460 (no corresponding foreign document)
- Patent document 18 Japanese Patent Application Laid-Open No. H5- 247460 (no corresponding foreign document)
- Patent document 19 Japanese Patent Application Laid-Open No. H7- 82551 (no corresponding foreign document) [Patent document 19]
- Patent document 20 Japanese Patent Application Laid-Open No. 6,010,796
- an object of the present invention to provide a novel phenanthroline compound. It is another object of the present invention to provide an organic light emitting device having a light output with an extremely high efficiency and a high luminance using a specific phenanthroline compound . It is still another object of the present invention to provide an extremely durable organic light emitting device.
- the present invention provides a phenanthroline compound represented by any one of the following general formulas [I] to [III] :
- Ri, R 2 , R 3 , R, R 5 and Re are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and ri and Ar 2 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ;
- R, R 3 , R 9 , Rio. Rn and R ⁇ 2 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar 3 and Ar are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ; and
- R i3 , R i4 , R 1 5 and Rie are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar 5 , Ar 6 , Ar 7 and Ar 8 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) .
- the fluorenyl group is preferably represented by the following general formula [IV] :
- R ⁇ 7 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom; and Ris and R ⁇ 9 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted heterocyclic group) .
- the fluoranthenyl group is preferably represented by the following general formula [V] :
- R 20 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom
- the perylenyl group is preferably represented by the following general formula [VI] :
- R 21 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom
- carbazolyl group is preferably represented by the following general formula [VII] :
- R 22 and R 23 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
- the present invention provides an organic light emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the above-mentioned phenanthroline compounds, interposed between the pair of electrodes.
- Fig. 1 is a sectional view illustrating an example of the organic light emitting device according to the present invention
- Fig. 2 is a sectional view illustrating another example of the organic light emitting device according to the present invention
- Fig. 3 is a sectional view illustrating still another example of the organic light emitting device according to the present invention.
- Fig. 4 is a sectional view illustrating yet another example of the organic light emitting device according to the present invention.
- Fig. 5 is a sectional view illustrating yet still another example of the organic light emitting device according to the present invention.
- Fig. 6 is a sectional view illustrating yet again another example of the organic light emitting device according to the present invention.
- the phenanthroline compounds of the present invention will be first described.
- the phenanthroline compounds of the present invention are represented by the above general formulas [I] to [III], wherein a fluorenyl group is represented by the above general formula [IV], a fluoranthenyl group by the above general formula [V] , a perylenyl group by the above general formula [VI] and a carbazolyl group by the above general formula [VII] .
- the alkyl group includes methyl, ethyl, n- propyl, iso-propyl, n-butyl, ter-butyl, octyl or the like.
- the aralkyl group includes benzyl, phenethyl or the like.
- the aryl group includes phenyl, biphenyl, terphenyl or the like.
- the heterocyclic group includes thienyl, pyrolyl, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thidiazolyl, terthienyl or the like.
- the substituted amino group includes dimethylamino, diehtylamino, dibenzylamino, diphenylamino, ditolylamino, dianisolylamino or the like.
- the halogen atom includes fluorine, chlorine, bromine, iodine or the like.
- the substituent groups that the above substituent groups may have include alkyl groups such as methyl, ethyl and propyl; aralkyl groups such as benzyl and phenethyl; aryl groups such as phenyl and biphenyl; heterocyclic groups such as thienyl, pyrolyl and pyridyl; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and dianisolylamino; alkoxyl groups such as methoxyl, ethoxyl, propoxyl and phenoxyl; cyano group; and halogen atoms such as fluorine, chlorine, bromine and iodine.
- the phenanthroline compound of the present invention can be synthesized by generally known methods, in which it can be obtained by the synthesis such as the Suzuki coupling method using a palladium catalyst (e.g., Chem. Rev. 1995, 95, 2457-2483) through a phenanthroline compound intermediate that is obtained by the methods, for example, described in J. Org, Chem., 16, 941-945 (1951); Tetrahedron, Lett., 36, 3489-3490 (1995) and the like.
- a palladium catalyst e.g., Chem. Rev. 1995, 95, 2457-2483
- the phenanthroline compound of the present invention has superior electron transporting property and durability to the conventional compounds and is useful as a layer comprising an organic compound of an organic light emitting device, particularly as an electron transporting layer and a light emitting layer. Moreover, the layers formed by a vacuum evaporation process or a solution coating process are difficult to be crystallized and are excellent in long-term stability.
- the organic light emitting device of the present invention comprises a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the phenanthroline compounds represented by the general formula [I], [II] and [III], interposed between the pair of electrodes.
- At least an electron transporting layer or a light emitting layer of the layer (s) comprised of an organic compound comprises at least one of the above-mentioned phenanthrolines .
- the phenanthroline compound represented by the above general formulas [I] to [III] is formed between the anode and the cathode by a vacuum evaporation process or a solution coating process.
- the organic layer is preferably formed in a thin film having a thickness of less than 10 ⁇ r ⁇ , preferably 0.5 ⁇ r ⁇ or less, more preferably from 0.01 to 0.5 ⁇ m.
- Figs. 1 to 6 are views illustrating preferred examples of the organic light emitting device of the present invention.
- Fig. 1 is a sectional view illustrating one example of the organic light emitting device of the present invention.
- the device of Fig. 1 has the structure in which an anode 2, a light emitting layer 3 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure shown in Fig. 1 is useful when employing a compound having hole transportability, electron transportability and light emitting property singularly within itself, or when employing compounds having respective characteristics in mixture.
- Fig. 2 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 2 has the structure in which an anode 2, a hole transporting layer 5, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure shown in Fig. 2 is useful when a material having a hole transportability and/or electron transportability is used for respective layers as a light emitting substance in combination with a hole transporting or electron transporting substance having no light emitting property.
- the light emitting layer comprises either the hole transporting layer 5 or the electron transporting layer 6.
- Fig. 3 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 3 has the structure in which an anode 2, a hole transporting layer 5, a light emitting layer 3, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure is to separate a carrier transporting function and a light emitting function, and is used in suitable combination with compounds having the respective properties of hole transporting property, electron transporting property and light emitting property.
- the freedom of selection of materials is extremely increased, and various compounds having different emission wavelengths can be used to allow diversification of the luminescent hue. Further, carriers or excitons can be effectively confined in the central light emitting layer 3 to improve the light emission efficiency.
- Fig. 4 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 4 has the structure in which a hole injecting layer 7 is inserted to the anode 2 side as compared with the structure shown in Fig. 3.
- the structure shown in Fig. 1 is effective for improving adhesiveness of the anode 2 to the hole transporting layer 5 or improving the hole injecting property and is also effective for driving at a reduced voltage.
- Figs. 5 and 6 are sectional views illustrating other examples of the organic light emitting device of the present invention.
- the devices of Figs. 5 and 6 have the structures in which a layer (hole-blocking layer 8) for blocking holes or excitons from passing through to the cathode 4 side is inserted between the light emitting layer 3 and the electron transporting layer 6 as compared with Figs. 3 and 4.
- the structure is effective for improving the light emission efficiency by using a compound having a very high ionization potential as the hole blocking layer 8.
- Figs. 1 to 6 merely show very basic device structures, and the structures of the organic light emitting device using the compounds of the present invention are not limited thereto. It is possible to take various structures, for example, to provide an insulating layer at an interface between an electrode and an organic layer, to provide an adhesion layer or an interference layer or to compose a hole transporting layer of two layers having different ionization potentials.
- the phenanthroline compounds represented by the general formulas [I] to [III] used in the present invention are excellent in electron transporting property and durability compared with the conventional compounds, and can be used in any one of the structures shown in Figs. 1 to 6.
- the present invention uses the phenanthroline compounds represented by the general formulas [I] to [III] as constituent components for an electron transporting layer or a light emitting layer, already known hole transporting compounds, light emitting compounds or electron transporting compounds can also be used together as needed
- M Cu, Mg, AlCI, TiO, SiCI 2 , Zn , Sn, m-MTDATA MnCI, GaCI, etc
- the layers containing the phenanthroline compounds represented by the general formulas [I] to [III] and the layers containing other organic compounds are generally formed into thin films by a vacuum evaporation process or a coating process in which they are dissolved in a suitable solvent.
- a coating process it is also possible to form the film in combination with a suitable binder resin.
- the binder resin can be selected from a wide range of binder resins, and include, for example, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, polyarylate resins, polystyrene resins, acrylic resins, methacrylic resins, butyral resins, polyvinylacetal resins, diallylphthalate resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins and the like. In addition, one of them or a mixture of two or more of them may be used in the form of a homopolymer or a copolymer.
- the materials for the anode preferably have a large work function, and metals such as, for example, gold, platinum, nickel, palladium, cobalt, selenium, vanadium and alloys thereof and metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides can be used.
- metals such as, for example, gold, platinum, nickel, palladium, cobalt, selenium, vanadium and alloys thereof and metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides
- metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides
- conductive polymers such as polyaniline, polypyrrole, polythiophene and poyphenylene sulfide can be used. These electrode materials can be used singularly or in combination.
- the materials for the cathode preferably have a small work function, and metals such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminium, indium, silver, lead, tin and chrome and alloys thereof can be used. Metal oxides such as indium tin oxides (ITO) can also be used.
- the cathode may have either a one- layer structure or a multilayer structure.
- the substrate for use in the present invention includes, but not limited to, metal substrates, opaque substrates such as ceramic substrates, and transparent substrates such as glass, quartz and pla,stic sheets. Moreover, it is possible to control the color of emitted light using a color filter film, a fluorescent color conversion filter film, a dielectric reflecting film and the like for the substrate .
- a protective layer or an encapsulant layer can also be provided on the prepared device for the purpose of preventing contact with oxygen, moisture and the like.
- the protective layer includes an inorganic material film such as a diamond thin film, a metal oxide film or a metal nitride film; a polymeric film such as of fluororesin, polyparaxylene, polyethylene, silicone resin and polystyrene resin; a photo-curable resin or the like.
- the device itself can be covered with glass, a gas-impermeable film, metal or the like and packaged with a suitable encapsulant resin.
- a device having the structure shown in Fig. 3 was prepared.
- ITO indium tin oxide
- IPA isopropyl alcohol
- a chloroform solution of the compound represented by the following structural formula was applied by a spin-coating process to form a film having a thickness of 30 nm, thus forming the hole transporting layer 5.
- the Ir complex represented by the following structural formula and Exemplary Compound No. 1 as the instant phenanthroline compound (weight ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3.
- the degree of the vacuum at the evaporation was 1.0 x 10 ⁇ 4 Pa and the film formation rate was 0.2-0.3 nm/sec,
- trisquinolinol aluminium was deposited by a vacuum evaporation process in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 "4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- a vacuum evaporation material consisting of aluminium and lithium (lithium concentration of 1 atomic %) was used to form a metal layer film having a thickness of 50 nm on the above organic layer by a vacuum evaporation process, and further by the vacuum evaporation process an aluminium layer having a thickness of 150 nm was formed.
- the degree of the vacuum at the evaporation was 1.0 x 10 "4 Pa and the film formation rate was 1.0-1.2 nm/sec.
- the resultant structure was covered with a protective glass plate in a nitrogen atmosphere and sealed with an acrylic resin adhesive.
- the thus obtained device was applied with a DC voltage of 10 V using the ITO electrode (anode 2) as a positive electrode and the Al-Li electrode (cathode 4) as a negative electrode, the current passed through the device at a current density of 18.0 mA/cm 2 and emission of green light was observed at a luminance of 4,500 cd/m 2 .
- a device of the structure shown in Fig. 3 was prepared.
- the hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
- coumarin and trisquinolinol aluminium (polymerization ratio of 1:20) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- Exemplary Compound No. 3 was deposited in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec. Then, the device was sealed after the cathode 4 was formed in the same manner as in Example 1.
- a device with the structure shown in Fig. 3 was prepared.
- the hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
- the Ir complex represented by the following structural formula and the carbazole compound represented by the following structural formula (polymerization ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3
- the degree of the vacuum at the evaporation was 1.0 x 10 ⁇ 4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- Exemplary Compound No. 5 was deposited in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- the device was then sealed after the cathode 4 was formed in the same manner as in Example 1.
- the organic light emitting devices using the phenanthroline compounds represented by the general formulas [I] to [III] provide the emission having a high luminance at a low applied voltage and are also excellent in durability.
- the organic layers comprising the phenanthroline compounds of the present invention are excellent as an electron transporting layer as well as a light emitting layer.
Priority Applications (3)
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US10/527,192 US7550594B2 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
AU2003260955A AU2003260955A1 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
US12/436,507 US7982213B2 (en) | 2002-09-19 | 2009-05-06 | Phenanthroline compound and organic light emitting device using same |
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JPNO.2002-272408 | 2002-09-19 | ||
JP2002272408A JP4261855B2 (ja) | 2002-09-19 | 2002-09-19 | フェナントロリン化合物及びそれを用いた有機発光素子 |
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US10527192 A-371-Of-International | 2003-09-09 | ||
US12/436,507 Division US7982213B2 (en) | 2002-09-19 | 2009-05-06 | Phenanthroline compound and organic light emitting device using same |
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Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007064484A2 (en) * | 2005-11-30 | 2007-06-07 | Eastman Kodak Company | Electroluminescent device containing a phenanthroline derivative |
US7517596B2 (en) * | 2004-11-29 | 2009-04-14 | Canon Kabushiki Kaisha | Phenanthroline compound and light-emitting device |
EP2072517A1 (de) * | 2007-12-21 | 2009-06-24 | Novaled AG | Asymmetrische Phenanthroline, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
CN100566489C (zh) * | 2004-12-01 | 2009-12-02 | 株式会社半导体能源研究所 | 发光元件、发光装置以及电子设备 |
EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
US7750159B2 (en) | 2004-07-07 | 2010-07-06 | Semiconductor Energy Laboratory Co., Ltd. | Phenanthroline derivative and light emitting element and light emitting device using the same |
US7750340B2 (en) * | 2003-04-30 | 2010-07-06 | Canon Kabushiki Kaisha | Light-emitting device |
US7833634B2 (en) * | 2005-06-21 | 2010-11-16 | Canon Kabushiki Kaisha | 1,8-naphthyridine compound and organic light-emitting device using the same |
WO2011030566A1 (en) * | 2009-09-14 | 2011-03-17 | Eisai R&D Management Co., Ltd. | Phenanthroline derivatives and their use as ligands |
WO2011046182A1 (ja) | 2009-10-16 | 2011-04-21 | 出光興産株式会社 | 含フルオレン芳香族化合物、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US7931975B2 (en) | 2008-11-07 | 2011-04-26 | Global Oled Technology Llc | Electroluminescent device containing a flouranthene compound |
WO2012124310A1 (en) | 2011-03-11 | 2012-09-20 | B.R.A.H.M.S Gmbh | Rare earth metal complex having phenanthroline compound as ligand |
EP2299508A3 (en) * | 2004-11-24 | 2014-04-23 | The Trustees of Princeton University | Organic photosensitive optoelectronic device having a phenanthroline exciton blocking layer |
US8748013B2 (en) | 2003-03-20 | 2014-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Electroluminescent device |
US8962155B2 (en) | 2007-11-02 | 2015-02-24 | Toray Industries, Inc. | Light emitting device based on a pyrromethene compound |
CN104603137A (zh) * | 2012-09-12 | 2015-05-06 | 出光兴产株式会社 | 新型化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
WO2015064969A2 (ko) * | 2013-10-29 | 2015-05-07 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
CN105646480A (zh) * | 2014-11-28 | 2016-06-08 | 机光科技股份有限公司 | 啡啉类化合物及其用途 |
US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
CN107207503A (zh) * | 2015-01-29 | 2017-09-26 | 东丽株式会社 | 菲咯啉衍生物、含有其的电子装置、发光元件及光电转换元件 |
CN111574505A (zh) * | 2020-05-22 | 2020-08-25 | 西安瑞联新材料股份有限公司 | 一种以苯并[c]噌啉为受体的化合物及其应用 |
CN116514778A (zh) * | 2023-06-26 | 2023-08-01 | 季华实验室 | 一种有机电子传输材料、有机电致发光器件 |
EP4223744A1 (en) * | 2022-02-08 | 2023-08-09 | Gwangju Institute of Science and Technology | Novel phenanthroline-based compound and optoelectronic device comprising the same |
Families Citing this family (114)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4427947B2 (ja) * | 2002-11-18 | 2010-03-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP4707082B2 (ja) * | 2002-11-26 | 2011-06-22 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
JP4356463B2 (ja) * | 2004-01-29 | 2009-11-04 | ソニー株式会社 | 有機発光材料および有機電界発光素子 |
JP4533015B2 (ja) * | 2004-06-15 | 2010-08-25 | キヤノン株式会社 | 化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2006128624A (ja) * | 2004-09-29 | 2006-05-18 | Canon Inc | 発光素子 |
JP4478555B2 (ja) * | 2004-11-30 | 2010-06-09 | キヤノン株式会社 | 金属錯体、発光素子及び画像表示装置 |
TWI321968B (en) | 2005-07-15 | 2010-03-11 | Lg Chemical Ltd | Organic light meitting device and method for manufacturing the same |
JP4770699B2 (ja) * | 2005-12-16 | 2011-09-14 | ソニー株式会社 | 表示素子 |
JP2007308477A (ja) * | 2006-04-20 | 2007-11-29 | Canon Inc | 化合物および有機発光素子 |
JP4227628B2 (ja) * | 2006-04-25 | 2009-02-18 | キヤノン株式会社 | 化合物および有機発光素子 |
US7754348B2 (en) * | 2007-04-25 | 2010-07-13 | Luminescene Technology Corp. | Phenanthroline compound and organic light emitting device using the same |
JP5159164B2 (ja) * | 2007-05-14 | 2013-03-06 | キヤノン株式会社 | ベンゾ[ghi]フルオランテン誘導体及びこれを用いた有機発光素子 |
US8076009B2 (en) * | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
US8420229B2 (en) * | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
US8431242B2 (en) | 2007-10-26 | 2013-04-30 | Global Oled Technology, Llc. | OLED device with certain fluoranthene host |
US20090110956A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with electron transport material combination |
US8129039B2 (en) * | 2007-10-26 | 2012-03-06 | Global Oled Technology, Llc | Phosphorescent OLED device with certain fluoranthene host |
WO2009066600A1 (ja) * | 2007-11-19 | 2009-05-28 | Idemitsu Kosan Co., Ltd. | モノベンゾクリセン誘導体、及びそれを含む有機エレクトロルミネッセンス素子用材料、並びにそれを用いた有機エレクトロルミネッセンス素子 |
KR101003267B1 (ko) | 2008-01-18 | 2010-12-21 | 주식회사 엘지화학 | 유기발광소자 및 이의 제조 방법 |
JP4830126B2 (ja) * | 2008-03-22 | 2011-12-07 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP4830127B2 (ja) * | 2008-03-22 | 2011-12-07 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
EP2299786B1 (en) | 2008-05-16 | 2014-03-26 | LG Chem, Ltd. | Stacked organic light-emitting diode |
KR101069520B1 (ko) | 2008-10-01 | 2011-09-30 | 주식회사 엘지화학 | 유기발광소자 및 이의 제조방법 |
EP2206716A1 (en) * | 2008-11-27 | 2010-07-14 | Solvay S.A. | Host material for light-emitting diodes |
US8088500B2 (en) * | 2008-11-12 | 2012-01-03 | Global Oled Technology Llc | OLED device with fluoranthene electron injection materials |
US7968215B2 (en) * | 2008-12-09 | 2011-06-28 | Global Oled Technology Llc | OLED device with cyclobutene electron injection materials |
EP2361009A4 (en) * | 2008-12-22 | 2012-12-05 | Du Pont | ELECTRONIC DEVICE WITH A PHENANTHROLINE DERIVATIVE |
US8216697B2 (en) * | 2009-02-13 | 2012-07-10 | Global Oled Technology Llc | OLED with fluoranthene-macrocyclic materials |
JP5349105B2 (ja) * | 2009-03-25 | 2013-11-20 | 株式会社東芝 | 有機電界発光素子 |
US20100244677A1 (en) * | 2009-03-31 | 2010-09-30 | Begley William J | Oled device containing a silyl-fluoranthene derivative |
JP5171734B2 (ja) * | 2009-06-04 | 2013-03-27 | 株式会社半導体エネルギー研究所 | 電界発光素子および発光装置 |
JP5722238B2 (ja) | 2010-01-15 | 2015-05-20 | 出光興産株式会社 | 含窒素複素環誘導体及びそれを含んでなる有機エレクトロルミネッセンス素子 |
JP5757615B2 (ja) * | 2011-03-10 | 2015-07-29 | 国立研究開発法人物質・材料研究機構 | 配位数4の金属及びビスフェナントロリン誘導体を含む有機/金属ハイブリッドポリマー、その配位子、及びその製造方法 |
WO2013035329A1 (ja) * | 2011-09-09 | 2013-03-14 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
JP2013110224A (ja) * | 2011-11-18 | 2013-06-06 | Mitsubishi Chemicals Corp | 光電変換素子、太陽電池、及び太陽電池モジュール |
KR101722027B1 (ko) | 2012-05-03 | 2017-04-03 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
JP6134786B2 (ja) | 2012-05-31 | 2017-05-24 | エルジー ディスプレイ カンパニー リミテッド | 有機電界発光素子 |
CN104335378B (zh) | 2012-05-31 | 2017-08-29 | 乐金显示有限公司 | 有机电致发光装置 |
CN104321896B (zh) | 2012-05-31 | 2017-07-14 | 乐金显示有限公司 | 堆叠式有机发光二极管 |
US9859517B2 (en) * | 2012-09-07 | 2018-01-02 | Nitto Denko Corporation | White organic light-emitting diode |
KR102120894B1 (ko) | 2013-05-03 | 2020-06-10 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US10033007B2 (en) | 2013-06-07 | 2018-07-24 | Lg Display Co., Ltd. | Organic light emitting diode |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
US9768390B2 (en) | 2015-03-26 | 2017-09-19 | Feng-wen Yen | Phenanthroline derivative for organic electroluminescent device |
US9692003B2 (en) * | 2015-04-15 | 2017-06-27 | Feng-wen Yen | Phenanthroline derivative and use thereof |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102536248B1 (ko) | 2017-06-21 | 2023-05-25 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102415376B1 (ko) | 2017-08-04 | 2022-07-01 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101926770B1 (ko) * | 2018-03-05 | 2018-12-07 | 주식회사 진웅산업 | 페난트롤린 화합물 및 이를 포함하는 유기발광소자 |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
CN110144213A (zh) * | 2019-05-31 | 2019-08-20 | 北京诚志永华显示科技有限公司 | 有机电致发光材料、有机电致发光器件 |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2024034301A1 (ja) * | 2022-08-09 | 2024-02-15 | 株式会社日本触媒 | フェナントロリン化合物およびそれを用いた有機薄膜、有機半導体素子 |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362645A3 (en) | 2022-10-27 | 2024-05-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362630A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362631A3 (en) | 2022-10-27 | 2024-05-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
EP1097980A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Bathophenanthroline compound and process for preparing same |
JP2001267080A (ja) * | 2000-01-14 | 2001-09-28 | Toray Ind Inc | 発光素子 |
JP2002050481A (ja) * | 2000-08-04 | 2002-02-15 | Toray Ind Inc | 発光素子 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US4720432A (en) * | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
US4885211A (en) * | 1987-02-11 | 1989-12-05 | Eastman Kodak Company | Electroluminescent device with improved cathode |
US5130603A (en) * | 1989-03-20 | 1992-07-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
JP2815472B2 (ja) * | 1990-01-22 | 1998-10-27 | パイオニア株式会社 | 電界発光素子 |
EP0443861B2 (en) * | 1990-02-23 | 2008-05-28 | Sumitomo Chemical Company, Limited | Organic electroluminescence device |
GB9018698D0 (en) * | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
US5382477A (en) * | 1991-02-27 | 1995-01-17 | Sanyo Electric Co., Ltd. | Organic electroluminescent element and process for producing the same |
US5151629A (en) * | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
JPH05202356A (ja) | 1991-09-11 | 1993-08-10 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
JP3328731B2 (ja) | 1991-12-05 | 2002-09-30 | 住友化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
US5393614A (en) * | 1992-04-03 | 1995-02-28 | Pioneer Electronic Corporation | Organic electroluminescence device |
US5514878A (en) * | 1994-03-18 | 1996-05-07 | Holmes; Andrew B. | Polymers for electroluminescent devices |
JPH0782551A (ja) | 1993-09-09 | 1995-03-28 | Nisshinbo Ind Inc | 有機エレクトロルミネッセンス素子 |
US5409783A (en) * | 1994-02-24 | 1995-04-25 | Eastman Kodak Company | Red-emitting organic electroluminescent device |
JPH09202878A (ja) | 1996-01-25 | 1997-08-05 | Nippon Telegr & Teleph Corp <Ntt> | 近紫外・紫外波長帯発光素子 |
JPH09227576A (ja) | 1996-02-23 | 1997-09-02 | Sony Corp | 金属複核錯体、その製造方法及び光学的素子 |
JPH1079297A (ja) * | 1996-07-09 | 1998-03-24 | Sony Corp | 電界発光素子 |
HU228700B1 (en) | 1998-07-22 | 2013-05-28 | Stichting Dienst Landbouwkundi | Streptococcus suis vaccines and diagnostic tests |
JPWO2003076549A1 (ja) * | 2002-03-08 | 2005-07-07 | キヤノン株式会社 | 金属配位化合物を用いた電界発光素子 |
-
2002
- 2002-09-19 JP JP2002272408A patent/JP4261855B2/ja not_active Expired - Fee Related
-
2003
- 2003-09-09 AU AU2003260955A patent/AU2003260955A1/en not_active Abandoned
- 2003-09-09 US US10/527,192 patent/US7550594B2/en active Active
- 2003-09-09 WO PCT/JP2003/011485 patent/WO2004026870A1/en active Application Filing
-
2009
- 2009-05-06 US US12/436,507 patent/US7982213B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
EP1097980A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Bathophenanthroline compound and process for preparing same |
JP2001267080A (ja) * | 2000-01-14 | 2001-09-28 | Toray Ind Inc | 発光素子 |
JP2002050481A (ja) * | 2000-08-04 | 2002-02-15 | Toray Ind Inc | 発光素子 |
Non-Patent Citations (1)
Title |
---|
ITO, T: "Synthesis of phenanthroline delivatives and their application to organic EL devices.", POLYMER PREPRINTS, JAPAN, vol. 51, no. 11, 18 September 2002 (2002-09-18), pages 2859 - 2860, XP002974180 * |
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JP2004107263A (ja) | 2004-04-08 |
US7550594B2 (en) | 2009-06-23 |
US20060097227A1 (en) | 2006-05-11 |
US20090218940A1 (en) | 2009-09-03 |
AU2003260955A1 (en) | 2004-04-08 |
US7982213B2 (en) | 2011-07-19 |
JP4261855B2 (ja) | 2009-04-30 |
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