WO2020080849A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2020080849A1
WO2020080849A1 PCT/KR2019/013658 KR2019013658W WO2020080849A1 WO 2020080849 A1 WO2020080849 A1 WO 2020080849A1 KR 2019013658 W KR2019013658 W KR 2019013658W WO 2020080849 A1 WO2020080849 A1 WO 2020080849A1
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compound
group
substituted
unsubstituted
formula
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윤정민
김공겸
구기동
오중석
오상민
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주식회사 엘지화학
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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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—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
    • H10K85/657—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, 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.
  • Patent Document US Patent Application Publication No. 2004-0251816
  • the present specification provides a compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by Formula 1 below.
  • A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocycle,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted alkyl group, or combine with each other to form a ring,
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a1 and a2 are integers from 0 to 4,
  • a3 and a4 are integers from 0 to 3
  • R 1 is the same as or different from each other
  • R 2 is the same as or different from each other
  • R 3 is the same as or different from each other
  • R 4 is the same as or different from each other.
  • the present specification is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device including the compound.
  • the compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using this, it is possible to improve efficiency, improve low driving voltage, and / or life characteristics in the organic light emitting device.
  • the compound according to an exemplary embodiment of the present specification can improve the efficiency and life of the OLED device by simultaneously controlling the electrical and luminescence properties, so that the compound of the existing simple spiro structure (for example, dimethylfluorene) Compared to the organic light emitting device employing, it may have high efficiency, low driving voltage, high brightness, and long life.
  • the compound of the existing simple spiro structure for example, dimethylfluorene
  • FIG. 1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.
  • FIG. 2 shows an organic light emitting diode according to an exemplary embodiment of the present specification.
  • FIG 3 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocycle,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted alkyl group, or combine with each other to form a ring with each other,
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a1 and a2 are integers from 0 to 4,
  • a3 and a4 are integers from 0 to 3
  • R 1 is the same as or different from each other
  • R 2 is the same as or different from each other
  • R 3 is the same as or different from each other
  • R 4 is the same as or different from each other.
  • the compound according to the exemplary embodiment of the present specification includes fluorene in which two adamantines are substituted in the core (A), so that the core structure has large bulkiness and rigidity, and is excellent.
  • the luminous efficiency increases and the thermal stability is excellent due to the sublimation and stability of the chemical structure.
  • substitution 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 to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substitution includes two hydrogen atoms bonded to a carbon atom of a compound, each of which is replaced with a different substituent to combine with each other to form a ring.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile 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 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents.
  • the "substituent in which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms.
  • Specific examples include methyl groups; 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-ethyl butyl 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; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-oct
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms.
  • the amine group is -NH 2 ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluoren
  • the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc 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; tert-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.
  • 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 is preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms.
  • a phenyl group; Biphenyl group; It may be a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited.
  • a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group, and the like, but is not limited thereto.
  • two substituents of carbon number 9 of the fluorenyl group may be bonded to each other to form a spiro structure such as 9,9-dimethylfluorenyl group or 9,9-diphenylfluorenyl group.
  • a spiro structure such as 9,9-dimethylfluorenyl group or 9,9-diphenylfluorenyl group.
  • the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. You can. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • ring is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group, except for the divalent group.
  • heterocyclic groups can be applied to the heterocycle except that it is divalent.
  • 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 can be selected from the examples of the aryl group described above.
  • the heterocyclic group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se, SO, SO 2 and S, etc. It can contain.
  • the number of carbon atoms is not particularly limited, preferably 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • heteroaryl group examples include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Ph
  • A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocyclic ring.
  • the aromatic ring may be applied to the description of the aromatic hydrocarbon ring described above.
  • A is a substituted or unsubstituted divalent aromatic ring having 6 to 60 carbon atoms;
  • a substituted or unsubstituted hetero element is a divalent heterocycle having 2 to 60 carbon atoms containing at least one of N, O, S, SO and SO 2 .
  • the amine group bound to A may be bonded to the core structure of A or a substituent.
  • A may be represented by [A1] a-[A2] b-[A3] c, wherein A1 to A3 are the same as or different from each other, and each independently substituted or unsubstituted Aromatic ring, a, b and c are 0 or 1, respectively, and a + b + c is an integer from 1 to 3.
  • A has a structure of [A1] a-[A2] b-[A3] c, it may be combined in the order of [phenylene]-[fluorenylene]-[phenylene], and number 9 of fluorenylene It may have a structure in which a divalent phenylene is bonded to a carbon atom.
  • A is a substituted or unsubstituted divalent 1 to 8 ring aromatic ring; Or a substituted or unsubstituted divalent 1 to 8 ring heterocycle.
  • A is a substituted or unsubstituted divalent 1 to 8 ring condensed aromatic ring; Or a substituted or unsubstituted divalent 1 to 8 ring condensed heterocycle.
  • A is represented by any one of the following [Chemical Formula 1-1] to [Chemical Formula 1-10].
  • X 1 to X 16 are the same as or different from each other, and each independently O; S; SO; SO 2 ; Or CR'R ",
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; nitrile group; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted silyl group; substituted or An unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted ring,
  • n1 to n9, and m1 to m9 are integers from 0 to 2
  • rings in parentheses may overlap.
  • A is represented by one of the following structural formulas.
  • X is O; S; SO; SO 2 ; Or CR'R ".
  • X 1 to X 14 are the same as or different from each other, and each independently O; S; SO; SO 2 ; Or CR'R ".
  • the R 'and R are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Or, they combine with each other to form a substituted or unsubstituted C 2 to C 60 ring.
  • R 'and R are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 60 carbon atoms, or in combination with each other, having 2 to 60 carbon atoms. Form a ring.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A heteroaryl group containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A heteroaryl group having 2 to 60 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A heteroaryl group having 2 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A heteroaryl group having 2 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • the 'substituted or unsubstituted' is deuterium; Halogen group; Nitrile group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 30 carbon atoms; A silyl group having 1 to 30 carbon atoms; And it means that one or more selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms is substituted or unsubstituted with a linked substituent.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted butyl group.
  • the 'substituted or unsubstituted' is deuterium; Halogen group; Nitrile group; Methyl group; Ethyl group; Butyl group; Phenyl group; Biphenyl group; Toughness group; Naphthyl group; Trimethylsilyl group; Triphenylsilyl group; Dimethylfluorenyl group; Dibenzofuranyl group; Dibenzothiophene group; And one or more substituents selected from the group consisting of carbazole, substituted or unsubstituted.
  • R 1 and R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R 1 and R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted silyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R 1 and R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R 1 and R 4 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Butyl group; Cyclopentyl group; Cyclohexyl group; Or a phenyl group.
  • a1 and a2 are 0 or 1, respectively.
  • a3 and a4 are 0 or 1, respectively.
  • Chemical Formula 1 is any one selected from the following compounds.
  • the organic light emitting device of the present invention comprises a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer may include the above-described compound.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.
  • FIG. 1 a structure of an organic light emitting device in which the first electrode 2, the organic material layer 3, and the second electrode 4 are sequentially stacked on the substrate 1 is illustrated.
  • FIG 1 illustrates an organic light emitting device and is not limited thereto.
  • FIG. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 5, and a second electrode 4 are sequentially stacked on a substrate 1.
  • FIG. 2 illustrates an organic light emitting device, and is not limited thereto, and may further include an additional organic material layer between the first electrode 2 and the light emitting layer 5 and the light emitting layer 5 and the second electrode 4. have.
  • FIG. 3 a first electrode 2, a hole injection layer 6, a hole transport layer-1 (7), a hole transport layer-2 (8), a light emitting layer 5, an electron transport layer 9 and a first electrode on the substrate 1 are shown in FIG.
  • the structure of the organic light emitting device in which the two electrodes 4 are sequentially stacked is illustrated.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 above.
  • the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant (host: dopant) in a mass ratio of 99.9: 0.1 to 80:20.
  • the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant (host: dopant) in a mass ratio of 99.9: 0.1 to 90:10.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a dopant.
  • the organic material layer includes at least one layer of a hole injection layer, a hole transport layer, and a hole injection and transport layer, and at least one layer of the hole injection layer, a hole transport layer, and a hole injection and transport layer is The compound of Formula 1 may be included.
  • the organic material layer includes at least one layer of an electron injection layer, an electron transport layer, and an electron injection and transport layer, and at least one layer of the electron injection layer, the electron transport layer, and the electron injection and transport layer is The compound of Formula 1 may be included.
  • the organic material layer includes one or more of the electron blocking layer and the hole blocking layer, and the electron blocking layer and / or the hole blocking layer may include the compound of 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 materials and methods known in the art, except that at least one layer of the organic material layer is formed using the compound.
  • the present specification also provides a method of manufacturing an organic light emitting device formed using the compound.
  • the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and then form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer containing the compound of Formula 1, and then use a material that can be used as a cathode thereon. It can be produced by vapor deposition.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • a hole injection material can be well injected from the anode at a low voltage, and it is preferable that the hole injection material has a high occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic material layer.
  • HOMO occupied molecular orbital
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable as a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • the dopant material examples include an aromatic compound, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound.
  • a compound in which at least one arylvinyl group is substituted with an arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted.
  • aryl group a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
  • examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • 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 light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that prevents the cathode from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
  • the compound represented by Formula 1 may be prepared by a manufacturing method according to the multi-step reaction of Scheme 1 below.
  • Scheme 1 below may be more specific in the production examples to be described later.
  • a glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves.
  • a dispersing agent a product of Fischer Co. was used, and distilled water was used by Millipore Co. Distilled water filtered secondarily was used as a filter of the product. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
  • the following HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer.
  • the following HT-A 1000 Pa was vacuum-deposited as a hole transport layer, and the following HT-B 100 Pa was deposited.
  • the compound 1 of Preparation Example 1 was doped with 4 wt% as a dopant in the following H-A as a host as a light emitting layer, and then vacuum-deposited to a thickness of 200 Pa.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • LiF was 0.2 ⁇ / sec
  • aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
  • Example 2 to 120 and Comparative example 1 to 8 Preparation of organic light emitting device
  • Example 1 When manufacturing the organic light emitting device of Example 1, using the compounds of Table 1 and Table 2 below instead of HA as a light emitting layer host, using the compounds of Table 1 and Table 2 instead of Compound 1 of Preparation Example 1 as a light emitting layer dopant An organic light emitting device was manufactured in the same manner as in Example 1 except for the above.
  • the driving voltage and luminous efficiency of the organic light emitting devices of Examples 1 to 120 and Comparative Examples 1 to 8 were measured at a current density of 10 mA / cm 2 , and 95% of the initial luminance at a current density of 20 mA / cm 2 was Time (LT95) was measured.
  • the results are shown in Table 1 and Table 2 below.
  • Examples 1 to 120 of the present application have lower driving voltages of devices than Comparative Examples 1 to 8, and are very excellent in efficiency and lifespan characteristics.

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/013658 2018-10-17 2019-10-17 Composé et dispositif électroluminescent organique le comprenant WO2020080849A1 (fr)

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WO2020248755A1 (fr) * 2019-06-14 2020-12-17 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, dispositif électroluminescent organique et dispositif de conversion photoélectrique
EP3845522A1 (fr) * 2019-12-31 2021-07-07 Shaanxi Lighte Optoelectronics Material Co., Ltd. Composé contenant de l'azote, élément électronique et dispositif électronique
CN113321589A (zh) * 2020-02-28 2021-08-31 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
WO2021170008A1 (fr) * 2020-02-28 2021-09-02 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, composant électronique et dispositif électronique
KR20220100986A (ko) * 2020-04-27 2022-07-18 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 질소 함유 화합물, 전자 소자 및 전자 장치
WO2022157599A1 (fr) * 2021-01-22 2022-07-28 株式会社半導体エネルギー研究所 Composé organique, dispositif luminescent, appareil luminescent, appareil électronique et dispositif d'éclairage
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WO2020248755A1 (fr) * 2019-06-14 2020-12-17 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, dispositif électroluminescent organique et dispositif de conversion photoélectrique
US11611043B1 (en) 2019-06-14 2023-03-21 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic component and electronic device
US10985324B2 (en) 2019-06-14 2021-04-20 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, organic electroluminescent device and photoelectric conversion device
CN111875505B (zh) * 2019-12-20 2021-10-08 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置
WO2021120835A1 (fr) * 2019-12-20 2021-06-24 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, dispositif électroluminescent organique et appareil électronique
US11608311B2 (en) 2019-12-20 2023-03-21 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, organic electroluminescent device, and electronic apparatus
CN111875505A (zh) * 2019-12-20 2020-11-03 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置
US11203584B2 (en) 2019-12-31 2021-12-21 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic element and electronic device
WO2021135207A1 (fr) * 2019-12-31 2021-07-08 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, élément électronique et dispositif électronique
EP3845522A1 (fr) * 2019-12-31 2021-07-07 Shaanxi Lighte Optoelectronics Material Co., Ltd. Composé contenant de l'azote, élément électronique et dispositif électronique
US11827615B2 (en) 2019-12-31 2023-11-28 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic element and electronic device
CN113321589A (zh) * 2020-02-28 2021-08-31 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
WO2021170008A1 (fr) * 2020-02-28 2021-09-02 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, composant électronique et dispositif électronique
CN113321589B (zh) * 2020-02-28 2023-03-28 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
KR102512339B1 (ko) 2020-04-27 2023-03-23 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 질소 함유 화합물, 전자 소자 및 전자 장치
KR20220100986A (ko) * 2020-04-27 2022-07-18 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 질소 함유 화합물, 전자 소자 및 전자 장치
CN111777517A (zh) * 2020-04-30 2020-10-16 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN111777517B (zh) * 2020-04-30 2021-06-01 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
US11718583B2 (en) 2020-04-30 2023-08-08 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic component using same and electronic device
WO2021218588A1 (fr) * 2020-04-30 2021-11-04 陕西莱特光电材料股份有限公司 Composé contenant de l'azote, composant électronique l'utilisant et dispositif électronique
CN111848501A (zh) * 2020-05-08 2020-10-30 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN111848501B (zh) * 2020-05-08 2021-06-01 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
US11691952B2 (en) 2020-05-08 2023-07-04 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, and electronic element and electronic device using same
WO2022157599A1 (fr) * 2021-01-22 2022-07-28 株式会社半導体エネルギー研究所 Composé organique, dispositif luminescent, appareil luminescent, appareil électronique et dispositif d'éclairage

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