WO2019240470A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2019240470A1
WO2019240470A1 PCT/KR2019/007021 KR2019007021W WO2019240470A1 WO 2019240470 A1 WO2019240470 A1 WO 2019240470A1 KR 2019007021 W KR2019007021 W KR 2019007021W WO 2019240470 A1 WO2019240470 A1 WO 2019240470A1
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group
compound
light emitting
substituted
unsubstituted
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French (fr)
Korean (ko)
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김진주
홍완표
윤홍식
이동훈
차용범
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주식회사 엘지화학
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Priority to CN201980013737.8A priority Critical patent/CN111770920B/zh
Publication of WO2019240470A1 publication Critical patent/WO2019240470A1/ko

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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
    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/10—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 two hetero rings linked by a carbon chain containing aromatic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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 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 two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as 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.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted indole group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dihydroindenocarbazole group; A substituted or unsubstituted dihydroindoloindole group; A substituted or unsubstituted dihydroindenocarbazole group; Substituted or unsubstituted hexahydropyridoquinoline group; Substituted or unsubstituted triphenylsilyl group; Or a substituted or unsubstituted tetraphenylsilane group.
  • the present application 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 includes the compound described above.
  • the compound according to the exemplary embodiment of the present application is used in an organic light emitting device to increase the brightness of the organic light emitting device, increase the lifespan, lower the driving voltage, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound Can be improved.
  • the substituent When the substituent is bonded to the 1,4 positions of the triphenylene, it has a symmetrical structure on both sides of the triphenylene having a flat structure so that the solubility is not good and the sublimation temperature also tends to be high. Falling problem occurs. Therefore, the compound according to the present invention has a asymmetric structure when the substituent is bonded to the 1,3 position of the triphenylene, giving a steric effect to increase the solubility and lower the sublimation temperature during device deposition Improve thermal stability
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, and a hole transport layer 6.
  • An example of an organic light emitting device in which the light emitting layer 3, the hole blocking layer 7, the electron transport layer 8, and the cathode 4 are sequentially stacked is illustrated.
  • the solubility can be increased due to the steric effect and the sublimation temperature is lower than that of the compound at the 1,4 position. Can be.
  • the substituent is bonded only to the first or the third position, when having a substituent at the 1, 3 position at the same time, there is an advantage that it is easy to control the energy level by introducing more various substituents.
  • substituted means that a hydrogen atom bonded to a 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 a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked 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 linked.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
  • Specific 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, cyclohexylmethyl, octyl, n-o
  • 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, but are not limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
  • the polycyclic aryl group may be naphthyl group, anthracene group, phenanthrene group, pyrenyl group, peryleneyl group, chrysene group, fluorene group, etc., but is not limited thereto.
  • the heteroaryl group includes one or more atoms other than carbon and hetero atoms, and specifically, the hetero atoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have.
  • carbon number of a heteroaryl group is not specifically limited, It is preferable that it is C2-C60 or C2-C30.
  • heteroaryl group examples include thiophene group, furan group, pyrrole 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, benzo
  • the arylene group refers to a divalent group having two bonding positions in the aryl group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • L1 and L2 are direct bonds.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an indole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; Carbazole groups unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A benzocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindolocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindoloindole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindenocarbazol
  • Ar1 and Ar2 are the same as or different from each other, and each independently an indole group unsubstituted or substituted with an alkyl group or an aryl group; Carbazole groups unsubstituted or substituted with alkyl or aryl groups; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A dihydroindolocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A dihydroindoloindole group unsubstituted or substituted with an alkyl group or an aryl group; A dihydroindenocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; Hexahydropyridoquinoline group unsubstituted or substituted with an alkyl group or an aryl group; Triphenylsilyl group unsub
  • the alkyl group is an alkyl group having 1 to 10 carbon atoms.
  • the aryl group is an aryl group having 1 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the following structural formulas.
  • R4 is the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
  • n is an integer from 1 to 10
  • R 4 in parentheses is the same as or different from each other.
  • R4 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R4 is hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted butyl group; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • R4 is hydrogen; Methyl group; tert-butyl group; Phenyl group; Or a naphthyl group.
  • Ar1 and Ar2 are the same as each other.
  • Ar1 and Ar2 are different from each other.
  • the compound represented by Formula 1 is selected from the following structural formulas.
  • the compound according to an exemplary embodiment of the present application may be prepared by the manufacturing method described below.
  • the compound of Formula 1 may have a core structure as shown in Scheme 1 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • a and B are halogen and may be the same or different. Typically can be synthesized through the Suzuki or Buchwald reaction used in the art.
  • the maximum emission wavelength of the compound is 400 to 700nm.
  • the maximum emission wavelength of the compound is 500 to 540m.
  • the maximum emission wavelength of the compound is 510 to 525m.
  • the maximum emission wavelength of the compound is 515 to 520m.
  • the present specification provides an organic light emitting device including the compound described above.
  • the 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 includes the compound.
  • the organic material layer of the organic light emitting device of the present application 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 may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound
  • the light emitting layer is a green light emitting layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host.
  • the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include another organic compound, a metal, or a metal compound as a dopant.
  • the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include an iridium-based dopant.
  • the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include a phosphorescent dopant.
  • the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include a red or green phosphorescent dopant.
  • the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include an iridium-based phosphorescent dopant.
  • the light emitting layer includes the compound and the dopant in a weight ratio of 1:99 to 99: 1.
  • the light emitting layer includes the compound and the dopant in a weight ratio of 2: 1 to 99: 1.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
  • the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises the compound.
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the 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, the electron transport layer, or the electron injection and transport layer includes the compound.
  • the organic light emitting device comprises 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. 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, wherein at least one of the two or more organic material layers comprises the compound.
  • the organic light emitting diode may be an organic light emitting diode 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 material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, and a hole transport layer 6.
  • An example of an organic light emitting device in which the light emitting layer 3, the hole blocking layer 7, the electron transport layer 8, and the cathode 4 are sequentially stacked is illustrated.
  • the organic light emitting device of the present application 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 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 may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • an organic material 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 of Formula 1 may be formed as an organic material 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, spray method, roll 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 (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 and the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode.
  • the hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a 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.
  • 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.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based 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.
  • the hole transport material is a material that can transport holes from an anode or a hole injection layer and transfer them to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • 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.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • 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-containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, 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 the electrons to the light emitting layer is provided. Suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including 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 in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the 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 the derivatives thereof, metal Complex compounds, 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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer for blocking the arrival of the cathode of 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 complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • the intermediate 4-1 (9.3g, 19.36mmol), bromotriphenylsilane (13.1g, 38.731mmol) and 4 mol% of tetrakistriphenylphosphinepalladium (Tetrakis (triphenylphosphine) palladium) were added to 50 ml of dioxane and potassium carbonate. (16.1g, 116.16mmol) was dissolved in 25ml of water and mixed. After stirring for 12 hours at 100 °C, the reaction was terminated and cooled to room temperature to separate the water and the organic layer. Take only the organic layer and add anhydrous magnesium sulfate. Silica pad filtration, solution purification under reduced pressure and column purification gave 10.4 g (72% yield) of compound 4.
  • the intermediate 6-1 (7.7g, 14.9mmol), (4-bromophenyl) triphenylsilane (6.2g, 14.9mmol) and tetrakistriphenylphosphinepalladium (Tetrakis (triphenylphosphine) palladium) 2mol% tetrahydro 50 ml of furan was added and potassium carbonate (6.2 g, 44.7 mmol) was dissolved in 25 ml of water and mixed. After stirring for 12 hours at 80 °C, the reaction was terminated and cooled to room temperature to separate the water and the organic layer. Take only the organic layer and add anhydrous magnesium sulfate. Silica pad filtration and solution purification under reduced pressure were followed by column purification to give 7.6 g (70% yield) of compound 6.
  • 60 ml of xylene was prepared using the intermediate 7-1 (10.9 g, 21.66 mmol) and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole (6.1 g, 21.66 mmol).
  • sodium-tert-butoxide 2.5g, 25.99mmol
  • 1 mol% of bis (tri-tert-butylphosphine) palladium was slowly added dropwise. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 8.8 g (54% yield) of compound 8.
  • a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned.
  • ITO Indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing 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.
  • M-MTDATA 60 nm) / TCTA (80 nm) / Host + 10% by weight Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) on the prepared ITO transparent electrode
  • a light emitting device was constructed in the order of) / Al (200 nm).
  • the structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP are as follows.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 8 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 9 was used instead of compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using GH 1 instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that GH 2 was used instead of compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using GH 3 instead of compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using GH 4 instead of compound 1 in Experimental Example 1-1.
  • the EL peak means the maximum emission wavelength ( ⁇ max), and the measuring method is as follows.
  • the photoluminescence spectrum of the solution state was measured using LS-55 of Perkin Elmer, and the emission spectrum of the excitation wavelength at 300 nm is 400 to 700 nm.
  • High performance liquid chromatography grade (HPLC grade) tetrahydrofuran (THF) was used as the solvent.
  • GH 2 used in Comparative Example 1-2 is a high-voltage, low-compound compared to Examples 1-1 to 1-9 where Ar1 is bonded to the position 3 of the triphenylene and Ar1 and Ar2 are bonded to the position 1 and 3; It was confirmed that efficiency appeared.
  • Comparative Example 1-3 used a compound GH 3 having an aryl group bonded to position 1 of the triphenylene, a substituent corresponding to the definition of Ar1 and Ar2 of the present invention at position 4, and Comparative Example 1-4 Compound GH 4 in which the substituents corresponding to the definitions of Ar1 and Ar2 of the present invention are bonded to positions 2 and 11 of triphenylene is used.
  • the compounds of Examples 1-1 to 1-9 in which Ar1 and Ar2 were bonded to positions 1 and 3 of the present invention have characteristics of low voltage and high efficiency.

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  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
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KR20090132352A (ko) * 2008-06-20 2009-12-30 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광소자
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