WO2012067415A2 - Composé et dispositif électronique organique l'utilisant, et terminal comprenant le dispositif électronique organique - Google Patents
Composé et dispositif électronique organique l'utilisant, et terminal comprenant le dispositif électronique organique Download PDFInfo
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- WO2012067415A2 WO2012067415A2 PCT/KR2011/008732 KR2011008732W WO2012067415A2 WO 2012067415 A2 WO2012067415 A2 WO 2012067415A2 KR 2011008732 W KR2011008732 W KR 2011008732W WO 2012067415 A2 WO2012067415 A2 WO 2012067415A2
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- OQVCPJXWPMKXAS-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)cc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)cc(-c2ccccc2)n1 OQVCPJXWPMKXAS-UHFFFAOYSA-N 0.000 description 1
- CCRYOXJDIQMMIU-UHFFFAOYSA-N c(cc1)ccc1-c1cc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)cc(-c2ccccn2)c1 Chemical compound c(cc1)ccc1-c1cc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)cc(-c2ccccn2)c1 CCRYOXJDIQMMIU-UHFFFAOYSA-N 0.000 description 1
- VDNPUNQIXMYNOC-UHFFFAOYSA-N c(cc1)ccc1-c1cc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)cc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)cc(-c2ccccc2)n1 VDNPUNQIXMYNOC-UHFFFAOYSA-N 0.000 description 1
- AOIAANZENIWJAK-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)c1 AOIAANZENIWJAK-UHFFFAOYSA-N 0.000 description 1
- PUIXPDCFRMIEJT-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)ccc2N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)n1 PUIXPDCFRMIEJT-UHFFFAOYSA-N 0.000 description 1
- HYQNXRSBRBWCPR-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)c1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)c1 HYQNXRSBRBWCPR-UHFFFAOYSA-N 0.000 description 1
- ADCORORFRRLACF-UHFFFAOYSA-N c(cc1)ccc1-c1nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2c4cccc2)nc(-c2ccccc2)n1 ADCORORFRRLACF-UHFFFAOYSA-N 0.000 description 1
- QDAIQEQEDDIJRR-UHFFFAOYSA-N c(cc1)ccc1-c1nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1nc(N(c2ccc3)c(cccc4)c4-[n]4c2c3c2ccccc42)nc(-c2ccccc2)c1 QDAIQEQEDDIJRR-UHFFFAOYSA-N 0.000 description 1
- AKQOCYAPRXGFNZ-UHFFFAOYSA-N c(cc12)ccc1[n]1-c(cccc3)c3N(c3cc(-c4ccccn4)cc(-c4cccnc4)c3)c3cccc2c13 Chemical compound c(cc12)ccc1[n]1-c(cccc3)c3N(c3cc(-c4ccccn4)cc(-c4cccnc4)c3)c3cccc2c13 AKQOCYAPRXGFNZ-UHFFFAOYSA-N 0.000 description 1
- XVTCIANLZBSRHC-UHFFFAOYSA-N c(cc12)ccc1[n]1-c(cccc3)c3N(c3cc(-c4cccnc4)nc(-c4cccnc4)c3)c3cccc2c13 Chemical compound c(cc12)ccc1[n]1-c(cccc3)c3N(c3cc(-c4cccnc4)nc(-c4cccnc4)c3)c3cccc2c13 XVTCIANLZBSRHC-UHFFFAOYSA-N 0.000 description 1
- DQAWUPWJXNPLPW-UHFFFAOYSA-N c(cc1c2c3c4ccc2)ccc1[n]3-c(cccc1)c1N4c1nc(-c2ccccn2)cc(-c2ccccn2)n1 Chemical compound c(cc1c2c3c4ccc2)ccc1[n]3-c(cccc1)c1N4c1nc(-c2ccccn2)cc(-c2ccccn2)n1 DQAWUPWJXNPLPW-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a compound, an organic electric element using the same, and a terminal thereof.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
- Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.
- the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
- the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
- a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high-efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to 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, etc., is supported by a stable and efficient material.
- a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
- the present invention for solving the above problems of the background art hole injection material, hole transport material, suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, according to the compound containing quinoxalinocarbazole It has been found to be useful as a luminescent material and / or an electron transporting material and as a host material for phosphorescent dopants of various colors, depending on the compound containing quinoxalinocarbazole.
- an object of the present invention is to provide a compound containing quinoxalinocarbazole, an organic electronic device using the same, and an electronic device including the organic electronic device.
- the present invention provides a compound of the formula:
- the present invention can provide a compound containing quinoxalinocarbazole, an organic electronic device using the same, and an electronic device or a terminal including the organic electronic device.
- the present invention is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue and white depending on the compound containing quinoxalinocarbazole.
- a hole injection material such as red, green, blue and white depending on the compound containing quinoxalinocarbazole.
- it may exhibit a useful effect as a host material of phosphorescent dopants of various colors.
- 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
- substrate 102 anode
- the present invention can provide a compound represented by the following formula (1).
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, Thiol group, substituted or unsubstituted C1-C50 alkyl group, substituted or unsubstituted C1-C50 alkoxy group, substituted or unsubstituted C1-C50 alkenyl group, substituted or unsubstituted C5-C60 aryl Benzene groups, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon At least one substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one sulfur (S
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each combine with an adjacent group to form a substituted or unsubstituted saturated or unsaturated ring can do.
- R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 May each combine with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring.
- X is a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted C5-C60 arylene group, a substituted or unsubstituted C5-C5 Substitutes containing at least one aryl group of 60, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted C 5 to 60 carbon atoms containing at least one unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si).
- S sulfur
- N nitrogen
- O oxygen
- P phosphorus
- Si silicon
- n may have an integer of 1 to 3, but is not limited thereto.
- the compound having the structural formula may be used in a solution process.
- the compound may form an organic material layer of an organic electric device, which will be described later, by a soluble process.
- the present invention may provide a compound represented by one of the following Chemical Formulas 2 to 4.
- Chemical Formulas 2 to 4 X may be the same as Chemical Formula 1, but is not limited thereto.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 may be the same as in Formula 1, but are not limited thereto.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each combine with an adjacent group to form a substituted or unsubstituted saturated or unsaturated ring can do.
- R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 May each combine with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring.
- substituents in Chemical Formulas 1 to 5 may be substituted or unsubstituted again even if not mentioned above, so that the substituents may be substituted with other substituents or substituents.
- organic electric devices exist in which compounds including substituted or unsubstituted quinoxalinocarbazoles described with reference to Chemical Formulas 1 to 5 are used as the organic material layer.
- the organic electroluminescent device in which the compounds may be used for the substituted or unsubstituted quinoxalinocarbazole described with reference to Chemical Formulas 1 to 5 may be, for example, an organic light emitting diode (OLED), an organic solar cell, or an organic photoconductor (OPC) drum.
- organic transistors organic transistors (organic TFTs).
- the organic electroluminescent device (OLED) is described as an example of the organic electroluminescent device to which the substituted or unsubstituted quinoxalinocarbazole described with reference to Chemical Formulas 1 to 5 can be applied, but the present invention is not limited thereto.
- the compounds described above may be applied to the organic electric device.
- Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 5 Provided is a light emitting device.
- 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
- the organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 5. It can be prepared as.
- FIGS. 1 to 6 The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto.
- reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.
- the organic light emitting diode further includes a hole blocking layer (HBL) that blocks hole movement, an electron blocking layer (EBL) that blocks electrons from moving, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located.
- the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
- the substituted or unsubstituted quinoxalinocarbazole described with reference to Formulas 1 to 5 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
- the compound containing a substituted or unsubstituted quinoxalinocarbazole described with reference to Formulas 1 to 5 may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, It may be used in place of one or more of the light emitting auxiliary layer and the protective layer, or may be used to form a layer with them.
- the organic layer may be used not only in one layer but also in two or more layers.
- a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material and a passivation (kepping) material It can be used as, in particular can be used as a host or dopant in the light emitting material and the host / dopant alone, can be used as a hole injection, a hole transport layer.
- the organic light emitting device is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- PVD physical vapor deposition
- An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
- PVD physical vapor deposition
- an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
- the organic material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
- An organic light emitting display device is a soluble process such as spin coating or ink jet process of the compound containing the substituted or unsubstituted quinoxalinocarbazole described above May be used.
- the substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
- An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon.
- the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
- the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the hole injection layer is located on the anode.
- the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
- the hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer is positioned on the hole injection layer.
- the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
- Tg glass transition temperature
- Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene and silicon germanium oxide.
- NPD or NPB
- spiro-arylamine compounds perylene-arylamine compounds
- azacycloheptatriene compounds bis (diphenylvinylphenyl) anthracene
- silicon germanium oxide silicon germanium oxide
- the organic light emitting layer is positioned on the hole transport layer.
- the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency.
- an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene.
- PPV polyphenylene vinylene
- a polymer such as poly fluorene can be used for
- the electron transport layer is positioned on the organic light emitting layer.
- Such an electron transport layer requires a material having high electron injection efficiency and efficiently transporting injected electrons from a cathode positioned thereon. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron injection layer is stacked on the electron transport layer.
- the electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like.
- the electron injection layer may be formed in a thickness range of 100 ⁇ 300 ⁇ .
- the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
- the material used as the cathode it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection.
- a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
- electrodes having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
- hole injection materials and holes suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, according to the compound including substituted or unsubstituted quinoxalinocarbazole described with reference to Chemical Formulas 1 to 5 It can be used as a transport material, a light emitting material, an electron transport material and an electron injection material, and can be used as a host or dopant material of various colors.
- the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
- the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
- This terminal means a current or future wired or wireless communication terminal.
- the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.
- the compounds were synthesized according to the synthesis method described above, and the examples in which the compounds were applied to an organic material layer of an organic electroluminescent device, for example, an organic electroluminescent device, were compared with those of commonly used compounds.
- a copper phthalocyanine (hereinafter abbreviated as CuPc) film was first vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.
- a-NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
- tris (2-phenylpyridine) iridium (abbreviated as I r (ppy) 3 hereinafter) was added as a phosphorescent Ir metal complex dopant.
- concentration of I r (ppy) 3 in the light emitting layer was 5% by weight.
- (1,1'bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm in a hole blocking layer, followed by electrons.
- Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq 3 ) was formed into an injection layer to a thickness of 40 nm.
- LiF an alkali metal halide
- Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
- CBP a compound represented by the following formula
- the organic electroluminescent device using the compound for organic electroluminescent devices of the present invention is not only high efficiency and color purity is improved, but also a long life green light emission is obtained green phosphorescent host material of the organic light emitting device It can be used to significantly improve the luminous efficiency and lifetime.
- the compounds of the present invention can achieve the same effect even when used in other organic material layers of the organic light emitting device, for example, a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer.
- a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer.
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Abstract
La présente invention concerne un composé et un dispositif électronique organique l'utilisant, ainsi qu'un terminal comprenant le dispositif électronique organique.
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Application Number | Priority Date | Filing Date | Title |
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KR10-2010-0115398 | 2010-11-19 | ||
KR1020100115398A KR101305934B1 (ko) | 2010-11-19 | 2010-11-19 | 화합물 및 이를 이용한 유기전기소자, 그 단말 |
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WO2012067415A2 true WO2012067415A2 (fr) | 2012-05-24 |
WO2012067415A3 WO2012067415A3 (fr) | 2012-09-07 |
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Cited By (6)
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JP2012248663A (ja) * | 2011-05-27 | 2012-12-13 | Konica Minolta Holdings Inc | 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、照明装置、並びに化合物 |
WO2014189122A1 (fr) * | 2013-05-24 | 2014-11-27 | 国立大学法人九州大学 | Composé, matériau électroluminescent et élément électroluminescent organique |
WO2015016200A1 (fr) * | 2013-08-01 | 2015-02-05 | 国立大学法人九州大学 | Composé, matériau électroluminescent et élément électroluminescent organique |
US20150060788A1 (en) * | 2013-09-05 | 2015-03-05 | Dong-Kyu Ryu | Compound for an organic optoelectric device, organic optoelectric device including the same, and display device including the optoelectric device |
CN104471020A (zh) * | 2012-07-10 | 2015-03-25 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
JPWO2014034535A1 (ja) * | 2012-08-30 | 2016-08-08 | 国立大学法人九州大学 | 発光材料、化合物、およびそれらを用いた有機発光素子 |
Families Citing this family (6)
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US9831441B2 (en) * | 2012-10-31 | 2017-11-28 | Merck Patent Gmbh | Electronic device |
KR102139781B1 (ko) * | 2013-06-03 | 2020-07-30 | 에스에프씨 주식회사 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
WO2015167225A1 (fr) * | 2014-04-29 | 2015-11-05 | 주식회사 엘지화학 | Cellule solaire organique et son procédé de fabrication |
US10636979B2 (en) * | 2014-12-23 | 2020-04-28 | Merck Patent Gmbh | Heterocyclic compounds with dibenzazapine structures |
KR101962420B1 (ko) * | 2015-12-08 | 2019-03-26 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
KR20210038789A (ko) | 2019-09-30 | 2021-04-08 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2012248663A (ja) * | 2011-05-27 | 2012-12-13 | Konica Minolta Holdings Inc | 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、照明装置、並びに化合物 |
CN104471020B (zh) * | 2012-07-10 | 2017-03-08 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
US10622567B2 (en) | 2012-07-10 | 2020-04-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN104471020A (zh) * | 2012-07-10 | 2015-03-25 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
JP2015530357A (ja) * | 2012-07-10 | 2015-10-15 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンスデバイス用の材料 |
JPWO2014034535A1 (ja) * | 2012-08-30 | 2016-08-08 | 国立大学法人九州大学 | 発光材料、化合物、およびそれらを用いた有機発光素子 |
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WO2014189122A1 (fr) * | 2013-05-24 | 2014-11-27 | 国立大学法人九州大学 | Composé, matériau électroluminescent et élément électroluminescent organique |
JPWO2015016200A1 (ja) * | 2013-08-01 | 2017-03-02 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
EP3029033A1 (fr) * | 2013-08-01 | 2016-06-08 | Kyushu University, National University Corporation | Composé, matériau électroluminescent et élément électroluminescent organique |
WO2015016200A1 (fr) * | 2013-08-01 | 2015-02-05 | 国立大学法人九州大学 | Composé, matériau électroluminescent et élément électroluminescent organique |
CN105531271A (zh) * | 2013-08-01 | 2016-04-27 | 国立大学法人九州大学 | 化合物、发光材料及有机发光元件 |
EP3029033A4 (fr) * | 2013-08-01 | 2017-04-05 | Kyushu University, National University Corporation | Composé, matériau électroluminescent et élément électroluminescent organique |
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Also Published As
Publication number | Publication date |
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KR20120054154A (ko) | 2012-05-30 |
WO2012067415A3 (fr) | 2012-09-07 |
KR101305934B1 (ko) | 2013-09-12 |
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