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WO2019164340A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019164340A1
WO2019164340A1 PCT/KR2019/002223 KR2019002223W WO2019164340A1 WO 2019164340 A1 WO2019164340 A1 WO 2019164340A1 KR 2019002223 W KR2019002223 W KR 2019002223W WO 2019164340 A1 WO2019164340 A1 WO 2019164340A1
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group
substituted
unsubstituted
light emitting
formula
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Korean (ko)
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서상덕
홍성길
차용범
김성소
천민승
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LG Chem Ltd
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device formed using the heterocyclic compound.
  • organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present specification provides a heterocyclic compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
  • X and Y are the same as or different from each other, and each independently represent a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring, and in combination with each other, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, Or a heterocycle including substituted or unsubstituted O or S,
  • A1 and A2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • R1 is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted alkoxy group , A substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring,
  • a is an integer of 0 to 3
  • another exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound.
  • the heterocyclic compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the same, the efficiency of the organic light emitting device may be improved, and high color purity may be obtained.
  • FIG. 1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked 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 linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic.
  • carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferable that it is C1-C20. More specifically, it is preferable that it is C1-C10.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • the amine group may be an arylamine group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
  • Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.
  • R2, R3, R6 and R7 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 silyl group, substituted or unsubstituted amine group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring,
  • Z1 and Z2 are the same as or different from each other, and each independently O or S,
  • b, c, f and g are integers from 0 to 4,
  • Chemical Formula 1 is represented by any one selected from the following Chemical Formulas 4 to 6.
  • Z3 is O or S
  • R2 to R7 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 silyl group, substituted or unsubstituted amine group, substituted or unsubstituted Alkoxy group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring,
  • b1 and c1 are each an integer of 0 to 3
  • d and e are each an integer of 0 to 8
  • the R2, R3, R8 and R9 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 silyl A group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring. Can be formed.
  • the R2, R3, R8 and R9 are the same as or different from each other, and each independently hydrogen; Nitrile group; Halogen group; An aryl group unsubstituted or substituted with a silyl group or an alkyl group; An alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or an N, O, or S-containing heteroaryl group having 3 to 10 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • the R2 and R3 are the same as or different from each other, and each independently hydrogen; An alkyl group; Or an alkylsilyl group.
  • the R2 and R3 are the same as or different from each other, and each independently hydrogen; An alkyl group; Or an alkylsilyl group.
  • the R2 and R3 are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; An alkylsilyl group having 1 to 10 carbon atoms.
  • the R2 and R3 are the same as or different from each other, and each independently hydrogen; Terbutyl group; Or trimethylsilyl group.
  • R1 is hydrogen; An alkyl group having 1 to 10 carbon atoms; A cycloalkyl group having 3 to 10 carbon atoms; Silyl groups substituted with alkyl groups having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 3 to 20 carbon atoms.
  • R1 is hydrogen; An alkyl group having 1 to 10 carbon atoms; A cycloalkyl group having 3 to 10 carbon atoms; Silyl groups substituted with alkyl groups having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group containing N, O, or S having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group.
  • R1 is hydrogen; Methyl group; Ethyl group; Profile group; Butyl group; Terbutyl group; An amine group unsubstituted or substituted with a phenyl group; Carbazole groups; Cyclohexyl group; Trimethylsilyl group; It is a phenophoto group, a phenothiazine group, or a dimethyldihydroacridine group.
  • R1 is hydrogen; Methyl group; Terbutyl group; An amine group unsubstituted or substituted with a phenyl group; Carbazole groups; Cyclohexyl group; Trimethylsilyl group; It is a phenophoto group, a phenothiazine group, or a dimethyldihydroacridine group.
  • the R4 and R5 are the same as or different from each other, each independently represent an aryl group having 6 to 30 carbon atoms.
  • R4 and R5 is a phenyl group.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen or an alkyl group.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen or an alkyl group having 1 to 10 carbon atoms.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen, methyl, ethyl, propyl, butyl, pentyl, or hexyl.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen or a methyl group.
  • the R8 and R9 are the same as or different from each other, and each independently hydrogen; An alkyl group; Alkylsilyl group; Or an alkoxy group.
  • the R8 and R9 are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; An alkylsilyl group having 1 to 10 carbon atoms; Or an alkoxy group having 1 to 10 carbon atoms.
  • the R8 and R9 are the same as or different from each other, and each independently hydrogen; Terbutyl group; Trimethylsilyl group; Or a methoxy group.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • A1 and A2 are the same as or different from each other, and each independently contain a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted N, O, or S It is a C3-C20 heteroaryl group.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted polycyclic polycyclic group having 6 to 20 carbon atoms Monocyclic heteroaryl group having 3 to 20 carbon atoms containing an aryl group, substituted or unsubstituted N, O, or S, or polycyclic having 3 to 20 carbon atoms containing substituted or unsubstituted N, O, or S Heteroaryl group.
  • A1 and A2 are the same as or different from each other, and each independently a monocyclic having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or an alkylsilyl group having 1 to 10 carbon atoms Aryl group; Or a C6-C20 polycyclic aryl group unsubstituted or substituted with a C1-C10 alkyl group or a C1-C10 alkylsilyl group.
  • A1 and A2 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and the monocyclic or polycyclic aryl group having 6 to 20 carbon atoms is a methyl group, Substituted or unsubstituted with one or more substituents selected from the group consisting of ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, pentyl group, hexyl group, and trimethylsilyl group.
  • A1 and A2 are the same as or different from each other, and each independently a phenyl group or a biphenyl group, and the phenyl group or biphenyl group is one selected from the group consisting of a methyl group, a terbutyl group, or a trimethylsilyl group It is substituted by the above substituent.
  • heterocyclic compound of Formula 1 may be represented by any one of the following structural formula.
  • the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include a heterocyclic compound of Chemical Formula 1.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention 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 and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and one or more of the layers may include the compound.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
  • the first electrode 2 the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, and the electron injection layer
  • the structure of the organic light emitting device in which 10) and the second electrode 4 are sequentially stacked is illustrated.
  • 1 and 2 illustrate an organic light emitting diode and are not limited thereto.
  • the organic light emitting device has a structure in which a substrate, a first electrode, an organic material layer, and a second electrode are sequentially stacked.
  • the organic light emitting device has a structure in which a substrate, a first electrode, a hole injection layer, an electron blocking layer, a light emitting layer, an electron injection layer, and a second electrode are sequentially stacked.
  • the organic light emitting device has a structure in which a substrate, a first electrode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron injection layer, and a second electrode are sequentially stacked.
  • the organic light emitting device has a structure in which a substrate, a first electrode, a hole injection layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode are sequentially stacked.
  • the organic light emitting device has a structure in which a substrate, a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode are sequentially stacked. .
  • the organic material layer including the heterocyclic compound of Formula 1 may include a light emitting layer, and may include the heterocyclic compound of Formula 1 in the light emitting layer.
  • the organic material layer including the heterocyclic compound of Formula 1 may include a light emitting layer, and may include the heterocyclic compound of Formula 1 as a dopant of the light emitting layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a host and a dopant in a weight ratio of 99: 1 to 1:99.
  • the organic material layer including the heterocyclic compound of Formula 1 includes a light emitting layer, and includes a host and a dopant in a weight ratio of 99: 1 to 50:50 in the light emitting layer.
  • the organic material layer including the heterocyclic compound of Formula 1 may include a light emitting layer, and an organic compound may be used as a host of the light emitting layer.
  • the organic material layer including the heterocyclic compound of Formula 1 may include a light emitting layer, and an anthracene-based organic compound may be used as a host of the light emitting layer.
  • the organic material layer including the heterocyclic compound of Formula 1 includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer is the heterocyclic ring It may include a compound.
  • the organic material layer including the heterocyclic compound of Formula 1 includes an electron injection layer, an electron transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer or the hole blocking layer is the heterocyclic ring. It may include a compound.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate.
  • PVD metal vapor deposition
  • 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 a heterocyclic compound of the formula (1), and then used as a cathode thereon It can be prepared by depositing.
  • 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 anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2: Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, 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.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include heterocyclic compounds, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may 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 heterocyclic compound.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting 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 present specification also provides a method of manufacturing an organic light emitting device formed using the heterocyclic compound.
  • preparing a substrate Forming a cathode or anode on the substrate; Forming at least one organic layer on the cathode or anode; And forming an anode or a cathode on the organic layer, wherein at least one layer of the organic layer is formed using the heterocyclic compound.
  • Dopant materials include aromatic heterocyclic compounds, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic heterocyclic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • 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 transporting material is a material that can inject electrons well from the cathode and transfer the electrons to the light emitting layer. Suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer for preventing the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,400 ⁇ was placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • Fischer Co. Decon TM CON705 product was used as a detergent, and distilled water was filtered secondly with a 0.22 ⁇ m sterilizing filter from Millerpore Co ..
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried and then transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • HI-A and LG-101 were thermally vacuum deposited to a thickness of 650 kPa and 50 kPa, respectively, on the prepared ITO transparent electrode to form a hole injection layer.
  • the following HT-A was vacuum deposited to a thickness of 600 kPa as the hole transport layer
  • the following HT-B was thermally vacuum deposited to a thickness of 50 kPa as the electron blocking layer.
  • BH-A and Compound 1 were vacuum deposited in a light emitting layer at a thickness of 200 kPa in a weight ratio of 96: 4.
  • a compound represented by ET and Liq was thermally vacuum deposited to a thickness of 360 kPa in a weight ratio of 1: 1 as the electron transporting layer, and then the compound represented by Liq was vacuum deposited to a thickness of 5 kPa to form an electron injection layer.
  • Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 and aluminum was deposited at a thickness of 1000 kW to form a cathode, thereby manufacturing an organic light emitting device.
  • the organic light emitting diodes of Examples 2 to 6, Comparative Example 1, and Comparative Example 2 were manufactured by the same method as Example 1, except that the compounds shown in Table 1 were used instead of the dopant materials in Example 1. Each was produced.
  • the current was applied to the organic light emitting diodes manufactured in Examples 1 to 6 and Comparative Examples 1 to 2, and the voltage, efficiency, and lifetime (T95) were measured, and the results are shown in Table 1 below.
  • voltage and efficiency were measured by applying a current density of 10 mA / cm 2 and T95 means the time until the initial luminance drops to 95% at a current density of 20 mA / cm 2 .

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1, et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/002223 2018-02-23 2019-02-22 Composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2019164340A1 (fr)

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JP2024170578A (ja) * 2019-01-11 2024-12-10 三星ディスプレイ株式會社 有機電界発光素子及び有機電界発光素子用多環化合物

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EP4291000A4 (fr) * 2021-11-26 2024-10-09 Kunshan Go-Visionox Opto-Electronics Co., Ltd. Dispositif électroluminescent organique et dispositif d'affichage

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