WO2020171531A1 - Compound and organic light emitting device comprising same - Google Patents

Compound and organic light emitting device comprising same Download PDF

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WO2020171531A1
WO2020171531A1 PCT/KR2020/002295 KR2020002295W WO2020171531A1 WO 2020171531 A1 WO2020171531 A1 WO 2020171531A1 KR 2020002295 W KR2020002295 W KR 2020002295W WO 2020171531 A1 WO2020171531 A1 WO 2020171531A1
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formula
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PCT/KR2020/002295
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French (fr)
Korean (ko)
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서상덕
정민우
이동훈
장분재
이정하
한수진
박슬찬
황성현
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주식회사 엘지화학
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Priority to CN202080005502.7A priority Critical patent/CN112805277B/en
Publication of WO2020171531A1 publication Critical patent/WO2020171531A1/en

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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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon 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 in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 to X 3 are each N or CR 21 , at least one is N,
  • L 1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • L 2 is a direct bond; Or a substituted or unsubstituted arylene group,
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
  • At least one of R 1 and R 2 includes an aryl group condensed by two or more rings,
  • R and R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r is an integer from 1 to 4,
  • R is the same or different
  • Ar is a substituted or unsubstituted aryl group condensed by two or more rings.
  • first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 do.
  • the compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light emitting device.
  • 1 to 3 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
  • a nitrogen-containing heterocycle serving as an electron acceptor in the same benzene ring of dibenzofuran is located at position 1 of dibenzofuran, and a unit serving as an electron donor is a nitrogen-containing heterocycle and meta or It is substituted at the para position. Since the electron donor unit and the electron acceptor unit exist in the same molecule at the same time, it is advantageous for both holes and electron transport, and because they are located in the meta or para position of each other, the steric hindrance effect is less than the ortho position, so the stability of the material is high. When used as a material, the effect of high efficiency and long life can be obtained.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent.
  • the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heterocyclic group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms.
  • 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-methylbutyl group; 1-ethylbutyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 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-octy
  • the cycloalkyl group is not particularly limited, but it is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms.
  • the silyl group may be represented by the formula of -SiR 101 R 102 R 103 , wherein R 101 , R 102 and R 103 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyldimethylsilyl group; Propyldimethylsilyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group and the like, but are not limited thereto.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms 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; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-phenant
  • the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms.
  • the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms.
  • the monocyclic aryl group is a phenyl group; Biphenyl group; It may be a terphenyl group or the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited.
  • the polycyclic aryl group includes a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenalenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group or the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • 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 or a polycyclic aryl group.
  • the arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 1 to 30.
  • heterocyclic groups include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridyl group, xanthenyl group, phenan
  • the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another exemplary embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.
  • heteroaryl group is aromatic, and the above description of the heterocyclic group may be applied.
  • the description of the aryl group may be applied except that the aromatic hydrocarbon ring is a monovalent group.
  • the arylene group and the heteroarylene group are divalent groups, and descriptions of the aryl groups and heteroaryl groups may be applied, respectively, except that they are monovalent groups.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • I can.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.
  • X 1 to X 3 are each independently N or CR 21 , and at least one is N.
  • X 1 and X 3 are N.
  • X 2 is N.
  • X 2 is CR 21 .
  • X 1 to X 3 are N.
  • R and R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R and R 21 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.
  • R and R 21 are each independently hydrogen; Or deuterium.
  • R and R 21 are hydrogen.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and at least one of R 1 and R 2 is a bicyclic or more condensed aryl group Include.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, and at least one of R 1 and R 2 includes a bicyclic or more condensed aryl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and at least one of R 1 and R 2 includes a naphthyl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, and at least one of R 1 and R 2 includes a naphthyl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or a naphthyl group unsubstituted or substituted with a phenyl group, and at least one of R 1 and R 2 includes a naphthyl group.
  • R 1 is a phenyl group
  • R 2 is a phenyl group substituted with a naphthyl group
  • a phenyl group substituted or unsubstituted naphthyl group
  • R 1 is a naphthyl group
  • R 2 is a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or a naphthyl group.
  • L 1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L 1 is a direct bond; A substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group.
  • L 1 is a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.
  • L 1 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L 1 is a direct bond; Or a phenylene group.
  • L 1 is a direct bond.
  • L 1 is a phenylene group.
  • L 2 is a direct bond; Or a substituted or unsubstituted arylene group.
  • L 2 is a direct bond; Or a substituted or unsubstituted C6 to C40 arylene group.
  • L 2 is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L 2 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L 2 is a direct bond; Or a phenylene group.
  • L 2 is a direct bond.
  • L 2 is a phenylene group.
  • Ar is a substituted or unsubstituted aryl group condensed by two or more rings.
  • Ar is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
  • Ar is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
  • Ar is a naphthyl group unsubstituted or substituted with an aryl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
  • Ar is a naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Triphenylenyl group; Or a fluoranthenyl group.
  • the compound represented by Formula 1 is represented by the following Formula 1-1 or 1-2.
  • the compound represented by Formula 1 is selected from the following compounds.
  • the first electrode A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes an emission layer
  • the emission layer includes a compound represented by Formula 1 above.
  • the organic material layer includes an emission layer
  • the emission layer includes a host
  • the host is a compound represented by Formula 1 above.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1
  • the emission layer including the compound represented by Formula 1 has green or red color.
  • it has an emission wavelength in the range of 450 nm to 700 nm.
  • green when green, it has an emission wavelength in the region of 450 nm to 600 nm, and when it is red, it has an emission wavelength in the region of 600 nm to 700 nm.
  • the organic material layer may include an emission layer, and the emission layer may further include a compound represented by Formula 2 below.
  • A is an aromatic hydrocarbon ring
  • L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar 11 is a substituted or unsubstituted aryl group
  • Ar 12 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n is an integer from 1 to 10
  • R 11 are the same as or different from each other.
  • A is a monocyclic aromatic hydrocarbon ring.
  • A is a benzene ring.
  • Formula 2 may be represented by any one of Formulas 2-1 to 2-4 below.
  • L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.
  • L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C40 arylene group.
  • L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L 11 and L 12 are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L 11 and L 12 are each independently a direct bond; Phenylene group; Or a biphenylene group.
  • Ar 11 is a substituted or unsubstituted C6 to C60 aryl group.
  • Ar 11 is a substituted or unsubstituted C6 to C40 aryl group.
  • Ar 11 is a substituted or unsubstituted C6 to C20 aryl group.
  • Ar 11 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
  • Ar 11 is a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group.
  • Ar 12 is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar 12 is a substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
  • Ar 12 is a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar 12 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar 12 is a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C3 to C40 cycloalkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C1 to C10 alkoxy group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C1 to C10 alkoxy group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R 11 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R 11 is hydrogen
  • the compound represented by Formula 2 may be any one selected from the following compounds.
  • the content ratio (weight ratio) of the compound represented by Formula 1 and the compound represented by Formula 2 is 10:90 to 90:10, 30:70 to 70:30, or 50: 50 to 70:30.
  • the emission layer may include a dopant together with the compound represented by Chemical Formula 1.
  • the dopant may be a fluorescent or phosphorescent dopant.
  • the dopant may be a phosphorescent dopant.
  • the emission layer may include a metal complex as a phosphorescent dopant together with the compound represented by Formula 1 above.
  • the emission layer may include an iridium-based (Ir) dopant as a phosphorescent dopant together with the compound represented by Formula 1 above.
  • Ir iridium-based
  • the iridium-based (Ir) dopant is as follows, but is not limited thereto.
  • the dopant may be included in an amount of 0.01 to 30 parts by weight, 0.01 to 10 parts by weight, and 0.01 to 5 parts by weight based on 100 parts by weight of the host.
  • the organic material layer includes two or more emission layers, and at least one of the two or more emission layers includes the compound represented by Formula 1 above.
  • the emission layer including the compound represented by Chemical Formula 1 has a green color, and the emission layer not including the compound represented by Chemical Formula 1 may include a blue, red, or green emission compound known in the art.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 to 3. 1 to 3 illustrate an organic light-emitting device, but are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101.
  • the compound represented by Formula 1 is included in the emission layer.
  • FIG. 2 shows a structure of an organic light emitting diode in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. It is illustrated.
  • the compound represented by Formula 1 is included in at least one of the organic material layers.
  • the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, and a light emitting layer.
  • a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, and an electron transport layer on the substrate 101 108), an electron injection layer 109, and a second electrode 110 are sequentially stacked in an organic light-emitting device.
  • the compound represented by Formula 1 is included in at least one of the organic material layers.
  • the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • Metals such as vanadium, chromium, copper, zinc, 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; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamine group.
  • the substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the emission material of the emission layer is capable of emitting light in the visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • the material a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • an additional light-emitting layer is provided separately from the light-emitting layer containing the compound represented by Formula 1, it is preferable that the light-emitting material of the additional light-emitting layer is also the aforementioned material.
  • Examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.
  • Alq3 8-hydroxyquinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.
  • the hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect to the light emitting layer or the light emitting material. In addition, a material excellent in ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Further, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the emission layer is preferable, and a material having high mobility for electrons is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material, as used according to the prior art.
  • suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injection material has an excellent ability to transport electrons, has an effect of receiving electrons from a cathode, and an excellent electron injection effect to a light emitting layer or a light emitting material. In addition, a material that prevents the excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • 8-hydroxyquinolinato lithium bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer.
  • Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.
  • intermediate A (15.0g, 45.6mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.0g, 50.2mmol) were mixed with THF (tetra). Hydrofuran) was put into 300ml, stirred and refluxed. Thereafter, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, and stirred sufficiently, and then tetrakis (triphenylphosphine) palladium (0) (1.6 g, 1.4 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • compound 1-1 (15.0g, 31mmol) and naphthalen-2-ylboronic acid (5.9g, 34.1mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (17.1g, 124mmol) was dissolved in 51 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (1.1 g, 0.9 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO Indium Tin Oxide
  • Fischer Co. product was used as a detergent
  • distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A and hexaazatriphenylene (HAT-CN) were sequentially thermally vacuum deposited to a thickness of 800 ⁇ and 50 ⁇ , respectively, to form a hole injection layer.
  • the following HT-A as a hole transport layer was vacuum-deposited to a thickness of 800 ⁇
  • EB-A as an electron blocking layer was thermally vacuum-deposited to a thickness of 600 ⁇ .
  • the compound 1 prepared above and the following RD compound were vacuum-deposited at a weight ratio of 97:3 to a thickness of 400 ⁇ to form a light emitting layer.
  • the following ET-A and Liq were thermally vacuum deposited to a thickness of 360 ⁇ at a ratio of 1:1, and then Liq was vacuum deposited to a thickness of 5 ⁇ to form an electron transport and injection layer.
  • the electron injection layer magnesium and silver were deposited to a thickness of 160 ⁇ in a weight ratio of 1:4 to form a cathode, thereby fabricating an organic light-emitting device.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 ⁇ /sec, and the deposition rate of silver and magnesium was 2 ⁇ /sec. Maintaining -7 ⁇ 5 ⁇ 10 -6 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
  • the organic light-emitting devices prepared in the above Experimental Examples and Comparative Experimental Examples were stored in an oven at 100° C. for 30 minutes and subjected to heat treatment, and then voltage, efficiency, and life (T95) were measured by applying a current, and the results are shown in Table 1 below. . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
  • the compound represented by Formula 1 has a structure in which a nitrogen-containing heterocycle serving as an electron acceptor is bonded to position 1 of dibenzofuran, and two or more condensed aryl groups are connected in the meta or para direction.
  • two or more condensed aryl groups exist in the structure as two or more condensed aryl groups are connected to the nitrogen-containing heterocycle.
  • Structures with only one condensed aryl group such as RH-A, RH-C, RH-F, and RH-G Compared with, the glass transition temperature is increased and the thermal stability of the thin film state is increased.

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Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light-emitting device comprising the same
본 명세서는 2019년 2월 19일 한국 특허청에 제출된 한국 특허 출원 제10-2019-0019011호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0019011 filed with the Korean Intellectual Property Office on February 19, 2019, the entire contents of which are incorporated herein.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. Development of a new material for the organic light emitting device as described above is continuously required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a compound and an organic light emitting device including the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.The present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
Figure PCTKR2020002295-appb-I000001
Figure PCTKR2020002295-appb-I000001
상기 화학식 1에 있어서,In Formula 1,
X1 내지 X3은 각각 N 또는 CR21이며, 적어도 하나는 N이고,X 1 to X 3 are each N or CR 21 , at least one is N,
L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L 1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
L2는 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L 2 is a direct bond; Or a substituted or unsubstituted arylene group,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고,R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함하며,At least one of R 1 and R 2 includes an aryl group condensed by two or more rings,
R 및 R21은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R and R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r은 1 내지 4의 정수이고,r is an integer from 1 to 4,
r이 2 이상일 경우, R은 같거나 상이하며,When r is 2 or more, R is the same or different,
Ar은 치환 또는 비치환되고 2환 이상 축합된 아릴기이다.Ar is a substituted or unsubstituted aryl group condensed by two or more rings.
또한, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 do.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다.The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light emitting device.
도 1 내지 3은 본 명세서의 일 실시상태에 따르는 유기 발광 소자를 도시한 것이다.1 to 3 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
101: 기판101: substrate
102: 제1 전극102: first electrode
103: 정공 주입층103: hole injection layer
104: 정공 수송층104: hole transport layer
105: 전자 저지층105: electron blocking layer
106: 발광층106: light emitting layer
107: 정공 저지층107: hole blocking layer
108: 전자 수송층108: electron transport layer
109: 전자 주입층109: electron injection layer
110: 제2 전극110: second electrode
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 화합물을 제공한다.The present specification provides a compound represented by Chemical Formula 1.
상기 화학식 1로 표시되는 화합물은 디벤조퓨란의 같은 벤젠고리에 전자 받개 역할을 하는 함질소헤테로고리가 디벤조퓨란의 1번 위치에 위치하고, 전자 주개 역할을 하는 유닛이 함질소헤테로고리와 메타 혹은 파라 위치에 치환되어 있다. 전자 주개 유닛과 전자 받개 유닛이 동일 분자 내 동시에 존재함으로써 정공과 전자 수송에 모두 유리하며, 서로 메타 혹은 파라 위치에 위치함으로써 오쏘 위치보다 입체 장애 효과가 적어 물질의 안정성이 높아 유기 발광 소자의 유기물층의 재료로 사용 시 고효율 및 장수명의 효과를 얻을 수 있다.In the compound represented by Formula 1, a nitrogen-containing heterocycle serving as an electron acceptor in the same benzene ring of dibenzofuran is located at position 1 of dibenzofuran, and a unit serving as an electron donor is a nitrogen-containing heterocycle and meta or It is substituted at the para position. Since the electron donor unit and the electron acceptor unit exist in the same molecule at the same time, it is advantageous for both holes and electron transport, and because they are located in the meta or para position of each other, the steric hindrance effect is less than the ortho position, so the stability of the material is high. When used as a material, the effect of high efficiency and long life can be obtained.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be positioned "on" another member, this includes not only a case where a member is in contact with another member, but also a case where another member exists between the two members.
본 명세서에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents in the present specification are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치, 즉 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 아릴기로 치환된 아릴기, 헤테로고리기로 치환된 아릴기, 아릴기로 치환된 헤테로고리기, 알킬기로 치환된 아릴기 등일 수 있다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heterocyclic group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적으로 탄소수 1 내지 20인 것이 바람직하다. 더 구체적으로는 탄소수 1 내지 10인 것이 바람직하다. 구체적인 예로는 메틸기; 에틸기; 프로필기; n-프로필기; 이소프로필기; 부틸기; n-부틸기; 이소부틸기; tert-부틸기; sec-부틸기; 1-메틸부틸기; 1-에틸부틸기; 펜틸기; n-펜틸기; 이소펜틸기; 네오펜틸기; tert-펜틸기; 헥실기; n-헥실기; 1-메틸펜틸기; 2-메틸펜틸기; 4-메틸-2-펜틸기; 3,3-디메틸부틸기; 2-에틸부틸기; 헵틸기; n-헵틸기; 1-메틸헥실기; 시클로펜틸메틸기; 시클로헥실메틸기; 옥틸기; n-옥틸기; tert-옥틸기; 1-메틸헵틸기; 2-에틸헥실기; 2-프로필펜틸기; n-노닐기; 2,2-디메틸헵틸기; 1-에틸프로필기; 1,1-디메틸프로필기; 이소헥실기; 2-메틸펜틸기; 4-메틸헥실기; 5-메틸헥실기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. 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-methylbutyl group; 1-ethylbutyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 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 group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 탄소수 3 내지 20인 것이 더 바람직하다. 구체적으로 시클로프로필기; 시클로부틸기; 시클로펜틸기; 3-메틸시클로펜틸기; 2,3-디메틸시클로펜틸기; 시클로헥실기; 3-메틸시클로헥실기; 4-메틸시클로헥실기; 2,3-디메틸시클로헥실기; 3,4,5-트리메틸시클로헥실기; 4-tert-부틸시클로헥실기; 시클로헵틸기; 시클로옥틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but it is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 실릴기는 -SiR101R102R103의 화학식으로 표시될 수 있고, 상기 R101, R102 및 R103는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기; 트리에틸실릴기; t-부틸디메틸실릴기; 비닐디메틸실릴기; 프로필디메틸실릴기; 트리페닐실릴기; 디페닐실릴기; 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group may be represented by the formula of -SiR 101 R 102 R 103 , wherein R 101 , R 102 and R 103 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyldimethylsilyl group; Propyldimethylsilyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group and the like, but are not limited thereto.
본 명세서에 있어서, 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 탄소수 1 내지 20인 것이 바람직하다. 더 구체적으로 탄소수 1 내지 10인 것이 바람직하다. 구체적으로, 메톡시기; 에톡시기; n-프로폭시기; 이소프로폭시기; i-프로필옥시기; n-부톡시기; 이소부톡시기; tert-부톡시기; sec-부톡시기; n-펜틸옥시기; 네오펜틸옥시기; 이소펜틸옥시기; n-헥실옥시기; 3,3-디메틸부틸옥시기; 2-에틸부틸옥시기; n-옥틸옥시기; n-노닐옥시기; n-데실옥시기; 벤질옥시기; p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; It may be a p-methylbenzyloxy group and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기; 디메틸아민기; 에틸아민기; 디에틸아민기; 페닐아민기; 나프틸아민기; 바이페닐아민기; 안트라세닐아민기; 9-메틸안트라세닐아민기; 디페닐아민기; N-페닐나프틸아민기; 디톨릴아민기; N-페닐톨릴아민기; 트리페닐아민기; N-페닐바이페닐아민기; N-페닐나프틸아민기; N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기; N-페닐페난트레닐아민기; N-바이페닐페난트레닐아민기; N-페닐플루오레닐아민기; N-페닐터페닐아민기; N-페난트레닐플루오레닐아민기; N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 탄소수 6 내지 20인 것이 더 바람직하다. 상기 아릴기는 단환식 또는 다환식일 수 있다. 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 더 구체적으로는 탄소수 6 내지 20인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기; 바이페닐기; 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하고 더 구체적으로 탄소수 10 내지 20인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기; 안트라세닐기; 페난트릴기; 트리페닐기; 파이레닐기; 페날레닐기; 페릴레닐기; 크라이세닐기; 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms. Specifically, the monocyclic aryl group is a phenyl group; Biphenyl group; It may be a terphenyl group or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms, and more specifically, it is preferable that it has 10-20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenalenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group or the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2020002295-appb-I000002
,
Figure PCTKR2020002295-appb-I000003
,
Figure PCTKR2020002295-appb-I000004
및
Figure PCTKR2020002295-appb-I000005
등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2020002295-appb-I000002
,
Figure PCTKR2020002295-appb-I000003
,
Figure PCTKR2020002295-appb-I000004
And
Figure PCTKR2020002295-appb-I000005
And the like, but is not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, 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 or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로 고리기의 탄소수는 1 내지 30이다. 헤테로 고리기의 예로는 예로는 피리딜기, 피롤기, 피리미딜기, 피리다지닐기, 퓨라닐기, 티오페닐기, 이미다졸기, 피라졸기, 옥사졸기, 이소옥사졸기, 티아졸기, 이소티아졸기, 트리아졸기, 옥사디아졸기, 티아디아졸기, 디티아졸기, 테트라졸기, 피라닐기, 티오피라닐기, 피라지닐기, 옥사지닐기, 티아지닐기, 디옥시닐기, 트리아지닐기, 테트라지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 퀴놀릴기, 퀴나졸리닐기, 퀴녹살리닐기, 나프티리디닐기, 아크리딜기, 크산테닐기, 페난트리디닐기, 디아자나프탈레닐기, 트리아자인데닐기, 인돌기, 인돌리닐기, 인돌리지닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 벤조티아졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티오펜기, 벤조퓨라닐기, 디벤조티오페닐기, 디벤조퓨라닐기, 카바졸기, 벤조카바졸기, 디벤조카바졸기, 인돌로카바졸기, 인데노카바졸기, 페나지닐기, 이미다조피리딘기, 페녹사지닐기, 페난트리딘기, 페난트롤린(phenanthroline)기, 페노티아진(phenothiazine)기, 이미다조피리딘기, 이미다조페난트리딘기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 1 to 30. Examples of heterocyclic groups include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridyl group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazindenyl group, indole group , Indolinyl group, indolizinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazole group, benzocarbazole group, dibenzocarbazole group, indolocarbazole group, indenocarbazole group, phenazinyl group, imidazopyridine group, phenoxazinyl group , A phenanthridine group, a phenanthroline group, a phenothiazine group, an imidazopyridine group, an imidazophenanthridine group, and the like, but are not limited thereto.
본 명세서에 있어서, 헤테로고리기의 고리를 구성하는 원자수는 3 내지 25이다. 또 하나의 실시상태에 있어서, 헤테로고리기의 고리를 구성하는 원자수는 5 내지 17이다.In the present specification, the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another exemplary embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.
본 명세서에 있어서, 헤테로아릴기는 방향족이며, 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group may be applied.
본 명세서에 있어서, 방향족 탄화수소 고리는 1가기인 것을 제외하고 상기 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group may be applied except that the aromatic hydrocarbon ring is a monovalent group.
본 명세서에 있어서, 아릴렌기 및 헤테로아릴렌기는 2가기이며, 1가기인 것을 제외하고 각각 상기 아릴기 및 헤테로아릴기에 관한 설명이 적용될 수 있다.In the present specification, the arylene group and the heteroarylene group are divalent groups, and descriptions of the aryl groups and heteroaryl groups may be applied, respectively, except that they are monovalent groups.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3은 각각 독립적으로, N 또는 CR21이며, 적어도 하나 이상은 N이다.In the exemplary embodiment of the present specification, X 1 to X 3 are each independently N or CR 21 , and at least one is N.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X3은 N이다.In the exemplary embodiment of the present specification, X 1 and X 3 are N.
본 명세서의 일 실시상태에 있어서, 상기 X2는 N이다.In the exemplary embodiment of the present specification, X 2 is N.
본 명세서의 일 실시상태에 있어서, 상기 X2는 CR21이다.In the exemplary embodiment of the present specification, X 2 is CR 21 .
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3은 N이다.In the exemplary embodiment of the present specification, X 1 to X 3 are N.
본 명세서의 일 실시상태에 있어서, 상기 R 및 R21은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In the exemplary embodiment of the present specification, R and R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 R 및 R21은 각각 독립적으로, 수소; 중수소; 또는 치환 또는 비치환된 알킬기이다.In the exemplary embodiment of the present specification, R and R 21 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 R 및 R21은 각각 독립적으로, 수소; 또는 중수소이다.In the exemplary embodiment of the present specification, R and R 21 are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R 및 R21은 수소이다.In the exemplary embodiment of the present specification, R and R 21 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and at least one of R 1 and R 2 is a bicyclic or more condensed aryl group Include.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C60의 아릴기이고, R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C40의 아릴기이고, R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C20의 아릴기이고, R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R 1 and R 2 is bicyclic or more Condensed aryl groups are included.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 또는 치환 또는 비치환된 나프틸기이고, R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, and at least one of R 1 and R 2 includes a bicyclic or more condensed aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and at least one of R 1 and R 2 includes a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C60의 아릴기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C40의 아릴기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 내지 C20의 아릴기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R 1 and R 2 is a naphthyl group. Include.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 또는 치환 또는 비치환된 나프틸기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, and at least one of R 1 and R 2 includes a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 나프틸기로 치환 또는 비치환된 페닐기; 비페닐기; 또는 페닐기로 치환 또는 비치환된 나프틸기이고, R1 및 R2 중 적어도 하나는 나프틸기를 포함한다.In the exemplary embodiment of the present specification, R 1 and R 2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or a naphthyl group unsubstituted or substituted with a phenyl group, and at least one of R 1 and R 2 includes a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 페닐기이고, R2는 나프틸기로 치환된 페닐기; 또는 페닐기로 치환 또는 비치환된 나프틸기이다.In the exemplary embodiment of the present specification, R 1 is a phenyl group, R 2 is a phenyl group substituted with a naphthyl group; Or a phenyl group substituted or unsubstituted naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 나프틸기이고, R2는 나프틸기로 치환 또는 비치환된 페닐기; 비페닐기; 또는 나프틸기이다.In the exemplary embodiment of the present specification, R 1 is a naphthyl group, and R 2 is a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L 1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합; 치환 또는 비치환된 C6 내지 C30의 아릴렌기; 또는 치환 또는 비치환된 C2 내지 C30의 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L 1 is a direct bond; A substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합; 또는 치환 또는 비치환된 C6 내지 C30의 아릴렌기이다.In the exemplary embodiment of the present specification, L 1 is a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합; 또는 치환 또는 비치환된 페닐렌기이다.In the exemplary embodiment of the present specification, L 1 is a direct bond; Or a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합; 또는 페닐렌기이다.In the exemplary embodiment of the present specification, L 1 is a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합이다.In the exemplary embodiment of the present specification, L 1 is a direct bond.
본 명세서의 일 실시상태에 있어서, 상기 L1은 페닐렌기이다.In the exemplary embodiment of the present specification, L 1 is a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.In the exemplary embodiment of the present specification, L 2 is a direct bond; Or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합; 또는 치환 또는 비치환된 C6 내지 C40의 아릴렌기이다.In the exemplary embodiment of the present specification, L 2 is a direct bond; Or a substituted or unsubstituted C6 to C40 arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합; 또는 치환 또는 비치환된 C6 내지 C20의 아릴렌기이다.In the exemplary embodiment of the present specification, L 2 is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합; 또는 치환 또는 비치환된 페닐렌기이다.In the exemplary embodiment of the present specification, L 2 is a direct bond; Or a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합; 또는 페닐렌기이다.In the exemplary embodiment of the present specification, L 2 is a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합이다.In the exemplary embodiment of the present specification, L 2 is a direct bond.
본 명세서의 일 실시상태에 있어서, 상기 L2는 페닐렌기이다.In the exemplary embodiment of the present specification, L 2 is a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환되고 2환 이상 축합된 아릴기이다.In the exemplary embodiment of the present specification, Ar is a substituted or unsubstituted aryl group condensed by two or more rings.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 파이레닐기; 치환 또는 비치환된 트리페닐레닐기; 또는 치환 또는 비치환된 플루오란테닐기이다.In the exemplary embodiment of the present specification, Ar is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 또는 치환 또는 비치환된 플루오란테닐기이다.In the exemplary embodiment of the present specification, Ar is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 아릴기로 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 또는 치환 또는 비치환된 플루오란테닐기이다.In the exemplary embodiment of the present specification, Ar is a naphthyl group unsubstituted or substituted with an aryl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 페닐기로 치환 또는 비치환된 나프틸기; 페난트레닐기; 트리페닐레닐기; 또는 플루오란테닐기이다.In the exemplary embodiment of the present specification, Ar is a naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Triphenylenyl group; Or a fluoranthenyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 또는 1-2로 표시된다.In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by the following Formula 1-1 or 1-2.
[화학식 1-1][Formula 1-1]
Figure PCTKR2020002295-appb-I000006
Figure PCTKR2020002295-appb-I000006
[화학식 1-2][Formula 1-2]
Figure PCTKR2020002295-appb-I000007
Figure PCTKR2020002295-appb-I000007
상기 화학식 1-1 및 1-2에 있어서, 각 치환기의 정의는 상기 화학식 1과 동일하다.In Formulas 1-1 and 1-2, the definition of each substituent is the same as in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택된다.In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.
Figure PCTKR2020002295-appb-I000008
Figure PCTKR2020002295-appb-I000008
Figure PCTKR2020002295-appb-I000009
Figure PCTKR2020002295-appb-I000009
Figure PCTKR2020002295-appb-I000010
Figure PCTKR2020002295-appb-I000010
Figure PCTKR2020002295-appb-I000011
Figure PCTKR2020002295-appb-I000011
Figure PCTKR2020002295-appb-I000012
Figure PCTKR2020002295-appb-I000012
Figure PCTKR2020002295-appb-I000013
Figure PCTKR2020002295-appb-I000013
Figure PCTKR2020002295-appb-I000014
Figure PCTKR2020002295-appb-I000014
Figure PCTKR2020002295-appb-I000015
Figure PCTKR2020002295-appb-I000015
Figure PCTKR2020002295-appb-I000016
Figure PCTKR2020002295-appb-I000016
Figure PCTKR2020002295-appb-I000017
Figure PCTKR2020002295-appb-I000017
Figure PCTKR2020002295-appb-I000018
Figure PCTKR2020002295-appb-I000018
Figure PCTKR2020002295-appb-I000019
Figure PCTKR2020002295-appb-I000019
Figure PCTKR2020002295-appb-I000020
Figure PCTKR2020002295-appb-I000020
Figure PCTKR2020002295-appb-I000021
Figure PCTKR2020002295-appb-I000021
Figure PCTKR2020002295-appb-I000022
Figure PCTKR2020002295-appb-I000022
Figure PCTKR2020002295-appb-I000023
Figure PCTKR2020002295-appb-I000023
Figure PCTKR2020002295-appb-I000024
Figure PCTKR2020002295-appb-I000024
Figure PCTKR2020002295-appb-I000025
Figure PCTKR2020002295-appb-I000025
Figure PCTKR2020002295-appb-I000026
Figure PCTKR2020002295-appb-I000026
Figure PCTKR2020002295-appb-I000027
Figure PCTKR2020002295-appb-I000027
Figure PCTKR2020002295-appb-I000028
Figure PCTKR2020002295-appb-I000028
Figure PCTKR2020002295-appb-I000029
Figure PCTKR2020002295-appb-I000029
Figure PCTKR2020002295-appb-I000030
Figure PCTKR2020002295-appb-I000030
Figure PCTKR2020002295-appb-I000031
Figure PCTKR2020002295-appb-I000031
본 명세서의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 또는 2층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In one embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 저지층, 정공 저지층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다.In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 호스트를 포함하며, 상기 호스트는 상기 화학식 1로 표시되는 화합물이다.In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a host, and the host is a compound represented by Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하고, 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 녹색 혹은 적색을 띤다. 예컨대, 450 nm 내지 700 nm의 범위 내에 발광파장을 가진다. 구체적으로, 녹색을 띠는 경우, 450 nm 내지 600 nm의 영역에서 발광파장을 가지고, 적색을 띠는 경우, 600 nm 내지 700 nm의 영역에서 발광파장을 가진다.In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes the compound represented by Formula 1, and the emission layer including the compound represented by Formula 1 has green or red color. For example, it has an emission wavelength in the range of 450 nm to 700 nm. Specifically, when green, it has an emission wavelength in the region of 450 nm to 600 nm, and when it is red, it has an emission wavelength in the region of 600 nm to 700 nm.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 더 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may further include a compound represented by Formula 2 below.
[화학식 2][Formula 2]
Figure PCTKR2020002295-appb-I000032
Figure PCTKR2020002295-appb-I000032
상기 화학식 2에 있어서,In Formula 2,
A는 방향족 탄화수소 고리이고,A is an aromatic hydrocarbon ring,
L11 및 L12는 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar11는 치환 또는 비치환된 아릴기이고,Ar 11 is a substituted or unsubstituted aryl group,
Ar12는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar 12 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n은 1 내지 10의 정수이며,n is an integer from 1 to 10,
n이 2 이상인 경우, R11은 서로 같거나 상이하다.When n is 2 or more, R 11 are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, A는 단환의 방향족 탄화수소 고리이다.In an exemplary embodiment of the present specification, A is a monocyclic aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, A는 벤젠 고리이다.In an exemplary embodiment of the present specification, A is a benzene ring.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2는 하기 화학식 2-1 내지 2-4 중 어느 하나로 표시될 수 있다.In the exemplary embodiment of the present specification, Formula 2 may be represented by any one of Formulas 2-1 to 2-4 below.
[화학식 2-1][Formula 2-1]
Figure PCTKR2020002295-appb-I000033
Figure PCTKR2020002295-appb-I000033
[화학식 2-2][Formula 2-2]
Figure PCTKR2020002295-appb-I000034
Figure PCTKR2020002295-appb-I000034
[화학식 2-3][Formula 2-3]
Figure PCTKR2020002295-appb-I000035
Figure PCTKR2020002295-appb-I000035
[화학식 2-4][Formula 2-4]
Figure PCTKR2020002295-appb-I000036
Figure PCTKR2020002295-appb-I000036
상기 화학식 2-1 내지 2-4에 있어서, 각 치환기의 정의는 상기 화학식 2와 동일하다.In Formulas 2-1 to 2-4, the definition of each substituent is the same as in Formula 2.
본 명세서의 일 실시상태에 있어서, L11 및 L12는 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 C6 내지 C60 아릴렌기이다.In the exemplary embodiment of the present specification, L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.
본 명세서의 일 실시상태에 있어서, L11 및 L12는 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 C6 내지 C40 아릴렌기이다.In the exemplary embodiment of the present specification, L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C40 arylene group.
본 명세서의 일 실시상태에 있어서, L11 및 L12는 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이다.In the exemplary embodiment of the present specification, L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
본 명세서의 일 실시상태에 있어서, L11 및 L12는 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 비페닐렌기이다.In the exemplary embodiment of the present specification, L 11 and L 12 are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 있어서, L11 및 L12는 각각 독립적으로 직접결합; 페닐렌기; 또는 비페닐렌기이다.In the exemplary embodiment of the present specification, L 11 and L 12 are each independently a direct bond; Phenylene group; Or a biphenylene group.
본 명세서의 일 실시상태에 있어서, Ar11은 치환 또는 비치환된 C6 내지 C60의 아릴기이다.In the exemplary embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C60 aryl group.
본 명세서의 일 실시상태에 있어서, Ar11은 치환 또는 비치환된 C6 내지 C40의 아릴기이다.In the exemplary embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C40 aryl group.
본 명세서의 일 실시상태에 있어서, Ar11은 치환 또는 비치환된 C6 내지 C20의 아릴기이다.In the exemplary embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C20 aryl group.
본 명세서의 일 실시상태에 있어서, Ar11은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 또는 치환 또는 비치환된 플루오레닐기이다.In the exemplary embodiment of the present specification, Ar 11 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 있어서, Ar11은 아릴기로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 또는 알킬기로 치환 또는 비치환된 플루오레닐기이다.In the exemplary embodiment of the present specification, Ar 11 is a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group.
본 명세서의 일 실시상태에 있어서, Ar12는 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴기이다.In the exemplary embodiment of the present specification, Ar 12 is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
본 명세서의 일 실시상태에 있어서, Ar12는 치환 또는 비치환된 C6 내지 C40의 아릴기; 또는 치환 또는 비치환된 C2 내지 C40의 헤테로아릴기이다.In the exemplary embodiment of the present specification, Ar 12 is a substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
본 명세서의 일 실시상태에 있어서, Ar12는 치환 또는 비치환된 C6 내지 C20의 아릴기; 또는 치환 또는 비치환된 C2 내지 C20의 헤테로아릴기이다.In the exemplary embodiment of the present specification, Ar 12 is a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
본 명세서의 일 실시상태에 있어서, Ar12는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.In the exemplary embodiment of the present specification, Ar 12 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, Ar12는 아릴기로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 알킬기로 치환 또는 비치환된 플루오레닐기; 디벤조퓨란기; 또는 디벤조티오펜기이다.In the exemplary embodiment of the present specification, Ar 12 is a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Dibenzofuran group; Or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 C1 내지 C60의 알킬기; 치환 또는 비치환된 C1 내지 C60의 알콕시기; 치환 또는 비치환된 C2 내지 C60의 알케닐기; 치환 또는 비치환된 C2 내지 C60의 알키닐기; 치환 또는 비치환된 C3 내지 C60의 시클로알킬기; 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 C1 내지 C30의 알킬기; 치환 또는 비치환된 C1 내지 C30의 알콕시기; 치환 또는 비치환된 C2 내지 C30의 알케닐기; 치환 또는 비치환된 C2 내지 C30의 알키닐기; 치환 또는 비치환된 C3 내지 C40의 시클로알킬기; 치환 또는 비치환된 C6 내지 C40의 아릴기; 또는 치환 또는 비치환된 C2 내지 C40의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C3 to C40 cycloalkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 C1 내지 C10의 알킬기; 치환 또는 비치환된 C1 내지 C10의 알콕시기; 치환 또는 비치환된 C2 내지 C10의 알케닐기; 치환 또는 비치환된 C2 내지 C10의 알키닐기; 치환 또는 비치환된 C3 내지 C20의 시클로알킬기; 치환 또는 비치환된 C6 내지 C20의 아릴기; 또는 치환 또는 비치환된 C2 내지 C20의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C1 to C10 alkoxy group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 C1 내지 C10의 알킬기; 치환 또는 비치환된 C1 내지 C10의 알콕시기; 치환 또는 비치환된 C2 내지 C10의 알케닐기; 치환 또는 비치환된 C2 내지 C10의 알키닐기; 치환 또는 비치환된 C3 내지 C20의 시클로알킬기; 치환 또는 비치환된 C6 내지 C20의 아릴기; 또는 치환 또는 비치환된 C2 내지 C20의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C1 to C10 alkoxy group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In an exemplary embodiment of the present specification, R 11 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, R11은 수소이다.In an exemplary embodiment of the present specification, R 11 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2로 표시되는 화합물은 하기 화합물들 중에서 선택되는 어느 하나일 수 있다.In the exemplary embodiment of the present specification, the compound represented by Formula 2 may be any one selected from the following compounds.
Figure PCTKR2020002295-appb-I000037
Figure PCTKR2020002295-appb-I000037
Figure PCTKR2020002295-appb-I000038
Figure PCTKR2020002295-appb-I000038
Figure PCTKR2020002295-appb-I000039
Figure PCTKR2020002295-appb-I000039
Figure PCTKR2020002295-appb-I000040
Figure PCTKR2020002295-appb-I000040
Figure PCTKR2020002295-appb-I000041
Figure PCTKR2020002295-appb-I000041
Figure PCTKR2020002295-appb-I000042
Figure PCTKR2020002295-appb-I000042
Figure PCTKR2020002295-appb-I000043
Figure PCTKR2020002295-appb-I000043
Figure PCTKR2020002295-appb-I000044
Figure PCTKR2020002295-appb-I000044
Figure PCTKR2020002295-appb-I000045
Figure PCTKR2020002295-appb-I000045
Figure PCTKR2020002295-appb-I000046
Figure PCTKR2020002295-appb-I000046
Figure PCTKR2020002295-appb-I000047
Figure PCTKR2020002295-appb-I000047
Figure PCTKR2020002295-appb-I000048
Figure PCTKR2020002295-appb-I000048
Figure PCTKR2020002295-appb-I000049
Figure PCTKR2020002295-appb-I000049
Figure PCTKR2020002295-appb-I000050
Figure PCTKR2020002295-appb-I000050
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물과 상기 화학식 2로 표시되는 화합물의 함량비(중량비)는 10:90 내지 90:10, 30:70 내지 70:30, 또는 50:50 내지 70:30이다.In an exemplary embodiment of the present specification, the content ratio (weight ratio) of the compound represented by Formula 1 and the compound represented by Formula 2 is 10:90 to 90:10, 30:70 to 70:30, or 50: 50 to 70:30.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물과 함께 도펀트를 포함할 수 있다.In the exemplary embodiment of the present specification, the emission layer may include a dopant together with the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 도펀트는 형광 또는 인광 도펀트일 수 있다.In the exemplary embodiment of the present specification, the dopant may be a fluorescent or phosphorescent dopant.
본 명세서의 일 실시상태에 있어서, 상기 도펀트는 인광 도펀트일 수 있다.In the exemplary embodiment of the present specification, the dopant may be a phosphorescent dopant.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물과 함께 인광 도펀트로서 금속 착체를 포함할 수 있다.In the exemplary embodiment of the present specification, the emission layer may include a metal complex as a phosphorescent dopant together with the compound represented by Formula 1 above.
또 하나의 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물과 함께 인광 도펀트로서 이리듐계(Ir) 도펀트를 포함할 수 있다.In another exemplary embodiment, the emission layer may include an iridium-based (Ir) dopant as a phosphorescent dopant together with the compound represented by Formula 1 above.
상기 이리듐계(Ir) 도펀트는 하기와 같으나, 이에만 한정되는 것은 아니다.The iridium-based (Ir) dopant is as follows, but is not limited thereto.
Figure PCTKR2020002295-appb-I000051
Figure PCTKR2020002295-appb-I000051
Figure PCTKR2020002295-appb-I000052
Figure PCTKR2020002295-appb-I000052
Figure PCTKR2020002295-appb-I000053
Figure PCTKR2020002295-appb-I000053
Figure PCTKR2020002295-appb-I000054
Figure PCTKR2020002295-appb-I000054
상기 발광층이 도펀트를 포함하는 경우, 도펀트는 호스트 100 중량부 대비 0.01 내지 30 중량부, 0.01 내지 10 중량부, 0.01 내지 5 중량부로 포함될 수 있다.When the light emitting layer includes a dopant, the dopant may be included in an amount of 0.01 to 30 parts by weight, 0.01 to 10 parts by weight, and 0.01 to 5 parts by weight based on 100 parts by weight of the host.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 발광층을 포함하고, 상기 2층 이상의 발광층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 녹색을 띠며, 상기 화학식 1로 표시되는 화합물을 포함하지 않은 발광층은 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer includes two or more emission layers, and at least one of the two or more emission layers includes the compound represented by Formula 1 above. The emission layer including the compound represented by Chemical Formula 1 has a green color, and the emission layer not including the compound represented by Chemical Formula 1 may include a blue, red, or green emission compound known in the art.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극 또는 음극이다.In the exemplary embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 있어서, 상기 제2 전극은 음극 또는 양극이다.In the exemplary embodiment of the present specification, the second electrode is a cathode or an anode.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 내지 3에 예시되어 있다. 상기 도 1 내지 도 3은 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다.For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3. 1 to 3 illustrate an organic light-emitting device, but are not limited thereto.
도 1에는 기판(101) 위에 제1 전극(102), 발광층(106) 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 발광층에 포함된다.1 illustrates a structure of an organic light-emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by Formula 1 is included in the emission layer.
도 2에는 기판(101) 위에 제1 전극(102), 정공 주입층(103), 정공 수송층(104), 발광층(106), 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 본 발명의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 상기 유기물층 중 1층 이상에 포함된다. 또 하나의 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 정공 주입층, 정공 수송층 및 발광층 중 1층 이상에 포함된다.FIG. 2 shows a structure of an organic light emitting diode in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. It is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in at least one of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, and a light emitting layer.
도 3에는 기판(101) 위에 제1 전극(102), 정공 주입층(103), 정공 수송층(104), 전자 저지층(105), 발광층(106), 정공 저지층(107), 전자 수송층(108), 전자 주입층(109), 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 본 발명의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 상기 유기물층 중 1층 이상에 포함된다. 또 하나의 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 정공 주입층, 정공 수송층, 전자 저지층, 발광층, 정공 저지층, 전자 수송층 및 전자 주입층 중 1층 이상에 포함된다.3, a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, and an electron transport layer on the substrate 101 108), an electron injection layer 109, and a second electrode 110 are sequentially stacked in an organic light-emitting device. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in at least one of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질, 유기물층 및 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다.For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, 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.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다.In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다.In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다.As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Metals such as vanadium, chromium, copper, zinc, 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; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다.The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다.Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamine group. The substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
본 명세서에서, 상기 화학식 1로 표시되는 화합물이 발광층 이외의 유기물층에 포함될 경우, 발광층의 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 또한, 상기 화학식 1로 표시되는 화합물을 포함하는 발광층과 별도로 추가의 발광층이 구비되는 경우, 추가의 발광층의 발광 물질 또한 전술한 물질인 것이 바람직하다.In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the emission layer, the emission material of the emission layer is capable of emitting light in the visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively. As the material, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. In addition, when an additional light-emitting layer is provided separately from the light-emitting layer containing the compound represented by Formula 1, it is preferable that the light-emitting material of the additional light-emitting layer is also the aforementioned material.
상기 발광 물질로는 예를 들어, 8-히드록시퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 및 루브렌 등이 있으나, 이에 한정되는 것은 아니다.Examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.
상기 정공 주입층은 전극으로부터 정공을 수취하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 양극으로부터 정공 수취 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에 서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정 되는 것은 아니다.The hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect to the light emitting layer or the light emitting material. In addition, a material excellent in ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Further, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 음극 물질과 함께 사용할 수 있다. 특히, 적절한 음극 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is preferable, and a material having high mobility for electrons is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material, as used according to the prior art. In particular, suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 전자 주입물로는 전자를 수송하는 능력이 우수하고, 음극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤이 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되는 것은 아니다.The electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injection material has an excellent ability to transport electrons, has an effect of receiving electrons from a cathode, and an excellent electron injection effect to a light emitting layer or a light emitting material. In addition, a material that prevents the excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로는 8-히드록시퀴놀리나토 리튬, 비스(8-히드록시퀴놀리나토)아연, 비스(8-히드록시퀴놀리나토)구리, 비스(8-히드록시퀴놀리나토)망간, 트리스(8-히드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-히드록시퀴놀리나토)알루미늄, 트리스(8-히드록시퀴놀리나토)갈륨, 비스(10-히드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-히드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.As the metal complex compound, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
상기 전자 저지층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. 상기 정공 저지층은 정공의 음극으로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다.The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes. The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The manufacturing method of the compound of Formula 1 and the manufacturing of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
[합성예][Synthesis Example]
합성예 A: 중간체 A의 합성Synthesis Example A: Synthesis of Intermediate A
Figure PCTKR2020002295-appb-I000055
Figure PCTKR2020002295-appb-I000055
질소 분위기에서 1-브로모-3-클로로디벤조[b,d]퓨란 (15.0g, 53.3mmol)과 비스(피나콜라토)디보론 (14.9g, 58.6mmol)을 1,4-디옥산 300ml에 환류시키며 교반하였다. 이후 포타슙 아세테이트 (7.8g, 79.9mmol)를 투입하고 충분히 교반한 후 비스(디벤질리덴아세톤)팔라듐(0) (0.9g, 1.6mmol) 및 트리시클로헥실포스핀 (0.9g, 3.2mmol)을 투입하였다. 10시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척한 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 A를 12.4g 제조하였다. (수율 71%, MS[M+H]+= 330)In a nitrogen atmosphere, 1-bromo-3-chlorodibenzo[b,d]furan (15.0g, 53.3mmol) and bis(pinacolato)diboron (14.9g, 58.6mmol) were added to 300ml of 1,4-dioxane. The mixture was stirred while refluxing. Thereafter, potashup acetate (7.8 g, 79.9 mmol) was added and sufficiently stirred, and then bis (dibenzylideneacetone) palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. Was put in. After reacting for 10 hours, cooling to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of Intermediate A. (Yield 71%, MS[M+H] + = 330)
합성예 B: 중간체 B의 합성Synthesis Example B: Synthesis of Intermediate B
Figure PCTKR2020002295-appb-I000056
Figure PCTKR2020002295-appb-I000056
합성예 A에서, 1-브로모-3-클로로디벤조[b,d]퓨란을 1-브로모-4-클로로디벤조[b,d]퓨란으로 변경하여 사용한 것을 제외하고는, 중간체 A의 제조 방법과 동일한 제조 방법으로 중간체 B를 제조하였다. (MS[M+H]+= 330)In Synthesis Example A, except that 1-bromo-3-chlorodibenzo[b,d]furan was changed to 1-bromo-4-chlorodibenzo[b,d]furan and used, Intermediate B was prepared by the same production method as the production method. (MS[M+H] + = 330)
합성예 1: 화합물 1의 합성Synthesis Example 1: Synthesis of Compound 1
단계 1) 화합물 1-1의 합성Step 1) Synthesis of Compound 1-1
Figure PCTKR2020002295-appb-I000057
Figure PCTKR2020002295-appb-I000057
질소 분위기에서 중간체 A (15.0g, 45.6mmol)와 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진 (16.0g, 50.2mmol)을 THF(테트라하이드로퓨란) 300ml에 넣고 교반 및 환류하였다. 이후 포타슘 카보네이트(25.2g, 182.6mmol)를 물 76ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(0) (1.6g, 1.4mmol)을 투입하였다. 12시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척한 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1을 17.0g 제조하였다. (수율 77%, MS[M+H]+= 485)In a nitrogen atmosphere, intermediate A (15.0g, 45.6mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.0g, 50.2mmol) were mixed with THF (tetra). Hydrofuran) was put into 300ml, stirred and refluxed. Thereafter, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, and stirred sufficiently, and then tetrakis (triphenylphosphine) palladium (0) (1.6 g, 1.4 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.0 g of compound 1-1. (Yield 77%, MS[M+H] + = 485)
단계 2) 화합물 1의 합성Step 2) Synthesis of Compound 1
Figure PCTKR2020002295-appb-I000058
Figure PCTKR2020002295-appb-I000058
질소 분위기에서 화합물 1-1 (15.0g, 31mmol)와 나프탈렌-2-일보론산 (5.9g, 34.1mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이후 포타슘 카보네이트 (17.1g, 124mmol)를 물 51ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(0) (1.1g, 0.9mmol)을 투입하였다. 12시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척한 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 1을 7.7g 제조하였다. (수율 43%, MS[M+H]+= 577)In a nitrogen atmosphere, compound 1-1 (15.0g, 31mmol) and naphthalen-2-ylboronic acid (5.9g, 34.1mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (17.1g, 124mmol) was dissolved in 51 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (1.1 g, 0.9 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 7.7 g of compound 1 was prepared through sublimation purification. (Yield 43%, MS[M+H] + = 577)
합성예 2: 화합물 2의 합성Synthesis Example 2: Synthesis of Compound 2
Figure PCTKR2020002295-appb-I000059
Figure PCTKR2020002295-appb-I000059
합성예 1에서, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4,6-디(나프탈렌-2-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 나프탈렌-1-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2를 제조하였다. (MS[M+H]+= 627)In Synthesis Example 1, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was converted to 2-chloro-4,6-di(naphthalen-2-yl)-1 Compound 2 was prepared in the same manner as in the preparation method of Compound 1, except that 3,5-triazine was used, and naphthalen-2-ylboronic acid was changed to naphthalen-1-ylboronic acid. (MS[M+H] + = 627)
합성예 3: 화합물 3의 합성Synthesis Example 3: Synthesis of Compound 3
Figure PCTKR2020002295-appb-I000060
Figure PCTKR2020002295-appb-I000060
합성예 1에서, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-(4-(나프탈렌-2-일)페닐)-6-페닐-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 페난트렌-9-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3을 제조하였다. (MS[M+H]+= 703)In Synthesis Example 1, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was converted to 2-chloro-4-(4-(naphthalen-2-yl)phenyl) -6-phenyl-1,3,5-triazine, except that naphthalen-2-ylboronic acid was changed to phenanthrene-9-ylboronic acid, and was used in the same manner as in the preparation method of compound 1, Was prepared. (MS[M+H] + = 703)
합성예 4: 화합물 4의 합성Synthesis Example 4: Synthesis of Compound 4
Figure PCTKR2020002295-appb-I000061
Figure PCTKR2020002295-appb-I000061
합성예 1에서, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-([1,1'-비페닐]-4-일)-4-클로로-6-(나프탈렌-2-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 트리페닐렌-2-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4를 제조하였다. (MS[M+H]+= 753)In Synthesis Example 1, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was converted to 2-([1,1'-biphenyl]-4-yl)- Compound 1, except that 4-chloro-6-(naphthalen-2-yl)-1,3,5-triazine, and naphthalen-2-ylboronic acid was changed to triphenylene-2-ylboronic acid. Compound 4 was prepared in the same manner as in the manufacturing method of. (MS[M+H] + = 753)
합성예 5: 화합물 5의 합성Synthesis Example 5: Synthesis of Compound 5
Figure PCTKR2020002295-appb-I000062
Figure PCTKR2020002295-appb-I000062
합성예 1에서, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 (4-페닐나프탈렌-1-일)보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 5를 제조하였다. (MS[M+H]+= 653)In Synthesis Example 1, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was converted to 2-chloro-4-(naphthalen-2-yl)-6-phenyl- Compound 5 in the same manner as in the preparation method of Compound 1, except that 1,3,5-triazine and naphthalen-2-ylboronic acid was changed to (4-phenylnaphthalen-1-yl) boronic acid. Was prepared. (MS[M+H] + = 653)
합성예 6: 화합물 6의 합성Synthesis Example 6: Synthesis of Compound 6
Figure PCTKR2020002295-appb-I000063
Figure PCTKR2020002295-appb-I000063
합성예 1에서, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-페닐-6-(4-페닐나프탈렌-1-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 플루오란텐-3-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 6을 제조하였다. (MS[M+H]+= 727)In Synthesis Example 1, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was converted to 2-chloro-4-phenyl-6-(4-phenylnaphthalene-1- Compound 6 was prepared in the same manner as in the preparation method of Compound 1, except that one) -1,3,5-triazine and naphthalen-2-ylboronic acid were changed to fluoranthene-3-ylboronic acid. Was prepared. (MS[M+H] + = 727)
합성예 7: 화합물 7의 합성Synthesis Example 7: Synthesis of Compound 7
Figure PCTKR2020002295-appb-I000064
Figure PCTKR2020002295-appb-I000064
합성예 1에서, 중간체 A를 중간체 B로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 7을 제조하였다. (MS[M+H]+= 577)In Synthesis Example 1, compound 7 was prepared in the same manner as in the preparation method of compound 1, except that intermediate A was changed to intermediate B and used. (MS[M+H] + = 577)
합성예 8: 화합물 8의 합성Synthesis Example 8: Synthesis of Compound 8
Figure PCTKR2020002295-appb-I000065
Figure PCTKR2020002295-appb-I000065
합성예 1에서, 중간체 A를 중간체 B로, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-(나프탈렌-1-일)-6-(나프탈렌-2-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 나프탈렌-1-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 8을 제조하였다. (MS[M+H]+= 627)In Synthesis Example 1, intermediate A to intermediate B, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine to 2-chloro-4- (naphthalene-1- A method for preparing compound 1, except that one)-6-(naphthalen-2-yl)-1,3,5-triazine and naphthalen-2-ylboronic acid was changed to naphthalen-1-ylboronic acid. Compound 8 was prepared in the same manner as described above. (MS[M+H] + = 627)
합성예 9: 화합물 9의 합성Synthesis Example 9: Synthesis of Compound 9
Figure PCTKR2020002295-appb-I000066
Figure PCTKR2020002295-appb-I000066
합성예 1에서, 중간체 A를 중간체 B로, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-(4-(나프탈렌-1-일)페닐)-6-페닐-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 페난트렌-9-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 9를 제조하였다. (MS[M+H]+= 703)In Synthesis Example 1, intermediate A to intermediate B, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine to 2-chloro-4- (4- (naphthalene) -1-yl)phenyl)-6-phenyl-1,3,5-triazine, except that naphthalen-2-ylboronic acid was changed to phenanthrene-9-ylboronic acid, and the preparation method of compound 1 Compound 9 was prepared by the same method as described above. (MS[M+H] + = 703)
합성예 10: 화합물 10의 합성Synthesis Example 10: Synthesis of Compound 10
Figure PCTKR2020002295-appb-I000067
Figure PCTKR2020002295-appb-I000067
합성예 1에서, 중간체 A를 중간체 B로, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-페닐-6-(6-페닐나프탈렌-2-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 트리페닐렌-2-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 10을 제조하였다. (MS[M+H]+= 753)In Synthesis Example 1, intermediate A was used as intermediate B and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was used as 2-chloro-4-phenyl-6-( 6-phenylnaphthalen-2-yl)-1,3,5-triazine, except that naphthalen-2-ylboronic acid was changed to triphenylen-2-ylboronic acid, and the method for preparing compound 1 and Compound 10 was prepared by the same method. (MS[M+H] + = 753)
합성예 11: 화합물 11의 합성Synthesis Example 11: Synthesis of Compound 11
Figure PCTKR2020002295-appb-I000068
Figure PCTKR2020002295-appb-I000068
합성예 1에서, 중간체 A를 중간체 B로, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 (4-(나프탈렌-1-일)페닐)보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 11을 제조하였다. (MS[M+H]+= 653)In Synthesis Example 1, intermediate A to intermediate B, 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1,3,5-triazine to 2-chloro-4- (naphthalene-2- Except for the use of mono)-6-phenyl-1,3,5-triazine and naphthalen-2-ylboronic acid to (4-(naphthalen-1-yl)phenyl)boronic acid, Compound 11 was prepared by the same production method as the production method. (MS[M+H] + = 653)
합성예 12: 화합물 12의 합성Synthesis Example 12: Synthesis of Compound 12
Figure PCTKR2020002295-appb-I000069
Figure PCTKR2020002295-appb-I000069
합성예 1에서, 중간체 A를 중간체 B로, 2-클로로-4-(나프탈렌-2-일)-6-페닐-1,3,5-트리아진을 2-([1,1'-비페닐]-3-일)-4-클로로-6-(나프탈렌-2-일)-1,3,5-트리아진으로, 나프탈렌-2-일보론산을 플루오란텐-3-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 12를 제조하였다. (MS[M+H]+= 727)In Synthesis Example 1, intermediate A is used as intermediate B, and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine is used as 2-([1,1'-biphenyl). ]-3-yl)-4-chloro-6-(naphthalen-2-yl)-1,3,5-triazine and naphthalen-2-ylboronic acid to fluoranthene-3-ylboronic acid Except for that, compound 12 was prepared by the same method as the method of preparing compound 1. (MS[M+H] + = 727)
[실험예][Experimental Example]
실험예 1-1Experimental Example 1-1
ITO(Indium Tin Oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 HI-A과 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT-CN)를 각각 800Å, 50Å의 두께로 순차적으로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공수송층으로 하기 HT-A를 800Å 두께로 진공 증착한 후 전자저지층으로 하기 EB-A를 600Å의 두께로 열 진공 증착하였다. 상기 전자저지층 위에, 앞서 제조한 화합물 1과 하기 RD 화합물을 97:3의 중량비로 400 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 위에, 하기 ET-A와 Liq를 1:1의 비율로 360Å의 두께로 열 진공 증착하고 이어서 Liq를 5Å의 두께로 진공 증착하여 전자 수송 및 주입층을 형성하였다. 상기 전자주입층 위에, 마그네슘과 은을 1:4의 중량비로 160 Å의 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.On the prepared ITO transparent electrode, the following HI-A and hexaazatriphenylene (HAT-CN) were sequentially thermally vacuum deposited to a thickness of 800Å and 50Å, respectively, to form a hole injection layer. The following HT-A as a hole transport layer was vacuum-deposited to a thickness of 800Å, and then EB-A as an electron blocking layer was thermally vacuum-deposited to a thickness of 600Å. On the electron blocking layer, the compound 1 prepared above and the following RD compound were vacuum-deposited at a weight ratio of 97:3 to a thickness of 400 Å to form a light emitting layer. On the light emitting layer, the following ET-A and Liq were thermally vacuum deposited to a thickness of 360Å at a ratio of 1:1, and then Liq was vacuum deposited to a thickness of 5Å to form an electron transport and injection layer. On the electron injection layer, magnesium and silver were deposited to a thickness of 160 Å in a weight ratio of 1:4 to form a cathode, thereby fabricating an organic light-emitting device.
Figure PCTKR2020002295-appb-I000070
Figure PCTKR2020002295-appb-I000070
상기의 과정에서 유기물의 증착속도는 0.4~0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 은과 마그네슘은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2Х10-7 ~ 5Х10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4~0.7 Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 Å/sec, and the deposition rate of silver and magnesium was 2 Å/sec. Maintaining -7 ~ 5Х10 -6 torr, an organic light emitting device was manufactured.
실험예 1-2 내지 실험예 1-12Experimental Example 1-2 to Experimental Example 1-12
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
비교실험예 1-1 내지 1-9Comparative Experimental Examples 1-1 to 1-9
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서, 화합물 RH-A, RH-B, RH-C, RH-D, RH-E, RH-F, RH-G, RH-H 및 RH-I는 각각 하기와 같다.An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1 below, compounds RH-A, RH-B, RH-C, RH-D, RH-E, RH-F, RH-G, RH-H and RH-I are as follows, respectively.
Figure PCTKR2020002295-appb-I000071
Figure PCTKR2020002295-appb-I000071
실험예 2-1 내지 2-4Experimental Examples 2-1 to 2-4
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 각 화합물의 비율은 중량비를 의미하며, 화합물 PRH-1과 PRH-2는 각각 하기와 같다. An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1 below, the ratio of each compound means a weight ratio, and compounds PRH-1 and PRH-2 are as follows, respectively.
Figure PCTKR2020002295-appb-I000072
Figure PCTKR2020002295-appb-I000072
비교실험예 2-1 내지 2-4Comparative Experimental Examples 2-1 to 2-4
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 각 화합물의 비율은 중량비를 의미하며, 화합물 RH-A, RH-D, RH-E, RH-F, PRH-1 및 PRH-2는 앞서 설명한 바와 같다. An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1 below, the ratio of each compound refers to a weight ratio, and compounds RH-A, RH-D, RH-E, RH-F, PRH-1 and PRH-2 are as described above.
상기 실험예 및 비교실험예에서 제조한 유기 발광 소자를 100℃ 오븐에서 30분간 보관하여 열처리한 후, 전류를 인가하여 전압, 효율, 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 전압 및 효율은 10 mA/cm2의 전류 밀도를 인가하여 측정하였다. 또한, 하기 표 1의 T95는 전류 밀도 20 mA/cm2에서 초기 휘도가 95%로 저하할 때까지 측정한 시간을 의미한다.The organic light-emitting devices prepared in the above Experimental Examples and Comparative Experimental Examples were stored in an oven at 100° C. for 30 minutes and subjected to heat treatment, and then voltage, efficiency, and life (T95) were measured by applying a current, and the results are shown in Table 1 below. . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
발광층(호스트)Emissive layer (host) 전압(V)Voltage(V) 효율(cd/A)Efficiency (cd/A) 수명(T95, hr)Life (T95, hr)
실험예 1-1Experimental Example 1-1 화합물 1Compound 1 4.514.51 16.516.5 8383
실험예 1-2Experimental Example 1-2 화합물 2Compound 2 4.564.56 17.017.0 8080
실험예 1-3Experimental Example 1-3 화합물 3Compound 3 4.534.53 16.116.1 8888
실험예 1-4Experimental Example 1-4 화합물 4Compound 4 4.524.52 16.316.3 8585
실험예 1-5Experimental Example 1-5 화합물 5Compound 5 4.594.59 16.816.8 7979
실험예 1-6Experimental Example 1-6 화합물 6Compound 6 4.504.50 16.116.1 8282
실험예 1-7Experimental Example 1-7 화합물 7Compound 7 4.624.62 17.617.6 7272
실험예 1-8Experimental Example 1-8 화합물 8Compound 8 4.664.66 18.118.1 7070
실험예 1-9Experimental Example 1-9 화합물 9Compound 9 4.614.61 17.217.2 7878
실험예 1-10Experimental Example 1-10 화합물 10Compound 10 4.624.62 17.417.4 7676
실험예 1-11Experimental Example 1-11 화합물 11Compound 11 4.634.63 17.617.6 7777
실험예 1-12Experimental Example 1-12 화합물 12Compound 12 4.604.60 17.117.1 8181
비교실험예 1-1Comparative Experimental Example 1-1 RH-ARH-A 5.215.21 12.412.4 4343
비교실험예 1-2Comparative Experimental Example 1-2 RH-BRH-B 4.724.72 7.67.6 2828
비교실험예 1-3Comparative Experimental Example 1-3 RH-CRH-C 5.265.26 12.012.0 4141
비교실험예 1-4Comparative Experimental Example 1-4 RH-DRH-D 4.854.85 14.314.3 6666
비교실험예 1-5Comparative Experimental Example 1-5 RH-ERH-E 4.774.77 14.514.5 6060
비교실험예 1-6Comparative Experimental Example 1-6 RH-FRH-F 4.914.91 13.613.6 5757
비교실험예 1-7Comparative Experimental Example 1-7 RH-GRH-G 5.305.30 13.413.4 4949
비교실험예 1-8Comparative Experimental Example 1-8 RH-HRH-H 5.075.07 14.914.9 3737
비교실험예 1-9Comparative Experimental Example 1-9 RH-IRH-I 5.725.72 4.34.3 1010
실험예 2-1Experimental Example 2-1 PRH-1:화합물 1(40:60)PRH-1: Compound 1 (40:60) 3.853.85 20.520.5 162162
실험예 2-2Experimental Example 2-2 PRH-1:화합물 7(40:60)PRH-1: Compound 7 (40:60) 3.903.90 21.121.1 150150
실험예 2-3Experimental Example 2-3 PRH-2:화합물 3(40:60)PRH-2: Compound 3 (40:60) 3.733.73 21.321.3 156156
실험예 2-4Experimental Example 2-4 PRH-2:화합물 11(40:60)PRH-2: Compound 11 (40:60) 3.823.82 21.821.8 141141
비교실험예 2-1Comparative Experimental Example 2-1 PRH-1:RH-A(40:60)PRH-1:RH-A(40:60) 4.664.66 15.715.7 7373
비교실험예 2-2Comparative Experimental Example 2-2 PRH-1:RH-D(40:60)PRH-1:RH-D(40:60) 4.864.86 12.412.4 5050
비교실험예 2-3Comparative Experimental Example 2-3 PRH-2:RH-E(40:60)PRH-2:RH-E(40:60) 4.134.13 17.317.3 8383
비교실험예 2-4Comparative Experimental Example 2-4 PRH-2:RH-F(40:60)PRH-2:RH-F(40:60) 4.334.33 17.117.1 7777
화학식 1로 표시되는 화합물은 디벤조퓨란의 1번 위치에 전자받개 역할을 하는 함질소헤테로고리가 결합되고 여기에 메타 혹은 파라 방향으로 2환 이상의 축합 아릴기가 연결된 구조를 가지고 있다. 특히, 함질소헤테로고리에도 2환 이상의 축합 아릴기가 연결되어 있어 구조 안에 둘 이상의 축합 아릴기가 존재하는데, RH-A, RH-C, RH-F, RH-G와 같이 축합 아릴기가 하나만 있는 구조들과 비교해 유리 전이 온도가 높아져 박막 상태의 열안정성이 높아진다. RH-A, RH-C, RH-F, RH-G의 구조를 적용한 소자의 경우 열처리 시 낮은 유리 전이 온도로 인해 박막 내 분자 배열의 변화가 일어날 수 있어 표 1에서 보는 바와 같이 소자의 전압 상승, 효율 및 수명의 저하를 초래한다. RH-B의 파이렌 고리와 같은 경우 높은 열안정성을 보여주지만 삼중항 에너지가 너무 낮아져 도펀트로의 에너지 전달에 불리하여 효율이 떨어진다. 따라서, 삼중항 에너지가 너무 낮지 않으면서도 높은 열안정성을 갖으려면 화학식 1과 같이 적당한 축합 아릴기가 구조 내 둘 이상 위치해야 함을 알 수 있다.The compound represented by Formula 1 has a structure in which a nitrogen-containing heterocycle serving as an electron acceptor is bonded to position 1 of dibenzofuran, and two or more condensed aryl groups are connected in the meta or para direction. In particular, two or more condensed aryl groups exist in the structure as two or more condensed aryl groups are connected to the nitrogen-containing heterocycle. Structures with only one condensed aryl group such as RH-A, RH-C, RH-F, and RH-G Compared with, the glass transition temperature is increased and the thermal stability of the thin film state is increased. In the case of devices to which the structures of RH-A, RH-C, RH-F, and RH-G are applied, the molecular arrangement in the thin film may change due to the low glass transition temperature during heat treatment, so the voltage of the device increases as shown in Table 1. , Lead to a decrease in efficiency and life. In the case of the pyrene ring of RH-B, it shows high thermal stability, but the triplet energy is too low, which is disadvantageous in energy transfer to the dopant, resulting in poor efficiency. Therefore, it can be seen that in order to have high thermal stability while the triplet energy is not too low, two or more suitable condensed aryl groups as shown in Formula 1 must be located in the structure.
RH-D 혹은 RH-E와 같이 축합 아릴기가 축합 헤테로아릴기인 경우 분자의 전자의 수송 능력이 떨어져 소자 내부의 전하 균형이 무너져 소자 특성이 저하됨을 알 수 있다. 또한, RH-H와 같이 오쏘로 결합되어 있는 경우 두 치환기 간의 상호 작용에 의해 디벤조퓨란과의 결합력이 약해져 소자 수명 저하가 나타난다. 디벤조퓨란의 2번 위치는 LUMO가 비어있는 자리로 이 위치에 트리아진이 결합하는 RH-I와 같은 구조는 디벤조퓨란과 트리아진 사이의 전자 전달이 안돼 비교실험예 1-9에서 보듯이 모든 소자 특성의 저하가 현격히 나타남을 알 수 있다. It can be seen that when a condensed aryl group such as RH-D or RH-E is a condensed heteroaryl group, the electron transport capacity of the molecule decreases, and the charge balance inside the device is broken, resulting in a decrease in device characteristics. In addition, in the case of ortho-bonding such as RH-H, the bonding strength with dibenzofuran is weakened due to the interaction between the two substituents, resulting in a decrease in device life. The 2nd position of dibenzofuran is the position where LUMO is empty, and the structure like RH-I in which triazine binds to this position does not allow electron transfer between dibenzofuran and triazine, as shown in Comparative Experiment 1-9. It can be seen that the deterioration of the device characteristics appears markedly.
특히, 실험예 2-1 내지 2-4와 같이 화학식 2로 표시되는 화합물과 함께 호스트로서 사용하여 exciplex를 형성하는 경우, 전체적인 소자 특성의 향상이 나타나는데 이 경우도 화학식 1의 화합물이 저전압, 고효율, 및 장수명의 특성 효과가 더 크게 나타남을 확인할 수 있다.In particular, when an exciplex is formed by using as a host with the compound represented by Formula 2 as in Experimental Examples 2-1 to 2-4, the overall device characteristics are improved. In this case, the compound of Formula 1 is also low voltage, high efficiency, And it can be seen that the characteristic effect of the long life appears larger.

Claims (12)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2020002295-appb-I000073
    Figure PCTKR2020002295-appb-I000073
    상기 화학식 1에 있어서,In Formula 1,
    X1 내지 X3은 각각 N 또는 CR21이며, 적어도 하나는 N이고,X 1 to X 3 are each N or CR 21 , at least one is N,
    L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L 1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    L2는 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L 2 is a direct bond; Or a substituted or unsubstituted arylene group,
    R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고,R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
    R1 및 R2 중 적어도 하나는 2환 이상 축합된 아릴기를 포함하며,At least one of R 1 and R 2 includes an aryl group condensed by two or more rings,
    R 및 R21은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R and R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    r은 1 내지 4의 정수이고,r is an integer from 1 to 4,
    r이 2 이상일 경우, R은 같거나 상이하며,When r is 2 or more, R is the same or different,
    Ar은 치환 또는 비치환되고 2환 이상 축합된 아릴기이다.Ar is a substituted or unsubstituted aryl group condensed by two or more rings.
  2. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 또는 1-2로 표시되는 것인 화합물:The compound represented by Formula 1 is a compound represented by the following Formula 1-1 or 1-2:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2020002295-appb-I000074
    Figure PCTKR2020002295-appb-I000074
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2020002295-appb-I000075
    Figure PCTKR2020002295-appb-I000075
    상기 화학식 1-1 및 1-2에 있어서, 각 치환기의 정의는 상기 화학식 1과 동일하다.In Formulas 1-1 and 1-2, the definition of each substituent is the same as in Formula 1.
  3. 청구항 1에 있어서,The method according to claim 1,
    상기 L1 및 L2는 각각 독립적으로, 직접결합; 또는 치환 또는 비치환된 페닐렌기인 것인 화합물.L 1 and L 2 are each independently a direct bond; Or a substituted or unsubstituted phenylene group.
  4. 청구항 1에 있어서,The method according to claim 1,
    상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 또는 치환 또는 비치환된 나프틸기인 것인 화합물.R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  5. 청구항 1에 있어서,The method according to claim 1,
    상기 Ar은 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 또는 치환 또는 비치환된 플루오란테닐기인 것인 화합물.Ar is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluoranthenyl group.
  6. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나인 것인 화합물:The compound represented by Formula 1 is any one selected from the following compounds:
    Figure PCTKR2020002295-appb-I000076
    Figure PCTKR2020002295-appb-I000076
    Figure PCTKR2020002295-appb-I000077
    Figure PCTKR2020002295-appb-I000077
    Figure PCTKR2020002295-appb-I000078
    Figure PCTKR2020002295-appb-I000078
    Figure PCTKR2020002295-appb-I000079
    Figure PCTKR2020002295-appb-I000079
    Figure PCTKR2020002295-appb-I000080
    Figure PCTKR2020002295-appb-I000080
    Figure PCTKR2020002295-appb-I000081
    Figure PCTKR2020002295-appb-I000081
    Figure PCTKR2020002295-appb-I000082
    Figure PCTKR2020002295-appb-I000082
    Figure PCTKR2020002295-appb-I000083
    Figure PCTKR2020002295-appb-I000083
    Figure PCTKR2020002295-appb-I000084
    Figure PCTKR2020002295-appb-I000084
    Figure PCTKR2020002295-appb-I000085
    Figure PCTKR2020002295-appb-I000085
    Figure PCTKR2020002295-appb-I000086
    Figure PCTKR2020002295-appb-I000086
    Figure PCTKR2020002295-appb-I000087
    Figure PCTKR2020002295-appb-I000087
    Figure PCTKR2020002295-appb-I000088
    Figure PCTKR2020002295-appb-I000088
    Figure PCTKR2020002295-appb-I000089
    Figure PCTKR2020002295-appb-I000089
    Figure PCTKR2020002295-appb-I000090
    Figure PCTKR2020002295-appb-I000090
    Figure PCTKR2020002295-appb-I000091
    Figure PCTKR2020002295-appb-I000091
    Figure PCTKR2020002295-appb-I000092
    Figure PCTKR2020002295-appb-I000092
    Figure PCTKR2020002295-appb-I000093
    Figure PCTKR2020002295-appb-I000093
    Figure PCTKR2020002295-appb-I000094
    Figure PCTKR2020002295-appb-I000094
    Figure PCTKR2020002295-appb-I000095
    Figure PCTKR2020002295-appb-I000095
    Figure PCTKR2020002295-appb-I000096
    Figure PCTKR2020002295-appb-I000096
    Figure PCTKR2020002295-appb-I000097
    Figure PCTKR2020002295-appb-I000097
    Figure PCTKR2020002295-appb-I000098
    Figure PCTKR2020002295-appb-I000098
    Figure PCTKR2020002295-appb-I000099
    .
    Figure PCTKR2020002295-appb-I000099
    .
  7. 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 6 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 6 Light-emitting element.
  8. 청구항 7에 있어서, The method of claim 7,
    상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an emission layer, and the emission layer includes the compound.
  9. 청구항 7에 있어서,The method of claim 7,
    상기 유기물층은 발광층을 포함하고, 상기 발광층은 호스트 물질을 포함하며, 상기 호스트 물질은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an emission layer, the emission layer includes a host material, and the host material includes the compound.
  10. 청구항 8에 있어서,The method of claim 8,
    상기 발광층은 하기 화학식 2로 표시되는 화합물을 더 포함하는 것인 유기 발광 소자: The light emitting layer is an organic light emitting device further comprising a compound represented by the following formula (2):
    [화학식 2][Formula 2]
    Figure PCTKR2020002295-appb-I000100
    Figure PCTKR2020002295-appb-I000100
    상기 화학식 2에 있어서,In Formula 2,
    A는 방향족 탄화수소 고리이고,A is an aromatic hydrocarbon ring,
    L11 및 L12는 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,L 11 and L 12 are each independently a direct bond; Or a substituted or unsubstituted arylene group,
    Ar11는 치환 또는 비치환된 아릴기이고,Ar 11 is a substituted or unsubstituted aryl group,
    Ar12는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar 12 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    R11은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    n은 1 내지 10의 정수이며,n is an integer from 1 to 10,
    n이 2 이상인 경우, R11은 서로 같거나 상이하다.When n is 2 or more, R 11 are the same as or different from each other.
  11. 청구항 10에 있어서, The method of claim 10,
    상기 화학식 2는 하기 화합물 중 어느 하나로 표시되는 것인 유기 발광 소자:Formula 2 is an organic light-emitting device represented by any one of the following compounds:
    Figure PCTKR2020002295-appb-I000101
    Figure PCTKR2020002295-appb-I000101
    Figure PCTKR2020002295-appb-I000102
    Figure PCTKR2020002295-appb-I000102
    Figure PCTKR2020002295-appb-I000103
    Figure PCTKR2020002295-appb-I000103
    Figure PCTKR2020002295-appb-I000104
    Figure PCTKR2020002295-appb-I000104
    Figure PCTKR2020002295-appb-I000105
    Figure PCTKR2020002295-appb-I000105
    Figure PCTKR2020002295-appb-I000106
    Figure PCTKR2020002295-appb-I000106
    Figure PCTKR2020002295-appb-I000107
    Figure PCTKR2020002295-appb-I000107
    Figure PCTKR2020002295-appb-I000108
    Figure PCTKR2020002295-appb-I000108
    Figure PCTKR2020002295-appb-I000109
    Figure PCTKR2020002295-appb-I000109
    Figure PCTKR2020002295-appb-I000110
    Figure PCTKR2020002295-appb-I000110
    Figure PCTKR2020002295-appb-I000111
    Figure PCTKR2020002295-appb-I000111
    Figure PCTKR2020002295-appb-I000112
    Figure PCTKR2020002295-appb-I000112
    Figure PCTKR2020002295-appb-I000113
    Figure PCTKR2020002295-appb-I000113
    Figure PCTKR2020002295-appb-I000114
    .
    Figure PCTKR2020002295-appb-I000114
    .
  12. 청구항 7에 있어서,The method of claim 7,
    상기 유기물층은 발광층, 정공 주입층, 정공 수송층, 전자 주입층, 전자 수송층, 전자 저지층 및 정공 저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.The organic material layer further comprises one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
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WO2021182834A1 (en) * 2020-03-09 2021-09-16 주식회사 엘지화학 Novel compound and organic light-emitting device using same
US11696501B2 (en) * 2020-10-26 2023-07-04 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
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