WO2014104535A1 - Composé pour dispositif organique optoélectronique, diode organique électroluminescente le comprenant et appareil d'affichage comprenant ladite diode organique électroluminescente - Google Patents

Composé pour dispositif organique optoélectronique, diode organique électroluminescente le comprenant et appareil d'affichage comprenant ladite diode organique électroluminescente Download PDF

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WO2014104535A1
WO2014104535A1 PCT/KR2013/008219 KR2013008219W WO2014104535A1 WO 2014104535 A1 WO2014104535 A1 WO 2014104535A1 KR 2013008219 W KR2013008219 W KR 2013008219W WO 2014104535 A1 WO2014104535 A1 WO 2014104535A1
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substituted
unsubstituted
group
organic
compound
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신창주
강동민
원종우
이남헌
정수영
정호국
채미영
김현정
정우석
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제일모직 주식회사
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • H10K50/14—Carrier transporting layers
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    • H10K50/17—Carrier injection layers
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • 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
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • a compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device is provided.
  • 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 operation principle.
  • an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes.
  • the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, organic photo conductor drums, and organic transistor posts, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.
  • OLEDs organic light emitting diodes
  • organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an 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 is generally functional between an anode and a cathode. It has a structure in which an organic layer is inserted. Where the organic layer is
  • the organic light emitting device is often composed of a multi-layer structure composed of different materials, for example, 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 a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors according to light emission colors.
  • the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the decay effect.
  • the host / dopant system can be used as a light emitting material.
  • the organic layer of the material 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 dopant in the light emitting material
  • the back should be supported by a stable and efficient material.
  • the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, development of new materials is continuously required. The need for such material development is
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum deposition method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode uses the inkjet or spin coating method, and the initial investment cost is low. Large area has an advantage.
  • 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 cyan is good, and since it does not need a backlight, the thickness and weight can be reduced to 1/3 level of LCD.
  • the response speed is 1000 times faster than LCD, it is possible to realize perfect video without afterimage. Therefore, it is expected to be spotlighted as an optimal display in line with the recent multimedia era, and based on these advantages, it has achieved rapid technological development of 80 times since its first development in the late 1980s : more than 100 times of life, and recently, 40 inches. Increasingly, the size of organic light emitting diode panels is being announced rapidly.
  • An organic light emitting device including the compound for an organic optoelectronic device and a display device including the organic light emitting device are provided.
  • a compound for an organic optoelectronic device is provided.
  • Ar 1 , ⁇ 2 , ⁇ 1, ⁇ 2 and R 1 to R 3 are as defined in the following detailed description.
  • an anode In one embodiment of the present invention, an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode
  • At least one of the organic thin film layer provides an organic light emitting device comprising the compound for the organic optoelectronic device.
  • 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 low
  • FIG. 1 and 2 are cross-sectional views showing various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • substituted means that at least one hydrogen in a substituent or compound is a hydrogen, halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or unsubstituted.
  • C1 such as a ring C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, pullouro group, trifluoromethyl group, etc.
  • C10 tripolouroalkyl group or cyano group To C10 tripolouroalkyl group or cyano group.
  • substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to Two adjacent substituents among C1 to C10 trifluorouroalkyl groups such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, and a trifluoromethyl group or a cyano group may be fused to form a ring. have.
  • 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” means an aliphatic hydrocarbon group.
  • the alkyl group may be any unsaturated “saturated alkyl group” which contains any double 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 that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a real pillar.
  • aryl group means that all the elements of the cyclic substituent have P—orbital And a substituent in which these P-orbitals form conjugates, and include monocyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • Heteroaryl group means containing 1 to 3 hetero atoms selected from the group consisting of N, O, 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.
  • the hole property refers to a property of having a conduction property along the HOMO level to facilitate the injection and movement of the hole formed in the anode into the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
  • the electronic property refers to a property that has conductive properties along the LUMO level, thereby facilitating injection of electrons formed in the cathode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of attracting electrons.
  • formula (1) represented by the following formula (1)
  • the compound for organic optoelectronic devices can be provided.
  • Ar 1 and Ar 2 are independently of each other, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group
  • L 1 and L 2 are independently from each other, substituted Or a ⁇ C6 alkenylene group in C2, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof
  • nl and ⁇ 2 are each independently 0 to An integer of any one of 5 and at least one of AT 1 or Ar 2 is a substituted or unsubstituted C2 to C30 heteroaryl group
  • At least one of L 1 or L 2 is a substituted or unsubstituted C2 to C30 heteroarylene group
  • R 1 to R 3 are independently of each other, hydrogen, hydrogen,
  • a heterocyclothiol group a substituted or unsubstituted C1 to C20 uraide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.
  • the compound represented by Chemical Formula 1 may have a core structure including three fused rings including a hetero atom. In the case of such a core structure, it may have high heat resistance and electron mobility may be improved.
  • the compound for an organic optoelectronic device represented by the formula (1) is a variety of other substituents to the substituents substituted in the core portion and the core portion
  • the introduction can lead to compounds having various energy band gaps.
  • the hole transfer ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in electrochemical and thermal stability. It is possible to improve the life characteristics when driving the device.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, substituted or unsubstituted naph Tyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted
  • Triphenylenyl group substituted or unsubstituted perylenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted Substituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazoleyl group , Substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted
  • the conjugation length can be determined, from which the triplet energy bend 3 ⁇ 4 can be adjusted. Through this, it is possible to realize the characteristics of the material required in the organic optoelectronic device.
  • triplet energy bandgap can be adjusted by changing the binding position of olso, para and meta.
  • L 1 and L 2 are a substituted or unsubstituted phenylene group, substituted Or an unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrene Nylene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted peryleneyl group.
  • L 'and L 2 may be, independently of each other, a phenylene group.
  • L 1 to L 3 is a phenylene group
  • both core portions may be bonded to an oth, meta, or para based on the phenylene group.
  • L 1 and L 2 may be independently a substituted or unsubstituted pyrimidinylene group.
  • L 1 and L 2 may have high heat resistance, and electron mobility may be improved.
  • L 1 is a substituted or unsubstituted C2 to C30 heteroarylene group
  • ⁇ may be an integer of any one of 1 to 5. However, it is not limited thereto.
  • Ar 2 may be a substituted or unsubstituted C6 to C30 aryl group, and Ax 1 may be a substituted or unsubstituted C2 to C30 heteroaryl group. That is, the electronic properties of the entire compound can be controlled by adjusting the substituents of A ⁇ 1 and Ar 2 . More specifically, it is possible to improve the driving voltage in the device by reducing the energy difference between adjacent layers by controlling HOMO and LUMO energy, dipole moment, and molecular weight of all compounds.
  • Ax 1 and Ar 2 may be each independently a substituted or unsubstituted C6 to C30 fused aryl group or a substituted or unsubstituted C2 to C30 fused heteroaryl group.
  • the heat resistance of the molecule may be improved due to the fused ring, and at the same time, the electron mobility may be improved.
  • Ar 1 may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthrenyl group.
  • At least one of the said Ar 1 and Ar 2 has an electronic characteristic substitution Or an unsubstituted C2 to C30 heteroaryl group.
  • the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl.
  • Benzimidazolyl group substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl Groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted purinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted isoquinolinyl groups, substituted or unsubstituted phthalazinyl groups, substituted Or unsubstituted naphpyridinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted acridinyl group, substituted or unsubsti
  • the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted.
  • electron mobility may be improved while having an appropriate energy band gap, thereby improving efficiency and lifespan of the device.
  • the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be represented by any one of the following Formulas E-1 to E-5. However, this is not limited.
  • the compound for an organic optoelectronic device may be It can be either. However, it is not limited thereto.
  • 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 compound for the organic optoelectronic device An organic optoelectronic device is provided.
  • the compound for an organic optoelectronic device is used in an organic thin film layer
  • the organic thin film insect may be an electron injection layer or an electron transport 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 a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the organic light emitting diodes 100 and 200 have a structure including an anode 120, a cathode 110 and at least one organic thin film layer 105 interposed between the anode and the cathode.
  • the anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly performed into an organic thin film.
  • the positive electrode material may include metals such as nickel, platinum, banana, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, phosphate oxide, tin oxide ( ⁇ ⁇ ), indium zinc oxide ( Metal oxides such as IZO), and combinations of metals and oxides such as ZnO and A1 or Sn0 2 and Sb; poly (3-methylthiophene), poly (3,4- (ethylene-1) , 2-dioxy) thiophene Xpolyehtylenedioxythiophene (PEDT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto. More specifically, a transparent electrode containing nO (indiumtinoxide) may be used as the anode.
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is generally a material having a small work function to facilitate electron injection into the organic thin film layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, rhythm, yttrium, litope, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al. Multi-layered materials such as, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto. More specifically, the cathode such as aluminum Metal electrodes can be used.
  • 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.
  • the organic thin film layer 105 may exist only as a light emitting layer 130.
  • FIG. 2 is a two-layered organic light emitting layer 105 including a light emitting layer 230 including an electron transport layer and a hole transport layer 140.
  • 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, and holes
  • the transport layer 140 functions to improve the bonding property and the hole transporting property with the transparent electrode such as ⁇ .
  • the organic thin film layer 105 of FIG. 1 and FIG. 2 may further include an electron injection layer, an auxiliary electron transport layer, an electron transport layer, a hole transport layer, an auxiliary hole transport layer, a hole injection layer, and a combination thereof. .
  • the organic thin film layer 105 the organic thin film layer 105), the light emitting layer 130,
  • the hole transport layer 140 which is not shown but may further include an electron injection layer, auxiliary electron transport layer, electron transport layer, hole injection layer, auxiliary hole transport layer, hole transport layer, any one selected from the group consisting of One contains the said organic optoelectronic device material.
  • the organic light emitting device described above includes a dry film method such as vacuum evaporation, sputtering, plasma plating and silver plating after forming an anode on a substrate; Or spin gating, dipping,
  • the organic thin film layer After forming the organic thin film layer by a wet film method such as flow coating (flow coating), it can be produced by forming a cathode thereon.
  • a wet film method such as flow coating (flow coating)
  • a display device including the organic optoelectronic device is provided.
  • ⁇ As a positive electrode, ⁇ was used at a thickness of 1000 A, and as a negative electrode, aluminum (A1) was used at a thickness of 1000 A.
  • the anode is cut in a glass substrate having a sheet resistance value of 15 n / cm 2 to a size of 50 mm X 50 mm X 0.7 mm in acetone, isopropyl alcohol and pure water Ultrasonic cleaning was performed for 5 minutes each, followed by UV ozone cleaning for 30 minutes.
  • Liq is vacuum deposited to a thickness of 0.5 nm as an electron injection layer on the electron transport layer, and A1 is vacuum deposited to a thickness of 100 nm to form a Liq / Al electrode.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 2 instead of using the compound prepared in Example 1 as an electron transport layer.
  • Example 11
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 3 as an electron transport layer, instead of using the compound prepared in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound fire prepared in Example 4 instead of using the compound prepared in Example 1 as the electron transport layer.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 5 as an electron transport layer, instead of using the compound prepared in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 6 instead of using the compound prepared in Example 1 as an electron transport layer.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 7 instead of using the compound prepared in Example 1 as an electron transport layer.
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound prepared in Example 8 instead of using the compound prepared in Example 1 as an electron transport layer. Comparative Example 1
  • An organic light emitting diode was manufactured according to the same method as Example 9 except for using the compound represented by Chemical Formula R-1 as an electron transport layer, instead of using the compound prepared in Example 1.
  • the voltage from 0V to 10V
  • the voltage from 0V to 10V
  • the current efficiency (cd / A) and power efficiency (lm ⁇ V) of the same brightness (1000 cd / m2) are obtained using the brightness, current density, and voltage measured from (1) and (2).
  • organic light emitting device 110 the cathode

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé destiné à un dispositif organique optoélectronique, une diode organique électroluminescente le comprenant et un appareil d'affichage comprenant ladite diode organique électroluminescente et un composé destiné à un dispositif organique optoélectronique représenté par la formule chimique 1.
PCT/KR2013/008219 2012-12-31 2013-09-11 Composé pour dispositif organique optoélectronique, diode organique électroluminescente le comprenant et appareil d'affichage comprenant ladite diode organique électroluminescente WO2014104535A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20120158172 2012-12-31
KR10-2012-0158172 2012-12-31

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WO2014104535A1 true WO2014104535A1 (fr) 2014-07-03

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PCT/KR2013/008219 WO2014104535A1 (fr) 2012-12-31 2013-09-11 Composé pour dispositif organique optoélectronique, diode organique électroluminescente le comprenant et appareil d'affichage comprenant ladite diode organique électroluminescente

Country Status (2)

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KR (1) KR20140087996A (fr)
WO (1) WO2014104535A1 (fr)

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EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4231804A2 (fr) 2022-02-16 2023-08-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362645A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362631A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362630A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4369898A1 (fr) 2022-10-27 2024-05-15 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4376583A2 (fr) 2022-10-27 2024-05-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

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