WO2020256527A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2020256527A1
WO2020256527A1 PCT/KR2020/008090 KR2020008090W WO2020256527A1 WO 2020256527 A1 WO2020256527 A1 WO 2020256527A1 KR 2020008090 W KR2020008090 W KR 2020008090W WO 2020256527 A1 WO2020256527 A1 WO 2020256527A1
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compound
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formula
layer
mmol
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심재훈
김민준
이동훈
서상덕
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주식회사 엘지화학
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Priority claimed from KR1020200075129A external-priority patent/KR102413614B1/ko
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Priority to CN202080006730.6A priority Critical patent/CN113166125B/zh
Publication of WO2020256527A1 publication Critical patent/WO2020256527A1/fr

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    • 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
    • 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
    • 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
    • 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 using the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • 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 composed 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 0001 Korean Patent Publication No. 10-2013-073537
  • 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:
  • R 1 to R 4 are each independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl; Or two of these adjacent to each other may form a benzene ring,
  • R 5 and R 6 are each independently substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 5-60 including at least one hetero atom selected from the group consisting of N, O and S Heteroaryl,
  • A is a substituent represented by the following formula 1A,
  • X is O or S
  • R 11 to R 18 not connected to Formula 1 are each independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl; Alternatively, two adjacent two of these may be bonded to each other to form a benzene ring.
  • 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 comprises the compound of the present invention.
  • 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 described above may be used as a material for the light emitting layer.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron suppression layer 7, a hole blocking layer 8, an electron injection and transport layer ( 9) and an example of an organic light-emitting device comprising a cathode 4 is shown.
  • substituted or unsubstituted refers to deuterium (D); Halogen group; Nitrile 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 a substituted or unsubstituted substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O and S atoms,
  • 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. 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 phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Etc When the fluorenyl group is substituted, Etc.
  • Etc it is not limited thereto.
  • the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbons is not particularly limited, but it is preferably 2 to 60 carbon atoms.
  • the heterocyclic group 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 , Car
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine 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.
  • the description of the aforementioned heterocyclic group 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 aforementioned heterocyclic group 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 heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are bonded to each other.
  • the present invention provides a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 has a structure in which a benzocarbazolyl-based substituent and a triazine-based substituent are connected to the para position of a phenylene linker, and an additional A substituent (di(di) at a specific position of the phenylene linker (ortho position based on a triazine-based substituent)).
  • Benzofuranyl type, dibenzothiophenyl type has a structure containing.
  • the phenylene linker does not include additional substituents other than the benzocarbazolyl-based substituent, the triazine-based substituent, and the A substituent, that is, the remaining carbons of the phenylene linker are all hydrogen-substituted structures.
  • the compound represented by Formula 1 has high stability against electrons and holes due to this structure, and can stably maintain a balance between electrons and holes.
  • the compound of the present invention is employed as an emission layer in an organic light emitting device, it is preferable because it can exhibit characteristics of low driving voltage, high efficiency, and long life.
  • Formula 1 is a substituent represented by Formula 1A, and in Formula 1A, any one of R 11 to R 18 is linked to Formula 1 (connected to a phenylene linker), in this case, Formula 1 is the following Formula 1- It is represented by any one of 1 to 1-4:
  • R 1 to R 6 and R 11 to R 18 are as defined above.
  • the rest of R 11 to R 18 in Formula 1A that are not connected to Formula 1 are each independently hydrogen, deuterium, or phenyl; Or two adjacent ones of these are bonded to each other to form a benzene ring.
  • formula 1A is any one selected from the group consisting of:
  • Each R" is independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl
  • n 1 to 7.
  • each R" is independently hydrogen or phenyl.
  • m is 1 or 2.
  • R 1 and R 2 are bonded, R 2 and R 3 are bonded, or R It means that 3 and R 4 combine to form a benzene ring.
  • all the rest of the benzene ring not formed are hydrogen.
  • Formula 1 is represented by any one of the compounds represented by the following Formulas 2-1 to 2-4:
  • Each R' is independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl
  • n is an integer from 0 to 4,
  • R 5 and R 6 are as defined above.
  • R' is hydrogen or phenyl.
  • the R 5 and R 6 are each independently, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carba Zol-9-yl, or 9-phenyl-9H-carbazolyl.
  • the compound represented by Formula 1 is any one selected from the group consisting of:
  • the compound represented by Formula 1 can be prepared by a manufacturing method such as the following Scheme 1:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and A are as defined in Formula 1, X is halogen, preferably chloro or bromo.
  • reaction formula is a Suzuki coupling reaction
  • reaction conditions such as a reactant, a catalyst, a solvent, etc., used in the reaction may be appropriately changed according to the type and position of the substituent of Formula 1 of the present invention.
  • the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1.
  • 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 do.
  • 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 organic light-emitting device may be a normal type organic light-emitting device in which an anode, an emission layer, and a cathode are sequentially stacked on a substrate.
  • the organic light-emitting device may be an organic light-emitting device of an inverted type in which a cathode, an emission layer, and an anode are sequentially stacked on a substrate.
  • 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, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron injection and transport 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.
  • 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 light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron suppression layer, the hole blocking layer, and the electron injection and transport layer. Can be included.
  • 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, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode 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 light emitting layer.
  • a hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable.
  • Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the emission layer is a layer in which holes and electrons transported from the hole transport layer and the electron transport layer are combined to emit light in a visible light region
  • the organic light emitting device according to an embodiment includes the compound represented by Formula 1 in the emission layer.
  • the compound represented by Formula 1 is used as a host material in the emission layer.
  • 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 an additional host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • 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 light emitting layer may include the following iridium complex compound as a dopant material, but 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 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 such hole-blocking materials include: a subazine derivative including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
  • an electron transport material a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the 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 formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are 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 to this.
  • the electron transport layer and the electron injection layer may be provided in the form of an electron injection and transport layer that simultaneously serves as an electron transport layer and an electron injection layer for transporting received electrons to the emission layer.
  • 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.
  • naphthalen-2-amine 300.0 g (1.0 eq), 1-bromo-2-iodobenzene 592.7 g (1.0 eq), NaOtBu 302.0 g (1.5 eq), Pd(OAc) 2 4.70 g (0.01 eq), Xantphos 12.12 g ( 0.01 eq), 1,4-dioxane was dissolved in 5L and stirred under reflux. When the reaction was completed after 3 hours, the pressure was reduced to remove the solvent. After that, it was completely dissolved in ethylacetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, and the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 443.5 g of compound a-1. (Yield 71%, MS: [M+H] + 299)
  • the intermediate compound P (20 g, 29mmol), 1-phenyl-5H-benzo[b]carbazole (8.5g, 29 mmol), sodium tert-butoxide (5.6 g, 58 mmol) was added to Xylene 400 ml and stirred and Refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent.
  • the intermediate compound Q (20 g, 31.9 mmol), 1-phenyl-5H-benzo[b]carbazole (9.4 g, 31.9 mmol), sodium tert-butoxide (6.1 g, 63.9 mmol) was added to Xylene 400 ml and stirred. And refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing 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 HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 ⁇ , but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • an electron suppressing layer was formed by vacuum depositing the following EB-1 compound with a film thickness of 150 ⁇ on the hole transport layer.
  • the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed by vacuum depositing the following HB-1 compound with a thickness of 30 ⁇ on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ . Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 1,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • LiF lithium fluoride
  • the lifetime T95 refers to the time it takes for the luminance to decrease from initial luminance (6000 nit) to 95%.
  • the red organic light-emitting device of Comparative Example 1 used a material that has been widely used in the past, and has a structure using compound [EB-1] as an electron suppressing layer and RH-1/Dp-7 as a red light-emitting layer.
  • organic light emitting devices were manufactured using C-1 to C-12 instead of RH-1.
  • the compound of the present invention has high stability against electrons and holes, and when applied as a host of a red light-emitting layer, the driving voltage is significantly lower than that of the material used in the comparative example, and is excellent in terms of efficiency . Accordingly, it was confirmed that when the present compound was used, energy transfer from the host to the red dopant was excellent. In addition, when using the present compound, it was confirmed that the lifespan characteristics can be improved up to two times or more while maintaining high efficiency.
  • substrate 2 anode

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (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 dispositif électroluminescent organique l'utilisant.
PCT/KR2020/008090 2019-06-21 2020-06-22 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2020256527A1 (fr)

Priority Applications (1)

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CN202080006730.6A CN113166125B (zh) 2019-06-21 2020-06-22 化合物及利用其的有机发光器件

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KR20190074430 2019-06-21
KR10-2019-0074430 2019-06-21
KR1020200075129A KR102413614B1 (ko) 2019-06-21 2020-06-19 신규한 화합물 및 이를 이용한 유기발광 소자
KR10-2020-0075129 2020-06-19

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150022268A (ko) * 2013-08-22 2015-03-04 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
KR20150129282A (ko) * 2014-05-09 2015-11-19 주식회사 엠비케이 신규한 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자 및 전자 기기
KR20180066818A (ko) * 2016-12-09 2018-06-19 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
EP3476915A1 (fr) * 2017-10-30 2019-05-01 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques
KR20190047631A (ko) * 2017-10-27 2019-05-08 주식회사 엘지화학 헤테로고리 화합물을 이용한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150022268A (ko) * 2013-08-22 2015-03-04 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
KR20150129282A (ko) * 2014-05-09 2015-11-19 주식회사 엠비케이 신규한 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자 및 전자 기기
KR20180066818A (ko) * 2016-12-09 2018-06-19 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20190047631A (ko) * 2017-10-27 2019-05-08 주식회사 엘지화학 헤테로고리 화합물을 이용한 유기 발광 소자
EP3476915A1 (fr) * 2017-10-30 2019-05-01 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques

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