WO2021080368A1 - 신규한 화합물 및 이를 이용한 유기 발광 소자 - Google Patents

신규한 화합물 및 이를 이용한 유기 발광 소자 Download PDF

Info

Publication number
WO2021080368A1
WO2021080368A1 PCT/KR2020/014558 KR2020014558W WO2021080368A1 WO 2021080368 A1 WO2021080368 A1 WO 2021080368A1 KR 2020014558 W KR2020014558 W KR 2020014558W WO 2021080368 A1 WO2021080368 A1 WO 2021080368A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
substituted
layer
organic light
Prior art date
Application number
PCT/KR2020/014558
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
서상덕
정민우
이정하
한수진
박슬찬
황성현
이동훈
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202080013021.0A priority Critical patent/CN113423705B/zh
Publication of WO2021080368A1 publication Critical patent/WO2021080368A1/ko

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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 by using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An 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.
  • 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. When it falls back to the ground, it glows.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1):
  • X is O, or S
  • Y is N, or CH, provided that at least two of Y are N,
  • L is phenylene; Biphenyldiyl; Terphenyldiyl; Naphthalenediyl; Or-naphthyl is substituted phenylene, and L is unsubstituted or substituted with one or more deuterium,
  • R 1 is substituted or unsubstituted C 6-60 aryl, and the others are each independently hydrogen or deuterium,
  • R 2 is hydrogen or deuterium
  • Each R 3 is independently hydrogen or deuterium
  • R 4 is substituted or unsubstituted C 6-60 aryl
  • Each R 5 is independently hydrogen or deuterium
  • n is an integer of 1 to 3
  • n is each independently an integer of 1 to 4.
  • 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 do.
  • 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 shows an example of an organic light-emitting device comprising 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 I did it.
  • 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 heterocyclic 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 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 a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group.
  • 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, a phenyl boron group, and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhex
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 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.
  • the fluorenyl group is substituted, Can be, etc. However, it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but it is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples 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, phenan
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • the description of the aforementioned heterocyclic group may be applied.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are bonded to each other.
  • L is any one selected from the group consisting of:
  • one of R 1 is phenyl, phenyl substituted with 1 to 5 deuterium, biphenylyl, or naphthyl, and the others are each independently hydrogen or deuterium.
  • R 4 is phenyl, phenyl substituted with 1 to 5 deuterium, biphenylyl, or naphthyl.
  • the present invention provides a method for preparing a compound represented by Chemical Formula 1 as shown in Scheme 1 below.
  • reaction Scheme 1 the definition of the remaining substituents excluding X'is as defined above, and X'is halogen and more preferably chloro or bromo.
  • the reaction is an amine substitution reaction, and is 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 Formula 1 above.
  • 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 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 may include an emission layer, and the emission layer includes 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 light emitting layer further includes a compound represented by the following formula (2) in addition to the compound represented by the formula (1):
  • Ar 4 and Ar 5 are each independently a 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,
  • R 6 and R 7 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 including any one or more selected from the group consisting of N, O and S,
  • a and b are each independently an integer of 0 to 7.
  • Ar 4 and Ar 5 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
  • both R 6 and R 7 are hydrogen.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 1 above.
  • the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons includes the compound represented by Formula 1 above.
  • the organic material layer may include an emission layer and an electron transport layer
  • the electron 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 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the compound represented by Formula 1 may be included in 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 multilayered 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 thin film formation ability is preferable. It is preferable that 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 light-emitting material a material capable of emitting light in a visible light 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 for 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.
  • 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, periflanthene and the like 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, periflanthene and the like 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
  • styrylamine styryldiamine
  • styryltriamine examples of the metal complex
  • styryltetraamine examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
  • An electron transport material a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for 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 is excellent in thin film forming ability is preferable.
  • Complex compounds and nitrogen-containing 5-membered ring derivatives 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-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.
  • intermediate A-1 15 g, 38.2 mmol
  • phenylboronic acid 4.7 g, 38.2 mmol
  • THF 225 ml
  • potassium carbonate 15.9 g, 114.7 mmol
  • tetrakis (triphenylphosphine) palladium (0) 1.3 g, 1.1 mmol
  • intermediate A 15 g, 34.6 mmol
  • intermediate a 9.9 g, 34.6 mmol
  • potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml), stirred sufficiently, and tetrakis (triphenylphosphine) palladium (0) (1.2 g, 1 mmol) was added.
  • the mixture was cooled to room temperature, separated into an organic layer and an aqueous layer, and the organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO Indium Tin Oxide
  • Fischer Co. product was used as a detergent
  • distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HT-A compound and the following PD compound were thermally vacuum deposited to a thickness of 100 ⁇ at a weight ratio of 95:5, and then only the following HT-A compound was deposited to a thickness of 1150 ⁇ to form a hole transport layer. Formed.
  • the following HT-B compound was thermally vacuum deposited to a thickness of 450 ⁇ to form an electron blocking layer.
  • the compound 1 prepared above and the following GD compound were vacuum-deposited to a thickness of 400 ⁇ at a weight ratio of 85:15 to form a light emitting layer.
  • the following ET-A compound was vacuum deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • the following ET-B compound and the following Liq compound were thermally vacuum deposited to a thickness of 250 ⁇ at a weight ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 ⁇ at a weight ratio of 1:1.
  • an electron transport and injection layer was formed.
  • magnesium and silver were deposited to a thickness of 160 ⁇ in a weight ratio of 1:4 to form a cathode, thereby fabricating an organic light-emitting device.
  • the deposition rate of organic materials was maintained at 0.4 ⁇ 0.7 ⁇ /sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 ⁇ /sec, and the deposition rate of silver and magnesium was 2 ⁇ /sec. Maintaining ⁇ 10 -7 ⁇ 5 ⁇ 10 -6 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1.
  • the organic light-emitting devices prepared in the above Experimental Examples and Comparative Experimental Examples were stored in an oven at 110° C. for 30 minutes and subjected to heat treatment, and then voltage, efficiency, and life (T95) were measured by applying current, and the results are shown in Table 1 . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2. In addition, T95 in Table 1 below refers to the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2.
  • substrate 2 anode

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2020/014558 2019-10-24 2020-10-23 신규한 화합물 및 이를 이용한 유기 발광 소자 WO2021080368A1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202080013021.0A CN113423705B (zh) 2019-10-24 2020-10-23 化合物及利用其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020190133056A KR102506584B1 (ko) 2019-10-24 2019-10-24 신규한 화합물 및 이를 이용한 유기 발광 소자
KR10-2019-0133056 2019-10-24

Publications (1)

Publication Number Publication Date
WO2021080368A1 true WO2021080368A1 (ko) 2021-04-29

Family

ID=75620540

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2020/014558 WO2021080368A1 (ko) 2019-10-24 2020-10-23 신규한 화합물 및 이를 이용한 유기 발광 소자

Country Status (3)

Country Link
KR (1) KR102506584B1 (zh)
CN (1) CN113423705B (zh)
WO (1) WO2021080368A1 (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022177401A1 (ko) * 2021-02-22 2022-08-25 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
WO2023121096A1 (ko) * 2021-12-22 2023-06-29 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2024167355A1 (ko) * 2023-02-10 2024-08-15 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023055177A1 (ko) * 2021-10-01 2023-04-06 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자
KR20230102740A (ko) * 2021-12-30 2023-07-07 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR20230102743A (ko) * 2021-12-30 2023-07-07 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
CN117447458B (zh) * 2023-12-20 2024-02-27 江苏三月科技股份有限公司 一种有机化合物、组合物及有机电致发光器件
CN118561827B (zh) * 2024-07-31 2024-10-11 南京高光半导体材料有限公司 一种带有三嗪基的化合物及有机电致发光器件

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180063710A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20190000185A (ko) * 2017-06-22 2019-01-02 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR20190010350A (ko) * 2017-07-21 2019-01-30 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR101959821B1 (ko) * 2017-09-15 2019-03-20 엘티소재주식회사 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물
KR102044943B1 (ko) * 2018-05-28 2019-11-14 삼성에스디아이 주식회사 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2020157204A1 (en) * 2019-01-30 2020-08-06 Novaled Gmbh Composition, organic semiconductor layer and electronic device

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법
KR102384676B1 (ko) * 2019-06-12 2022-04-07 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180063710A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20190000185A (ko) * 2017-06-22 2019-01-02 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR20190010350A (ko) * 2017-07-21 2019-01-30 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR101959821B1 (ko) * 2017-09-15 2019-03-20 엘티소재주식회사 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물
KR102044943B1 (ko) * 2018-05-28 2019-11-14 삼성에스디아이 주식회사 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2020157204A1 (en) * 2019-01-30 2020-08-06 Novaled Gmbh Composition, organic semiconductor layer and electronic device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022177401A1 (ko) * 2021-02-22 2022-08-25 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
WO2023121096A1 (ko) * 2021-12-22 2023-06-29 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2024167355A1 (ko) * 2023-02-10 2024-08-15 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자

Also Published As

Publication number Publication date
KR102506584B1 (ko) 2023-03-03
CN113423705B (zh) 2024-05-07
KR20210048856A (ko) 2021-05-04
CN113423705A (zh) 2021-09-21

Similar Documents

Publication Publication Date Title
WO2021080368A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2020046049A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020111733A1 (ko) 유기 발광 소자
WO2021091173A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021066351A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021040467A1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
WO2021045347A1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2020185038A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2024010336A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2020111780A1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2020091468A1 (ko) 유기 발광 소자
WO2020111585A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022031028A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022031013A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022031016A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021162227A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022060047A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021210774A1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2021066350A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021033980A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021029715A1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2020149656A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020185054A9 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020111886A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020022779A1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20879496

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20879496

Country of ref document: EP

Kind code of ref document: A1