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WO2017078494A1 - Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé Download PDF

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WO2017078494A1
WO2017078494A1 PCT/KR2016/012728 KR2016012728W WO2017078494A1 WO 2017078494 A1 WO2017078494 A1 WO 2017078494A1 KR 2016012728 W KR2016012728 W KR 2016012728W WO 2017078494 A1 WO2017078494 A1 WO 2017078494A1
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박건유
오한국
마재열
이윤지
김동준
최대혁
이주동
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LT Materials Co Ltd
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Heesung Material Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • 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
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the 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
    • 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

Definitions

  • the present application relates to a heterocyclic compound and an organic light emitting device using the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting element has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound which may itself constitute a light emitting layer may be used, or a compound that may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used.
  • An exemplary embodiment of the present application provides a heterocyclic compound represented by any one of the following Chemical Formulas 1-3:
  • Ar1 to Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 Through C 60 Heteroaryl group,
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • n, o, p, q, r, s, t and u are each independently an integer of 0-4.
  • an organic light emitting device including an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, and one or more layers of the organic material layers are represented by any one of Chemical Formulas 1 to 3. It provides an organic light emitting device comprising a heterocyclic compound.
  • organic material layer including the heterocyclic compound further includes a compound represented by Formula 4 or 5 below:
  • L1 and L2 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted C 6 to C 60 arylene group,
  • Ar7 is a substituted or unsubstituted, C 2 Through C 60 Heteroaryl group containing at least one N,
  • Ar8 is represented by the following formula (6) or (7),
  • Y1 to Y4 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring; Or substituted or unsubstituted C 2 to C 60 aromatic heterocycle,
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • At least one of X1 to X3 is N, and the rest are each independently N or CR35,
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted C 2 to C 60 heteroaryl group.
  • the heterocyclic compound according to the exemplary embodiment of the present application may be used as an organic material layer material of the organic light emitting device.
  • the heterocyclic compound may be used as a material such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer in the organic light emitting device.
  • the heterocyclic compound represented by any one of Formulas 1 to 3 may be used as a material of an electron transporting layer, a hole transporting layer, or a light emitting layer of an organic light emitting device.
  • the driving voltage of the device may be lowered, the light efficiency may be improved, and the life characteristics of the device may be improved by thermal stability of the compound.
  • the organic light emitting device according to the exemplary embodiment of the present application, a heterocyclic compound represented by any one of Formulas 1 to 3 as a host material of the light emitting layer; And by including the compound represented by the formula (4) or 5 at the same time, it can exhibit a significantly improved characteristics of driving, efficiency, lifespan than the organic light emitting device to which a single compound as a host material.
  • 1 to 3 are diagrams schematically showing a laminated structure of an organic light emitting device according to an exemplary embodiment of the present application.
  • heterocyclic compound according to an exemplary embodiment of the present application is characterized in that represented by any one of the formulas (1) to (3). More specifically, the heterocyclic compound represented by any one of Formulas 1 to 3 may be used as an organic material layer material of the organic light emitting device by the structural features of the core structure and the substituent as described above.
  • R1 to R9 of Formulas 1 to 3 may each independently be hydrogen or deuterium.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent to which two phenyl groups are linked. Said additional substituents may be further substituted further.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cyclo An alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted C 2 to C 60 heteroaryl group.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; deuterium, halogen, -CN, C 1 to C 20 alkyl group, C 6 to C 60 aryl group, and C 2 to C 60 substituted heteroaryl or unsubstituted alkyl group of C 1 to C 60; an aryl group of deuterium, halogen, -CN, C 1 to C 20 alkyl group, C 6 to C 60 a, and C 2 A C 3 to C 60 cycloalkyl group unsubstituted or substituted with a C 6 to C 60 heteroaryl group; deuterium, halogen, —CN, an alkyl group of C 1 to C 20 , an aryl group of C 6 to C 60 , and C 2 to C 60 substituted or unsubstituted group heteroaryl C 6 to C 60 aryl group; or an alkyl group of deuterium, halogen, -CN, C 1 to
  • 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 substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. Carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl
  • the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • Specific examples thereof include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, and 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • Carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic means a group in which an aryl group is directly connected or condensed with another ring group.
  • the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like.
  • the aryl group includes a spiro group. Carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
  • aryl group examples include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre Neyl group, tetrasenyl group, pentaxenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof Etc., but is not limited thereto.
  • the spiro group is a group including a spiro structure, and may have 15 to 60 carbon atoms.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group.
  • the following spiro groups may include any of the groups of the following structural formula.
  • the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
  • Carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.
  • heteroaryl group examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl and thiazolyl Group, isothiazolyl group, triazolyl group, furazanyl group, oxdiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, deoxyyl group, triazinyl group, tetragenyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenan
  • the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkyl heteroaryl amine group; And it may be selected from the group consisting of arylheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore And a phenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • an arylene group means one having two bonding positions, that is, a divalent group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • a heteroarylene group means a thing which has two bonding positions, ie, a bivalent group, in a heteroaryl group.
  • the description of the aforementioned heteroaryl group can be applied except that they are each divalent.
  • the compound represented by any one of Formulas 1 to 3 may be represented by any one of the following compounds, but is not limited thereto.
  • compounds having the inherent properties of the substituents introduced may be synthesized by introducing various substituents into the structure of any one of Formulas 1 to 3.
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.
  • the heterocyclic compound has a high glass transition temperature (Tg) is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.
  • the heterocyclic compound according to one embodiment of the present application may be prepared by a multistage chemical reaction. Some intermediate compounds may be prepared first, and compounds of any one of formulas 1 to 3 may be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application may be prepared based on the preparation examples described below.
  • An exemplary embodiment of the present application provides an organic light emitting device including the compound represented by any one of Formulas 1 to 3.
  • an organic light emitting device comprising an anode, a cathode and one or more organic material layers provided between the anode and the cathode, the organic material layer comprises a light emitting layer, the light emitting layer is any one of the formulas (1) to Heterocyclic compounds represented by one; And it provides an organic light-emitting device comprising a compound represented by Formula 4 or 5.
  • Chemical Formula 6 may be represented by any one of the following structural formulas.
  • X 1 to X 6 in the structural formulas are the same as or different from each other, and each independently NR, S, O, or CR′R ′′,
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • n, o, p, q, r, and s are each independently the integer of 0-6.
  • Chemical Formula 7 may be represented by any one of the following structural formulas.
  • X7 and X8 in the above structural formula is the same as or different from each other, and each independently NR, S, O or CR'R ",
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • t is an integer of 0-7.
  • R10 to R15 of Chemical Formula 4 may be each independently hydrogen or deuterium.
  • the compound represented by Formula 4 may be represented by any one of the following compounds, but is not limited thereto.
  • any one of X1 to X3 of Formula 5 may be N, any two of X1 to X3 may be N, X1 to X3 may be all N.
  • R17 and R18 of Formula 5 are each independently a substituted or unsubstituted C 6 Through C 60 An aryl group; Or a substituted or unsubstituted C 2 Through C 60 It may be a heteroaryl group.
  • R19 to R21 of Chemical Formula 5 may be each independently hydrogen or deuterium.
  • any one of R22 to R26 of Chemical Formula 5 is -CN, and the others may each independently be hydrogen or deuterium.
  • the compound represented by Formula 5 may be represented by any one of the following compounds, but is not limited thereto.
  • An organic light emitting device is a heterocyclic compound represented by any one of the above-described formulas (1) to (3); And a compound represented by Formula 4 or 5 as a host material of the light emitting layer.
  • the dopant material of the light emitting layer may use a material known in the art.
  • Heterocyclic compound represented by any one of Formulas 1 to 3 in the host material 1 to 10 to 10 of the compound represented by the formula (4) or 5 may be 1: 8 to 8: 1, 1: 5 to 5: 1, 1: 2: may be 2: 1, 1: 1: may be, but is not limited thereto.
  • the host material may be a form in which two or more compounds are simply mixed, and a powder material may be mixed before the organic material layer of the organic light emitting device is formed, or a compound in a liquid state may be mixed at an appropriate temperature or more.
  • the host material is in a solid state below the melting point of each material, and can be maintained in the liquid phase by adjusting the temperature.
  • An organic light emitting device is a heterocyclic compound represented by any one of the above-mentioned Formulas 1 to 3; And except for forming one or more organic material layers using the compound represented by Formula 4 or 5, it may be prepared by a conventional method and material for manufacturing an organic light emitting device.
  • the heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the compound represented by Chemical Formulas 1 to 3 may be used as an electron transport layer, a hole blocking layer, or a light emitting layer in an organic light emitting device.
  • the compound represented by Chemical Formulas 1 to 3 may be used as a material of an electron transporting layer, a hole transporting layer, or a light emitting layer of an organic light emitting device.
  • the compounds represented by Formulas 1 to 3 may be used as a material of the light emitting layer in the organic light emitting device.
  • the compound represented by Chemical Formulas 1 to 3 may be used as a material of the phosphorescent host of the light emitting layer in the organic light emitting device.
  • organic material layer including the compound represented by Chemical Formulas 1 to 3 may further include other materials as necessary.
  • the compound represented by Chemical Formulas 1 to 3 may be used as a material of the charge generating layer in the organic light emitting device.
  • the compound represented by Chemical Formulas 1 to 3 may be used as an electron transporting layer, a hole blocking layer, or a light emitting layer in an organic light emitting device.
  • the compound represented by Chemical Formulas 1 to 3 may be used as a material of an electron transporting layer, a hole transporting layer, or a light emitting layer of an organic light emitting device.
  • the compounds represented by Formulas 1 to 3 may be used as a material of the light emitting layer in the organic light emitting device.
  • the compound represented by Formula 1 may be used as a material of the phosphorescent host of the light emitting layer in the organic light emitting device.
  • FIG. 1 to 3 illustrate a lamination order of an electrode and an organic material layer of an organic light emitting diode according to an exemplary embodiment of the present application.
  • these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can be applied to the present application.
  • an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
  • the present invention is not limited thereto, and as illustrated in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • a light emitting layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present application is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); 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] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer may be used.
  • 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.
  • hole injection material a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst amine derivatives such as tris (4-carbazoyl-9-ylphenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m-tolyl) amino] triphenylamine (m- MTDATA), 1,3,5-tris [4- (3-methylphenylphenylamino) phenyl] benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid, or poly (line) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Camphor sulfonic acid or polyaniline / Poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.
  • TCTA tri
  • pyrazoline derivatives arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.
  • Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthhraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.
  • LiF is representatively used in the art, but the present application is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • the heterocyclic compound according to the exemplary embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
  • the glass substrate coated with the thin film of ITO to a thickness of 1500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then treated with UVO for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition apparatus for organic deposition.
  • PT plasma cleaner
  • 2-TNATA (4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) was formed as a hole injection layer on ITO prepared as above, and NPB (N, N'-Di as a hole transport layer).
  • (1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine) was formed on the hole transport layer by thermal vacuum deposition to form a light emitting layer of 400 Pa.
  • the compound shown in the following table, which is a host, was used as a phosphorescent dopant with 7% doping of Ir (ppy) 3 (tris (2-phenylpyridine) iridium).
  • the organic electroluminescent device was manufactured by forming a cathode by vapor deposition.
  • the electroluminescent (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement results. T 90 was measured at cd / m 2 .
  • the characteristics of the organic EL device of the present invention is shown in Tables 8 and 9.
  • Ref 1,2,3 was influenced by nitrogen, which is a group giving electrons when substituted with carbazole-N at position 2 of dibenzofuran It is considered that the lifespan characteristics are poor because oxygen of the dibenzofuran in the para position is activated, the resonance is weakened and the stability of the molecule is reduced. In the case of Ref 4, if the heteroaryl group that pulls an electron at the dibenzofuran position 4 is substituted, the lifetime of the dibenzofuran group giving the electron destabilizes the electrons injected along the LUMO. .
  • Ref 5 has a molecular structure similar to that of the present invention, but when carbazole 3 is substituted at position 2 and 4 of dibenzofuran at the same time, the lifespan characteristics are deteriorated for the same reason as Ref 1,2,3. It seems to be.
  • the organic light emitting device As a result, in particular, the organic light emitting device according to an exemplary embodiment of the present application, the compound represented by any one of formulas 1 to 3 as a host material of the light emitting layer; And by including the compound represented by the formula (4) or 5 at the same time, it can exhibit a significantly improved characteristics of driving, efficiency, lifespan than the organic light emitting device to which a single compound as a host material.
  • the compound represented by the formula (4) or 5 at the same time, it can exhibit a significantly improved characteristics of driving, efficiency, lifespan than the organic light emitting device to which a single compound as a host material.
  • Comparative Examples 7 to 16 even though the light emitting layer is composed of two hosts, the hole and the electrons are not balanced, and thus the life characteristics are much lower than those of the Examples.
  • the organic light emitting device of the present invention includes a light emitting layer using a host and a phosphorescent dopant, and the host includes a host compound composed of a conventional single compound by being composed of a host compound (pn type) in which two or more compounds are mixed. There is an effect that has a lifespan characteristics superior to the organic light emitting device.
  • the pn type host of the present invention has the advantage of increasing the emission characteristics by adjusting the ratio of the host, which can be achieved by a suitable combination of P host with good hole mobility and n host with good electron mobility to be.

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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne : un composé hétérocyclique capable d'améliorer considérablement la durée de vie, l'efficacité, la stabilité électrochimique ainsi que la stabilité thermique d'un dispositif électroluminescent organique; et un dispositif électroluminescent organique renfermant ledit composé dans une couche de composé organique.
PCT/KR2016/012728 2015-11-06 2016-11-07 Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé Ceased WO2017078494A1 (fr)

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CN109385266A (zh) * 2017-08-04 2019-02-26 北京绿人科技有限责任公司 用于形成有机电致发光材料的组合物及其应用和有机电致发光器件及其制备方法
WO2019038448A1 (fr) * 2017-08-25 2019-02-28 Cynora Gmbh Molécules organiques contenant de la triazine destinées en particulier à être utilisées dans des dispositifs optoélectroniques
WO2019081433A1 (fr) * 2017-10-25 2019-05-02 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques
CN109928962A (zh) * 2017-12-18 2019-06-25 江苏三月光电科技有限公司 一种以咔唑为核心的化合物、制备方法及其在有机电致发光器件上的应用
JP2019108315A (ja) * 2017-12-20 2019-07-04 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用化合物、液状組成物、インク組成物、薄膜、及び有機エレクトロルミネッセンス素子
WO2020022860A1 (fr) * 2018-07-27 2020-01-30 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
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CN112041315A (zh) * 2018-07-27 2020-12-04 株式会社Lg化学 新的化合物和包含其的有机发光器件
WO2022140878A1 (fr) * 2020-12-28 2022-07-07 京东方科技集团股份有限公司 Dispositif électroluminescent organique et appareil d'affichage
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US12250879B2 (en) 2018-09-21 2025-03-11 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US12389793B2 (en) 2018-07-06 2025-08-12 Lg Chem, Ltd. Compound and organic light emitting device comprising the same

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CN110799507B (zh) * 2017-10-20 2023-04-14 株式会社Lg化学 化合物及包含其的有机发光器件
WO2019088751A1 (fr) * 2017-11-03 2019-05-09 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
WO2019143112A1 (fr) * 2018-01-16 2019-07-25 주식회사 두산 Dispositif électroluminescent organique
WO2019143110A1 (fr) * 2018-01-16 2019-07-25 주식회사 두산 Composé organique et élément électroluminescent organique l'utilisant
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KR102312963B1 (ko) * 2018-12-26 2021-10-14 엘티소재주식회사 화합물, 유기 광전자 소자 및 표시 장치
KR102359899B1 (ko) * 2019-02-01 2022-02-09 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

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CN108976212A (zh) * 2017-06-02 2018-12-11 北京鼎材科技有限公司 芴衍生物及其在有机发光材料中的应用
CN109385266A (zh) * 2017-08-04 2019-02-26 北京绿人科技有限责任公司 用于形成有机电致发光材料的组合物及其应用和有机电致发光器件及其制备方法
CN109385266B (zh) * 2017-08-04 2021-10-26 北京绿人科技有限责任公司 用于形成有机电致发光材料的组合物及其应用和有机电致发光器件及其制备方法
KR20200037361A (ko) * 2017-08-25 2020-04-08 시노라 게엠베하 유기 분자, 특히 광전자 장치에 사용하기 위한 유기 분자
CN111032648B (zh) * 2017-08-25 2023-06-27 三星显示有限公司 有机含三嗪分子，特别是用于光电子装置的有机含三嗪分子
WO2019038448A1 (fr) * 2017-08-25 2019-02-28 Cynora Gmbh Molécules organiques contenant de la triazine destinées en particulier à être utilisées dans des dispositifs optoélectroniques
KR102423189B1 (ko) 2017-08-25 2022-07-22 삼성디스플레이 주식회사 유기 분자, 특히 광전자 장치에 사용하기 위한 유기 분자
JP2020531491A (ja) * 2017-08-25 2020-11-05 サイノラ ゲゼルシャフト ミット ベシュレンクテル ハフツング トリアジンを含む有機分子、特に光電子デバイスに用いる有機分子
JP7077398B2 (ja) 2017-08-25 2022-05-30 サイノラ ゲゼルシャフト ミット ベシュレンクテル ハフツング トリアジンを含む有機分子、特に光電子デバイスに用いる有機分子
CN111032648A (zh) * 2017-08-25 2020-04-17 辛诺拉有限公司 有机含三嗪分子，特别是用于光电子装置的有机含三嗪分子
US11600783B2 (en) 2017-08-25 2023-03-07 Samsung Display Co., Ltd. Organic molecules for use in optoelectronic devices
CN111148738A (zh) * 2017-09-29 2020-05-12 三星Sdi株式会社 有机化合物、组合物、有机光电装置和显示装置
CN111148738B (zh) * 2017-09-29 2024-10-15 三星Sdi株式会社 有机化合物、组合物、有机光电装置和显示装置
WO2019081433A1 (fr) * 2017-10-25 2019-05-02 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques
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US11700767B2 (en) 2017-12-20 2023-07-11 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the condensed cyclic compound, and organic light-emitting device including the composition
JP7145608B2 (ja) 2017-12-20 2022-10-03 三星電子株式会社 有機エレクトロルミネッセンス素子用化合物、液状組成物、インク組成物、薄膜、及び有機エレクトロルミネッセンス素子
JP2019108315A (ja) * 2017-12-20 2019-07-04 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用化合物、液状組成物、インク組成物、薄膜、及び有機エレクトロルミネッセンス素子
CN111164182A (zh) * 2018-01-29 2020-05-15 株式会社Lg化学 有机发光器件
CN111164182B (zh) * 2018-01-29 2024-02-02 株式会社Lg化学 有机发光器件
US12389793B2 (en) 2018-07-06 2025-08-12 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
CN112041315B (zh) * 2018-07-27 2024-02-23 株式会社Lg化学 化合物和包含其的有机发光器件
WO2020022860A1 (fr) * 2018-07-27 2020-01-30 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
CN112041315A (zh) * 2018-07-27 2020-12-04 株式会社Lg化学 新的化合物和包含其的有机发光器件
US12453283B2 (en) 2018-07-27 2025-10-21 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12250879B2 (en) 2018-09-21 2025-03-11 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
WO2020111663A1 (fr) * 2018-11-26 2020-06-04 두산솔루스 주식회사 Composé organique et dispositif électroluminescent organique l'utilisant
CN111269219B (zh) * 2020-03-25 2023-05-30 烟台显华化工科技有限公司 一种有机发光材料及有机电致发光器件
CN111269219A (zh) * 2020-03-25 2020-06-12 烟台显华化工科技有限公司 一种有机发光材料及有机电致发光器件
WO2022140878A1 (fr) * 2020-12-28 2022-07-07 京东方科技集团股份有限公司 Dispositif électroluminescent organique et appareil d'affichage

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