WO2020071863A1 - Composé et diode électroluminescente organique le comprenant - Google Patents

Composé et diode électroluminescente organique le comprenant

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WO2020071863A1
WO2020071863A1 PCT/KR2019/013054 KR2019013054W WO2020071863A1 WO 2020071863 A1 WO2020071863 A1 WO 2020071863A1 KR 2019013054 W KR2019013054 W KR 2019013054W WO 2020071863 A1 WO2020071863 A1 WO 2020071863A1
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group
substituted
unsubstituted
formula
compound
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PCT/KR2019/013054
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Korean (ko)
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이정하
이동훈
장분재
정민우
한수진
박슬찬
황성현
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주식회사 엘지화학
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Priority to CN201980030795.1A priority Critical patent/CN112088159B/zh
Publication of WO2020071863A1 publication Critical patent/WO2020071863A1/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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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]
    • H10K50/17—Carrier injection layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in an organic thin film to form a pair, and then extinguish and emit light.
  • the organic thin film may be composed of a single layer or multiple layers if necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound that can itself constitute a light emitting layer may be used, or a compound capable of serving as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present specification provides a compound and an organic light emitting device including the same.
  • One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
  • At least 2 of X1 to X3 are N, the rest are CH,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Y1 is O or S
  • Y2 is O, S or NR
  • R and R1 to R10 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted dimethylfluorene group.
  • the present application is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.
  • the compound according to an exemplary embodiment of the present application is used in an organic light emitting device to increase the luminance of the organic light emitting device, increase the life, lower the driving voltage, improve the light efficiency, and improve the life characteristics of the device by thermal stability of the compound Can be improved.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked.
  • Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (8), hole blocking layer (9), electron transport layer (10) ,
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; Alkoxy groups; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, or substituted with two or more substituents among the exemplified substituents, or means having no substituents.
  • a substituent having two or more substituents 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.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 50.
  • Specific examples are 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, cyclohexylmethyl, octyl, n
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like. It is not.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 24 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, pyrenyl group, perylene group, chrysene group, fluorene group, but is not limited thereto.
  • the heteroaryl group includes one or more non-carbon atoms and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms.
  • heteroaryl group examples include thiophene group, furan group, pyrrol group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothi
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.
  • Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.
  • Ar1, Ar2, X1 to X3, L1, L2, Y2 and R1 to R10 are the same as those in formula (1).
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 6.
  • Ar1, Ar2, X1 to X3, L1, L2, Y1, R and R1 to R10 are the same as those in formula (1).
  • Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; A triphenylene group unsubstituted or substituted with an aryl group; A phenanthrene group unsubstituted or substituted with an aryl group; A fluorene group unsubstituted or substituted with an aryl group or an alkyl group; A carbazole group unsubstituted or substituted with an aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group unsubstituted or substituted with
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; A terphenyl group unsubstituted or substituted with a phenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; A triphenylene group unsubstituted or substituted with a phenyl group; A phenanthrene group unsubstituted or substituted with a phenyl group; A dimethyl fluorene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a phenyl group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Or a dibenzothi
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted fluorene group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; Or a naphthyl group unsubstituted or substituted with an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; A carbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group; Or a dibenzothiophene group
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Or a naphthylene group.
  • R and R1 to R10 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; A phenanthrene group unsubstituted or substituted with an aryl group; Or a dimethylfluorene group unsubstituted or substituted with an aryl group.
  • R and R1 to R10 are the same as or different from each other, and each independently hydrogen;
  • R and R1 to R10 are the same as or different from each other, and each independently hydrogen; Or it is selected from the following structural formula.
  • R5 is hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted dimethylfluorene group.
  • R5 is hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.
  • R5 is hydrogen; Phenyl group; Biphenyl group; Or a terphenyl group.
  • R1 to R4 and R6 to R10 are hydrogen.
  • the compound represented by Chemical Formula 1 is selected from the following structural formulas.
  • the present specification provides an organic light emitting device comprising the above-described compound.
  • the 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 layer of the organic material layer includes the compound.
  • the organic material layer of the organic light emitting device of the present application may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device 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 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 includes a light emitting layer, and the light emitting layer contains the compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a host, and further includes another host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a host, and further includes a host and a dopant.
  • the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a first host, and further includes a second host.
  • the light emitting layer includes a first host and a second host in a weight ratio of 8: 2 to 2: 8, and the first host is a compound of Formula 1 above.
  • the light emitting layer includes a first host and a second host in a weight ratio of 1: 1, and the first host is a compound of Formula 1 above.
  • the second host is a carbazole-based compound.
  • the second host is a biscarbazole-based compound.
  • the light emitting layer further includes a dopant.
  • the light emitting layer includes a first host and a second host, and further includes a dopant.
  • the dopant is included in 1 to 20 parts by weight based on 100 parts by weight of the host.
  • the dopant is an iridium-based compound.
  • the dopant compound may be selected from the following structural formulas, but is not limited thereto.
  • the organic material layer includes a hole injection layer or a hole transport layer.
  • the organic material layer includes an electron blocking layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, and an electron blocking layer.
  • the organic material layer includes a hole transport layer, and the hole transport layer includes two or more layers.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or a hole transport layer contains the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer includes the compound.
  • the organic material layer includes a hole blocking layer.
  • the organic material layer includes an electron transport and injection layer.
  • the organic material layer includes an electron transport and injection layer, and the electron transport and injection layer includes two or more layers.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. It includes two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers comprises the compound.
  • the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIG. 1 the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIG. 1.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked.
  • Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (8), hole blocking layer (9) electron transport layer (10),
  • the structure of the organic light emitting device in which the electron injection layer 11 and the cathode 4 are sequentially stacked is illustrated. In such a structure, the compound may be included in the light emitting layer 8, but is not limited thereto.
  • the organic light emitting device of the present application may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a light emitting layer and an electron transport layer it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound of Formula 1 may be formed into 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • an organic material layer and an anode material may be sequentially deposited on a substrate to form an organic light emitting device (International Patent Application Publication No. 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 positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention 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); ZnO: Al or SnO 2 : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
  • the cathode material is preferably 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 is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer.
  • a compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and which has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transport material a hole can be transported to the light emitting layer by transporting holes from an anode or a hole injection layer, and the mobility of holes is large.
  • the material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • the light emitting layer may include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include compounds, dibenzofuran derivatives, and ladder-type furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, 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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
  • Dibenzothiophene-4-ylboronic acid (20.0 g, 87.7 mmol) and 2-chloro-4,6-diphenyltriazine (23.5 g, 87.7 mmol) in tetrahydrofuran 200 in a 500 mL round-bottom flask in a nitrogen atmosphere.
  • 1.5M aqueous potassium carbonate solution 100 mL was added, tetrakis- (triphenylphosphine) palladium (0.44 g, 0.9 mmol) was added, followed by heating and stirring for 7 hours.
  • intermediate A7 (8.5 g, 16 mmol) and 2-chloro-thiazole (3.0 g, 18 mmol) were added to 120 ml of dioxane, stirred and refluxed. Thereafter, cesium carbonate (15.8 g, 48.5 mmol) was dissolved in 50 ml of water, stirred sufficiently, and bis (tri- t -butylphosphine) palladium (0) (0.1 g, 0.3 mmol) was added. After the reaction for 6 hours, the temperature was reduced to room temperature and filtered. The filtrate was extracted with dichlorobenzene and water, and then the organic layer was dried using magnesium sulfate.
  • the following HI-A was thermally vacuum-deposited to a thickness of 100 Pa to form a hole injection layer. Subsequently, only the HT-A material was thermally vacuum-deposited to a thickness of 800 Pa to form a hole transport layer, and an HT-B compound was vacuum deposited to a thickness of 500 Pa to the hole transport layer to form an electron blocking layer. Subsequently, H1 was used as the first host of the emission layer in a weight ratio of 40:60 as the first host, and 6% by weight of GD of the two host weights was vacuum-deposited to a thickness of 350 MPa. Subsequently, the following ET-A was vacuum-deposited to a thickness of 50 MPa as a hole blocking layer.
  • ET-B and Liq as the electron transport layer were thermally vacuum-deposited to a thickness of 250 MPa at a ratio of 1: 1, and then vacuum-deposited to a thickness of 30 MPa to form an electron injection layer.
  • a cathode was formed by depositing aluminum to a thickness of 1000 MPa, thereby manufacturing an organic light emitting device.
  • the organic light-emitting device according to the embodiment has a 15% efficiency and longer lifespan by about 2 times compared to the organic light-emitting device according to Comparative Example 6 using a commonly used phosphorescent host material, Compound C6. It was confirmed that the compound having a. In addition, it exhibited low voltage, high efficiency, and long life characteristics compared to the compound (C1) in which only the triazine substituent is substituted or the compound (C2, C3) in which only the benzoimidazole (or benzothiazole or benzoxazole) substituent is substituted. In addition, when comparing Comparative Example 5 and Experimental Example 10, the compound of the present invention exhibited a long life property, which was confirmed to be different depending on the substitution position of dibenzofuran.

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  • 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 composé de formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/013054 2018-10-04 2019-10-04 Composé et diode électroluminescente organique le comprenant WO2020071863A1 (fr)

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CN116023372A (zh) * 2021-10-22 2023-04-28 烟台显华化工科技有限公司 一种苯并噁唑联吸电片段的化合物和电子传输材料

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KR101385216B1 (ko) * 2012-11-07 2014-04-14 주식회사 엘엠에스 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치
KR20170057660A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자
KR20180071621A (ko) * 2016-12-20 2018-06-28 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물

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DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
TW202340153A (zh) 2016-04-11 2023-10-16 德商麥克專利有限公司 具有二苯并呋喃及／或二苯并噻吩結構之雜環化合物
CN110878054A (zh) 2018-09-06 2020-03-13 北京鼎材科技有限公司 一种咪唑类化合物及其应用

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KR20100118690A (ko) * 2009-04-29 2010-11-08 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20130116041A (ko) * 2012-04-13 2013-10-22 주식회사 엘지화학 새로운 함질소 헤테로환 화합물 및 이를 이용한 유기 전자 소자
KR101385216B1 (ko) * 2012-11-07 2014-04-14 주식회사 엘엠에스 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치
KR20170057660A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자
KR20180071621A (ko) * 2016-12-20 2018-06-28 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물

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KR20200038876A (ko) 2020-04-14
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KR102228753B1 (ko) 2021-03-17

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