WO2021029634A1 - Nouveau composé, et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé, et élément électroluminescent organique l'utilisant Download PDF

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WO2021029634A1
WO2021029634A1 PCT/KR2020/010536 KR2020010536W WO2021029634A1 WO 2021029634 A1 WO2021029634 A1 WO 2021029634A1 KR 2020010536 W KR2020010536 W KR 2020010536W WO 2021029634 A1 WO2021029634 A1 WO 2021029634A1
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substituted
group
compound
deuterium
unsubstituted
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PCT/KR2020/010536
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Korean (ko)
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박슬찬
이동훈
장분재
서상덕
정민우
이정하
한수진
황성현
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주식회사 엘지화학
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Priority claimed from KR1020200097410A external-priority patent/KR102478094B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202410674524.2A priority Critical patent/CN118666816A/zh
Priority to CN202080005412.8A priority patent/CN112771037A/zh
Publication of WO2021029634A1 publication Critical patent/WO2021029634A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula 1:
  • X is O or S
  • X 1 to X 3 are each independently CH or N, but at least one of X 1 to X 3 is N,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted N, O, and C 2- containing one or more heteroatoms selected from the group consisting of 60 heteroaryl,
  • R 1 to R 3 are each independently selected from the group consisting of hydrogen (H), deuterium (D), substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted N, O, and S. C 2-60 heteroaryl containing one or more heteroatoms,
  • At least one of R 1 to R 3 is deuterium (D); At least one of Ar 1 , Ar 2 and R 1 to R 3 is C 6-60 aryl substituted with one or more deuterium (D),
  • n and m are each independently an integer of 1 to 3
  • o is an integer from 1 to 8.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and a cathode 6 is shown as an example of an organic light-emitting device.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituent
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhex
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and the like, but is not limited thereto.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine 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, be
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • heteroaryl among heteroarylamines the above-described description of heteroaryl may be applied.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
  • the present invention provides a compound represented by Chemical Formula 1.
  • X 1 to X 3 are each independently CH or N, but at least one of X 1 to X 3 is N. For example, all of X 1 to X 3 may be N.
  • the compound represented by Formula 1 has dibenzofuran or dibenzothiophene as a core, and is based on a structure in which 1,3,5-triazine and carbazole are bonded to both sides of the core.
  • the bonding position of 1,3,5-triazine is not particularly limited, but the bonding position of carbazole of carbazole is limited to carbon 7 of the core.
  • the binding position of such carbazole is capable of controlling the energy barrier with the organic material layer by controlling the HOMO and LUMO energy levels of the compound without deteriorating the function of other substituents (ie, 1,3,5-triazine). It corresponds to the structure.
  • the compound represented by Formula 1 contains at least one deuterium (D) in the molecule, and it is possible to more stably control the energy barrier with the organic material layer.
  • the compound represented by Formula 1 includes a structure in which 1,3,5-triazine and carbazole are bonded to both sides of a dibenzofuran or dibenzothiophene core, a bonding position of the carbazole, and at least one in the molecule. Due to the synergistic effect of deuterium, it is applied as a host material of the light emitting layer in the organic electroluminescent device to realize low voltage, high efficiency, and particularly long life.
  • the compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4:
  • X is O or S.
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-30 aryl; Or it may be a substituted or unsubstituted C 2-30 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, phenyl carbazol-9-yl, or 9 -Phenyl-9H-carbazolyl;
  • Each of Ar 1 and Ar 2 may be independently unsubstituted or substituted with one or more deuterium (D).
  • R 1 to R 3 are each independently hydrogen (H), deuterium (D), substituted or unsubstituted C 6-30 aryl; Or it may be a substituted or unsubstituted C 2-30 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
  • R 1 and R 2 may each independently be hydrogen (H), deuterium (D), or phenyl unsubstituted or substituted with one or more deuterium (D).
  • R 3 is hydrogen (H), deuterium (D), phenyl unsubstituted or substituted with one or more deuterium (D), dibenzofuranyl unsubstituted or substituted with one or more deuterium (D), or It may be a dibenzothiophenyl ring or substituted with one or more deuterium (D).
  • n and m are each independently an integer of 1 to 3; o is an integer from 1 to 8.
  • the compound may be one in which at least one or more, specifically two or more, for example, five or more deuterium (D) are present in the molecule.
  • the compound may increase the device life in proportion to the number of deuterium in the molecule. Specifically, when a compound having two or more, for example, five or more than one having one deuterium in the molecule is applied, the life of the device may be further increased. In other words, as a compound having a larger number of deuterium in a molecule is used, the device life tends to be longer.
  • At least one of R 1 to R 3 may be deuterium (D).
  • at least one of Ar 1 , Ar 2 and R 1 to R 3 may be C 6-30 aryl substituted with one or more deuterium (D).
  • At least one of R 1 to R 3 is deuterium (D); At least one of Ar 1 , Ar 2 and R 1 to R 3 may be phenyl substituted with one or more deuterium (D) or biphenylyl substituted with one or more deuterium (D).
  • the phenyl substituted with at least one deuterium (D) and biphenylyl substituted with at least one deuterium (D) are each substituted with phenyl substituted with 5 deuterium (D) and 5 deuterium (D) It may be biphenylyl.
  • the compound represented by Formula 1 may be prepared according to a series of processes of Reaction Schemes 1-1 to 1-3 below.
  • the present invention provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention 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, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Including the indicated compound.
  • the organic material layer may include an emission layer, and the emission layer includes the compound represented by Chemical Formula 1.
  • the emission layer may further include a compound represented by Formula 2 below.
  • Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 2-60 hetero containing any one or more selected from the group consisting of N, O and S Aryl,
  • R 4 and R 5 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 6-60 aryl, or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S ,
  • a and b are each independently an integer of 1 to 7.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, phenyl biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl; Both R 4 and R 5 may be hydrogen.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, phenyl biphenylyl, naphthyl, or dimethylfluorenyl; Both R 4 and R 5 may be hydrogen.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the emission layer, and an electron transport layer and an electron injection layer between the emission layer and the second electrode in addition to the emission layer as an organic material layer. It can have a structure to However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.
  • the first electrode is an anode and the second electrode is a cathode, and an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate (normal type). It can be a device.
  • the first electrode is a cathode and the second electrode is an anode, and a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. It may be a light emitting device.
  • FIGS. 1 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
  • the compound represented by Formula 1 may be included in the hole transport layer.
  • the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.
  • the organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
  • an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer may be formed thereon, and then a material that can be used as a cathode may be deposited thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material.
  • a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable.
  • the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes.
  • the material is suitable.
  • the hole transport material the compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used, but the present invention is not limited thereto. .
  • the electron suppression layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. It refers to the layer that plays a role in improving the value.
  • the electron-suppressing layer includes an electron-blocking material, and examples of such an electron-blocking material include a compound represented by Formula 1 or an arylamine-based organic material, but are not limited thereto.
  • the light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • the emission layer may include a host material and a dopant material.
  • the host material may further contain a condensed aromatic ring derivative or a heterocyclic-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by increasing the probability of hole-electron coupling by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role.
  • the hole-blocking layer includes a hole-blocking material, and examples of the hole-blocking material include: a subazine derivative including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but is not limited thereto.
  • the electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer.
  • an electron injection and transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable.
  • specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives and the like, but are not limited thereto.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or a nitrogen-containing 5-membered cyclic derivative, but may be used together, but is not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • 6-bromo-3-chlorodibenzo[b,d]furan (20 g, 71 mmol) and bis (pinacolato) diboron (18 g, 71 mmol) were added to 400 ml of Diox and stirred and refluxed. Thereafter, tri-potassium phosphate (45.2 g, 213.1 mmol) was added and sufficiently stirred, and then palladium dibenzylidene acetone palladium (1.2 g, 2.1 mmol) and tricyclohexylphosphine (1.2 g, 4.3 mmol) were added. After reacting for 6 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled.
  • A-1 (20 g, 45.6 mmol) and 3-phenyl-9H-carbazole (11.1 g, 45.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. Thereafter, sodium tertiary-butoxide (13.1 g, 136.7 mmol) was added, stirred sufficiently, and bis(tri tertiary-butylphosphine) palladium (0.7 g, 1.4 mmol) was added. After reacting for 2 hours, after cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO Indium Tin Oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HT-A and 5% by weight of PD were thermally vacuum deposited to a thickness of 100 ⁇ , and then only the HT-A material was deposited to a thickness of 1150 ⁇ to form a hole transport layer.
  • the following HT-B as an electron blocking layer was thermally vacuum deposited to a thickness of 450 ⁇ .
  • a host was formed using Compound 1 as the first host and GH-A as the second host in a weight ratio of 40:60, and vacuum evaporation was performed to a thickness of 400 ⁇ using 15% by weight of GD of the host as a dopant.
  • the following ET-A was vacuum deposited to a thickness of 50 ⁇ .
  • the following ET-B and Liq were thermally vacuum-deposited at a thickness of 250 ⁇ in a ratio of 2:1, and then LiF and magnesium were vacuum-deposited at a thickness of 30 ⁇ at a ratio of 1:1.
  • Magnesium and silver were deposited on the electron injection layer to a thickness of 160 ⁇ at a ratio of 1:4 to form a cathode, thereby manufacturing an organic light emitting device.
  • Organic light emitting devices of Examples 2 to 14 and Comparative Examples 1 to 6 were fabricated using the same method as in Example 1, except that the host material was changed to the compound shown in Table 1 below. At this time, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.
  • the organic light-emitting devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6 were heat-treated in an oven at 100° C. for 30 minutes and then taken out, and a current was applied to measure voltage, efficiency, and life (T95), and the results are as follows. It is shown in Table 1. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm 2 , and T95 means the time (hr) until the initial luminance decreases to 95% at the current density of 20 mA/cm 2 .
  • Example 1 Compound 1 4.40 57.3 95
  • Example 2 Compound 2 4.56 58.2 91
  • Example 3 Compound 3 4.26 55.7 89
  • Example 4 Compound 4 4.54 60.1 84
  • Example 5 Compound 5 4.42 59.3 93
  • Example 6 Compound 6 4.53 57.8
  • Example 7 Compound 7 4.38 53.4
  • Example 8 Compound 8 4.62 55.2
  • Example 9 Compound 9 4.65 58.1
  • Example 10 Compound 10 4.45 57.3 81
  • Example 11 Compound 11 4.64 58.4 85
  • Example 12 Compound 12 4.51 59.0 100
  • Example 13 Compound 13 4.50 57.3
  • Example 14 Compound 14 4.43 58.2 97 Comparative Example 1 CE 1 4.66 58.0 65 Comparative Example 2 CE 2 4.53 57.6 66 Comparative Example 3 CE 3 4.64 55.2 65 Comparative Example 4 CE 4 4.70 54.6 62 Comparative Example 5
  • an organic electroluminescent device in which the compound represented by Formula 1 is applied as a host material of an emission layer has advantages in voltage and efficiency, and in particular, can implement long life characteristics.
  • Comparative Examples 2 and 4 respectively, a compound having the same or similar skeleton as in Comparative Examples 5 and 6, but having a different binding position of carbazole, was applied as a host material of the light emitting layer.
  • Examples 11 and 9 a compound having the same or similar skeleton as those of Comparative Examples 2 and 4, but having a different deuterium substitution and a different binding position of carbazole, was applied as a host material of the emission layer.
  • Examples 8 and 9 compounds having the same or similar skeletons as those of Comparative Examples 3 and 4 but having different deuterium substitutions were applied as host materials.
  • Examples 8 and 9 compared to Comparative Examples 3 and 4, respectively, it was confirmed that the voltage of the device was decreased, the efficiency was improved, and in particular, the lifetime was increased.
  • Examples 11 and 12 compounds having the same or similar skeleton as those of Comparative Examples 1 and 2 but different in whether or not substituted with deuterium was applied as a host material.
  • Examples 11 and 12 compared to Comparative Examples 1 and 2, respectively, it was confirmed that the voltage of the device was decreased, the efficiency was improved, and in particular, the lifetime was increased.
  • the compound represented by Formula 1 above has a structure in which 1,3,5-triazine and carbazole are bonded to both sides of a dibenzofuran or dibenzothiophene core, and the bonding position of the carbazole ( Bonded to carbon 7), and one or more (specifically, two or more, for example, five or more) in a molecule.It is applied as a host material of the light-emitting layer in an organic electroluminescent device and has low voltage, high efficiency, especially It can be seen that long life characteristics can be implemented.
  • an organic electroluminescent device in which the compound represented by Formula 1 described above is applied as a host material of the emission layer can obtain advantages in voltage and efficiency, and in particular, can implement long life characteristics.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer

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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)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé, et un élément électroluminescent organique l'utilisant.
PCT/KR2020/010536 2019-08-13 2020-08-10 Nouveau composé, et élément électroluminescent organique l'utilisant WO2021029634A1 (fr)

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CN202410674524.2A CN118666816A (zh) 2019-08-13 2020-08-10 化合物及包含其的有机发光器件
CN202080005412.8A CN112771037A (zh) 2019-08-13 2020-08-10 新型化合物及包含其的有机发光器件

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EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
JP7562921B2 (ja) 2021-02-22 2024-10-08 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子

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CN109535138A (zh) * 2017-09-22 2019-03-29 北京绿人科技有限责任公司 含氘代苯基的三嗪化合物及其应用和有机电致发光器件
KR20200012798A (ko) * 2018-07-27 2020-02-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

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KR20180108425A (ko) * 2017-03-24 2018-10-04 희성소재 (주) 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20190030963A (ko) * 2017-09-15 2019-03-25 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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KR20200012798A (ko) * 2018-07-27 2020-02-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7562921B2 (ja) 2021-02-22 2024-10-08 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
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