WO2019194615A1 - Composé polycyclique et dispositif électronique organique le comprenant - Google Patents

Composé polycyclique et dispositif électronique organique le comprenant Download PDF

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WO2019194615A1
WO2019194615A1 PCT/KR2019/004029 KR2019004029W WO2019194615A1 WO 2019194615 A1 WO2019194615 A1 WO 2019194615A1 KR 2019004029 W KR2019004029 W KR 2019004029W WO 2019194615 A1 WO2019194615 A1 WO 2019194615A1
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group
substituted
unsubstituted
layer
carbon atoms
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Korean (ko)
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금수정
윤정민
구기동
이기곤
김명곤
김경희
김공겸
이형진
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주식회사 엘지화학
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Priority to CN201980007580.8A priority Critical patent/CN111556865B/zh
Publication of WO2019194615A1 publication Critical patent/WO2019194615A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
    • H10K85/631—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
    • H10K85/657—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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present specification relates to a compound and an organic electronic device including the same.
  • the organic electronic device is an organic light emitting device.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the material used in the organic light emitting device may be classified into a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material and the like according to the use.
  • a hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
  • an organic material having an n-type property that is, an organic material which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used.
  • the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloal
  • Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n1 is an integer of 0 to 3, when n1 is 2 or more, two or more R1 are the same as or different from each other,
  • n2 is an integer of 0 to 5, and when n2 is 2 or more, two or more R2 are the same or different from each other.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.
  • the compound described herein can be used as the material of the organic material layer of the organic electronic device.
  • an organic electronic device including a compound according to at least one embodiment it is possible to obtain an organic electronic device having high efficiency and long life.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the present specification provides a compound represented by the following Formula 1.
  • the compound represented by Chemical Formula 1 is used in the organic material layer of the organic electronic device, since the structure of the luminophore is simple and rigid, the full width at half maximum is relatively improved, thereby achieving high efficiency.
  • dibenzofuran is more chemically stable, when manufacturing an organic electronic device comprising the compound represented by the formula (1) of the present invention, the life characteristics of the organic electronic device are always.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloal
  • Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n1 is an integer of 0 to 3, when n1 is 2 or more, two or more R1 are the same as or different from each other,
  • n2 is an integer of 0 to 5, and when n2 is 2 or more, two or more R2 are the same or different from each other.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted or unsubstituted
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the silyl group may be represented by a chemical formula of -SiY 1 Y 2 Y 3 , wherein Y 1 , Y 2 and Y 3 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.
  • the boron group may be represented by a chemical formula of -BY 4 Y 5 , wherein Y 4 and Y 5 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another 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.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group and the like, but are not limited thereto.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .
  • Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
  • aryl group in the aryloxy group may be described with reference to the aryl group described below.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, and the like, but are not limited thereto.
  • the alkylamine group is not particularly limited, but may be 1 to 40, according to one embodiment may be 1 to 20.
  • Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, and the like, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, diphenylamine group, phenylnaphthylamine group, biphenylphenylamine group, dibiphenylamine group, and fluorine. And a phenylphenyl group, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group, may be a polycyclic heteroaryl group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.
  • arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.
  • an alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, benzofluorenyl group, triphenylenyl group, etc. It is not limited to this.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • heterocyclic group examples include, for example, pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, carbazole group, Benzocarbazole groups, naphthobenzofuranyl groups, benzonaphthothiophenyl groups and the like, but are not limited thereto.
  • the hydrocarbon ring group may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the description of the aforementioned aryl group may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring The description of the cycloalkyl group described above may be applied except that is not a monovalent group.
  • an example of the condensed ring of the aromatic and aliphatic is hydronaphthalene, specifically 1,2,3,4-tetrahydronaphthalene ( ).
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the compound of the present invention may have a maximum emission peak of 430 nm to 470 nm, and when the compound includes the compound in the light emitting layer of the organic electronic device, it emits blue light.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Substituted or unsubstituted methyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Methyl group; Cyclohexyl group; Or a phenyl group.
  • n1 is an integer of 0 to 2.
  • n1 is 0 or 1.
  • n2 is an integer of 0 to 2.
  • n2 is 0 or 1.
  • Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted 3 to 60 hydrocarbon ring groups; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted hydronaphthalene; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted carbazole group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substitution Or a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an unsubstituted heterocyclic group or a substituent to which two or more substituents are linked;
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituent to which two or more substituents are linked; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A biphenyl group
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, or a phenyl group a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a tert-butylphenyl group and a carbazole group or a substituent to which two or more substituents are linked; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups A biphenyl group unsubstit
  • Formula 1 may be represented by any one of the following compounds.
  • the compound of Formula 1 may be prepared in the core structure through the same process as in the following scheme. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • the substance to make can be synthesize
  • the organic electronic device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the organic electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic material layer is formed using the above-described compound.
  • the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and a glass transistor.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • 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 is a hole injection layer, a hole transport layer, a hole injection layer and a hole transport layer at the same time, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and an electron transport layer simultaneously It may have a structure including the.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include the above-described compound.
  • the organic material layer may include a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer may include the above-described compound.
  • the hole injection layer or the hole transport layer may be made of only the above-described compounds, but the compound may be present in a mixed or doped state with other hole injection layers or hole transport layer materials known in the art.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound described above.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above as a dopant of the light emitting layer and further include a host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the above-described compound as a dopant of the light emitting layer, and may further include the following Chemical Formula 1-A as a host.
  • A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • q1 is an integer of 0-7, and when q1 is two or more, two or more R11 is same or different from each other.
  • A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • A3 is hydrogen
  • A1 is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.
  • A1 is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms;
  • A1 is hydrogen; A phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.
  • A2 is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • A2 is hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • A2 is hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cyclo
  • A2 is hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • R11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R11 is hydrogen
  • q1 is an integer of 0 to 2.
  • q1 is 0 or 1.
  • Chemical Formula 1-A may be represented by any one of the following compounds.
  • the content of the dopant may be 1 part by weight to 10 parts by weight based on 100 parts by weight of the host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and includes at least two of the compounds represented by the following Chemical Formulas 1-B and 1-C as hosts. It may further include.
  • A4 to A8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,
  • A9 is a substituted or unsubstituted heterocyclic group
  • L4 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R12 and R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • A4 to A8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • A4 to A8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • A6 and A8 are hydrogen.
  • A5 and A7 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • A5 and A7 are the same as or different from each other, and each independently hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl
  • A5 and A7 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.
  • A4 is hydrogen; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • A4 is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • A4 is hydrogen; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with a methyl group.
  • A9 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • A9 is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • A9 is a substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.
  • A9 is a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or an indolocarbazole group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • A9 is a dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.
  • L4 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L4 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • the L4 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • the L4 to L9 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L4 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • the L4 to L9 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • R12 and R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R12 and R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R12 and R13 are hydrogen.
  • q2 is an integer of 0 to 7, and when q2 is 2 or more, two or more R12 are the same or different from each other.
  • q2 is an integer of 0 to 2.
  • q2 is 0 or 1.
  • q3 is an integer of 0 to 7, and when q3 is 2 or more, two or more R13 are the same as or different from each other.
  • q3 is an integer of 0 to 2.
  • q3 is 0 or 1.
  • Chemical Formula 1-B may be represented by any one of the following compounds.
  • Chemical Formula 1-C may be represented by any one of the following compounds.
  • the compound of the present invention is included as a dopant of the light emitting layer, and includes two or more of the compounds represented by Formulas 1-B and 1-C as a host, the content of the dopant is 1 part by weight based on 100 parts by weight of the host. It may be 10 parts by weight.
  • the compound may be included as a dopant of the emission layer, and the compound represented by Formula 1-B and the compound represented by Formula 1-C may be included as a host of the emission layer.
  • the mixed weight ratio of (1-B: 1-C) may be 95: 5 to 5:95.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound as a dopant of the light emitting layer, includes a fluorescent host or a phosphorescent host, and includes another organic compound, metal or metal compound as a dopant. It may include.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer and further include a dopant.
  • the organic material layer may include an electron suppression layer, and the electron suppression layer may include the aforementioned compound.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in Figs. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which 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 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7 or the electron transport layer (8).
  • the organic light emitting device is a metal oxide or a metal oxide or alloy thereof having a conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation To form an anode, and a hole injection layer, a hole transport layer, a hole injection and hole transport at the same time, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer and a layer for simultaneously injecting and transporting electrons
  • PVD physical vapor deposition
  • a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer and a layer for simultaneously injecting and transporting electrons After forming an organic material layer comprising a, 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 organic material layer may be a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, and the like.
  • the present invention is not limited thereto and may have a single layer structure.
  • the organic material layer using a variety of polymer materials less or more by a solvent process (e.g. spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method) rather than deposition It can be prepared in a number of layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable as an anode material so that hole injection can be smoothly performed into an organic material layer.
  • the positive electrode 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); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, the highest occupied hole injection material
  • the molecular orbital is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole injection layer may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristic from being lowered.
  • the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a hole transporting material a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the hole transport layer may be formed in one or more layers in the organic light emitting device. have.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron suppression layer may be provided between the hole transport layer and the light emitting layer.
  • the electron suppression layer may be a compound described above or a material known in the art.
  • the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • light emitting dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium) and PQIr (tris (1-phenylquinoline) iridium Phosphor, such as octaethylporphyrin platinum (PtOEP), or a fluorescent substance such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but is not limited thereto.
  • a phosphor such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a phosphor such as Alq3 (tris (8-hydroxyquinolino) aluminum
  • the present invention is not limited thereto.
  • a light emitting dopant may be a phosphor such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, ditylbenzene (DSB) or distriarylene (DSA).
  • a fluorescent material such as PFO-based polymer, PPV-based polymer may be used, but is not limited thereto.
  • a hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transporting layer is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. If the thickness of the electron transporting layer is 50 nm or less, the thickness of the electron transporting layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage to this.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • As the electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and The compound which is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • the compound HAT was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound HT-A 1000 Pa was vacuum-deposited on the hole transport layer, and the compound HT-B 100 Pa was subsequently deposited.
  • the light emitting layer was vacuum deposited to a thickness of 200 ⁇ at 2 wt% with BH-1 and dopant as a host.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • LiF was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-3 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-6 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-8 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-11 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-13 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for further including Compound BH-2 (weight ratio of BH-1 and BH-2: 1: 1).
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound D-1 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound D-2 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound D-3 instead of the compound BD-2.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound D-4 instead of the compound BD-2.
  • the organic light emitting diodes of Examples 1 to 7 and Comparative Examples 1 to 4 measured driving voltage, luminous efficiency and color coordinates at a current density of 10 mA / cm 2 , and 95% of the initial luminance at a current density of 20 mA / cm 2 .
  • the time to become (LT95) was measured. The results are shown in Table 1 below.

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Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électronique organique le comprenant.
PCT/KR2019/004029 2018-04-05 2019-04-05 Composé polycyclique et dispositif électronique organique le comprenant WO2019194615A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113248462A (zh) * 2021-05-12 2021-08-13 长春海谱润斯科技股份有限公司 一种有机电致发光器件
KR20230135591A (ko) 2021-01-26 2023-09-25 이데미쓰 고산 가부시키가이샤 조성물, 분체, 유기 일렉트로루미네센스 소자, 유기일렉트로루미네센스 소자의 제조 방법 및 전자 기기

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104672126A (zh) * 2014-12-31 2015-06-03 北京鼎材科技有限公司 一种苯并萘并五元杂环衍生物及其应用
KR20160141361A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR20160141360A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR101789998B1 (ko) * 2016-05-26 2017-10-25 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180018327A (ko) * 2016-08-09 2018-02-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기전계 발광 소자

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6095391B2 (ja) 2013-02-06 2017-03-15 キヤノン株式会社 有機発光素子
CN107698601B (zh) * 2016-08-09 2022-01-04 株式会社Lg化学 杂环化合物及包含其的有机电致发光元件

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104672126A (zh) * 2014-12-31 2015-06-03 北京鼎材科技有限公司 一种苯并萘并五元杂环衍生物及其应用
KR20160141361A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR20160141360A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR101789998B1 (ko) * 2016-05-26 2017-10-25 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180018327A (ko) * 2016-08-09 2018-02-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기전계 발광 소자

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230135591A (ko) 2021-01-26 2023-09-25 이데미쓰 고산 가부시키가이샤 조성물, 분체, 유기 일렉트로루미네센스 소자, 유기일렉트로루미네센스 소자의 제조 방법 및 전자 기기
CN113248462A (zh) * 2021-05-12 2021-08-13 长春海谱润斯科技股份有限公司 一种有机电致发光器件
CN113248462B (zh) * 2021-05-12 2022-03-25 长春海谱润斯科技股份有限公司 一种有机电致发光器件

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