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WO2020080872A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2020080872A1
WO2020080872A1 PCT/KR2019/013722 KR2019013722W WO2020080872A1 WO 2020080872 A1 WO2020080872 A1 WO 2020080872A1 KR 2019013722 W KR2019013722 W KR 2019013722W WO 2020080872 A1 WO2020080872 A1 WO 2020080872A1
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light emitting
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Korean (ko)
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윤정민
김공겸
구기동
오중석
오상민
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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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • 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
    • 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 heterocyclic 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, 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 heterocyclic compound and an organic light emitting device including the same.
  • the present invention provides a heterocyclic compound represented by Formula 1 below.
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 , R 51 to R 55 , And R 61 to R 64 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 cycloalkyl group, substituted or unsubstituted alkoxy group, substituted Or an unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or adjacent Combines with a substituent to form a substituted or unsubstituted ring,
  • 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 includes the above-described heterocyclic compound. to provide.
  • the heterocyclic 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 lifespan characteristics in the organic light emitting device.
  • the heterocyclic compound of the present specification has a small half width in structure, it can exhibit high efficiency characteristics in a device.
  • 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.
  • the present specification provides a heterocyclic compound represented by Chemical Formula 1 above.
  • the existing spiro structure has a right-angled structure based on the carbon atom in the center, or limits the characteristics of enhancing luminous efficiency by suppressing the interaction between molecules and controlling the wavelength using simple cyclization compounds such as dimethylfluorene. It is possible to improve the efficiency and lifetime of the OLED device by controlling the electrical and luminescence properties using new materials including adamantane.
  • the core including boron and nitrogen has a small half width, and thus exhibits high efficiency characteristics in the device.
  • 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.
  • substituted or unsubstituted refers to deuterium; 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 may be represented by the formula of -NRdRe, wherein Rd and Re are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; It may be a substituted or unsubstituted heterocyclic group, but is not limited thereto. Further, the number of carbon atoms of the amine group is not 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; A substituted or unsubstituted cycloalkyl group; 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 60 carbon atoms, more preferably 6 to 30 carbon atoms.
  • the aryl group may be monocyclic or polycyclic.
  • 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
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 , R 51 to R 55 and R 61 to R 64 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 cycloalkyl group, substituted or unsubstituted Alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted amine group, substituted or unsubstituted boron group, substituted or unsubstituted aryl group, substituted or unsubstituted hetero A ring group, or combine with an adjacent substituent to form a substituted or unsubstituted ring, and R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 ,
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 , And R 51 to R 55 , a substituent that does not bind to Formula 2; And R 61 to R 64 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cyclo group having 3 to 30 carbon atoms.
  • Alkyl group substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted silyl group having 1 to 60 carbon atoms, substituted or unsubstituted amine group having 1 to 30 carbon atoms, substituted or unsubstituted 6 to 60 carbon atoms
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, silyl group having 1 to 30 carbon atoms, carbon number 1 It means that one or more selected from the group consisting of an amine group having 30 to 30, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms is substituted or unsubstituted with a connected substituent.
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 , And R 51 to R 55 , a substituent that does not bind to Formula 2; And R 61 to R 64 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted Or an unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group , Substituted or unsubsti
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted Substituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted methoxy group, substituted or unsubstituted ethoxy group, substituted Or an unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamine group, a substituted or unsub
  • Chemical Formula 1 is represented by one of the following Chemical Formulas 1-1 to 1-7.
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43, R 51 to R 55 , and R 61 to R 64 are as defined in Formulas 1 and 2,
  • R 71 to R 74 , R 81 to R 84 , R 91 to R 94 , And Ra to Re 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 cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted A substituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or in combination with an adjacent substituent, substituted or unsubstituted Form a ring,
  • a and c are each an integer from 0 to 3
  • b and f are each 0 or 1
  • d and e are each an integer from 0 to 2
  • the R 71 To R 74 , R 81 to R 84 , R 91 to R 94 , And Ra to Re are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted Or an unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or by combining with an adjacent substituent, a substituted or
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, silyl group having 1 to 30 carbon atoms, carbon number 1 It means that one or more selected from the group consisting of an amine group having 30 to 30, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms is substituted or unsubstituted with a connected substituent.
  • R 71 To R 74 , R 81 To R 84 , R 91 To R 94 , And Ra to Re are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted Substituted butyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted methoxy group, substituted Or an unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsub
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted Substituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted methoxy group, substituted or unsubstituted ethoxy group, substituted Or an unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamine group, a substituted or unsub
  • Chemical Formula 1 is represented by one of the following Chemical Formulas 2-1 to 2-5.
  • R 11 to R 14 , R 21 to R 24 , R 31 to R 35 , R 41 to R 43 , and R 51 to R 55 are as defined in Chemical Formulas 1 and 2,
  • X 1 and X 2 are the same as or different from each other, and each independently O, S or NR,
  • R, R 101 to R 111 , and R 201 to R 228 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 cycloalkyl group, substituted Or an unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or Unsubstituted heterocyclic group,
  • n1 to n9 are each an integer of 0 to 2
  • n10 and n11 are each an integer from 0 to 4,
  • n1 to n11 are each 2 or more, the substituents in parentheses are the same as or different from each other.
  • the R, R 101 to R 111 and R 201 to R 228 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted carbon number 1 To 20 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted silyl groups having 1 to 60 carbon atoms, substituted or unsubstituted carbon atoms It is an amine group of 1 to 30, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or bonded to each other with adjacent substituents to have 3 or more unsubstituted or substituted carbon atoms.
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, silyl group having 1 to 30 carbon atoms, carbon number 1 It means that one or more selected from the group consisting of an amine group having 30 to 30, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms is substituted or unsubstituted with a connected substituent.
  • R, R 101 to R 111 and R 201 to R 228 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group , Substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group , Substituted or unsubstituted cyclohexyl group, substituted or unsubstituted methoxy group, substituted or unsubstituted ethoxy group, substituted or unsubstituted trimethylsilyl group, substituted or unsubstituted triphenylsilyl group, substituted or unsubstituted triphen
  • the 'substituted or unsubstituted' is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted Substituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted methoxy group, substituted or unsubstituted ethoxy group, substituted Or an unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamine group, a substituted or unsub
  • Chemical Formula 1 is any one selected from the following compounds.
  • D deuterium Me is a methyl group
  • Ph means a phenyl group.
  • 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 aforementioned heterocyclic 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 heterocyclic compound represented by Chemical 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 in a mass ratio of 99.9: 0.1 to 90:10.
  • 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 in a mass ratio of 99.5: 0.5 to 95: 5.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1 as a dopant.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1 as a dopant in the light emitting layer.
  • 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 It may include a heterocyclic compound of the formula (1).
  • 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 It may include a heterocyclic compound of the formula (1).
  • 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 heterocyclic 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 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 present specification also provides a method for manufacturing an organic light emitting device formed using the heterocyclic 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.
  • a glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1300 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice for 10 minutes with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • the following compound HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Thereafter, the following compound HT-A 1000A was vacuum-deposited as a first hole transport layer, and subsequently the following compound HT-B 100 ⁇ was deposited as a second hole transport layer.
  • the host BH-A and the dopant Compound 1 were vacuum deposited at a weight ratio of 95: 5 to form a 200 mm thick light emitting layer.
  • the deposition rate of the organic material in the above process, 0.4 to 1.0 was maintained ⁇ / sec, the lithium fluoride of the cathode was maintained at the deposition speed of 0.3 ⁇ / sec of aluminum is 2 ⁇ / sec, the deposition upon the degree of vacuum is 1 ⁇ 10 - By maintaining 7 to 5 ⁇ 10 -8 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the host and dopant compounds described in Table 1 below were used as the light-emitting layer material in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the host and dopant compounds described in Table 1 below were used as the light-emitting layer material in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the host and dopant compounds described in Table 1 below were used as the light-emitting layer material in Example 1. Specifically, the host used the first host and the second host in a 1: 1 weight ratio instead of the BH-A of Example 1.

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Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une première électrode, une seconde électrode disposée en face de la première électrode, une ou au moins deux couches organiques disposées entre la première électrode et la seconde électrode, au moins l'une des couches organiques comprenant un composé hétérocyclique représenté par la formule chimique 1.
PCT/KR2019/013722 2018-10-18 2019-10-18 Composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2020080872A1 (fr)

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