WO2018216913A1 - 신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자 - Google Patents

신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자 Download PDF

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WO2018216913A1
WO2018216913A1 PCT/KR2018/004809 KR2018004809W WO2018216913A1 WO 2018216913 A1 WO2018216913 A1 WO 2018216913A1 KR 2018004809 W KR2018004809 W KR 2018004809W WO 2018216913 A1 WO2018216913 A1 WO 2018216913A1
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εΐ69ΐζ
8ϊοζ
oav
compound
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차용범
이성재
김연환
전상영
한수진
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주식회사 엘지화학
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Publication of WO2018216913A1 publication Critical patent/WO2018216913A1/ko

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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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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
    • H10K50/171—Electron injection layers

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. .
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • Ri and 3 ⁇ 4 are hydrogen or connected to each other
  • Xi to X 3 are each independently N, or CH, provided that at least one of 3 ⁇ 4 to 3 ⁇ 4 is N,
  • An and Ar 2 are each independently; Substituted or unsubstituted C 6 -60 aryl; Or substituted or unsubstituted C 2 -60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, 0 and 3,
  • Ar 3 is substituted or unsubstituted C 6 -60 aryl; Carbazolyl; 9-phenylcarbazolyl; Dibenzofuranyl; Dibenzothiophenyl; Or a ring group represented by Formula 2 below:
  • Yi and Y 2 are each independently ⁇ , or CH, provided that at least one of ⁇ and ⁇ 2 is ⁇ ,
  • ⁇ 0, or S
  • Ar 4 is substituted or unsubstituted C 6 -60 aryl; Or substituted or unsubstituted C 2 -60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, 0 and S,
  • R is hydrogen; Substituted or unsubstituted C 6 -60 aryl; Or substituted or unsubstituted C 2 -60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, 0 and ' S,
  • n is an integer of 1-4.
  • the present invention is a first electrode; A low 12 electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting device, and organic. In the light emitting device, efficiency, low driving voltage, and / or lifetime characteristics can be improved.
  • the compound represented by Chemical 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 element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the present invention provides a compound represented by Chemical Formula 1.
  • substituted or unsubstituted is deuterium halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group alkylthioxy group Arylthioxy group; alkyl sulfoxy group; a3 ⁇ 4 sulfoxy group; silyl group; boron group alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group alkylaryl group; alkylamine group; aralkylamine group; hetero An arylamine group, an arylamine group, an arylphosphine group, or an unsubstituted or substituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N,
  • the compound may be a compound having the following structure, but is not limited thereto.
  • Anidi- the oxygen of the ester group may be substituted with a linear, 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,
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, 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.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromide or iodine.
  • the alkyl group may be linear or branched chain, carbon number 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, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4- 1-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, Heptyl, n-heptyl, 1-methylnuclear, cyclopentylmethyl, cyclonuctylmethyl, octyl, n —octyl, ter t -octyl, 1—methylheptyl, 2-ethyl
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, it 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—part Tenyl, 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 (dijonyl-1 -yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but is not limited to these.
  • the cycloalkyl group is not particularly limited, preferably 3 to 60 carbon atoms, according to one embodiment, the cycloalkyl group is 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.
  • aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • 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, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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. When the fluorenyl group is substituted '
  • the heterocyclic group is a heterocyclic group containing one or more of 0, N, Si, and S as heterologous elements, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine and acridil pyri.
  • the aryl group in 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 alkyl group described above.
  • the heteroaryl amine increases heteroaryl can be applied to the description of the above-mentioned heterocyclic groups.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the arylene is a divalent group
  • the description of the aryl group described above may be applied.
  • the heteroarylene is a divalent group
  • the description of the aforementioned heterocyclic group may be applied.
  • the hydrocarbon ring is not a monovalent group, except that two substituents are bonded to each other to form the aforementioned aryl group or cycloalkyl group. The description may apply.
  • the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • Chemical Formula 1 according to the bonding position, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-4:
  • An and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluore Nil, dibenzofuranyl, carbazolyl, 9-phenylcarbazolyl, or dibenzothiophenyl. More preferably, An and Ar 2 are each independently phenyl or biphenylyl.
  • Ar 3 is phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl phenanthrenyl, anthracenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, 9- Phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl.
  • Ar 4 is phenyl, biphenylyl, naphthyl, dimethylfluorenyl, diphenylpletuenyl, dibenzo Furanyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl.
  • R is hydrogen. Representative examples of the compound represented by Formula 1 are as follows:
  • the compound represented by Chemical Formula 1 may be prepared by the same method as in Scheme 1 below.
  • reaction formula 1 is a Suzuki coupling reaction, in which the compound represented by Chemical Formula 1-a and the compound represented by Chemical Formula 1-b are reacted in the presence of a palladium catalyst and a base to prepare a compound represented by Chemical Formula 1 It's a reaction.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1 to provide an organic light emitting device. do.
  • the organic material layer of the organic light emitting device of the present invention may be formed of a single layer structure, but may be formed of 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 the organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole is represented by the formula (1) It includes a compound represented.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
  • the electron transport layer, the electron injection layer: or the layer at the same time the electron transport and electron injection comprises a compound represented by the formula (1).
  • the organic layer includes a light emitting layer and an electron transport layer,
  • the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention 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 organic light emitting device having an inverted type in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 show an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport 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 layer of the organic material layer 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a crab 2 electrode on a substrate.
  • PVD physical vapor deposition
  • an alloy of It may be prepared by forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then 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 Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (W0 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 anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); A combination of a metal such as ZnO: AI or SN0 2 : Sb and an ' oxide; Conductive polymers such as poly (3 ′ methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline, but are not limited thereto. no.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material Metals such as magnesium, carbon, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiP7Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • HOMO highest occupied molecul ar orbi tal) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer.
  • the hole injecting material is a metal porphyrin (porphyr in), oligothiophene, an aryl amine-based, organic, hex nitrile hex-aza triphenyl organic materials alkylene series, quinacridone (quinacr idone) organic substance in the series, perylene ( perylene) organic materials, anthraquinone 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 transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, strylamine compound 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 periplanthene having an arylamino group
  • the styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted.
  • styryl amine, styryl di are substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, 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 light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include A 1 complex of 8-hydroxyquinoline; A complex containing the 1 Q 3 '; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer is used according to the prior art As can be used with any desired cathode material.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, etherboom and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, metal Complex compounds and nitrogen-containing five-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) ( 0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium
  • the present invention 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. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • Tetrahydrofuran 240 was added to compound FC11.26 g, 15.53 ⁇ l), and compound a2 (3.95 g, 14.79 ⁇ l ol) in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolved in mL, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.51 g, 0.44 mmol) was added thereto, and the mixture was heated and stirred for 4 hours.
  • Preparation 12 (7.60 g, 65%).
  • IT0 indium tin oxide
  • IT0 indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • the ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the compound represented by the following formula HAT was thermally vacuum deposited to a thickness of 150 A on the prepared ITO transparent electrode to form a hole injection layer.
  • a compound represented by the following Chemical Formula EB1 was vacuum deposited on the hole transport layer with a film thickness of 100 A to form an electron blocking layer.
  • a compound represented by the following formula BH and a compound represented by the following formula BD were deposited at a weight ratio of 25: 1 to form a light emitting layer with a thickness of 200 A.
  • a hole blocking layer was formed by vacuum depositing a compound represented by the following Chemical Formula HB1 with a film thickness of 50 A on the light emitting layer. Subsequently, the compound prepared in Preparation Example 1 and the compound represented by LiQ below were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 310 A. Lithium fluoride (LiF) with a thickness of 12 A on the electron injection and transport layer sequentially and aluminum to 1,000 A thickness A cathode was formed under deposition.
  • LiF Lithium fluoride
  • the organic light emitting device was manufactured by the same method as Example 1-1, using the compound shown in Table 1 below instead of the compound prepared in Preparation Example 1. ⁇ Comparative Examples 1-1 to 1-4
  • Example 1-1 Manufactured in the same manner as in Example 1-1.
  • An organic light emitting device was manufactured by using the compound shown in Table 1 below instead of the compound prepared in Preparation Example 1.
  • ETl, ET2, ET3, and ET4 used in Table 1 are as follows.
  • T95 refers to the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
  • the organic light emitting device was manufactured by the same method as Comparative Example 2-1, using a compound represented by the following Chemical Formula GH2 instead of the compound represented by the Chemical Formula GH1.
  • the organic light emitting device was manufactured by the same method as Comparative Example 2-1, but using the compound shown in Table 2 below instead of the compound represented by Formula GH1.
  • Experimental Example 2
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 ni t).
  • Comparative Example 2-2 GH2 4.28 98.45 (0.254, 0.702) 210
  • Table 2 in the case of an organic light emitting device manufactured using the compound of the present invention as a green light emitting layer, the efficiency, driving voltage, and / Or excellent properties in terms of stability.
  • nuorene-9, 8-indoloacr idine Asymmetric compounds of the present invention in which an aryl group is connected at position 3 and an electron withdrawing substituent is connected at position 5 are organic light emitting compounds prepared using the compound of the comparative example as a host of the green light emitting layer. It shows lower voltage and higher efficiency than the device.
  • Table 2 it was confirmed that the other compounds in the present invention can be applied to the organic light emitting device excellent in the light emitting ability.

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KR102633124B1 (ko) * 2019-10-07 2024-02-01 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102633769B1 (ko) * 2019-10-18 2024-02-02 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102639657B1 (ko) * 2019-10-18 2024-02-21 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102633801B1 (ko) * 2019-10-23 2024-02-02 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102427162B1 (ko) * 2019-11-11 2022-07-29 주식회사 엘지화학 유기 발광 소자
CN114144902B (zh) * 2020-04-09 2024-10-15 株式会社Lg化学 有机发光器件

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