WO2024076117A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2024076117A1
WO2024076117A1 PCT/KR2023/015175 KR2023015175W WO2024076117A1 WO 2024076117 A1 WO2024076117 A1 WO 2024076117A1 KR 2023015175 W KR2023015175 W KR 2023015175W WO 2024076117 A1 WO2024076117 A1 WO 2024076117A1
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현서용
빈종관
이승재
박관희
장준영
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(주)피엔에이치테크
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers
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    • 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
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • 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
    • H10K85/615—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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings

Definitions

  • the present invention relates to organic compounds, and more specifically, to organic compounds employed in organic layers such as electron blocking layers in organic light-emitting devices, and to organic light-emitting devices whose device characteristics, such as low-voltage operation, long life, and luminous efficiency, are significantly improved by employing the same. It's about.
  • Organic light emitting devices not only can be formed on transparent substrates, but also can be driven at low voltages of 10 V or less compared to plasma display panels or inorganic electroluminescence (EL) displays, and consume relatively little power. , It has the advantage of excellent color and can display three colors of green, blue, and red, so it has recently been the subject of much attention as a next-generation display device.
  • the materials that make up the organic layer within the device such as hole injection material, hole transport material, hole blocking material, light emitting material, electron transport material, electron injection material, and electron blocking material, are required.
  • Support by stable and efficient materials should be a priority, but the development of stable and efficient organic layer materials for organic light-emitting devices has not yet been sufficiently developed.
  • the present invention aims to provide an organic compound that can be used as an organic layer material such as an electron blocking layer in an organic light-emitting device to significantly improve device characteristics such as low-voltage driving characteristics, long life, and luminous efficiency, and an organic light-emitting device containing the same. do.
  • the present invention provides an organic compound represented by the following [Chemical Formula I] and an organic light-emitting device containing the same.
  • the organic light-emitting device employing the organic compound according to the present invention in an organic layer such as an electron blocking layer is significantly superior to conventional devices in device characteristics such as low-voltage operation, long lifespan, and luminous efficiency, and can be usefully used in various lighting devices and display devices. You can.
  • the present invention relates to an organic compound represented by the following [Chemical Formula I], which structurally (i) contains specific positions (positions 4 and 6) of the dibenzofuran (thiophene) or fluorene structure, that is, Ar 1 and Ar It is characterized by introducing an aryl group at position 2 , and (ii) by introducing an aryl (heteroaryl)amine group at position 2 by directly bonding it without an additional linking group.
  • [Chemical Formula I which structurally (i) contains specific positions (positions 4 and 6) of the dibenzofuran (thiophene) or fluorene structure, that is, Ar 1 and Ar It is characterized by introducing an aryl group at position 2 , and (ii) by introducing an aryl (heteroaryl)amine group at position 2 by directly bonding it without an additional linking group.
  • an organic light-emitting device with significantly improved device characteristics such as low-voltage driving, long life, and luminous efficiency when used in various organic layers in the organic light-emitting device, preferably in the electron blocking layer.
  • Ar 1 and Ar 2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R 1 to R 5 are the same as or different from each other and are each independently hydrogen or deuterium.
  • X is O, S or CR 6 R 7 , the R 6 and R 7 are the same or different with each other, respectively, independently of hydrogen, heavy hydrogen, cyano group, halogen group, alkyl groups of 1 to 20 carbon ate or shifted or beached. or an unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • R 6 and R 7 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • L is a divalent linking group, which is a single bond or one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and n is an integer of 0 to 3. And when n is 2 or more, the plurality of Ls are the same or different from each other.
  • Ar 3 and Ar 4 are the same or different from each other and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • substituted or unsubstituted means that R 6 , R 7 , L and Ar 1 to Ar 4 are each a deuterium group, a cyano group, a halogen group, or a hydroxy group. , nitro group, alkyl group, alkoxy group, halogenated alkoxy group, cycloalkyl group, heterocycloalkyl group, aryl group, fluorenyl group, heteroaryl group, silyl group and amine group, or the above substituents It means that two or more substituents are substituted with a linked substituent, or do not have any substituents.
  • a substituted aryl group refers to a phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc. substituted with another substituent such as deuterium.
  • substituted heteroaryl group refers to pyridyl group, thiophenyl group, triazine group, quinoline group, phenanthroline group, imidazole group, thiazole group, oxazole group, carbazole group and condensed heterocyclic groups thereof, such as This means that benzquinoline group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc. are also substituted with other substituents such as deuterium.
  • the compound represented by [Formula I] according to the present invention may contain at least one or more deuterium in [Formula I], and accordingly, any one or more of R 1 to R 7 This may be deuterium, and R 6 , R 7 , L and Ar 1 to Ar 4 defined above may have one or more deuterium as an additional substituent.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, 2-e
  • the alkoxy group may be straight chain or branched chain.
  • the number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20, which is within a range that does not cause steric hindrance.
  • neopentyloxy group isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.
  • the alkyl group and the alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group, respectively, and the alkyl group or alkoxy group refers to an alkyl group or alkoxy group substituted with a deuterium or halogen group.
  • the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. It also includes a polycyclic aryl group structure fused with cycloalkyl, etc., and the monocyclic aryl group Examples of phenyl group, biphenyl group, terphenyl group, stilbene group, etc. Examples of polycyclic aryl groups include naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, and chrysenyl group. , fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.
  • fluorene in a fluorenyl group or fluorene moiety is a structure in which two ring organic compounds are connected through one atom, for example , , etc.
  • open fluorene structure where open fluorene is a structure in which one ring compound is disconnected from a structure in which two ring organic compounds are connected through one atom, for example , etc.
  • the carbon atom of the ring may be substituted with one or more heteroatoms selected from N, S, and O, for example , , , etc.
  • the fluorenyl group may have a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring, etc. are further condensed to the above linked structure or open structure.
  • pyrimidyl group triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxaziny
  • the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc.
  • Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxysilyl.
  • Examples include phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.
  • halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).
  • cycloalkyl groups refer to and include monocyclic, polycyclic and spiro alkyl radicals, and preferably contain ring carbon atoms having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, and bicyclo. It includes heptyl, spirodecyl, spiroundecyl, adamantyl, etc., and the cycloalkyl group may be optionally substituted.
  • heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si and Se, It is preferably selected from O, N or S, and specifically, when it contains N, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc.
  • the amine group may be -NH 2 , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc.
  • an arylamine group refers to an amine substituted with aryl
  • an alkylamine group refers to an amine substituted with alkyl.
  • the arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups.
  • arylamine group examples include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group or a polycyclic heteroaryl group.
  • the arylamine group containing two or more heteroaryl groups, and the arylheteroarylamine group include a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group). It may contain both an aryl group) and a polycyclic aryl group (heteroaryl group).
  • the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the above-mentioned aryl group and heteroaryl group.
  • the organic compound according to the present invention represented by [Chemical Formula I] can be used as an organic layer of an organic light-emitting device due to its structural specificity, and more specifically, electron blocking of the organic layer depending on the characteristics of various substituents introduced. It can be used as a material for layers, etc.
  • Preferred specific examples of the compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited to these.
  • organic compounds with unique properties of the skeletal structure and substituents can be synthesized.
  • an organic compound material that satisfies the conditions required for each organic layer can be manufactured.
  • device characteristics such as luminous efficiency of the device can be further improved.
  • the organic compound according to the present invention can be applied to an organic light-emitting device according to a conventional manufacturing method.
  • the organic light emitting device may have a structure including a first electrode, a second electrode, and an organic layer disposed between them, except that the organic compound according to the present invention is used in the organic layer of the device. It can be manufactured using conventional device manufacturing methods and materials.
  • the organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, etc.
  • it is not limited to this and may include fewer or more organic layers.
  • the organic light emitting device may include a hole injection layer, a hole transport layer, a light emitting layer, etc. formed on an anode, and may also include a hole blocking layer, an electron injection layer, an electron transport layer, an electron blocking layer, It may include a light emitting auxiliary layer, etc., but is not limited thereto.
  • the organic layer may include an electron blocking layer, etc., and one or more of the layers may include the organic compound represented by [Chemical Formula I].
  • the organic light emitting device deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. is deposited to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc. is formed thereon, and then an organic layer that can be used as a cathode is formed thereon. It can be manufactured by depositing the material.
  • PVD physical vapor deposition
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
  • the organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc., but is not limited to this and may have a single layer structure.
  • the organic layer uses a variety of polymer materials and is formed using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, to form a smaller number of layers. It can be manufactured in layers.
  • the anode is usually preferably a material with a large work function to ensure smooth hole injection into the organic layer.
  • anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , conductive polymers such as polypyrrole and polyaniline, but are not limited to these.
  • the cathode is generally preferably made of a material with a low work function to facilitate electron injection into the organic layer.
  • cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof, multilayers such as LiF/Al or LiO 2 /Al. Structural materials, etc., but are not limited to these.
  • the hole injection layer is a material that can easily receive holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene, quinacridone-based organic substances, perylene-based organic substances, Examples include anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
  • the hole transport layer is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • the electron blocking layer is a layer that blocks the movement of electrons and can be formed on the hole transport layer.
  • An electron blocking layer that can block the movement of electrons without affecting the transport of holes can be used.
  • a light-emitting layer may be formed on the electron blocking layer, and a hole blocking layer, an electron transport layer, and an electron injection layer may be formed.
  • the hole blocking layer can be used to prevent the movement of holes without affecting the transport of electrons.
  • An example of such a hole blocking layer is TPBi (1,3,5-tri(1-phenyl-1H-benzo). [d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl4,7-diphenyl-1,10-phenanthroline), CBP (4,4-bis(N-carbazolyl)-1,1'-biphenyl ), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole), PTCBI (bisbenzimidazo[2,1-a:1',2-b']anthra [2,1,9-def:6,5,10-d'e'f']diisoguinoline-10,21-dione) or BPhen (4,7-diphenyl-1,10-phenanthroline), etc. It is not limited.
  • the light-emitting layer is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited to these.
  • PV poly(p-phenylenevinylene)
  • the electron injection layer can be one that has high injection efficiency of electrons transferred from the cathode.
  • electron injection layers include, but are not limited to, lithium quinolate (Liq).
  • the electron transport layer is a material that can easily receive electrons from the cathode and transfer them to the light emitting layer, and a material with high electron mobility is suitable.
  • a material with high electron mobility includes, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
  • the organic light emitting device may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.
  • organic compound according to the present invention can function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.
  • Synthesis example 5 Synthesis of Compound 141
  • the ITO transparent electrode is patterned so that the light emitting area is 2 mm ⁇ 2 mm using an ITO glass substrate to which the ITO transparent electrode is attached on a glass substrate of 25 mm ⁇ 25 mm ⁇ 0.7 mm. and then washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 ⁇ 10 -6 torr, organic materials and metals were deposited on the ITO in the following structure.
  • an organic light emitting device having the following device structure by employing the compound implemented according to the present invention in an electron blocking layer, the light emitted by the compound implemented according to the present invention and the organic light emitting device containing the same in the electron blocking layer and driving characteristics were measured.
  • ITO / hole injection layer HAT-CN, 5 nm
  • hole transport layer HT1, 100 nm
  • electron blocking layer 10 nm
  • emission layer 20 nm
  • electron transport layer E1:Liq, 30 nm
  • LiF LiF ( 1 nm) / Al (100 nm)
  • [HAT-CN] was deposited to a thickness of 5 nm on the top of the ITO transparent electrode to form a hole injection layer, and then [HT1] was deposited to a thickness of 100 nm to form a hole transport layer.
  • the compound according to the present invention shown in [Table 1] below was deposited to a thickness of 10 nm to form an electron blocking layer, and the emitting layer was formed at a thickness of 20 nm using [BH1] as the host compound and [BD1] as the dopant compound. It was formed by vapor deposition.
  • an organic light-emitting device was manufactured by forming an Al film to a thickness of 100 nm.
  • the organic light emitting device for Comparative Device Example 1 was manufactured in the same manner as the device structures of Examples 1 to 48 except that [EB1] below was used instead of the compound according to the present invention in the electron blocking layer.
  • the organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as the device structures of Examples 1 to 48 except that [EB2] below was used instead of the compound according to the present invention in the electron blocking layer.
  • the organic light-emitting device for Comparative Device Example 3 was manufactured in the same manner as the device structures of Examples 1 to 48, except that [EB3] below was used in the electron blocking layer instead of the compound according to the present invention.
  • the organic light emitting device for Device Comparative Example 4 was manufactured in the same manner as the device structures of Examples 1 to 48 except that [EB4] below was used instead of the compound according to the present invention in the electron blocking layer.
  • the organic light-emitting device for Comparative Device Example 5 was manufactured in the same manner as the device structures of Examples 1 to 48, except that [EB5] below was used in the electron blocking layer instead of the compound according to the present invention.
  • the driving voltage, current efficiency, and color coordinates of the organic light emitting devices manufactured according to the above examples and comparative examples were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and were measured at 1,000 nit.
  • the standard result values are shown in [Table 1] below.
  • the present invention is an organic compound employed in an organic layer provided in an organic light-emitting device, and when used in particular in the electron blocking layer of an organic light-emitting device, low-voltage operation is possible compared to conventional devices, and device characteristics such as long lifespan and luminous efficiency are possible. Since this significantly improved organic light emitting device can be implemented, it can be used industrially in various display devices such as lighting devices as well as flat panel, flexible, wearable, and virtual or augmented reality displays.

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

Abstract

La présente invention concerne un composé organique utilisé dans une couche organique disposée dans un élément électroluminescent organique. En particulier, le composé organique peut être utilisé dans une couche de blocage d'électrons d'un élément électroluminescent organique, ce qui permet d'obtenir un élément électroluminescent organique qui peut être entraîné à une tension inférieure à celle des éléments existants et qui présente des caractéristiques d'élément significativement améliorées telles que des caractéristiques de longue durée de vie et une efficacité lumineuse élevée, et ainsi le composé organique peut être utilisé de manière efficace sur le plan commercial dans des éléments d'éclairage ainsi que divers éléments d'affichage tels que des écrans plats, flexibles, portables et de réalité virtuelle ou augmentée.
PCT/KR2023/015175 2022-10-05 2023-10-04 Composé organique et élément électroluminescent organique le comprenant WO2024076117A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017100967A1 (fr) * 2015-12-14 2017-06-22 武汉尚赛光电科技有限公司 Dérivé de benzo[c]phénanthrène présentant une structure de donneur-accepteur d'électrons et utilisation correspondante et dispositif électroluminescent
KR20190134356A (ko) * 2018-05-25 2019-12-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20200127628A (ko) * 2019-05-03 2020-11-11 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치
CN114014764A (zh) * 2021-11-16 2022-02-08 阜阳欣奕华材料科技有限公司 含有三亚苯基团的有机化合物、电致发光器件和显示装置
CN116496168A (zh) * 2023-06-29 2023-07-28 吉林奥来德光电材料股份有限公司 一种发光辅助材料及有机电致发光器件

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017100967A1 (fr) * 2015-12-14 2017-06-22 武汉尚赛光电科技有限公司 Dérivé de benzo[c]phénanthrène présentant une structure de donneur-accepteur d'électrons et utilisation correspondante et dispositif électroluminescent
KR20190134356A (ko) * 2018-05-25 2019-12-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20200127628A (ko) * 2019-05-03 2020-11-11 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치
CN114014764A (zh) * 2021-11-16 2022-02-08 阜阳欣奕华材料科技有限公司 含有三亚苯基团的有机化合物、电致发光器件和显示装置
CN116496168A (zh) * 2023-06-29 2023-07-28 吉林奥来德光电材料股份有限公司 一种发光辅助材料及有机电致发光器件

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