WO2020171530A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2020171530A1
WO2020171530A1 PCT/KR2020/002294 KR2020002294W WO2020171530A1 WO 2020171530 A1 WO2020171530 A1 WO 2020171530A1 KR 2020002294 W KR2020002294 W KR 2020002294W WO 2020171530 A1 WO2020171530 A1 WO 2020171530A1
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서상덕
정민우
이동훈
장분재
이정하
한수진
박슬찬
황성현
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주식회사 엘지화학
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Priority to CN202080006309.5A priority Critical patent/CN113166124A/zh
Publication of WO2020171530A1 publication Critical patent/WO2020171530A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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 ring containing N serving as an electron acceptor in the same benzene ring of dibenzofuran is located at position 3 of dibenzofuran, substituted or unsubstituted serving as an electron donor, and two or more rings
  • the condensed aryl group is substituted at the 1 position of dibenzofuran. 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 meta positions, the steric hindrance effect is less than that of the ortho position, so the stability of the material is high. High efficiency and long life can be obtained when used.
  • 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 group examples 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, tetrazol 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.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • 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 2 are N.
  • X 3 is N.
  • X 3 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; Substituted or unsubstituted cycloalkyl*; 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 any one of the following Formulas 1-1 to 1-4.
  • 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 may be green or red.
  • the emission layer including the compound represented by Formula 1 has an emission wavelength in a region of 500 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 Brene, 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 Brene, 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.
  • compound 1-1 (15.0g, 45.6mmol) and bis(pinacolato)diboron (12.7g, 50.2mmol) were stirred while refluxing in 300ml of 1,4-dioxane. After that, potassium acetate (6.7 g, 68.4 mmol) was added and sufficiently stirred, and then bis (dibenzylideneacetone) palladium (0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. Was put in. After reacting for 8 hours, cooling to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled.
  • a glass substrate coated with a thin film of 1,400 ⁇ of ITO Indium Tin Oxide
  • 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
  • the deposition rate of silver and magnesium was 2 ⁇ /sec.
  • An organic light-emitting device was manufactured by maintaining ⁇ 10 -7 to 5 ⁇ 10 -6 torr.
  • 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 Chemical Formula 1 has a structure in which a nitrogen-containing heterocycle serving as an electron acceptor is bonded to position 3 of dibenzofuran, and two or more fused aryl groups are connected in the meta direction.
  • two or more condensed aryl groups exist in the structure as two or more condensed aryl groups are also connected to the nitrogen-containing heterocycle.
  • the thermal stability of the state increases.
  • a change in the molecular arrangement in the thin film may occur due to a low glass transition temperature during heat treatment, resulting in an increase in the voltage of the device and a decrease in efficiency and lifetime as shown in Table 1. do.

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/002294 2019-02-19 2020-02-18 Composé et dispositif électroluminescent organique le comprenant WO2020171530A1 (fr)

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