WO2020122671A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2020122671A1
WO2020122671A1 PCT/KR2019/017713 KR2019017713W WO2020122671A1 WO 2020122671 A1 WO2020122671 A1 WO 2020122671A1 KR 2019017713 W KR2019017713 W KR 2019017713W WO 2020122671 A1 WO2020122671 A1 WO 2020122671A1
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present specification
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French (fr)
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김경희
금수정
홍완표
서상덕
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주식회사 엘지화학
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Priority to CN201980016113.1A priority Critical patent/CN111788198B/zh
Publication of WO2020122671A1 publication Critical patent/WO2020122671A1/ko

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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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light 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, or the like.
  • the present specification is intended to provide a compound and an organic light emitting device including the same.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring,
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is 1 or 2, when 2 R7 is the same or different from each other,
  • r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.
  • the compound according to one embodiment of the present specification is used in an organic light emitting device, so that the driving voltage of the organic light emitting device can be lowered, and light efficiency can be improved.
  • the life characteristics of the device can be improved by the thermal stability of the compound.
  • 1 to 3 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • the compound represented by Chemical Formula 1 has a core structure in which benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene, and an arylamine group is connected to the core structure.
  • the cyclohexane ring in the core structure increases the solubility of the substance, facilitating the synthesis of the compound.
  • the luminous efficiency is high because the molecular orientation value is higher than when one cyclohexane ring is condensed and two cyclohexane rings are condensed.
  • the compound represented by Chemical Formula 1 includes two amine groups, and thus has higher luminous efficiency of the device due to increased radiative transition probability (Oscillator strength) compared to a structure that does not contain an amine group or contains one amine group.
  • Cn means n carbon atoms.
  • Cn-Cm means “n to m carbon atoms”.
  • 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 can be substituted, 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; Halogen group; Nitro group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine group; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups containing one or more of N, O, and S atoms, or two or more substituents of the above-exemplified substituents are substituted with linked substituents, or have no substituents.
  • the “substituted or unsubstituted” is deuterium; Halogen group; Nitro group; Nitrile group; C1-C10 alkyl group; C3-C10 cycloalkyl group; Silyl group; Amine group; C6-30 aryl group; And one or more substituents selected from the group consisting of C2-30 heteroaryl groups including one or more of N, O, and S atoms, or substituted with a substituent linked by two or more substituents of the above-described substituents, or It means that it does not have any substituents.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30.
  • Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1- Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, cyclopen
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms.
  • an aryl group means a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative.
  • aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and planar
  • a group derived from aromatic hydrocarbon means a structure in which aromatic hydrocarbon or cyclic aliphatic hydrocarbon is condensed in aromatic hydrocarbon.
  • the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other.
  • the aryl group is not particularly limited, and has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, the aryl group may be monocyclic or polycyclic.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
  • the substituted fluorenyl group includes all compounds in which the substituents of the pentane ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring.
  • the substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited to this.
  • the heteroaryl group is a heteroatom containing one or more of N, O, and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 or 2 to 20 carbon atoms. Do.
  • heteroaryl group examples include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyrido pyrimidine group, pyrido pyrimidine group pyrazine), pyrazino pyrazine, isoquinoline group, indole group, pyrido indole, indo pyrimidine, 5H-indeno pyrimidine, carbazole group, benzoxazole group, benzimidazole group , Benzothiazole group, benzocarbazole group, benzo
  • an arylene group means one having two bonding positions on the aryl group, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent 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.
  • 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 substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted 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 non-monovalent.
  • the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.
  • the heterocycle is a non-carbon atom, and contains one or more heteroatoms.
  • the heteroatom may include one or more atoms selected from the group consisting of O, N, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C5 alkyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group unsubstituted or substituted with deuterium, or adjacent substituents combine to form a fluorene ring unsubstituted or substituted with deuterium.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or it may be a phenyl group, or adjacent substituents may combine to form a fluorene ring.
  • R1 is hydrogen; Or deuterium.
  • R2 is hydrogen; Or deuterium.
  • R1 and R2 are the same as or different from each other.
  • R3 is hydrogen; Or deuterium.
  • R4 is hydrogen; Or deuterium.
  • R3 and R4 combine with each other to form a C2-C20 ring.
  • R3 and R4 are phenyl groups, and combine with each other to form a fluorene ring.
  • R3 and R4 are the same as or different from each other.
  • R5 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R6 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R5 and R6 are the same as or different from each other.
  • R7 and R8 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with X1; Or a C2-C30 heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group with X1; Or a C2-C20 heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 5 ring heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A carbazole group unsubstituted or substituted with X2; A benzocarbazole group unsubstituted or substituted with X2; A dibenzofuran group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; Or an indolocarbazole group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; Or a naphthobenzothiophene group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group And a C6-C20 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of silyl groups or two or more groups selected from the group connected thereto; Or C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C1-C5 alkyl group and C3-C10 cycloalkyl group, or two or more groups selected from the group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C5 alkyl groups, or two or more groups selected from the group are connected C6-C20 aryl group unsubstituted or substituted with a substituent; Or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C5 alkyl groups or two or more groups selected from the group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, or C1-C5 alkyl group substituted with deuterium, substituted with halogen group C1-C5 alkyl group, C3-C10 cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with a halogen group, a C1-C5 alkyl group, or a trimethylsilyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a C1-C5 alkyl group; A fluorenyl group unsubstituted or substituted with a C1-C5 alkyl group; A C1-C5 alkyl group substituted or unsubstit
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, alkyl group of C1-C5, alkyl group of C1-C5 substituted with deuterium, or halogen group A substituted or unsubstituted phenyl group with an alkyl group of C1-C5; Biphenyl group; Terphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; A dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • Ar1 to Ar4 are the same or different from each other, and each independently deuterium, halogen group, nitrile group, methyl group, tert-butyl group, methyl group substituted with deuterium, trifluoromethyl group, cyclohexyl
  • Ar1 to Ar4 are the same as or different from each other, and each independently substituted with deuterium, a halogen group, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a trifluoromethyl group.
  • Ar1 is a substituted or unsubstituted aryl group
  • Ar2 is a substituted or unsubstituted heteroaryl group
  • Ar3 is a substituted or unsubstituted aryl group
  • Ar4 is a substituted or unsubstituted heteroaryl group
  • Ar1 is a substituted or unsubstituted heteroaryl group
  • Ar2 is a substituted or unsubstituted aryl group
  • Ar3 is a substituted or unsubstituted heteroaryl group
  • Ar4 is a substituted or unsubstituted aryl group
  • At least one of Ar1 and Ar2 may be represented by the following Chemical Formula A1.
  • At least one of Ar3 and Ar4 may be represented by the following Chemical Formula A1.
  • Q1 is C(T2)(T3); S; Or O,
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent substituents to form a substituted or unsubstituted ring,
  • t1 is an integer from 0 to 7, and when t1 is 2 or more, T1 is the same as or different from each other.
  • T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C5 alkyl group.
  • T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.
  • T1 is hydrogen; Or deuterium, or two adjacent T1's combine with each other to form a benzene ring.
  • At least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
  • At least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
  • At least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • Ar1 and Ar3 are the same as each other.
  • Ar2 and Ar4 are the same as each other.
  • Ar1 and Ar2 are the same or different from each other.
  • Ar3 and Ar4 are the same or different from each other.
  • Ar1 to Ar4 are the same as or different from each other, and are any one selected from Groups A or B below.
  • the group A is substituted or unsubstituted by X1
  • the group B is substituted or unsubstituted by X2.
  • X1 and X2 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups and C1-C5 alkyl groups, or two or more groups selected from the group are connected It is a substituent.
  • X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A C1-C5 alkyl group unsubstituted or substituted with deuterium or halogen; C3-C10 cycloalkyl group; A silyl group substituted with a C1-C5 alkyl group or a C6-C20 aryl group; Or it is a C6-C20 aryl group.
  • X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Methyl group; tert-butyl group; A methyl group substituted with deuterium; A methyl group substituted with a halogen group; Cyclohexyl group; Trimethylsilyl group; It is a dimethylphenylsilyl group.
  • X1 is a deuterium, halogen group, nitrile group, C1-C5 alkyl group, C1-C5 alkyl group substituted with deuterium, C1-C5 alkyl group substituted with halogen group, C3-C10 Cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group
  • X1 is a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, or a C1-C5 alkyl group substituted with a halogen group.
  • X2 is a C1-C5 alkyl group or C3-C10 cycloalkyl group.
  • X2 is a C1-C5 alkyl group.
  • r7 is 1 or 2, and in the case of 2, R7 is the same or different from each other.
  • r7 is 2.
  • r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
  • r8 is 3.
  • -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same or different from each other.
  • -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by Chemical Formula 1-1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 5-1.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 6-1.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • the compound represented by Chemical Formula 1 is any one selected from the following compounds.
  • the compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later. Representative examples are described in the manufacturing examples described below, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change starting materials, reactants, reaction conditions, and the like.
  • a core structure may be prepared as in the following General Formula 1.
  • Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art. Substituents may be bonded as shown in General Formula 1, but are not limited thereto.
  • Ar1 to Ar4, R5 and R6 are the same as defined in Formula 1. Although R1 to R4, R7 and R8 are not indicated in the general formula, R1 to R4, R7 and R8 are substituted or reacted with the product produced by the general formula 1 in a manner known in the art. To R4, R7 and R8.
  • the present specification provides an organic light emitting device comprising the above-described compound.
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including 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 compound.
  • the'layer' is a meaning compatible with the'film' mainly used in the technical field, and refers to a coating covering a desired area.
  • the size of the'layer' is not limited, and each'layer' may have the same or different sizes. In an exemplary embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the meaning that a specific A material is included in the B layer means i) one or more A materials are included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B All of the layers included in one or more layers are included.
  • the meaning that the specific A material is included in the C layer or the D layer includes i) one or more of the C layers of one or more layers, ii) one or more of the D layers of the one or more layers, or iii ) It means both included in each of the C layer of one or more layers and the D layer of one or more layers.
  • the organic light emitting device may include an additional organic material layer in addition to the light emitting layer.
  • the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.
  • the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by Chemical Formula 1, and a light emitting layer including a compound represented by Chemical Formula 1 has a blue color.
  • the organic material layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Chemical Formula 1.
  • the light emitting layer including the compound represented by Chemical Formula 1 has a blue color, and the light emitting layer not containing the compound represented by Chemical Formula 1 may include a blue, red or green light emitting compound known in the art.
  • the organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; C6-C20arylene group; Or a C2-C20 heteroarylene group containing N, O, or S.
  • the arylene group or heteroarylene group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with deuterium; Or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4 ring aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
  • Ar21 and Ar22 are the same or different from each other, and each independently a substituted or unsubstituted deuterium monocyclic to 4 ring aryl group; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 and Ar22 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 terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofur
  • Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, or C1-C5 alkyl group.
  • Ar21 and Ar22 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 terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, and Ar21 and Ar22 may contain one or more deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Dibenzofuran group; Or a naphthobenzofuran group, and Ar21 and Ar22 may include one or more deuterium.
  • Ar21 and Ar22 are different from each other.
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted aryl group
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted heteroaryl group.
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is an aryl group unsubstituted or substituted with deuterium
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.
  • R22 is a group represented by -L23-Ar23.
  • R21 to R28 are the same as or different from each other, and each independently hydrogen or deuterium.
  • At least four of R21 to R28 are deuterium, and the rest are hydrogen.
  • R21 to R28 are hydrogen.
  • R21 to R28 are deuterium.
  • the compound represented by Chemical Formula H is any one selected from the following compounds.
  • Chemical Formula H is represented by the following Chemical Formula H-1.
  • L21, L22, R21, R23 to R28, Ar21 and Ar22 are as defined in Formula H,
  • L23 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar23 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L21 and L22 described above may be applied to L23.
  • Ar23 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group; Naphthylene group; Anthracene group; Phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Pyridine group; Or an isoquinoline group.
  • L23 is a direct bond; Phenylene group; Naphthylene group; Or a divalent thiophene group.
  • Ar23 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with deuterium; A naphthylene group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.
  • L23 is a direct bond; A phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • the compound represented by Chemical Formula H-1 is any one selected from the following compounds.
  • the organic light emitting device includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and a compound represented by Formula H as a host of the light emitting layer.
  • the content of the compound represented by Formula 1 is 0.01 parts by weight to 30 parts by weight; 0.1 to 20 parts by weight; Or 0.5 to 10 parts by weight.
  • the emission layer may further include a host material in addition to the compound represented by Chemical Formula H.
  • the host material (mixed host compound) further included may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.
  • the mixing ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95.
  • the light emitting layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H has a blue color.
  • the organic light emitting diode includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H.
  • the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color, and the light emitting layer not containing the compound represented by Formula 1 and the compound represented by Formula H is blue known in the art, Red or green luminescent compounds.
  • the organic material layer includes a hole injection layer or a hole transport layer.
  • the organic material layer includes an electron injection layer or an electron transport layer.
  • the organic material layer includes an electron blocking layer.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device is a hole injection layer, a hole transport layer. It further includes at least one layer or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Chemical Formula 1.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer simultaneously performing hole transport and hole injection, and an electron blocking layer.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 to 3. 1 to 3 illustrate an organic light emitting device and are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101.
  • the compound represented by Chemical Formula 1 is included in the light emitting layer.
  • a structure of an organic light emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101 is shown. Is illustrated.
  • the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer.
  • the compound represented by Chemical Formula 1 is included in one or more of the hole injection layer, the hole transport layer, and the light emitting layer.
  • the first electrode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, the electron transport layer on the substrate 101 ( 108), the structure of the organic light emitting device in which the electron injection layer 109 and the second electrode 110 are sequentially stacked is illustrated.
  • the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer.
  • the compound represented by Chemical Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is deposited by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be produced by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by the formula (1) or the compound represented by the formula (H) may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer.
  • Metals such as vanadium, chromium, copper, zinc, gold or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • 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.
  • 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.
  • the organic light emitting device may include an additional light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula H.
  • the additional emissive layer can include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having arylamine groups.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. Substituents are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • the compound represented by Chemical Formula 1 when included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and combined with holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • a material capable of emitting light in the visible light region a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxyquinoline aluminum complex Alq3
  • 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; And rubrene, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO high-occupied molecular orbital
  • the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organic matter; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.
  • 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 well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • a suitable negative electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents exciton generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and derivatives thereof, 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, and bis(8-hydroxyquinolinato) manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.
  • the hole blocking layer is a layer that blocks reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, 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 ITO (indium tin oxide) at a thickness of 1,500 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying, and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • the following chemical formula [HAT-CN] was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer.
  • the following formula [NPB] was vacuum-deposited to a thickness of 1,000 MPa on the hole injection layer to form a hole transport layer.
  • the following formula [HT-A] was vacuum deposited on the hole transport layer to a thickness of 200 Pa to form an electron blocking layer.
  • [BH-1] was vacuum-deposited to a thickness of 300 300 as a light emitting host on the electron blocking layer to form a light emitting layer. While depositing the light emitting layer was used as a blue light emitting dopant 3% by weight of the total weight of the host compound 100%.
  • [TPBI] and the following formula [LiQ] were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to form a first electron transport layer with a thickness of 200 Pa.
  • [LiF] was vacuum deposited on the first electron transport layer to form a second electron transport layer with a thickness of 100 mm 2. On the second electron transport layer, aluminum was deposited to a thickness of 1,000 mm 2 to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 1.0 ⁇ /sec
  • the LiF of the second electron transport layer was 0.3 0.3/sec
  • the aluminum of the negative electrode was maintained at a deposition rate of 2 ⁇ /sec.
  • An organic light-emitting device was manufactured by maintaining 1 ⁇ 10 -7 to 5 ⁇ 10 -8 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used as the host and the dopant of the emission layer in Example 1.
  • Compounds 1 to 17 according to an exemplary embodiment of the present invention have two arylamine groups while having a core structure in which a benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene.
  • Compound BD-1 of Comparative Example 1 has only one arylamine group
  • Compound BD-2 of Comparative Example 2 has a core structure in which two cyclohexane rings are condensed in naphthalene.
  • the devices of Examples 1 to 17 using the compound having the structure of Formula 1 have properties of blue high efficiency and long life compared to those of Comparative Examples 1 and 2.

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