WO2019143151A1 - Diode électroluminescente organique - Google Patents

Diode électroluminescente organique Download PDF

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WO2019143151A1
WO2019143151A1 PCT/KR2019/000703 KR2019000703W WO2019143151A1 WO 2019143151 A1 WO2019143151 A1 WO 2019143151A1 KR 2019000703 W KR2019000703 W KR 2019000703W WO 2019143151 A1 WO2019143151 A1 WO 2019143151A1
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group
substituted
unsubstituted
compound
formula
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PCT/KR2019/000703
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Korean (ko)
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차용범
서상덕
홍성길
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주식회사 엘지화학
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Priority to CN201980005363.5A priority Critical patent/CN111279502B/zh
Publication of WO2019143151A1 publication Critical patent/WO2019143151A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • This application relates to an organic light emitting device.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the present application provides an organic light emitting device.
  • the present invention relates to a positive electrode; A negative electrode opposed to the positive electrode; And an organic layer between the anode and the cathode,
  • the organic layer includes a light emitting layer
  • a first organic material layer provided between the anode and the light emitting layer; And a second organic material layer in contact with the light emitting layer between the first organic material layer and the light emitting layer,
  • the first organic layer comprises a compound represented by the following formula (1)
  • the second organic compound layer comprises a compound represented by the following general formula (2).
  • Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group
  • At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group
  • L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar5 and Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n is an integer of 0 to 8
  • R is hydrogen or when n is 2 or more, adjacent Rs are bonded to each other to form a ring
  • any one of Ar1 and Ar2; And any one of Ar3 and Ar4 is a 1-naphthyl group and the remaining Ar1 to Ar4 are unsubstituted phenyl groups.
  • the organic light emitting device has a low driving voltage and can improve the lifetime characteristics of the device by the thermal stability of the compound.
  • the compound represented by Chemical Formula 1 has low voltage and high efficiency characteristics when applied to a hole transporting layer and has a long life characteristic when a compound represented by Chemical Formula 2 is applied to an electron blocking layer.
  • the compound of formula (1) is bonded to an arylamine group on both sides of the biphenyl, wherein at least one of the aryl groups is a polycyclic aryl group, and the compound which binds to the arylamine is an aryl of monocyclic or a 1-naphthyl group,
  • the glass transition temperature is high and the stability is improved.
  • FIG. 1 to 3 show examples of an organic light emitting device according to one embodiment of the present invention.
  • the present specification discloses a battery comprising: a positive electrode; A negative electrode opposed to the positive electrode; And an organic layer between the anode and the cathode,
  • the organic layer includes a light emitting layer
  • first organic material layer comprises the compound represented by Formula 1,
  • the second organic compound layer includes a compound represented by Formula 2.
  • the compound represented by the formula (1) has an excellent effect on lifetime in the organic electronic device by bonding a polycyclic aryl group having a large molecular weight to Ar1 to Ar4 to increase the glass transition temperature.
  • a polycyclic aryl group having a large molecular weight to Ar1 to Ar4 to increase the glass transition temperature.
  • the current efficiency and lifetime of the organic light emitting device are simultaneously improved .
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; Cyano; A nitro group; A hydroxy group; An alkyl group; A cycloalkyl group; An alkenyl group; An alkoxy group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S, and the like.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, Group, an acridyl group, a hydroacridyl group (e.g., ), A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyrazinyl group, an isoquinolinyl group , An indole group, a carbazolyl group, a benzoxazolyl group, a
  • Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group,
  • At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group
  • any one of Ar1 and Ar2; And any one of Ar3 and Ar4 is a 1-naphthyl group and the remaining Ar1 to Ar4 are unsubstituted phenyl groups.
  • Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group,
  • At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group
  • Ar 1 to Ar 4 are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group, and at least one of Ar1 to Ar4 is a polycyclic aryl group substituted or unsubstituted with an aryl group, with the proviso that any one of Ar1 and Ar2; And when any one of Ar3 and Ar4 is a 1-naphthyl group, the remaining Ar1 to Ar4 are the same or different and are each a phenyl group substituted with an aryl group; A naphthyl group substituted or unsubstituted with an
  • Ar 1 to Ar 4 are the same or different from each other and are each independently a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A biphenyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; Or a terphenyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group, and at least one of Ar1 to Ar
  • At least one of Ar1 to Ar4 is a polycyclic aryl group.
  • At least one of Ar1 to Ar4 represents a naphthyl group; Phenanthrene; Or a triphenylene group.
  • At least one of Ar1 to Ar4 represents a naphthyl group; Phenanthrene; Or a triphenylene group.
  • Ar1 to Ar4 are the same as each other, and Ar1 and Ar4 are each a polycyclic aryl group.
  • Ar1 to Ar4 are the same as each other, Ar1 to Ar4 represent a naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar1 to Ar4 are the same as each other, Ar1 to Ar4 represent a naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; Or a phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group.
  • Ar1 to Ar3 are the same as each other and are different from Ar4, Ar1 to Ar3 are polycyclic aryl groups, Ar4 is a monocyclic aryl group substituted or unsubstituted with an aryl group; Or a polycyclic aryl group.
  • Ar1 to Ar3 are the same as each other and are different from Ar4, and Ar1 to Ar3 are naphthyl groups substituted or unsubstituted with an aryl group; Or phenanthrene which is substituted or unsubstituted with an aryl group, Ar4 is a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar1 to Ar3 are the same as each other and are different from Ar4, and Ar1 to Ar3 are a naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; Or a phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group, Ar4 is a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenant
  • Ar 1 and Ar 2 are the same as each other, Ar 3 and Ar 4 are the same as each other, Ar 1 and Ar 2 are different from A 3 and Ar 4, Ar 1 and Ar 2 are each a polycyclic aryl group, Ar3 and Ar4 are monocyclic aryl groups substituted or unsubstituted with an aryl group; Or a polycyclic aryl group.
  • Ar 1 and Ar 2 are the same as each other, Ar 3 and Ar 4 are the same as each other, Ar 1 and Ar 2 are different from A 3 and Ar 4, Ar 1 and Ar 2 are substituted with an aryl group, A naphthyl group; Or a phenanthrene group substituted or unsubstituted with an aryl group, Ar3 and Ar4 are a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar 1 and Ar 2 are the same as each other, Ar 3 and Ar 4 are the same as each other, Ar 1 and Ar 2 are different from A 3 and Ar 4, Ar 1 and Ar 2 are a phenyl group, a naphthyl group, A naphthyl group substituted or unsubstituted with a phenanthrene group; Or a phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group,
  • Ar3 and Ar4 are phenyl groups, naphthyl groups, phenyl groups substituted or unsubstituted with phenanthrene groups; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A biphenyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; Or a terphenyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group.
  • Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are the same as each other, Ar 1 and Ar 3 are different from Ar 2 and Ar 4, Ar 1 and Ar 3 are each a polycyclic aryl group, Ar2 and Ar4 are monocyclic aryl groups substituted or unsubstituted with an aryl group; Or a polycyclic aryl group,
  • Ar 1 and Ar 3 are 1-naphthyl groups
  • Ar 2 and Ar 4 are monocyclic aryl groups substituted with an aryl group; Or a polycyclic aryl group.
  • Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are the same as each other, Ar 1 and Ar 3 are different from Ar 2 and Ar 4, Ar 1 and Ar 3 are substituted with an aryl group, A naphthyl group; Or a phenanthrene group substituted or unsubstituted with an aryl group, Ar2 and Ar4 are a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group,
  • Ar 1 and Ar 3 are 1-naphthyl groups
  • Ar 2 and Ar 4 are phenyl groups substituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group, and Ar2 and Ar4 are phenyl groups substituted or unsubstituted with an aryl group.
  • Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are the same as each other, Ar 1 and Ar 3 are different from Ar 2 and Ar 4, Ar 1 and Ar 3 are each a phenyl group, a naphthyl group, A naphthyl group substituted or unsubstituted with a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; , Ar2 and Ar4 represent a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a
  • Ar1 and Ar2 are the same as each other, Ar3 and Ar4 are different from each other, Ar1 and Ar2 are different from Ar3 and Ar4, Ar1 and Ar2 are a polycyclic aryl group, Ar3 and Ar4 are monocyclic aryl groups substituted or unsubstituted with an aryl group; Or a polycyclic aryl group.
  • Ar 1 and Ar 2 are the same as each other, Ar 3 and Ar 4 are different from each other, Ar 1 and Ar 2 are different from Ar 3 and Ar 4, Ar 1 and Ar 2 are substituted with an aryl group, A naphthyl group; A phenanthrene group substituted or unsubstituted with an aryl group; , Ar3 and Ar4 represent a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar 1 and Ar 2 are the same as each other, Ar 3 and Ar 4 are different from each other, Ar 1 and Ar 2 are different from Ar 3 and Ar 4, Ar 1 and Ar 2 represent a phenyl group, a naphthyl group, A naphthyl group substituted or unsubstituted with a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; , Ar3 and Ar4 represent a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naph
  • Ar1 and Ar3 are the same as each other, Ar2 and Ar4 are different from each other, Ar1 and Ar3 are different from Ar2 and Ar4, Ar1 and Ar3 are a polycyclic aryl group, Ar2 and Ar4 are monocyclic aryl groups substituted or unsubstituted with an aryl group; Or a polycyclic aryl group.
  • Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are different from each other, Ar 1 and Ar 3 are different from Ar 2 and Ar 4, Ar 1 and Ar 3 are substituted with an aryl group, A naphthyl group; Or a phenanthrene group substituted or unsubstituted with an aryl group, Ar2 and Ar4 are a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar1 and Ar3 are the same, Ar2 and Ar4 are different from each other, Ar1 and Ar3 are different from Ar2 and Ar4, Ar1 and Ar3 are a phenyl group, A naphthyl group substituted or unsubstituted with a phenanthrene group; Or a phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group, Ar2 and Ar4 are a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthren
  • Ar2 to Ar4 are different from each other, Ar1 is different from Ar2 to Ar4, Ar1 is a polycyclic aryl group, Ar2 to Ar4 are substituted or unsubstituted aryl groups A monocyclic aryl group; Or a polycyclic aryl group.
  • Ar2 to Ar4 are different from each other, Ar1 is different from Ar2 to Ar4, Ar1 is a naphthyl group substituted or unsubstituted with an aryl group; Or a phenanthrene group substituted or unsubstituted with an aryl group, Ar2 to Ar4 are a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • Ar2 to Ar4 are different from each other, Ar1 is different from Ar2 to Ar4, Ar1 is a naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; Or a phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group, and Ar2 to Ar4 are a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a phenanthrene group; A naphthyl group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A phenanthrene group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group;
  • the formula (2) is represented by any one of the following formulas (2-1) to (2-1) to (2-3).
  • L1, L2, Ar5 and Ar6 are as defined in Formula (2).
  • Ar5 and Ar6 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar5 and Ar6 are the same or different and are each independently a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, or an aryl group; A naphthyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A phenanthrene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A biphenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A terphenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A triphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A fluorenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A flu
  • Ar5 and Ar6 are the same or different and each independently represents a phenyl group substituted or unsubstituted with a deuterium, a methyl group, a butyl group, a phenyl group, a naphthyl group, a phenanthrene group, or a dimethylfluorene group ;
  • Ar5 and Ar6 are the same or different and each independently represents a phenyl group substituted or unsubstituted with a deuterium, a methyl group, a butyl group, a phenyl group, a naphthyl group, or a dimethylfluorene group; A naphthyl group substituted or unsubstituted with a phenyl group or a naphthyl group; Phenanthrene; A biphenyl group; A terphenyl group; Triphenylene group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A dibenzofurane group; Or a dibenzothiophene group.
  • Ar1 to Ar6 are the same or different from each other, and each independently selected from the following structural formulas.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; Or a phenylene group.
  • L1 is a direct bond.
  • L2 is a direct bond or a phenylene group.
  • L2 is a direct bond or a para-phenylene group.
  • the compound represented by Formula 1 is selected from the following structural formulas.
  • the compound represented by Formula 2 is selected from the following structural formulas.
  • the first organic layer is a hole transporting layer.
  • the HOMO value of the hole transport layer is 5.3 eV to 5.7 eV.
  • the second organic layer is an electron blocking layer.
  • the thickness of the first organic layer is 100 to 2000 ANGSTROM.
  • the thickness of the first organic material layer is 100 to 1500 ANGSTROM.
  • the first organic layer is a hole transporting layer
  • the thickness of the hole transporting layer is 300 ANGSTROM to 2000 ANGSTROM.
  • the thickness of the second organic layer is 30 to 400 ANGSTROM.
  • the second organic layer is an electron blocking layer
  • the thickness of the electron blocking layer is 30 ANGSTROM to 200 ANGSTROM.
  • the hole transport layer and the second organic material layer are in contact with each other.
  • the first organic material layer and the second organic material layer are in contact with each other.
  • a third organic material layer is disposed between the cathode of the organic light emitting device and the light emitting layer, and the third organic material layer includes a compound represented by the following general formula (3).
  • L3 and L4 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar7 to Ar10 are the same or different and each independently represents a substituted or unsubstituted aryl group
  • At least one of X1 to X3 and at least one of X4 to X6 is N and the others are CH.
  • the third organic layer is an electron injection and transport layer.
  • the third organic compound layer is an electron injection layer.
  • the third organic material layer is an electron transporting layer.
  • the formula (3) is represented by any one of the following formulas (3-1) to (3-8).
  • At least one of X1 to X3 and at least one of X4 to X6 is N and the others are CH.
  • X1 to X3; And X4 to X6 are N;
  • L3 and L4 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted phenylene group.
  • L3 and L4 are the same or different from each other and are each independently a direct bond; Or a phenylene group.
  • L3 and L4 are the same or different from each other and are each independently a direct bond; para-phenylene group; Or meta-phenylene group.
  • Ar7 to Ar10 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorenyl group.
  • Ar7 to Ar10 are the same or different and each independently represents a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • Ar7 to Ar10 are the same or different from each other and are each independently a phenyl group; Or a biphenyl group.
  • Ar7 to Ar10 are the same or different from each other, and each independently selected from the following structural formulas.
  • the compound represented by Formula 3 is selected from the following structural formulas.
  • the light emitting layer includes a compound represented by the following general formula (4).
  • Ar11 and Ar12 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar11 and Ar12 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.
  • the light emitting layer comprises a compound represented by the following general formula (5).
  • Ar11 is a substituted or unsubstituted aryl group
  • Y is O or S
  • R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
  • Ar11 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted biphenyl group.
  • Ar11 represents a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; Or a biphenyl group substituted or unsubstituted with an aryl group.
  • Ar11 represents a phenyl group substituted or unsubstituted with a phenyl group or a naphthyl group; A naphthyl group substituted or unsubstituted with a phenyl group or a naphthyl group; A phenanthrene group substituted or unsubstituted with a phenyl group or a naphthyl group; Or a biphenyl group substituted or unsubstituted with a phenyl group or a naphthyl group.
  • Y is O.
  • Y is S.
  • R1 to R4 are hydrogen.
  • the compound represented by Formula 4 is selected from the following structural formulas.
  • the compound represented by Formula 5 is selected from the following structural formulas.
  • the organic light emitting device of the present invention may be manufactured by materials and methods known in the art, except that the organic light emitting device includes a first organic layer and a second organic layer.
  • the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate.
  • a metal PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode And forming an organic material layer including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron injecting and transporting layer on the hole transporting layer, and then depositing a material usable as a cathode thereon .
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer of the organic light emitting device of the present invention may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device may further include one or more layers selected from the group consisting of a hole injection layer, an electron transport layer, an electron injection layer, and a hole blocking layer.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but the present invention is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device in which a cathode 201, a first organic layer 301, a second organic layer 401, a light emitting layer 501, and a cathode 601 are sequentially stacked on a substrate 101 have.
  • 1 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer, and the first organic layer may include the compound of Formula 1, and the second organic layer may include the compound of Formula 2 But are not limited thereto.
  • FIG. 1 is an exemplary structure according to an embodiment of the present invention, wherein the first organic layer may include the compound of Formula 1, the second organic layer may include the compound of Formula 2, The light emitting layer may include the compound of Formula 3, but the present invention is not limited thereto.
  • the hole transport layer may include the compound of Formula 1 and the electron blocking layer may include the compound of Formula 2.
  • the electron injecting and transporting layer may include the compound of Formula 3
  • the light emitting layer may include the compound of Formula 4 or 5, but is not limited thereto.
  • the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material 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); A combination of a metal and an oxide such as ZnO: Al or SNO2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transporting layer is a layer for transporting holes from the hole injecting layer to the light emitting layer and may be a layer other than the first organic layer in the present specification.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and 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-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material includes an organic compound, a metal, or a metal compound.
  • Examples of the organic compound as the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, and a fluoranthene compound.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • the styrylamine compound examples include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal or metal compound a common metal or metal compound can be used. Specifically, metal complexes can be used. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • the organic light emitting diode according to the present invention may be an inverted type in which the lower electrode is a cathode, the upper electrode is a cathode, the lower electrode is a cathode, and the upper electrode is an anode.
  • the structure according to one embodiment of the present disclosure can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organophotoreceptors, organic transistors and the like.
  • the core structure of the compound represented by formula (1) according to one embodiment of the present invention can be prepared by conventional techniques.
  • the core structure of the compound represented by Formula 2 according to one embodiment of the present invention can be prepared through the following Reaction Scheme 1, but is not limited thereto.
  • L1, L2, Ar5, Ar6, R and n are the same as defined in Formula (1).
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum depositing a compound of the following formula [HI-1] and a compound of the following formula [HI-2] in a thickness of 100 ⁇ so as to have a molar ratio of 98: 2 on the prepared ITO transparent electrode.
  • HT-1 (1150 ANGSTROM), which is a material for transporting holes, was vacuum-deposited on the hole injection layer to form a hole transport layer.
  • the compound [HB-1] was vacuum deposited on the hole transporting layer to a thickness of 50 ANGSTROM to form a hole blocking layer.
  • the compound [ET-1] and the compound [LiQ] were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form a layer simultaneously injecting and transporting electrons at a thickness of 310 ⁇ .
  • Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 ⁇ on the electron injecting and transporting layer sequentially to form a cathode.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-1 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-2 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1-3 was used in place of Compound [HT-1] in Comparative Example 1-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that the above compound 2-1 was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1-1 except that the compound [2-2] was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 2-3 was used in place of the compound [EB-1] in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 2-4 was used instead of the compound [EB-1] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the above compound 4-1 was used instead of the compound [BH] in the above Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the above compound 4-2 was used instead of the compound [BH] in the above Comparative Example 1-1.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that Compound 1-1 was used in place of Compound [HT-1] in Comparative Example 1-1 and Compound 2-1 was used in place of Compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound 1-1 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-2 was used in place of the compound [EB-1]
  • An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that Compound 1-1 was used in place of Compound [HT-1] in Comparative Example 1-1 and Compound 2-4 was used in place of Compound [EB-1]
  • An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 was repeated except that the compound 1-2 was used instead of the compound [HT-1] in the above Comparative Example 1-1 and the compound 2-1 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound 1-2 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-2 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound 1-2 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-3 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound 1-2 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-4 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • Comparative Example 1-1 and Comparative Example 1-1 were repeated except that the compound 1-3 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-1 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner.
  • the compound 1-1 was used in place of the compound [HT-1] in the Comparative Example 1-1, the compound 2-2 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1.
  • the compound 1-1 was used in place of the compound [HT-1] in the above Comparative Example 1-1, the compound 2-2 was used in place of the compound [EB-1] An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1.
  • ET-1] was used in place of the compound [HT-1] in the above Comparative Example 1-1
  • the compound 2-2 was used in place of the compound [EB- 1 was used instead of the organic EL device of Comparative Example 1-1.
  • ET-1] was used in place of the compound [HT-1] in the above Comparative Example 1-1
  • the compound 2-2 was used in place of the compound [EB- 1 was used and Compound 4-1 was used instead of Compound [BH]
  • an organic light emitting device was prepared in the same manner as in Comparative Example 1-1.
  • An organic light emitting device was fabricated in the same manner as in Example 1-2, except that Compound HT-2 was used instead of Compound 1-1 in Example 1-2.
  • An organic light emitting device was fabricated in the same manner as in Example 1-2, except that Compound EB-2 was used instead of Compound 2-2 in Example 1-2.
  • An organic light emitting device was fabricated in the same manner as in Example 1-2, except that Compound EB-3 was used instead of Compound 2-2 in Example 1-2.
  • the blue organic light emitting device of Comparative Example 1-1 was a commonly used material, and the compound [HT-1] as the hole transporting layer, the compound [EB-1] as the electron blocking layer, the compound [ET -1], and the compound [BH] is used as the blue light emitting layer.
  • Comparative Examples 1-2 to 1-4 use a compound of Formula 1 according to one embodiment of the present invention in place of the compound [HT-1] used as a conventional hole transport layer, 5 to 1-8 used a compound of the formula 2 according to one embodiment of the present invention instead of the compound [EB-1] used as a conventional electron blocking layer, and Comparative Examples 1-9 used a conventional electron transport layer Instead of the compound [ET-1], the compound of the formula (3-1) according to one embodiment of the present invention was used.
  • Comparative Examples 1-10 and 1-11 the compound [BH] An organic light emitting device comprising compounds of formulas (1), (2), (3) and (4) was prepared using the compound of formula (4-1) according to one embodiment.
  • the driving voltage is lowered by 8 to 10%
  • the compound of formula (2) is used as an electron blocking layer
  • the luminous efficiency is increased by 8% and the lifetime is increased by more than 30% Results were obtained.
  • the lifetime was increased by 10 to 20%
  • the compound of Formula 4 was used as the blue light emitting layer, the lifetime was increased by 10 to 20% as well as the low voltage and high efficiency characteristics .
  • Examples 1-1 to 1-12 are organic light emitting devices using Formula 1 of the present invention as a hole transporting layer and Formula 2 of the present invention as an electron blocking layer.
  • the organic light emitting device exhibits 8% higher luminous efficiency and a longer lifetime of 30% than the organic light emitting device including the organic light emitting device of the present invention by 8 ⁇ 10% lower driving voltage.
  • the compound 1-1 was used as the hole transporting layer, and the organic light emitting device of Examples 1-1 to 1-4 using the compounds 2-1 to 2-4 as the electron blocking layer, 1-6 and 1- (3-aminophenyl) -1,2,3-triazole were used as the electron blocking layer and the compounds 1-1 to 1-3, which are the compounds of the present invention as the hole transporting layer, 10 < / RTI >
  • Examples 1-13 to 1-16 are devices in which the electron injecting and transporting layer and the blue light emitting layer are contained in the organic luminescent device of Example 1-2 or using the compounds 3-1 and 4-1 at the same time, However, it showed the best lifetime characteristics instead.
  • Comparative Example 1-13 is an organic light emitting device using a compound [EB-2] in which biphenyl and carbazole, which are substituents of Formula 2 in the present specification, are connected in the meta direction not in the ortho direction, And the life span also decreased by 20% or more.
  • Comparative Example 1-14 is an organic light-emitting device using a compound [EB-3] having an amine substituent bonded to a biphenyl, which is a substituent of the formula (2), as an electron transport layer, collapsing and greatly reducing the lifetime of the device .
  • the reason for this is that the compound [EB-3] containing three amine groups is too low in HOMO value, so that the adjacent luminescent layer and the barrier are greatly increased.
  • the compound satisfying the formula (1) is used for the hole transport layer by complementing the efficiency in the case where the 1-naphthyl group is bonded in order to compensate the lifetime by increasing the glass transition temperature by controlling the substituents of Ar 1 to Ar 4, 2 was used as an electron blocking layer to optimize current efficiency and lifetime in an organic light emitting device.

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Abstract

La présente invention concerne une diode électroluminescente organique comprenant : une électrode positive ; une électrode négative faisant face à l'électrode positive ; et une couche organique entre l'électrode positive et l'électrode négative. La couche organique comprend une couche électroluminescente, et comprend : une première couche organique disposée entre l'électrode positive et la couche électroluminescente ; et une seconde couche organique disposée entre la première couche organique et la couche électroluminescente et venant en contact avec la couche électroluminescente. La première couche organique comprend un composé représenté par la formule chimique (1). La seconde couche organique comprend un composé représenté par la formule chimique (2).
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KR20200065952A (ko) * 2018-11-30 2020-06-09 주식회사 엘지화학 유기 발광 소자
CN113994495A (zh) * 2019-08-14 2022-01-28 株式会社Lg化学 有机发光器件
WO2021029709A1 (fr) * 2019-08-14 2021-02-18 주식회사 엘지화학 Dispositif électroluminescent organique
US20230023811A1 (en) * 2019-09-26 2023-01-26 Idemitsu Kosan Co.,Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
KR102568228B1 (ko) * 2019-11-05 2023-08-18 주식회사 엘지화학 유기 발광 소자
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US20220310935A1 (en) * 2020-02-28 2022-09-29 Lg Chem, Ltd. Organic light-emitting device
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KR102631973B1 (ko) * 2020-03-31 2024-01-31 주식회사 엘지화학 유기 발광 소자
WO2023237073A1 (fr) * 2022-06-10 2023-12-14 浙江光昊光电科技有限公司 Composé organique d'amine aromatique et son utilisation dans un dispositif électronique organique
WO2023244000A1 (fr) * 2022-06-15 2023-12-21 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160129710A (ko) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 유기 발광 소자
KR20170036641A (ko) * 2015-09-24 2017-04-03 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20170042414A (ko) * 2015-10-08 2017-04-19 삼성디스플레이 주식회사 유기 발광 소자
KR20170134163A (ko) * 2016-05-27 2017-12-06 주식회사 엘지화학 유기 발광 소자
KR20170136842A (ko) * 2016-06-02 2017-12-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
WO2016027989A1 (fr) * 2014-08-20 2016-02-25 주식회사 엘지화학 Dispositif organique électroluminescent
KR101803599B1 (ko) * 2014-09-12 2017-12-01 주식회사 엘지화학 유기 발광 소자
KR101857518B1 (ko) * 2015-05-08 2018-05-15 머티어리얼사이언스 주식회사 유기전계발광소자
KR102654929B1 (ko) * 2016-05-10 2024-04-05 삼성디스플레이 주식회사 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160129710A (ko) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 유기 발광 소자
KR20170036641A (ko) * 2015-09-24 2017-04-03 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20170042414A (ko) * 2015-10-08 2017-04-19 삼성디스플레이 주식회사 유기 발광 소자
KR20170134163A (ko) * 2016-05-27 2017-12-06 주식회사 엘지화학 유기 발광 소자
KR20170136842A (ko) * 2016-06-02 2017-12-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

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