WO2013027906A1 - Composé pour un dispositif optoélectronique organique, élément électroluminescent organique le comprenant et dispositif d'affichage comprenant l'élément électroluminescent organique - Google Patents

Composé pour un dispositif optoélectronique organique, élément électroluminescent organique le comprenant et dispositif d'affichage comprenant l'élément électroluminescent organique Download PDF

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WO2013027906A1
WO2013027906A1 PCT/KR2012/001357 KR2012001357W WO2013027906A1 WO 2013027906 A1 WO2013027906 A1 WO 2013027906A1 KR 2012001357 W KR2012001357 W KR 2012001357W WO 2013027906 A1 WO2013027906 A1 WO 2013027906A1
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WO2013027906A9 (fr
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이호재
김영훈
유은선
김형선
민수현
채미영
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제일모직 주식회사
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    • H—ELECTRICITY
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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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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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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    • 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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1007—Non-condensed systems
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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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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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Definitions

  • the present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent life, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the 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 operation principle.
  • excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
  • 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, and an organic transistor, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.
  • organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • Such an organic light emitting device converts electrical energy into light by applying a current to an 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 is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, 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 realize 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 emission attenuation effect.
  • the host / dopant system can be used as a light emitting material.
  • materials constituting 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, etc.
  • a hole injection 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 a dopant in the light emitting material, etc.
  • a hole injection material such as 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, etc.
  • This stable and efficient material should be preceded, and 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 necessity of such a material development is the same in the other organic optoelectronic devices described above.
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has low initial investment cost. 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 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.
  • the luminous efficiency In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer.
  • the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.
  • a compound for an organic optoelectronic device which can play a role of hole injection and transport or electron injection and transport, and can act as a light emitting host with an appropriate dopant.
  • An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • the compound for an organic optoelectronic device may be represented by the following formula (2).
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • the compound for an organic optoelectronic device may be represented by the following formula (3).
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same
  • the compound for an organic optoelectronic device may be represented by the following formula (4).
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted Oxadiazolyl group, substituted or unsubstituted oxtriazolyl group, substituted or unsubstituted thiatriazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted Substituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substitute
  • the compound for an organic optoelectronic device may be represented by one of Formulas A1 to A28.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B1 to B28.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas C1 to C47.
  • the compound for an organic optoelectronic device may have a triplet excitation energy (T1) of 2.0 eV or more.
  • the organic optoelectronic device may be selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the organic light emitting device comprising 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 is the above-described organic optoelectronic device It provides an organic light emitting device comprising a compound for.
  • the organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
  • the compound for an organic optoelectronic device may be included in a hole transport layer or a hole injection layer.
  • the compound for an organic optoelectronic device may be included in a light emitting layer.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.
  • a display device including the organic light emitting diode described above is provided.
  • Such a compound can be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer.
  • the organic optoelectronic device using the same has excellent electrochemical and thermal stability, and has excellent life characteristics, and may have high luminous efficiency even at a low driving voltage.
  • 1 to 5 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 an embodiment of the present invention.
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C1 to C10 such as 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, fluoro group, trifluoromethyl group, etc. Substituted by a trifluoroalkyl group or a cyano group.
  • hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, O, 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 a "saturated alkyl group” meaning that it does not contain any alkenes or alkyne groups.
  • alkene group means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond
  • alkyne group means at least two carbon atoms of at least one carbon-carbon triple bond It means a functional group formed.
  • the alkyl group, whether saturated or unsaturated, may be branched, straight chain or cyclic.
  • the alkyl group may be an alkyl group that is C1 to C20.
  • the alkyl group may be a medium sized alkyl group which is C1 to C10.
  • the alkyl group may be a lower alkyl group which is C1 to C6.
  • a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • Typical alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl and cyclo It means a functional group which may be substituted with one or more groups individually and independently selected from pentyl group, cyclohexyl group and the like.
  • Aromatic group means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.
  • aryl group includes a monocyclic or fused ring polycyclic (ie, a ring that divides 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.
  • Spiro structure means a ring structure having one carbon as a contact point.
  • the spiro structure may also be used as a compound containing a spiro structure or a substituent including a spiro structure.
  • the hole property means a property that has a conduction property along the HOMO level, thereby facilitating injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.
  • the electronic characteristic means a characteristic that has conductivity characteristics along the LUMO level to facilitate the injection and movement of the electrons formed in the cathode into the light emitting layer.
  • the compound for an organic optoelectronic device has a structure in which a substituent is selectively bonded to a core portion to which two carbazoles are bonded.
  • Two of the substituents bonded to the core may be a substituent having excellent electronic properties.
  • the compound may satisfy the conditions required in the light emitting layer by reinforcing the electronic properties in the carbazole structure having excellent hole properties. More specifically, it can be used as a host material of the light emitting layer.
  • the compound for an organic optoelectronic device may be a compound having various energy band gaps by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.
  • the compound may be used as an electron injection layer and a transfer layer or a hole injection layer and a transfer layer.
  • the electron transport ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent life time when driving the organic photoelectric device due to excellent electrochemical and thermal stability. Properties can be improved.
  • a compound for an organic optoelectronic device represented by Formula 1 is provided.
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • the compound represented by Chemical Formula 1 may have a carbazole having excellent bipolar characteristics as a core.
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl Groups or combinations thereof.
  • a suitable combination of the substituents can be prepared a structure of the asymmetric bipolar (bipolar) characteristics, the structure of the asymmetric bipolar characteristics can be expected to improve the luminous efficiency and performance of the device by improving the major and electron transfer ability.
  • L 1 and L 2 are the same as or different from each other, and independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 aryl It may be a ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group or a combination thereof.
  • the substituent in which the pi bond exists among the substituents increases the triplet energy bandgap by controlling the pi conjugate length ( ⁇ -conjugation length) of the entire compound so that it can be very usefully applied to the light emitting layer of the organic photoelectric device as a phosphorescent host. can do.
  • the structure of the compound can be prepared in bulk by the control of the substituents, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.
  • Ar 1 and Ar 2 may be the same as or different from each other, and may independently have a substituted or unsubstituted heteroaryl group having electronic properties.
  • substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties include substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, and substituted Or an unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group , Substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following Formula 2.
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • the binding position of the carbazole which is the core may be bonded as shown in Formula 2.
  • the binding position may be an advantage in synthesizing the compound to one of the high reactivity of the carbazole or carbazole derivatives.
  • the compound for an organic optoelectronic device may be represented by the following formula (3).
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same
  • the structure is a structure in which the binding position of both carbazole groups is defined in the structure of the compound for an organic optoelectronic device represented by Formula 1 above.
  • This structure has the advantage of improving the bandgap and triplet energy bandgap because the molecular structure is more non-planarized to limit the conjugate length.
  • the compound for an organic optoelectronic device may be represented by the following formula (4).
  • R 1 to R 6 are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof
  • Ar 1 and Ar 2 are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties
  • L 1 and L 2 are the same or different from each other Independently, a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof
  • n and m are the same as
  • the structure of Formula 4 is a structure defining the binding position of both carbazole of the core in the structure of the formula (1).
  • Such a core structure may have an appropriate HOMO energy and has an advantage of easy synthesis.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas A1 to A28, but is not limited thereto.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B1 to B28, but is not limited thereto.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas C1 to C47, but is not limited thereto.
  • the compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 110 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This enables the implementation of high efficiency organic optoelectronic devices.
  • the compound for an organic optoelectronic device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport material.
  • Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
  • one embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.
  • the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like.
  • a compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, a gate, a source-drain electrode, or the like may be used as an electrode material. Can be used.
  • Another embodiment of the present invention is an organic light emitting device comprising 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 is an embodiment of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to.
  • the organic thin film layer which may include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. At least one of the layers includes the compound for an organic optoelectronic device according to the present invention.
  • the electron transport layer or the electron injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the compound for an organic optoelectronic device when included in a light emitting layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.
  • FIG. 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, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
  • 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 injected into the organic thin film layer.
  • the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO 2 and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably 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, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al.
  • Multilayer structure materials such as LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates an organic photoelectric 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 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 and an hole transport layer 140 including an electron transport layer as the 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 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.
  • FIG. 3 is a three-layered organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, and the organic thin film layer 105.
  • the light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.
  • FIG. 4 illustrates a four-layered organic light emitting diode 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105.
  • the hole injection layer 170 may improve adhesion to ITO used as an anode.
  • FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105.
  • the five-layer organic light emitting device 500 having five layers is present, and the organic light emitting device 500 is effective in lowering the voltage by separately forming the electron injection layer 160.
  • the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 are provided.
  • Any one selected from the group consisting of a combination includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and in particular, when included in the electron transport layer, a hole blocking layer (not shown). Since it is not necessary to form separately, it is desirable to provide an organic light emitting device having a simplified structure.
  • the compound for an organic optoelectronic device when included in the light emitting layers 130 and 230, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
  • the above-described organic light emitting device includes a dry film method such as an evaporation, sputtering, plasma plating and ion plating 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 light emitting diode is provided.
  • the reaction solution was poured into 2500 ml of water, stirred, and the solid precipitated in the reaction solution was washed with methanol and filtered under reduced pressure to obtain a solid.
  • the solid was dissolved in chlorobenzene and filtered through silica gel to obtain 67 g (yield 78%) of the intermediate compound (A).
  • reaction solution was slowly added dropwise to 2000 ml of water to solidify, and this was filtered to give a fleshy solid.
  • the solid was dissolved in 500 ml of dichloromethane, water was removed with anhydrous magnesium sulfate, and then filtered to obtain an organic solution layer.
  • reaction solution was added to 1000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removal of an appropriate amount of the organic solvent, and recrystallized in MeOH to give 25g (72% yield) of Compound A7.
  • the glass substrate coated with ITO (Indium tin oxide) 1500 thin film was washed with distilled water ultrasonic. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.
  • the prepared ITO transparent electrode as an anode, the following HTM compound was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 1200 ⁇ .
  • Example 1 Using the material (A1) synthesized in Example 1 as a host on the hole transport layer, and a phosphorescent green dopant of the following PhGD compound to 7% by weight to form a light emitting layer of 300 ⁇ thickness by vacuum deposition.
  • BAlq (Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum] 50um and Alq3 [Tris (8-hydroxyquinolinato) aluminium] 250 ⁇ Laminated sequentially to form an electron transport layer.
  • An organic light emitting device was manufactured by sequentially depositing LiF 5 ′ and Al 1000 ′ on the electron transport layer to form a cathode.
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 2 instead of the compound according to Example 1.
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 3 instead of the compound according to Example 1.
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 4 instead of the compound according to Example 1.
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 5 instead of the compound according to Example 1.
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound represented by the following Formula R1 instead of the compound according to Example 1.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2) above.
  • Table 1 summarizes the device evaluation results.
  • Example 1 Classification Host Drive voltage (Vd, V) Luminous Efficiency (Cd / A) Power efficiency (lm / W) Luminance (cd / m 2 ) Color coordinates CIEx Color coordinates Comparative Example 1 R1 7.0 49.24 22.09 3000 0.333 0.623 Example 6 A1 5.09 59.8 36.9 3000 0.340 0.622 Example 7 A7 5.04 58.4 36.4 3000 0.341 0.621 Example 8 B3 5.37 56.1 32.9 3000 0.339 0.623 Example 9 B11 5.21 53.5 32.3 3000 0.338 0.623 Example 10 C2 5.17 54.9 33.4 3000 0.338 0.623
  • the organic light emitting device according to Examples 6 to 10 is advantageous in terms of efficiency and driving voltage of the device.
  • the structure of the two carbazole binding sites of the core 3-3 '(A1 or A7) is 2-3 (the C2) or 2-2' (the B3 or B11) structure It can be seen that it is excellent in terms of efficiency.
  • hole injection layer 230 light emitting layer + electron transport layer

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Abstract

La présente invention porte sur un composé pour un dispositif optoélectronique organique, sur un élément électroluminescent organique le comprenant et sur un dispositif d'affichage comprenant l'élément électroluminescent organique. Le composé pour un dispositif optoélectronique organique répond à la formule chimique (1) et permet de fabriquer un dispositif optoélectronique organique ayant une durée de vie utile supérieure, du fait qu'il présente une stabilité électrochimique et thermique supérieure, et une efficacité lumineuse élevée même sous une faible tension de polarisation.
PCT/KR2012/001357 2011-08-19 2012-02-22 Composé pour un dispositif optoélectronique organique, élément électroluminescent organique le comprenant et dispositif d'affichage comprenant l'élément électroluminescent organique WO2013027906A1 (fr)

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US9306171B2 (en) 2011-12-05 2016-04-05 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device
US11746117B2 (en) 2018-11-27 2023-09-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12037337B2 (en) 2018-11-27 2024-07-16 Lg Chem, Ltd. Compound and organic light emitting device comprising the same

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KR102052076B1 (ko) * 2013-06-14 2019-12-05 삼성디스플레이 주식회사 유기 발광 소자
US10840454B2 (en) 2013-06-14 2020-11-17 Samsung Display Co., Ltd. Organic light-emitting devices
KR102084170B1 (ko) 2013-07-25 2020-03-04 삼성디스플레이 주식회사 유기발광소자, 이를 포함하는 유기 발광 표시장치 및 그 제조방법
KR102011907B1 (ko) * 2016-06-24 2019-08-19 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR102181240B1 (ko) * 2019-11-26 2020-11-23 삼성디스플레이 주식회사 유기 발광 소자

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CN103232843A (zh) * 2013-04-18 2013-08-07 烟台万润精细化工股份有限公司 一种电致发光材料及其应用
US11746117B2 (en) 2018-11-27 2023-09-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12037337B2 (en) 2018-11-27 2024-07-16 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
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