WO2014007565A1 - 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 - Google Patents
유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 Download PDFInfo
- Publication number
- WO2014007565A1 WO2014007565A1 PCT/KR2013/005954 KR2013005954W WO2014007565A1 WO 2014007565 A1 WO2014007565 A1 WO 2014007565A1 KR 2013005954 W KR2013005954 W KR 2013005954W WO 2014007565 A1 WO2014007565 A1 WO 2014007565A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- substituted
- unsubstituted
- group
- compound
- Prior art date
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
- H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- 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
- H10K85/30—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
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Definitions
- Display device including organic light emitting device
- It relates to a display device including an organic light emitting device.
- An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
- Organic optoelectronic devices can be divided into two types according to the principle of operation.
- exciton is formed in the organic layer by photons introduced from the external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes, respectively, to the current source (voltage source).
- current source voltage source
- the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
- Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, an organic transistor, and the like. Injection or transport materials, or light emitting materials.
- organic light emitting diodes are attracting attention as demand for flat panel displays increases.
- organic light emitting phenomenon is to convert electrical energy into light energy using organic material
- Such an organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
- the organic material layer has a multilayer structure composed of different materials in order to increase efficiency and stability of the organic light emitting device.
- it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- the material used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials depending on their functions.
- the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
- the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect.
- the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect.
- Host / dopant systems can be used.
- a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material
- the backing should be preceded by a stable and efficient material, and the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, the development of new materials is continuously required.
- the necessity of such a material development is the same in the other organic optoelectronic devices described above.
- the low molecular weight organic light emitting device is a device in the form of a thin film by vacuum deposition method Since it is manufactured, the efficiency and lifespan performance are good, and the polymer organic light emitting device has an advantage of low initial investment cost and large area using an inkjet or spin coating method.
- Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
- advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
- LCD liquid crystal display
- the response speed is 1000 times faster than the LCD in microseconds, it is possible to implement a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era. Based on these advantages, it has made rapid technological advancements of 80 times efficiency and 100 times life span since the first development in the late 1980s. Increasingly, large-scaled developments are being made with the introduction of organic light emitting diode panels.
- An organic light emitting device comprising the compound for an organic optoelectronic device and the
- a display device including an organic light emitting device is provided.
- R 1 to R 16 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 17 R 18 R 19 , wherein R 17 to R 19 are each independently a substituted or unsubstituted C1 to C6 alkyl group.
- R 1 to R 8 is a functional group represented by Formula 2, and any one of R 1 to R 8 is —SiR 17 R 18 R 19 .
- any one of R 9 to R 16 is a functional group represented by the following formula (2), and R 9 to R 16 , the other is-SiR 17 R 18 R 19 . .
- L is a bidentate ligand of a monovalent anion, which is a ligand that coordinates to this rhythm via a non-covalent electron pair of carbon or heteroatom, n and m are independently of each other any one of integers from 0 to 3, n + m is either an integer increase of 1 to 3.
- R 20 to R 24 are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group, and * is a part connected to a carbon atom Means.
- R 20 to R 24 includes an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, wherein at least one layer of the organic thin film layer comprises the organic optoelectronic device compound Element
- the organic thin film layer may be a light emitting layer.
- the compound for an organic optoelectronic device may be used as a dopant in a light emitting layer.
- a display device including the organic light emitting diode is provided.
- the organic optoelectronic device including the compound for an organic optoelectronic device has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.
- the compound for an organic optoelectronic device may be suitable for a solution process.
- FIG. 1 and 2 are cross-sectional views illustrating various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to one embodiment. [Best form for implementation of the invention]
- optionally substituted means separate there is no defined "one, in the substituent or compound, at least one hydrogen is deuterium, halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or Unsubstituted C3 to C40 silyl groups, C1 to C30 alkyl groups, C1 to C10 alkylsilyl groups, C3 to C30 cycloalkyl groups, C6 to C30 aryl groups, C1 to C20 alkoxy groups, fluoro groups, and trifluoromethyl groups Substituted C1 to C10 trifluoroalkyl group or cyano group and also substituted halogen, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 Silyl group, C1 to C30 alkyl group, C
- hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S, and P in one functional group, and the remainder is carbon.
- an "alkyl group” is aliphatic
- the alkyl group may be a "saturated alkyl group" that does not contain any double bonds or triple bonds.
- the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
- a C1 to C4 alkyl group means one to four carbon atoms in the alkyl chain, and methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
- Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, penyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus. It means a practical skill.
- Aryl group means a substituent in which all elements of a cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic (Ie, rings that share adjacent pairs of carbon atoms).
- Heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
- substituted or unsubstituted aryl group and / or substituted or unsubstituted heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted.
- Furanyl group substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrylyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or
- Thiadiazolyl group substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinal group, substituted or unsubstituted A quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a
- the hole characteristic means a property that has a conduction characteristic along the HOMO level and facilitates the injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
- the electronic characteristic means the characteristic which has an electroconductive characteristic along LUMO level, and makes the injection
- R 1 to R 16 each independently represent hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, "substituted or unsubstituted C6 to C20 aryl group, or unsubstituted R 17 to R 19 are each independently a substituted or unsubstituted C1 to C6 alkyl group.
- R 1 to R 8 is a functional group represented by the following Chemical Formula 2, and any one of R 1 to R 8 is —SiR 17 R 18 R 19 .
- any one of R 9 to R 16 is a functional group represented by the following formula (2), and R 9 to R 16 , the other is-SiR 17 R 18 R 19 .
- L is a bidentate ligand of a monovalent anion, is a ligand coordinating to this lithium via a non-covalent electron pair of carbon or heteroatom, n and m are independently integers of 0 to 3, n + m is any one of 1 to 3.
- Formula 2 is in the form of a substituted or unsubstituted phenyl group, in Formula 2 R : to R 24 are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 Is an aryl group, and * is a carbon atom It means the part to be connected.
- Compound for an organic optoelectronic device represented by Formula 1 is 2-phenylpyridine
- the main ligand of the skeleton must have a substituted or unsubstituted phenyl group represented by the formula (2), and must also have -SiR 17 R 18 R 19 .
- the main ligand refers to a ligand represented by the number n or m of ligands coordinated to the rhythm.
- the compound for an organic optoelectronic device represented by Chemical Formula 1 may have excellent heat resistance stability and lifespan characteristics and high luminous efficiency even at a low driving voltage.
- the efficiency at high current density is triplet.
- the dopant which is a light emitter manufactured in one embodiment, also has reduced intermolecular interactions due to the introduction of -SiR 17 R 18 R 19 and a phenyl group having high steric hindrance. The efficiency is thought to be very good.
- the deposition silver may also have an effect of reducing.
- One main ligand in Formula 1 has one -SiR 17 R 18 R 19 .
- n is any one integer of 1 to 3
- R 1 to R 4 is either a -SiR l7 R 18 R 19
- R 1 to R 4 are each of the remaining
- any one of R 5 to R 8 is a functional group represented by Formula 2, and the rest of R 5 to R 8 may be each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group.
- the compound for an organic optoelectronic device may realize excellent heat stability, lifetime characteristics, and luminous efficiency. Bulky substituents
- n is any one integer increasing 1 to 3
- R 2 is a -SiR l7 R ls R 19
- R 6 is a phenyl group
- the compound for an organic optoelectronic device is excellent in heat resistance stability, life characteristics and luminous efficiency.
- the light emitting device can be realized with high efficiency and long life.
- n is any one of integers of 1 to 3
- any one of R 1 to R 4 is a functional group represented by Formula 2
- any of R 1 to R 4 is -SiR. 17 R 18 R 19
- the remainder of R 1 to R 4 and R 5 to R 8 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group.
- the functional group represented by -SiR 17 ⁇ ⁇ 19 and the formula (2) may be bonded in the ortho, meta or para position.
- n in Formula 1 is any one of an integer of 1 to 3,
- R 2 is a phenyl group
- R 3 is —SiR 17 R 18 R 19
- R 1 , R 4 to R 8 may each independently be hydrogen, hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group.
- the compound for an organic optoelectronic device is excellent in heat resistance stability, life characteristics and luminous efficiency.
- n is any one of 1 to 3
- any one of R 1 to R 4 is -SiR 17 R 18 R 19
- the rest of R 1 to R 4 are each independently. Hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group.
- any one of R 5 to R 8 is represented by the formula (2)
- R 5 to R 8 increase remainder may be each independently hydrogen, dihydrogen, or a substituted or unsubstituted C1 to CH) alkyl group.
- m is any one of an integer of 1 to 3
- any one of R 9 to R 12 is a functional group represented by the formula (2)
- any other of R 9 to R 12 is -SiR 17 R 18 R 19
- R 9 to R 12 increase and R 13 to R 16 may be each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group.
- n is any one of an integer of 1 to 3
- at least one of R 1 to R 8 may be a substituted or unsubstituted C1 to C20 alkyl group, specifically an unsubstituted C1 to C10 alkyl group, for example a methyl group Can be. In this case, there is an effect excellent in thermal stability.
- R 17 to R 19 may each be a methyl group. That is, above-
- SiR 17 R 18 R 19 may be trimethylsilyl group.
- the compound for an organic optoelectronic device may implement excellent heat stability, lifetime characteristics and luminous efficiency.
- n + m may be 3.
- n or m in Formula 1 may be 3. This means that the ligand represented by L in the formula (1) is not included. In this case, the synthesis is easy and the compound may be stable. Therefore, by applying this it can be produced a light emitting device excellent in life characteristics.
- n + m may be 1 or 2. This means that at least one ligand represented by L in Formula 1 is included. In this case, the color of the compound can be adjusted.
- L is an auxiliary ligand, and the following Formula L-1 to Formula L-
- L 14 may be selected. However, this is only an example of a ligand represented by L, and the present invention is not limited thereto.
- an asterisk (*) denotes a position which combines with rhythm (Ir), and R 101 to R 103 independently of each other, hydrogen, hydrogen, halogen, or substituted C1 to C1-C14.
- An alkyl group of C30, an alkyl of C1 to C30 may be a substituted or unsubstituted aryl group of C6 to C30, or a halogen.
- 04 to R are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 Trialkylsilyl group having arylamino group, SF 5 , substituted or unsubstituted C1 to C30 alkyl group, Dialkylarylsilyl group having substituted or unsubstituted C1 to C30 alkyl group and C6 to C30 aryl group
- Rue to Rm may be independently of each other hydrogen, deuterium, C1 to C30 alkyl group, which is substituted or unsubstituted, C6 to C30 aryl group which is substituted or unsubstituted, alkyl of C1 to C30.
- Formula 1 may be any one of the following Formula M-1 to Formula M-40, Formula ⁇ _ ⁇ to Formula p-26, Formula Q-1 to Formula Q-46. This is an example of a structure in which one phenyl group and one trimethylsilyl group are substituted in the main ligand. However, this is only a specific example of the formula (1), the present invention is not limited thereto.
- an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least any one of the organic thin film layer comprising the compound for the organic optoelectronic device Provided is an organic optoelectronic device.
- the compound for an organic optoelectronic device is used in an organic thin film layer
- the organic thin film layer may be a light emitting layer.
- the organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device.
- the organic optoelectronic device may be an organic light emitting device.
- 1 to 5 are cross-sectional views of an organic light emitting device including the compound for an organic optoelectronic device according to an embodiment of the present invention.
- the organic light emitting diodes 100 and 200 according to the exemplary embodiment of the present invention may include an anode 120, a cathode 1 10, and at least one organic layer interposed between the anode and the cathode. It has a structure including the thin film layer 105.
- the anode 120 includes an anode material, which is typically
- a material having a large work function is preferable to facilitate hole injection into the organic thin film layer.
- the positive electrode material may include nickel, platinum, barnacle, crack, copper, zinc, metal such as gold, or an alloy thereof, zinc oxide, indium oxide,
- Metal oxides such as indium tin oxide ( ⁇ ) and indium zinc oxide (IZO); and combinations of metals and oxides such as ZnO and A1 or Sn0 2 and Sb; and poly (3-methylthiophene)
- Conductive polymers such as poly (3,4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole, and polyaniline, and the like, but are not limited thereto.
- a transparent electrode including indium tin oxide (ITO) may be used as the anode.
- the negative electrode 1 10 comprises a negative electrode material, which is usually
- the material has a small work function to facilitate electron injection into the organic thin film layer.
- the negative electrode material may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Multi-layered materials such as Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
- a metal electrode such as aluminum can be used as the cathode.
- FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105, and the organic thin film layer 105 is
- the light emitting layer 130 may be present only.
- FIG. 2 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 including an electron transport layer and a hole transport layer 140 as an organic thin film layer 105, as shown in FIG. 2.
- the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
- the light emitting layer 130 functions as an electron transporting layer
- the hole transporting layer 140 has a bonding property with a transparent electrode such as?
- an electron transport layer As the organic thin film layer 105 in FIG. 1 or FIG. 2, an electron transport layer, an electron injection layer, and a hole injection layer. It may be an organic light emitting device further including.
- the light emitting layers 130 and 230 constituting the organic thin film layer 105, the hole transport layer 140, or an electron transport layer, an electron injection layer, a hole injection layer, and combinations thereof, which may not be included, may be included. Any one selected from the group includes the compound for organic optoelectronic devices.
- the compound for an organic optoelectronic device may be used in the light emitting layers 130 and 230, and may be used as a green phosphorescent dopant material in the light emitting layer.
- the organic light emitting device described above after forming an anode on a substrate,
- the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
- a display device including the organic optoelectronic device is provided.
- Compound P-12 was synthesized in the same manner as in the preparation of Compound M-1, using 16.2 g (37.67 mmol) of K-1-3 and 34.3 g (1 13.02 mmol) of Compound 1 of Preparation Example 1, in a 250 mL back bottom flask. 4.8 g (30%) was obtained.
- ITO Indium tin oxide
- ITO Indium tin oxide
- distilled water ultrasonic.
- HTM N- (biphenyl-4-yl) -9,9-diphenyl-N- (4- (9-phenyl) represented by the following formula Z-1 on the ⁇ substrate using the prepared ⁇ ⁇ transparent electrode as the anode -9H-carbazole) -3-yl) phenyl) 9H-fluorene- 2 -amine
- HTM N- (biphenyl-4-yl) -9,9-diphenyl-N- (4- (9-phenyl) represented by the following formula Z-1 on the ⁇ substrate using the prepared ⁇ ⁇ transparent electrode as the anode -9H-carbazole) -3-yl) phenyl) 9H-fluorene- 2 -amine
- An organic light emitting diode was manufactured according to the same method as described above.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 2 instead of the dopant according to Preparation Example 1.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 3.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 4.
- An organic light emitting diode * was manufactured in the same manner as in Example 1, except for using the dopant according to Preparation Example 5.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for the dot using the dopant according to Preparation Example 6.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 7.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using a dopant according to Preparation Example 8. (Performance Measurement of Organic Light Emitting Diode)
- the current density change and luminance change according to voltage were measured, and the luminous efficiency was evaluated and life characteristics were evaluated.
- Specific measurement methods are as follows, and the results are shown in Table 1 below.
- the current value flowing through the unit device was measured using a current-voltmeter (Keithley2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
- the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
- a luminance meter Minolta Cs-IOOOA
- the current efficiency (cd / A) of the same brightness (9000 cd / m 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2).
- the lifetime is a measure of the time until the 3% luminous efficiency decreases at a luminance of 6000 cd / m 2.
- the present invention may not be limited to the above embodiments, but may be manufactured in various other forms, and a person of ordinary skill in the art to which the present invention pertains may change the technical spirit or essential features of the present invention without changing other specific features. It will be appreciated that it may be implemented in a form. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
- organic light emitting element 110 cathode
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015520065A JP6189431B2 (ja) | 2012-07-04 | 2013-07-04 | 有機光電子素子用化合物、これを含む有機発光素子および前記有機発光素子を含む表示装置 |
US14/390,570 US9882149B2 (en) | 2012-07-04 | 2013-07-04 | Compound for organic optoelectric device, organic optoelectronic device comprsing same, and display apparatus comprising organic optoelectric device |
CN201380033478.8A CN104428391B (zh) | 2012-07-04 | 2013-07-04 | 用于有机光电装置的化合物、包括它的有机光电装置和包括有机光电装置的显示设备 |
EP13812616.4A EP2871222B1 (en) | 2012-07-04 | 2013-07-04 | Compound for organic optoelectric device, organic optoelectric device comprising same, and display apparatus comprising organic optoelectric device |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20120073091 | 2012-07-04 | ||
KR10-2012-0073091 | 2012-07-04 | ||
KR20120124963 | 2012-11-06 | ||
KR10-2012-0124963 | 2012-11-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014007565A1 true WO2014007565A1 (ko) | 2014-01-09 |
Family
ID=49882259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2013/005954 WO2014007565A1 (ko) | 2012-07-04 | 2013-07-04 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9882149B2 (ko) |
EP (1) | EP2871222B1 (ko) |
JP (1) | JP6189431B2 (ko) |
KR (1) | KR101344787B1 (ko) |
CN (1) | CN104428391B (ko) |
WO (1) | WO2014007565A1 (ko) |
Cited By (85)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3000815A1 (en) * | 2014-09-26 | 2016-03-30 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
EP3010067A1 (en) * | 2014-10-17 | 2016-04-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
EP3010066A1 (en) * | 2014-10-17 | 2016-04-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN105529406A (zh) * | 2014-10-17 | 2016-04-27 | 三星显示有限公司 | 有机发光元件 |
EP3056504A1 (en) | 2015-02-16 | 2016-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3061763A1 (en) | 2015-02-27 | 2016-08-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3067361A1 (en) * | 2015-03-13 | 2016-09-14 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US20160268519A1 (en) * | 2015-03-13 | 2016-09-15 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
JP2016188202A (ja) * | 2015-03-13 | 2016-11-04 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機金属化合物及びこれを含む有機発光素子 |
EP3098229A1 (en) | 2015-05-15 | 2016-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3101021A1 (en) | 2015-06-01 | 2016-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3124488A1 (en) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3159350A1 (en) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3205658A1 (en) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3231809A2 (en) | 2016-04-11 | 2017-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261147A1 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261146A2 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3270435A2 (en) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3297051A1 (en) | 2016-09-14 | 2018-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3301088A1 (en) | 2016-10-03 | 2018-04-04 | Universal Display Corporation | Condensed pyridines as organic electroluminescent materials and devices |
EP3305796A1 (en) | 2016-10-07 | 2018-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3321258A1 (en) | 2016-11-09 | 2018-05-16 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3323822A1 (en) | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3345914A1 (en) | 2017-01-09 | 2018-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3354654A2 (en) | 2016-11-11 | 2018-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3381927A1 (en) | 2017-03-29 | 2018-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3401318A1 (en) | 2017-05-11 | 2018-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3418286A1 (en) | 2017-06-23 | 2018-12-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3444258A2 (en) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2019088281A1 (ja) | 2017-11-06 | 2019-05-09 | 保土谷化学工業株式会社 | インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
WO2019098234A1 (ja) | 2017-11-16 | 2019-05-23 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
EP3489243A1 (en) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480A2 (en) | 2017-11-29 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3492528A1 (en) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN110746422A (zh) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | 有机化合物、高聚物、混合物、组合物及其有机电子器件 |
EP3613751A1 (en) | 2018-08-22 | 2020-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3689889A1 (en) | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3690973A1 (en) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organic electroluminescent materials and devices |
KR20200096506A (ko) | 2017-12-05 | 2020-08-12 | 호도가야 가가쿠 고교 가부시키가이샤 | 아릴아민 화합물 및 유기 일렉트로루미네선스 소자 |
EP3715353A1 (en) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10826000B2 (en) | 2014-10-17 | 2020-11-03 | Samsung Display Co., Ltd. | Organic light-emitting device |
US10854827B2 (en) * | 2014-12-17 | 2020-12-01 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
EP3750897A1 (en) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3771717A1 (en) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3778614A1 (en) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112480180A (zh) * | 2019-09-11 | 2021-03-12 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件和包括所述有机发光器件的电子设备 |
EP3816175A1 (en) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3845545A1 (en) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858945A1 (en) | 2020-01-28 | 2021-08-04 | 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 |
EP4001287A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001286A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4016659A1 (en) | 2020-11-16 | 2022-06-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4019526A1 (en) | 2018-01-26 | 2022-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
EP4039692A1 (en) | 2021-02-03 | 2022-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4053137A1 (en) | 2021-03-05 | 2022-09-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4056578A1 (en) | 2021-03-12 | 2022-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059941A1 (en) | 2021-03-15 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4074723A1 (en) | 2021-04-05 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075530A1 (en) | 2021-04-14 | 2022-10-19 | 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 |
EP4079743A1 (en) | 2021-04-23 | 2022-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4086266A1 (en) | 2021-04-23 | 2022-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4112701A2 (en) | 2021-06-08 | 2023-01-04 | University of Southern California | Molecular alignment of homoleptic iridium phosphors |
US11594690B2 (en) | 2017-12-14 | 2023-02-28 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex, and polymer, mixture and formulation comprising same, and use thereof in electronic device |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4185086A1 (en) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11672167B2 (en) | 2015-03-13 | 2023-06-06 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US11674080B2 (en) | 2017-12-14 | 2023-06-13 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex, polymer, mixture, formulation and use thereof |
US11680059B2 (en) | 2017-12-21 | 2023-06-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture and application thereof in organic electronic devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11731994B2 (en) | 2018-12-05 | 2023-08-22 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
EP4231804A2 (en) | 2022-02-16 | 2023-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4242285A1 (en) | 2022-03-09 | 2023-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4265626A2 (en) | 2022-04-18 | 2023-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4282863A1 (en) | 2022-05-24 | 2023-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4299693A1 (en) | 2022-06-28 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4326030A1 (en) | 2022-08-17 | 2024-02-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362631A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362630A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362645A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102429869B1 (ko) * | 2014-10-17 | 2022-08-05 | 삼성전자주식회사 | 유기 발광 소자 |
KR102429870B1 (ko) * | 2014-10-17 | 2022-08-05 | 삼성전자주식회사 | 유기 발광 소자 |
KR102323210B1 (ko) | 2014-11-14 | 2021-11-08 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
US10003035B2 (en) | 2014-11-28 | 2018-06-19 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
EP3026056B1 (en) * | 2014-11-28 | 2017-11-08 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
KR102395990B1 (ko) * | 2014-12-30 | 2022-05-10 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
US9701671B2 (en) * | 2015-02-20 | 2017-07-11 | Canon Kabushiki Kaisha | Organic compound, electrochromic element containing the same, optical filter, lens unit, imaging device, and window component |
EP3133078B1 (en) * | 2015-08-18 | 2019-01-30 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
KR102541267B1 (ko) * | 2015-10-05 | 2023-06-12 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US20170141330A1 (en) * | 2015-11-17 | 2017-05-18 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
US20170155063A1 (en) * | 2015-11-26 | 2017-06-01 | Industrial Technology Research Institute | Organic metal compound, organic light-emitting devices employing the same |
CN106883270B (zh) | 2015-11-26 | 2019-03-26 | 财团法人工业技术研究院 | 有机金属化合物、包含其的有机发光装置 |
US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
TWI728594B (zh) * | 2019-12-13 | 2021-05-21 | 財團法人工業技術研究院 | 有機金屬化合物及包含其之有機發光裝置 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20060029866A (ko) * | 2004-10-04 | 2006-04-07 | 엘지전자 주식회사 | 유기 실리콘을 갖는 페닐 피리딘기를 포함하는 이리듐화합물계 발광 화합물 및 이를 발색 재료로서 사용하는유기전계발광소자 |
WO2008056799A1 (en) * | 2006-11-07 | 2008-05-15 | Showa Denko K.K. | Iridium complex compound, organic electroluminescent device obtained by using the same, and uses of the device |
KR20110065496A (ko) | 2008-09-03 | 2011-06-15 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
WO2012023947A1 (en) * | 2010-08-20 | 2012-02-23 | Universal Display Corporation | Bicarbazole compounds for oleds |
WO2012057138A1 (ja) * | 2010-10-28 | 2012-05-03 | 独立行政法人産業技術総合研究所 | トリスオルトメタル化イリジウム錯体の製造方法及びそれを用いた発光材料並びに発光素子 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7675228B2 (en) * | 2006-06-14 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with silylated, germanylated, and stannylated ligands, and devices made with such compounds |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
KR100907564B1 (ko) | 2007-06-29 | 2009-07-14 | 제일모직주식회사 | 유기전계발광 소자용 발광층 조성물 및 이를 이용한 유기전계발광 소자 |
KR100894135B1 (ko) | 2007-06-29 | 2009-04-20 | 제일모직주식회사 | 유기전계 발광소자용 금속착체 화합물 및 이를 이용한유기전계발광 표시소자 |
KR100933226B1 (ko) * | 2007-11-20 | 2009-12-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
KR100933225B1 (ko) | 2007-11-27 | 2009-12-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 인광 화합물 및 이를 발광재료로서 채용하고 있는유기발광소자 |
KR100966885B1 (ko) * | 2008-02-29 | 2010-06-30 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자 |
KR100946409B1 (ko) * | 2008-03-19 | 2010-03-09 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자 |
KR100880224B1 (ko) | 2008-06-20 | 2009-01-28 | 엘지디스플레이 주식회사 | 유기 실리콘을 갖는 페닐 피리딘기를 포함하는 이리듐화합물계 발광 화합물 및 이를 발색 재료로서 사용하는유기전계발광소자 |
KR20100047466A (ko) * | 2008-10-29 | 2010-05-10 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
JP4474493B1 (ja) | 2009-07-31 | 2010-06-02 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4500364B1 (ja) | 2009-08-31 | 2010-07-14 | 富士フイルム株式会社 | 有機電界発光素子 |
CN102421772B (zh) | 2010-04-20 | 2015-11-25 | 出光兴产株式会社 | 双咔唑衍生物、有机电致发光元件用材料及使用其的有机电致发光元件 |
KR20110122051A (ko) | 2010-05-03 | 2011-11-09 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
US20140054564A1 (en) | 2010-07-30 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Electroluminescent device using electroluminescent compound as luminescent material |
-
2013
- 2013-07-04 KR KR1020130078591A patent/KR101344787B1/ko active IP Right Grant
- 2013-07-04 WO PCT/KR2013/005954 patent/WO2014007565A1/ko active Application Filing
- 2013-07-04 EP EP13812616.4A patent/EP2871222B1/en active Active
- 2013-07-04 CN CN201380033478.8A patent/CN104428391B/zh active Active
- 2013-07-04 US US14/390,570 patent/US9882149B2/en active Active
- 2013-07-04 JP JP2015520065A patent/JP6189431B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20060029866A (ko) * | 2004-10-04 | 2006-04-07 | 엘지전자 주식회사 | 유기 실리콘을 갖는 페닐 피리딘기를 포함하는 이리듐화합물계 발광 화합물 및 이를 발색 재료로서 사용하는유기전계발광소자 |
WO2008056799A1 (en) * | 2006-11-07 | 2008-05-15 | Showa Denko K.K. | Iridium complex compound, organic electroluminescent device obtained by using the same, and uses of the device |
KR20110065496A (ko) | 2008-09-03 | 2011-06-15 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
WO2012023947A1 (en) * | 2010-08-20 | 2012-02-23 | Universal Display Corporation | Bicarbazole compounds for oleds |
WO2012057138A1 (ja) * | 2010-10-28 | 2012-05-03 | 独立行政法人産業技術総合研究所 | トリスオルトメタル化イリジウム錯体の製造方法及びそれを用いた発光材料並びに発光素子 |
Non-Patent Citations (2)
Title |
---|
ORGANIC ELECTRINICS, vol. 10, 2009, pages 1066 - 1073 |
See also references of EP2871222A4 |
Cited By (123)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016069379A (ja) * | 2014-09-26 | 2016-05-09 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機金属化合物及びそれを含む有機発光素子 |
US9490437B2 (en) | 2014-09-26 | 2016-11-08 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US10135009B2 (en) | 2014-09-26 | 2018-11-20 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
EP3000815A1 (en) * | 2014-09-26 | 2016-03-30 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
CN105529406B (zh) * | 2014-10-17 | 2019-06-04 | 三星显示有限公司 | 有机发光元件 |
CN105529406A (zh) * | 2014-10-17 | 2016-04-27 | 三星显示有限公司 | 有机发光元件 |
CN105529400B (zh) * | 2014-10-17 | 2020-08-18 | 三星显示有限公司 | 有机发光元件 |
CN105529400A (zh) * | 2014-10-17 | 2016-04-27 | 三星显示有限公司 | 有机发光元件 |
US10826000B2 (en) | 2014-10-17 | 2020-11-03 | Samsung Display Co., Ltd. | Organic light-emitting device |
EP3010066A1 (en) * | 2014-10-17 | 2016-04-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
EP3010067A1 (en) * | 2014-10-17 | 2016-04-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
US10854827B2 (en) * | 2014-12-17 | 2020-12-01 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
EP3056504A1 (en) | 2015-02-16 | 2016-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3061763A1 (en) | 2015-02-27 | 2016-08-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN105968142B (zh) * | 2015-03-13 | 2020-12-04 | 三星电子株式会社 | 有机金属化合物和包括其的有机发光器件 |
JP2016188202A (ja) * | 2015-03-13 | 2016-11-04 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機金属化合物及びこれを含む有機発光素子 |
JP2021102625A (ja) * | 2015-03-13 | 2021-07-15 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機金属化合物及びこれを含む有機発光素子 |
JP7102566B2 (ja) | 2015-03-13 | 2022-07-19 | 三星電子株式会社 | 有機金属化合物及びこれを含む有機発光素子 |
EP3067361A1 (en) * | 2015-03-13 | 2016-09-14 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US20160268519A1 (en) * | 2015-03-13 | 2016-09-15 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
JP2016169212A (ja) * | 2015-03-13 | 2016-09-23 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機金属化合物及びそれを含む有機発光素子 |
US11672167B2 (en) | 2015-03-13 | 2023-06-06 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
CN105968142A (zh) * | 2015-03-13 | 2016-09-28 | 三星电子株式会社 | 有机金属化合物和包括其的有机发光器件 |
EP3098229A1 (en) | 2015-05-15 | 2016-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3101021A1 (en) | 2015-06-01 | 2016-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3124488A1 (en) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3159350A1 (en) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3760635A1 (en) | 2015-09-03 | 2021-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858842A1 (en) | 2016-02-09 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3205658A1 (en) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4122941A1 (en) | 2016-04-11 | 2023-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3231809A2 (en) | 2016-04-11 | 2017-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4349935A2 (en) | 2016-06-20 | 2024-04-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3843171A1 (en) | 2016-06-20 | 2021-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3920254A1 (en) | 2016-06-20 | 2021-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3270435A2 (en) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261146A2 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261147A1 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3758084A1 (en) | 2016-06-20 | 2020-12-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3297051A1 (en) | 2016-09-14 | 2018-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3323822A1 (en) | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3301088A1 (en) | 2016-10-03 | 2018-04-04 | Universal Display Corporation | Condensed pyridines as organic electroluminescent materials and devices |
EP3305796A1 (en) | 2016-10-07 | 2018-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858844A1 (en) | 2016-10-07 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3789379A1 (en) | 2016-11-09 | 2021-03-10 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3321258A1 (en) | 2016-11-09 | 2018-05-16 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3354654A2 (en) | 2016-11-11 | 2018-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4092036A1 (en) | 2016-11-11 | 2022-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3689890A1 (en) | 2017-01-09 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212540A1 (en) | 2017-01-09 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3345914A1 (en) | 2017-01-09 | 2018-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3985012A1 (en) | 2017-03-29 | 2022-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3730506A1 (en) | 2017-03-29 | 2020-10-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3381927A1 (en) | 2017-03-29 | 2018-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4141010A1 (en) | 2017-05-11 | 2023-03-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3401318A1 (en) | 2017-05-11 | 2018-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3418286A1 (en) | 2017-06-23 | 2018-12-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4185086A1 (en) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3783006A1 (en) | 2017-08-10 | 2021-02-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3444258A2 (en) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2019088281A1 (ja) | 2017-11-06 | 2019-05-09 | 保土谷化学工業株式会社 | インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
KR20200084876A (ko) | 2017-11-06 | 2020-07-13 | 호도가야 가가쿠 고교 가부시키가이샤 | 인데노카르바졸 고리 구조를 갖는 화합물 및 유기 일렉트로루미네선스 소자 |
WO2019098234A1 (ja) | 2017-11-16 | 2019-05-23 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
KR20200088836A (ko) | 2017-11-16 | 2020-07-23 | 호도가야 가가쿠 고교 가부시키가이샤 | 유기 일렉트로루미네선스 소자 |
EP3878855A1 (en) | 2017-11-28 | 2021-09-15 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3489243A1 (en) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480A2 (en) | 2017-11-29 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3492528A1 (en) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20200096506A (ko) | 2017-12-05 | 2020-08-12 | 호도가야 가가쿠 고교 가부시키가이샤 | 아릴아민 화합물 및 유기 일렉트로루미네선스 소자 |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
US11594690B2 (en) | 2017-12-14 | 2023-02-28 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex, and polymer, mixture and formulation comprising same, and use thereof in electronic device |
US11674080B2 (en) | 2017-12-14 | 2023-06-13 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex, polymer, mixture, formulation and use thereof |
US11680059B2 (en) | 2017-12-21 | 2023-06-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture and application thereof in organic electronic devices |
EP4019526A1 (en) | 2018-01-26 | 2022-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4206210A1 (en) | 2018-08-22 | 2023-07-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3613751A1 (en) | 2018-08-22 | 2020-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11731994B2 (en) | 2018-12-05 | 2023-08-22 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
CN110746422A (zh) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | 有机化合物、高聚物、混合物、组合物及其有机电子器件 |
CN110746422B (zh) * | 2018-12-10 | 2023-01-10 | 广州华睿光电材料有限公司 | 有机化合物、高聚物、混合物、组合物及其有机电子器件 |
EP3690973A1 (en) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organic electroluminescent materials and devices |
EP4301117A2 (en) | 2019-02-01 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3689889A1 (en) | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4134371A2 (en) | 2019-03-26 | 2023-02-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3715353A1 (en) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3750897A1 (en) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4219515A1 (en) | 2019-07-30 | 2023-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3771717A1 (en) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3778614A1 (en) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112480180A (zh) * | 2019-09-11 | 2021-03-12 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件和包括所述有机发光器件的电子设备 |
EP3816175A1 (en) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4151644A1 (en) | 2020-01-06 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3845545A1 (en) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4294157A2 (en) | 2020-01-28 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858945A1 (en) | 2020-01-28 | 2021-08-04 | 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 |
EP4016659A1 (en) | 2020-11-16 | 2022-06-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001287A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4329463A2 (en) | 2020-11-24 | 2024-02-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001286A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4039692A1 (en) | 2021-02-03 | 2022-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4053137A1 (en) | 2021-03-05 | 2022-09-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4056578A1 (en) | 2021-03-12 | 2022-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059941A1 (en) | 2021-03-15 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4074723A1 (en) | 2021-04-05 | 2022-10-19 | 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 |
EP4075530A1 (en) | 2021-04-14 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4079743A1 (en) | 2021-04-23 | 2022-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4086266A1 (en) | 2021-04-23 | 2022-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4112701A2 (en) | 2021-06-08 | 2023-01-04 | 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 |
EP4231804A2 (en) | 2022-02-16 | 2023-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4242285A1 (en) | 2022-03-09 | 2023-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4265626A2 (en) | 2022-04-18 | 2023-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4282863A1 (en) | 2022-05-24 | 2023-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4299693A1 (en) | 2022-06-28 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4326030A1 (en) | 2022-08-17 | 2024-02-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362631A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362630A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362645A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
Also Published As
Publication number | Publication date |
---|---|
US20150090974A1 (en) | 2015-04-02 |
EP2871222B1 (en) | 2017-04-26 |
EP2871222A1 (en) | 2015-05-13 |
JP2015530356A (ja) | 2015-10-15 |
JP6189431B2 (ja) | 2017-08-30 |
KR101344787B1 (ko) | 2013-12-26 |
US9882149B2 (en) | 2018-01-30 |
EP2871222A4 (en) | 2016-04-06 |
CN104428391A (zh) | 2015-03-18 |
CN104428391B (zh) | 2017-06-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2014007565A1 (ko) | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 | |
KR101820865B1 (ko) | 유기광전자소자용 재료, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 | |
JP5707818B2 (ja) | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示素子、照明装置及び金属錯体化合物 | |
TWI500604B (zh) | 有機光電元件用組成物及有機光電元件及顯示元件 | |
JP5499972B2 (ja) | 有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子、これを用いた表示装置、照明装置 | |
CN110294703B (zh) | 用于有机光电器件的组合物、有机光电器件及显示器件 | |
EP2860783A1 (en) | Organic optoelectric device and display device | |
EP2871223A1 (en) | Composite for organic light-emitting diode, organic light-emitting layer including same, and organic light-emitting diode | |
KR20170102000A (ko) | 방향족 복소환 유도체, 그것을 사용한 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치 | |
CN109863614B (zh) | 有机电致发光元件及有机电致发光用材料 | |
WO2016068460A1 (ko) | 유기 광전자 소자 및 표시 장치 | |
WO2014104515A1 (ko) | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 | |
KR20120116282A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
JP6036696B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子の製造方法 | |
JP5692011B2 (ja) | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置、並びに照明装置 | |
WO2016068450A1 (ko) | 유기 광전자 소자 및 표시 장치 | |
JP5505315B2 (ja) | 有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子、これを用いた表示装置、照明装置、並びに複合縮環化合物 | |
JP5659972B2 (ja) | 有機エレクトロルミネッセンス素子および照明装置 | |
WO2014193033A1 (ko) | 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 | |
WO2014017094A1 (ja) | 有機エレクトロルミネッセンス素子 | |
JP5617645B2 (ja) | 有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子、これを用いた表示装置、照明装置 | |
WO2019066304A2 (ko) | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 | |
JP5609761B2 (ja) | プチセン系化合物、有機エレクトロルミネッセンス素子および照明装置 | |
JP2012169465A (ja) | 有機エレクトロルミネッセンス素子、該素子を用いた照明装置及び新規プチセン系化合物 | |
KR20200020061A (ko) | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13812616 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14390570 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2015520065 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REEP | Request for entry into the european phase |
Ref document number: 2013812616 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013812616 Country of ref document: EP |