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WO2019107710A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2019107710A1
WO2019107710A1 PCT/KR2018/010035 KR2018010035W WO2019107710A1 WO 2019107710 A1 WO2019107710 A1 WO 2019107710A1 KR 2018010035 W KR2018010035 W KR 2018010035W WO 2019107710 A1 WO2019107710 A1 WO 2019107710A1
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formula
group
compound
light emitting
layer
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Korean (ko)
Inventor
차용범
서상덕
홍성길
김성소
천민승
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LG Chem Ltd
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LG Chem Ltd
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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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present disclosure relates to an organic light emitting device.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the present invention provides an organic light emitting device.
  • the present specification discloses a battery pack comprising: a positive electrode; A negative electrode opposed to the positive electrode; A light emitting layer provided between the anode and the cathode; At least one first organic material layer disposed between the anode and the light emitting layer; And a second organic compound layer disposed between the cathode and the light emitting layer, wherein the first organic compound layer includes at least one of compounds represented by Chemical Formulas 1 and 2, 3 < / RTI >
  • Ar 1 to Ar 4 is a polycyclic aryl group and the rest are the same or different and are each independently a monocyclic aryl group,
  • Ar5 and Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Y1 is a group represented by any one of the following structures
  • X is O or S
  • R1 to R8 are hydrogen, or adjacent groups are bonded to each other to form an aromatic ring
  • At least one of X1 to X3 is N, and the others are CH,
  • At least one of X4 to X6 is N, and the others are CH,
  • L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar7 to Ar10 are the same or different and are each independently a substituted or unsubstituted aryl group.
  • the organic light emitting device can improve the low voltage, lifetime characteristics and / or efficiency characteristics of the device.
  • FIG 1 shows an organic light emitting device 10 according to an embodiment of the present invention.
  • FIG 2 shows an organic light emitting element 11 according to another embodiment of the present invention.
  • the present specification discloses a battery pack comprising: a positive electrode; A negative electrode opposed to the positive electrode; A light emitting layer provided between the anode and the cathode; At least one first organic material layer disposed between the anode and the light emitting layer; And a second organic compound layer disposed between the cathode and the light emitting layer, wherein the first organic compound layer includes at least one of the compounds represented by Chemical Formulas 1 and 2, 3 < / RTI >
  • the first organic layer includes a hole transporting layer and an electron blocking layer.
  • the electron blocking layer is provided between the anode and the light emitting layer
  • the hole transporting layer is provided between the electron blocking layer and the anode.
  • the first organic layer is a hole transporting layer or an electron blocking layer.
  • the first organic layer includes a hole transporting layer and an electron blocking layer
  • the hole transporting layer includes a compound represented by the above formula (1).
  • the first organic layer is a hole transporting layer
  • the hole transporting layer includes a compound represented by the general formula (1).
  • the formula (1) has a structure in which amine groups are bonded on both sides of a biphenylene core, and a non-covalent electron pair of an amine group bonded on both sides of biphenylene is conjugated with biphenylene
  • the hole transporting ability is excellent due to the structural characteristic of dispersing.
  • the compound in which any one of Ar1 to Ar4 in the formula (1) is a polycyclic aryl group has a relatively high glass transition temperature (Tg) as compared with a material used in a hole transport layer of a conventional material, There is an effect that the driving voltage is reduced when applied to a light emitting device.
  • Tg glass transition temperature
  • the compound has a low glass transition temperature (Tg) The efficiency decreases.
  • the first organic layer includes a hole transporting layer and an electron blocking layer
  • the electron blocking layer includes a compound represented by the general formula (2).
  • the first organic layer is an electron blocking layer
  • the electron blocking layer includes a compound represented by the general formula (2).
  • the formula (2) is a structure in which an amine group and a three-ring heteroaryl group are bonded to both sides of the biphenylene core, and each of the amine groups and The structure is characterized in that the non-covalent electron pair of N, O or S of the heteroaryl group of the ring is dispersed by the conjugation of biphenylene.
  • the carbazole, dibenzofuran and dibenzothiophene are substituted in the monoamine form in the monoamine form, the molecular symmetry is disrupted and the amorphous property is improved, The device has high device efficiency.
  • the first organic material layer includes a hole transporting layer and an electron blocking layer
  • the hole transporting layer includes a compound represented by Formula 1
  • the electron blocking layer is represented by Formula 2 ≪ / RTI >
  • the second organic layer is a layer that simultaneously performs electron injection, electron transport, or electron injection and transport, and the electron injection layer, electron transport layer, And the compound represented by the above formula (3).
  • the second organic layer is an electron transporting layer.
  • the second organic layer is an electron transporting layer
  • the electron transporting layer includes a compound represented by the above-mentioned general formula (3).
  • the second organic layer is a layer which simultaneously injects electrons and transports electrons.
  • the second organic material layer is a layer simultaneously injecting and transporting electrons
  • the electron transporting layer includes a compound represented by the general formula (3).
  • the monocyclic heteroaryl groups bonded to each other via naphthalene have an appropriate twist structure, and the electronic interaction due to conjugation is reduced so that the independent characteristics of the substituents are maintained Properly maintained conjugation is suitable for use as an electron transporting layer because of its structural features that can prevent the lifetime of the organic light emitting device from deteriorating due to excessive electron injection.
  • the above Formula 3 includes a naphthalene core substituted with triazine, which is excellent in the ability to inject electrons and has excellent thermal stability. Therefore, the organic light emitting device including the naphthalene core can improve driving voltage, luminous efficiency, and lifetime characteristics of the device.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; Ether group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted halogen group; A nit
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • Quot refers to a moiety bonded to another substituent or bond.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 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 ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the ether group may be substituted with a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms in the ether group.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
  • the amine group is -NH 2 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group.
  • the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenyl
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a linear or branched alkyl group.
  • the alkylamine group containing two or more of the alkyl groups may contain a straight chain alkyl group, a branched chain alkyl group, or a straight chain alkyl group and a branched chain alkyl group at the same time.
  • the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
  • the alkyl group in the N-alkylarylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above.
  • Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group.
  • Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyrenyl, phenalenyl, perylenyl, It is not.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group.
  • aryloxy group examples include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group.
  • the present invention is not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes at least one non-carbon atom and at least one hetero atom.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
  • the "aromatic ring” in the substituted or unsubstituted aromatic ring formed by bonding adjacent groups to each other, may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
  • the formula (1) is represented by any one of the following formulas (1-1) to (1-3).
  • Ar1 to Ar4 is the same as defined in the above formula (1).
  • any one of Ar1 to Ar4 is a naphthyl group; A phenanthrenyl group; Or a triphenylrenyl group, and the rest are the same or different from each other, and are each independently a phenyl group; A biphenyl group; Or a terphenyl group.
  • Ar 1 is a naphthyl group; A phenanthrenyl group; Or a triphenylenyl group, Ar2 to Ar4 are the same or different from each other and are each independently a phenyl group; A biphenyl group; Or a terphenyl group.
  • Ar2 represents a naphthyl group; A phenanthrenyl group; Or a triphenenyl group; Ar1, Ar3 and Ar4 are the same or different from each other, and are each independently a phenyl group; A biphenyl group; Or a terphenyl group.
  • Ar3 represents a naphthyl group; A phenanthrenyl group; Or a triphenylenyl group, Ar1, Ar2 and Ar4 are the same or different from each other and are each independently a phenyl group; A biphenyl group; Or a terphenyl group.
  • Ar4 represents a naphthyl group; A phenanthrenyl group; Or a triphenylenyl group, Ar1 to Ar3 are the same or different from each other, and are each independently a phenyl group; A biphenyl group; Or a terphenyl group.
  • Formula 1 is selected from the following compounds.
  • the formula (2) is represented by the following formula (2-1) or (2-2).
  • R1 to R8, X, Ar5 and Ar6 are the same as those defined in the above formula (2).
  • X is O.
  • X is S.
  • Ar5 and Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group.
  • Ar5 and Ar6 are the same or different and each independently an alkyl group, an aryl group, or an aryl group substituted or unsubstituted with a heteroaryl group.
  • Ar5 and Ar6 are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; Or a fluorenyl group substituted with an alkyl group.
  • Ar5 and Ar6 are the same or different and are each independently a phenyl group or a phenyl group substituted or unsubstituted with a biphenyl group; A phenyl group substituted with a dibenzofurane group; A phenyl group substituted with a dibenzothiophene group; A biphenyl group substituted or unsubstituted with a phenyl group; A terphenyl group; Or a fluorenyl group substituted with a methyl group.
  • adjacent groups among R1 to R8 are bonded to each other to form a benzene ring.
  • R 1 and R 2 combine with each other to form a benzene ring.
  • Formula 2 is selected from the following compounds.
  • the formula (3) is represented by any one of the following formulas (3-1) to (3-8).
  • X1 to X6, L1, L2 and Ar7 to Ar10 have the same meanings as defined in formula (3).
  • any one of X1 to X3 is N and the others are CH.
  • X1 is N
  • X2 and X3 are CH.
  • X2 is N
  • X1 and X3 are CH.
  • X3 is N, and X1 and X2 are CH.
  • any two of X1 to X3 are N and the others are CH.
  • X1 and X2 are N and X3 is CH.
  • X2 and X3 are N and X1 is CH.
  • X1 and X3 are N and X2 is CH.
  • X1 to X3 in Formula 3 are N.
  • any one of X4 to X6 is N and the remainder is CH.
  • X4 is N
  • X5 and X6 are CH.
  • X5 is N
  • X4 and X6 are CH.
  • X6 is N, and X4 and X5 are CH.
  • any two of X4 to X6 in Formula 3 is N and the remainder is CH.
  • X4 and X5 are N and X6 is CH.
  • X5 and X6 are N and X4 is CH.
  • X4 and X6 are N and X5 is CH.
  • X4 to X6 are N.
  • L 1 and L 2 are the same or different and are each independently a direct bond; Or an arylene group.
  • L 1 and L 2 are the same or different and are each independently a direct bond; Or a phenylene group.
  • Ar7 to Ar10 are the same or different and each independently an alkyl group or an aryl group substituted or unsubstituted with an aryl group.
  • Ar7 to Ar10 may be the same or different and are each independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group; Or a biphenyl group.
  • Ar7 to Ar10 are the same or different and are each independently a methyl group or a phenyl group substituted or unsubstituted with a phenyl group; Or a biphenyl group.
  • Formula 3 is selected from the following compounds.
  • the light emitting layer includes a compound represented by the following general formula (4).
  • Ar11 and Ar12 are the same or different and are each independently a substituted or unsubstituted aryl group.
  • Ar11 and Ar12 are the same or different and each independently an alkyl group or an aryl group substituted or unsubstituted with an aryl group.
  • Ar11 and Ar12 are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Anthracenyl group substituted with an aryl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A triphenylrenyl group; Or a phenanthrenyl group.
  • Ar11 and Ar12 are the same or different and are each independently a phenyl group, a phenyl group, a phenyl group, or a substituted or unsubstituted naphthyl group; A biphenyl group substituted or unsubstituted with a phenyl group; A terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Anthracenyl group substituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a phenanthrenyl group, or a triphenylenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A triphenylrenyl group; Or a phenanthrenyl group.
  • Formula 4 is selected from the following compounds.
  • the light emitting layer includes a compound represented by the following general formula (5).
  • Ar13 is a substituted or unsubstituted aryl group.
  • X 'in formula (5) is S.
  • Ar13 in the general formula (5) is an aryl group substituted or unsubstituted with an aryl group.
  • Ar13 represents a phenyl group substituted or unsubstituted with an aryl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Or a phenanthrenyl group.
  • Ar 13 represents a phenyl group, or a phenyl group substituted or unsubstituted with a naphthyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Or a phenanthrenyl group.
  • Formula 5 is selected from the following compounds.
  • the light emitting layer includes the compounds represented by Chemical Formulas 4 and 5.
  • the light emitting layer includes a compound represented by the general formula (4) or (5).
  • the light emitting layer includes a compound represented by the general formula (4).
  • the light emitting layer includes the compound represented by the general formula (5).
  • the light emitting layer includes the compound represented by the general formulas (4) and (5) as a host of the light emitting layer.
  • the host is a blue host.
  • the light emitting layer includes the compound represented by the general formula (4) or (5) as a host of the light emitting layer.
  • the light emitting layer includes the compound represented by Formula 4 as a host of the light emitting layer.
  • the light emitting layer includes the compound represented by the general formula (5) as a host of the light emitting layer.
  • the light emitting layer includes the compound represented by the general formula (4) as a blue host of the light emitting layer.
  • the light emitting layer includes the compound represented by Formula 5 as a blue host of the light emitting layer.
  • 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device 10 in which an anode 30, a light emitting layer 40, and a cathode 50 are sequentially stacked on a substrate 20.
  • 1 is an exemplary structure according to one embodiment of the present invention, and may further include another organic layer.
  • the organic light- 2 shows a structure in which an anode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transport layer 90, an electron injection layer 100, And a cathode 50 are successively laminated on a substrate 50.
  • the organic light- 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • the organic layers may be formed of the same material or different materials.
  • the organic luminescent device of the present invention is a device in which the first organic material layer contains at least one of the compounds represented by Chemical Formulas 1 and 2 and the second organic material layer includes the compound represented by Chemical Formula 3 May be prepared by materials and methods known in the art.
  • the organic light emitting device of the present invention can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate.
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material that can be used in the present invention 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); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of 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; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material ,
  • the migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer for transporting holes from the hole injection layer to the light emitting layer.
  • the organic light emitting device of the present invention includes an additional hole transport layer in addition to the hole transport layer including the compound represented by the above formula
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is preferable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the electron blocking layer is a layer capable of preventing the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device.
  • a known material may be used to form an appropriate portion between the light emitting layer and the electron injection layer.
  • the light emitting material of the light emitting layer is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having high quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; 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 heterocyclic compound.
  • Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound examples include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex examples include iridium complex, platinum complex, and the like, but are not limited thereto.
  • At least one selected from the following compounds may be used as the toptic material, but the present invention is not limited thereto.
  • the light emitting layer includes the dopant, and includes 0.1 wt% to 10 wt%, preferably 0.5 wt% to 4 wt% of the dopant.
  • the electron transporting material of the electron transporting layer is a layer which transports electrons from the electron injecting layer to the electron transporting layer and transports electrons.
  • the electron transporting material is a material capable of transferring electrons from the cathode well into the light emitting layer, and is preferably a material having high mobility to electrons. Specific examples include an 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 transporting layer can be used with any desired cathode material as used according to the prior art.
  • an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • the structure according to one embodiment of the present disclosure can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organophotoreceptors, organic transistors and the like.
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum depositing a compound of the following formula [HI-1] and a compound of the following formula [HI-2] in a thickness of 100 ⁇ so as to have a molar ratio of 98: 2 on the prepared ITO transparent electrode.
  • HT-1 (1150 ANGSTROM), which is a material for transporting holes, was vacuum-deposited on the hole injection layer to form a hole transport layer.
  • the compound [HB-1] was vacuum deposited on the hole transporting layer to a thickness of 50 ANGSTROM to form a hole blocking layer.
  • the compound [ET-1] and the compound [LiQ] were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form a layer simultaneously injecting and transporting electrons at a thickness of 310 ⁇ .
  • Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 ⁇ on the electron injecting and transporting layer sequentially to form a cathode.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-1 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-2 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-3 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-4 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that Compound 1-5 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that the above compound 2-1 was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1-1 except that the compound [2-2] was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 2-3 was used in place of Compound [EB-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 2-4 was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 3-2 was used instead of the compound [ET-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 3-3 was used in place of the compound [ET-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 3-4 was used in place of the compound [ET-1] in the above Comparative Example 1-1.
  • ET-1 was used in place of the compound [HT-1] in the above Comparative Example 1-1, the above compound 2-2 was used in place of the compound [EB- An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound [HT-2] was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 3-1 was used in place of the compound [ET- An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 except that the above compound [EB-2] was used in place of the compound [EB-1] in Comparative Example 1-1 and the above compound 3-2 was used in place of the compound [ET- An organic light emitting device was fabricated in the same manner.
  • the compound [ET-1] was used instead of the compound [ET-1] in place of the compound [ET- 2] was used in place of the organic EL device of Comparative Example 1-1.
  • Comparative Examples 1-7 to 1-10 were prepared by using compounds of Formula 2 according to one embodiment of the present invention instead of Compound [EB-1] used as a conventional electron blocking layer
  • 1-14 are organic light emitting devices comprising compounds of the formulas (1), (2) and (3), respectively, using the compound of the formula (3) according to one embodiment of the present invention, instead of the compound [ET- .
  • Examples 1-1 to 1-20 are organic light emitting devices using Formula 1 of the present invention as a hole transporting layer and using Formula 3 of the present specification as an electron transporting layer. In Examples 1-1 to 1-20, The driving voltage is lowered by about 10 to 12% and the lifetime of the light emitting device is longer than that of the organic light emitting devices of Comparative Examples 1-2 to 1-14 including Formula 1, Formula 2 and Formula 3, respectively, Respectively.
  • Examples 1-21 to 1-36 are organic light emitting devices in which Formula 2 of the present specification is used as a charge blocking layer and Formula 3 of the present specification is used as an electron transporting layer.
  • the organic light emitting device has a luminous efficiency as high as 5 to 8% or more and a lifetime of more than 30% as a whole as compared with the organic light emitting device including the organic light emitting devices of the above formulas 1, 2 and 3, respectively.
  • Example 1-37 exhibited the best characteristics as the organic light emitting device including the compound of the present invention as the hole transporting layer, the electron blocking layer of the present invention as the electron transporting layer, and the electron transporting layer as the electron transporting layer simultaneously.
  • Comparative Example 1-15 the compound [HT-2] in which two polycyclic aryl groups are bonded to the core structure of the present invention, which is widely used conventionally, is used as a hole transport layer, and Compound 3-1 of the present specification is compound When used instead of [ET-1], the voltage was increased by 10% or more.
  • the glass transition temperature (Tg) is 100 ° C or less, thermal stability is lowered and the lifetime of the organic light emitting device is greatly reduced and the efficiency is lowered.
  • Comparative Example 1-16 is an organic light-emitting device using a compound [EB-2] in which a heterocyclic group having three rings, which is a substituent of Formula 2, is connected in the para direction, not in the meta direction, The results were significantly reduced.
  • the organic light emitting device including at least one of the first organic material layer including at least one of the first and second organic materials and the second organic material including the second organic material has improved lifetime, I could confirm.

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Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant : une électrode positive ; une électrode négative disposée à l'opposé de l'électrode positive ; une couche électroluminescente disposée entre l'électrode positive et l'électrode négative ; au moins une première couche de matériau organique disposée entre l'électrode positive et la couche électroluminescente ; et une seconde couche de matériau organique disposée entre l'électrode négative et la couche électroluminescente, la première couche de matériau organique comprenant un composé de formule chimique 1 et/ou de formule chimique 2, et la seconde couche de matériau organique comprenant un composé de formule chimique 3.
PCT/KR2018/010035 2017-11-28 2018-08-30 Dispositif électroluminescent organique Ceased WO2019107710A1 (fr)

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