WO2021029715A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2021029715A1
WO2021029715A1 PCT/KR2020/010802 KR2020010802W WO2021029715A1 WO 2021029715 A1 WO2021029715 A1 WO 2021029715A1 KR 2020010802 W KR2020010802 W KR 2020010802W WO 2021029715 A1 WO2021029715 A1 WO 2021029715A1
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group
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layer
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오중석
이동훈
김민준
서상덕
김영석
심재훈
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주식회사 엘지화학
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Priority to CN202080006877.5A priority Critical patent/CN113166112A/zh
Publication of WO2021029715A1 publication Critical patent/WO2021029715A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • a voltage is applied between the two electrodes
  • holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel organic light emitting material and an organic light emitting device including the same.
  • the present invention provides a compound represented by the following formula 1:
  • Ar 1 is substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
  • L 1 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene including any one or more selected from the group consisting of N, O and S,
  • R 1 to R 10 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more selected from the group consisting of N, O and S, or two adjacent substituents of R 1 to R 10 are bonded to each other to C 6-60 aromatic ring; Or to form a C 2-60 heteroaromatic ring comprising any one or more selected from the group consisting of N, O and S,
  • R '1 and R' 2 are each independently hydrogen, heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted N, O and or C 2-60 heteroaryl comprising at least one selected from the group consisting of S, R '1 and R' 2 are combined with each other by -O- or -NRa- To form,
  • Ra is hydrogen; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • the compound represented by Formula 1 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 device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8) and a cathode (4).
  • An example of an organic light emitting device is shown.
  • FIG. 3 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9).
  • An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown.
  • the present invention provides a compound represented by Chemical Formula 1.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Etc When the fluorenyl group is substituted, Etc.
  • Etc it is not limited thereto.
  • the heteroaryl group is a heteroaryl group including one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms.
  • heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthro
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • the above description of the heteroaryl group may be applied.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the aforementioned heteroaryl group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heteroaryl is not a monovalent group, and the description of the heteroaryl group described above may be applied except that the heteroaryl group is formed by bonding of two substituents.
  • Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3:
  • Ar 1 , L 1 , R 1 to R 10 and Ra are as defined in Formula 1.
  • Ar 1 is substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted C 2-20 heteroaryl including any one or more selected from the group consisting of N, O and S,
  • Ar 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl carbazolyl, or phenyl benzocarbazolyl,
  • Ar 1 may be any one selected from the group consisting of:
  • L 1 is a single bond; Substituted or unsubstituted C 6-20 arylene; Or substituted or unsubstituted C 2-20 heteroarylene including any one or more selected from the group consisting of N, O and S,
  • L 1 may be any one selected from the group consisting of:
  • Ar 2 is substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
  • L 2 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene including any one or more selected from the group consisting of N, O and S.
  • L 1 may be any one selected from the group consisting of:
  • Ar 2 may be a substituted or unsubstituted C 6-20 aryl
  • Ar 2 may be phenyl or naphthyl.
  • L 2 is a single bond; Or it may be a substituted or unsubstituted C 6-60 arylene,
  • L 2 may be a single bond, phenylene, or naphthalenediyl.
  • R 1 to R 10 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-10 alkyl; Substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted C 2-20 heteroaryl including any one or more selected from the group consisting of N, O and S, or two adjacent substituents of R 1 to R 10 are bonded to each other to C 6-20 aromatic ring; Or it can form a C 2-20 heteroaromatic ring comprising any one or more selected from the group consisting of N, O and S,
  • R 1 to R 10 may each independently be hydrogen or deuterium
  • R 1 to R 10 may each be hydrogen.
  • Ra is substituted or unsubstituted C 6-20 aryl;
  • substituted or unsubstituted N, O and S may be a C 2-20 heteroaryl including any one or more selected from the group consisting of,
  • Ra may be phenyl
  • the compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below, for example, and other compounds may be prepared similarly.
  • Ar 1 , L 1 , R 1 to R 10 , R′ 1 and R′ 2 are as defined in Formula 1, X is halogen, and preferably X is chloro or bromo.
  • Reaction Scheme 1 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be changed as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1.
  • the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking 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 material layers.
  • the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.
  • the compound according to the present invention can be used as a host of a light emitting layer.
  • the organic material layer may include a hole transport layer, a hole injection layer, or a layer for simultaneously transporting and injecting holes, and the layer for simultaneously transporting and injecting holes is the above formula It may contain a compound represented by 1.
  • the electron transport layer, the electron injection layer, or a layer that simultaneously transports electrons and injects electrons may include the compound represented by Formula 1 above.
  • the organic material layer may include an emission layer and a hole transport layer, and the emission layer or the hole transport layer may include a compound represented by Formula 1 above.
  • the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 to 3 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 to 3.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • FIG. 3 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9).
  • An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown.
  • the compound represented by Formula 1 may be included in one or more 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 of the organic material layers includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material.
  • a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable.
  • the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable.
  • Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the electron blocking layer is a layer interposed between the hole transport layer and the light emitting layer in order to prevent electrons injected from the cathode from passing over to the hole transport layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer.
  • the electron blocking layer is preferably a material having less electron affinity than the electron transport layer.
  • the light-emitting material a material capable of emitting light in a 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 against fluorescence or phosphorescence is preferable.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the compound represented by Formula 1 may be included as a host material.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppressing layer.
  • a material having high ionization energy is preferable for the hole blocking layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
  • an electron transport material a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the 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.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • Compound HI-1 was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 ⁇ , but compound A-1 was p-doped at a concentration of 1.5 wt%.
  • the following compound HT-1 was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • the following compound EB-1 was vacuum-deposited with a film thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • the following compound RH-1 and the following compound Dp-39 were vacuum-deposited at a weight ratio of 98:2 on the compound EB-1 deposition film to form a light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed by vacuum deposition of Compound HB-1 below with a thickness of 30 ⁇ on the emission layer. Subsequently, the following compound ET-1 and the following compound LiQ were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ . Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a cathode.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2 * 10 Maintaining -7 to 5 * 10 -6 torr, an organic light emitting device was manufactured.
  • an exemplary embodiment of the present invention is superior in terms of driving voltage, current efficiency, and in particular lifetime, compared to an organic light-emitting device including the compounds of Comparative Examples 1 to 8 having a different parent body.
  • substrate 2 anode

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

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/010802 2019-08-13 2020-08-13 Nouveau composé et dispositif électroluminescent organique le comprenant WO2021029715A1 (fr)

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KR1020200101339A KR102441470B1 (ko) 2019-08-13 2020-08-12 신규한 화합물 및 이를 포함하는 유기발광 소자

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CN113121544A (zh) * 2021-04-01 2021-07-16 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用

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KR20150121337A (ko) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US20180175306A1 (en) * 2016-12-15 2018-06-21 Universal Display Corporation Organic Electroluminescent Materials and Devices
KR20190035475A (ko) * 2017-09-26 2019-04-03 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN110452182A (zh) * 2019-08-01 2019-11-15 浙江华显光电科技有限公司 一种主体化合物和使用该化合物的有机电致发光器件
CN110746401A (zh) * 2019-09-09 2020-02-04 浙江华显光电科技有限公司 一种磷光化合物和使用该化合物的有机发光二极管器件

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US20180175306A1 (en) * 2016-12-15 2018-06-21 Universal Display Corporation Organic Electroluminescent Materials and Devices
KR20190035475A (ko) * 2017-09-26 2019-04-03 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113121544A (zh) * 2021-04-01 2021-07-16 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用

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