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WO2020032719A1 - Nouveau composé et diode électroluminescente organique l'utilisant - Google Patents

Nouveau composé et diode électroluminescente organique l'utilisant Download PDF

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WO2020032719A1
WO2020032719A1 PCT/KR2019/010125 KR2019010125W WO2020032719A1 WO 2020032719 A1 WO2020032719 A1 WO 2020032719A1 KR 2019010125 W KR2019010125 W KR 2019010125W WO 2020032719 A1 WO2020032719 A1 WO 2020032719A1
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group
substituted
unsubstituted
formula
light emitting
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PCT/KR2019/010125
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Korean (ko)
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정민우
이동훈
장분재
이정하
한수진
박슬찬
황성현
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주식회사 엘지화학
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Priority claimed from KR1020190096889A external-priority patent/KR102236322B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980042862.1A priority Critical patent/CN112334472B/zh
Publication of WO2020032719A1 publication Critical patent/WO2020032719A1/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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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 heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention relates to a novel compound and an organic light emitting device using the same.
  • 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 brightness, 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 to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2013-073537
  • the present invention relates to a novel compound organic light-emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • L is a direct bond; Substituted or unsubstituted C 1-60 alkylene; Or substituted or unsubstituted C 6-60 arylene,
  • Ar is substituted or unsubstituted C 6-60 aryl
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 1-60 haloalkoxy; Tri (C 1-60 alkyl) silyl; Or substituted or unsubstituted C 6-60 aryl,
  • a1 is an integer of 0 to 7
  • a2 is an integer of 0 to 5
  • Y is O, S, CR 4 R 5 or NR 6 ,
  • R 4 and R 5 are each independently substituted or unsubstituted C 1-60 alkyl
  • R 6 is substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
  • Each R 3 is independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 1-60 haloalkyl; A substituted or unsubstituted C 1-60 haloalkoxy; Tri (C 1-60 alkyl) silyl; Or substituted or unsubstituted C 6-60 aryl,
  • a3 is an integer of 0-4.
  • 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 provides an organic light emitting device including the compound of the present invention.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • 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 consisting 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 the following formula (1).
  • L is a direct bond; Substituted or unsubstituted C 1-60 alkylene; Or substituted or unsubstituted C 6-60 arylene,
  • Ar is substituted or unsubstituted C 6-60 aryl
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 1-60 haloalkoxy; Tri (C 1-60 alkyl) silyl; Or substituted or unsubstituted C 6-60 aryl,
  • a1 is an integer of 0 to 7
  • a2 is an integer of 0 to 5
  • Y is O, S, CR 4 R 5 or NR 6 ,
  • R 4 and R 5 are each independently substituted or unsubstituted C 1-60 alkyl
  • R 6 is substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
  • Each R 3 is independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 1-60 haloalkoxy; Tri (C 1-60 alkyl) silyl; Or substituted or unsubstituted C 6-60 aryl,
  • a3 is an integer of 0-4.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O, and S atoms, or two or more substituents connected to the 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, and can be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a straight chain, branched chain or cyclic alkyl group 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.
  • 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 includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • 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, bromine 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, 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-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched chain, carbon number 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 preferably has 3 to 60 carbon atoms, and according to one 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 preferably has 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, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, And so on.
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but 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, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group
  • 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 of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in 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.
  • 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 aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • 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.
  • the compound represented by Chemical Formula 1 is any one selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8:
  • L, Ar, Y, R 1 , R 2 , R 3 , a1, a2, and a3 are as defined above.
  • L is a direct bond; Phenylene; Biphenylylene; Terphenylylene; Quarterphenylylene; Naphthylene; Phenanthrenylene; Triphenylenylene; Chrysylene; Fluoranthhenylene; Pyrenylene; Or triphenylenylene.
  • L is a direct bond; Phenylene; Biphenylylene; Or naphthylene, more preferably L is a direct bond; Or phenylene.
  • Ar is phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Chrysenyl; Fluoranthenyl; Pyrenyl; Or triphenylenyl.
  • Ar is phenyl; Biphenylyl; Or terphenylyl, more preferably Ar is phenyl.
  • R 1 and R 2 are each independently hydrogen.
  • a1 and a2 are integers of 0 to 2, more preferably 0 or 1.
  • R 4 and R 5 are each independently methyl.
  • R 6 is phenyl
  • R 3 is hydrogen
  • a3 is an integer of 0 to 2, more preferably 0 or 1.
  • the compound represented by Formula 1 is any one selected from the group consisting of:
  • an electron stability is increased by forming a bond between benzoxazole and a carbazole group, and at the same time, the effect may be further enhanced by interaction with the condensed carbazole group. Accordingly, when applied to the organic light emitting device, high efficiency, low driving voltage, high brightness and long life are realized.
  • the compound represented by Chemical Formula 1 may be prepared through the following Schemes 1-1 to 1-2.
  • Schemes 1-1 to 1-2 the remaining variables except X are as defined above, and X is halogen, preferably bromo or chloro.
  • Scheme 1-1 is an amine substitution reaction and a reaction for producing the Sub Compound by reacting a palladium catalyst in the presence of a base.
  • Scheme 1-2 is a Suzuki coupling reaction, in which a reactant is reacted with a palladium catalyst in the presence of a base to prepare a compound represented by Chemical Formula 1 of the present invention.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the present invention provides an organic light emitting device comprising a compound represented by the 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. 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 an 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, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above. It includes the 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 a layer for simultaneously injecting and transporting electrons includes a compound represented by the formula (1).
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability.
  • an n-type dopant used in the art may be mixed and used.
  • the organic layer may include a light emitting layer and an electron transport layer
  • the electron transport layer may include a compound represented by the 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 diode according to the present invention may be an organic light emitting diode having an inverted type structure 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 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 element composed of 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 light emitting layer.
  • the compound represented by 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 may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using 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.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by 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, 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 from a cathode material (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 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 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), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO 2 : 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 the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • 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 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 for receiving holes from the hole injection layer and transporting 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 and transferring them to the light emitting layer. This 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 receiving and combining holes and electrons from the hole transporting layer and the electron transporting 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-hydroxybenzo quinoline-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 may be a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and styrylamine compounds may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the above-described 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.
  • substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • 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 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 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 for injecting electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, 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 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 organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to 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.
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound sub 1-1 (30.4 g, 61%).
  • compound sub 1-1 (30.4 g, 90.8 mmol), bis (pinacolato) diboron (26.1 g, 99.8 mmol) and potassium acetate (17.8 g, 181.5 mmol) are mixed and added to 300 ml of dioxane And heated with stirring.
  • bis (dibenzylideneacetone) palladium 1.5 g, 3 mol%) and tricyclohexylphosphine (1.5 g, 6 mol%) were added thereto, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the temperature was lowered to room temperature and filtered.
  • compound sub 2-1 (36.1 g, 88.1 mmol), bis (pinacolato) diboron (24.9g, 96.9mmol) and potassium acetate (17.3 g, 176.1 mmol) are mixed and added to 300 ml of dioxane And heated with stirring.
  • bis (dibenzylideneacetone) palladium 1.5 g, 3 mol%) and tricyclohexylphosphine (1.5 g, 6 mol%) were added thereto, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the temperature was lowered to room temperature and filtered.
  • compound sub 1-2 (20.0 g, 46.9 mmol) 2-bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno [2,1-b] carbazole (20.5 g, 46.9 mmol) 200 ml of tetrahydrofuran was added and stirred and refluxed. Thereafter, potassium carbonate (19.5 g, 140.8 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.6 g, 3 mol%) was added thereto. After 4 hours the reaction was lowered to room temperature and filtered.
  • the glass substrate coated with ITO indium tin oxide having a thickness of 1,300 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a 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.
  • the following HI-1 compound was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 kPa on the hole injection layer, and an electron blocking layer was formed by vacuum depositing the following HT-2 compound to a thickness of 50 kPa on the HT-1 deposition film.
  • Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1 which were prepared in Preparation Example 1 as a light emitting layer on the HT-2 deposited film, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 kHz.
  • the following ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer. Formed. Aluminum was deposited to a thickness of 1000 ⁇ on the electron injection layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the aluminum was maintained at the deposition rate of 2 ⁇ / sec
  • the vacuum during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr It was.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Preparation Example 1 in Experimental Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Experiment 1, except that Compound 1 in Preparation Example 1 was used instead of Compound 1 of Preparation Example 1.
  • the compounds of CE1 to CE3 in Table 1 are as follows.
  • the organic light emitting diodes were measured voltage and efficiency at a current density of 10 mA / cm 2 , and lifespan was measured at a current density of 50 mA / cm 2 , and the results are shown in Table 1 below.
  • LT95 means 95% of initial luminance.
  • substrate 2 anode

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique l'utilisant.
PCT/KR2019/010125 2018-08-09 2019-08-09 Nouveau composé et diode électroluminescente organique l'utilisant WO2020032719A1 (fr)

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CN201980042862.1A CN112334472B (zh) 2018-08-09 2019-08-09 新型化合物及包含其的有机发光器件

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KR20180093318 2018-08-09
KR10-2018-0093318 2018-08-09
KR1020190096889A KR102236322B1 (ko) 2018-08-09 2019-08-08 신규한 화합물 및 이를 이용한 유기발광 소자
KR10-2019-0096889 2019-08-08

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120052879A (ko) * 2010-11-16 2012-05-24 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20140032823A (ko) * 2012-09-07 2014-03-17 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
US20150333274A1 (en) * 2012-12-14 2015-11-19 Merck Patent Gmbh Materials for electronic devices
KR20160046296A (ko) * 2014-10-17 2016-04-28 삼성디스플레이 주식회사 유기 발광 소자
KR20170093061A (ko) * 2016-02-03 2017-08-14 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120052879A (ko) * 2010-11-16 2012-05-24 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20140032823A (ko) * 2012-09-07 2014-03-17 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
US20150333274A1 (en) * 2012-12-14 2015-11-19 Merck Patent Gmbh Materials for electronic devices
KR20160046296A (ko) * 2014-10-17 2016-04-28 삼성디스플레이 주식회사 유기 발광 소자
KR20170093061A (ko) * 2016-02-03 2017-08-14 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

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