WO2019143151A1 - Organic light-emitting diode - Google Patents

Organic light-emitting diode 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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French (fr)
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/en
Publication of WO2019143151A1 publication Critical patent/WO2019143151A1/en

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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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—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
    • C—CHEMISTRY; METALLURGY
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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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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

The present application relates to an organic light-emitting diode comprising: a positive electrode; a negative electrode facing the positive electrode; and an organic layer between the positive electrode and the negative electrode. The organic layer comprises a light-emitting layer, and comprises: a first organic layer provided between the positive electrode and the light-emitting layer; and a second organic layer provided between the first organic layer and the light-emitting layer and coming in contact with the light-emitting layer. The first organic layer comprises a compound represented by chemical formula (1). The second organic layer comprises a compound represented by chemical formula (2).

Description

유기 발광 소자Organic light emitting device
본 출원은 유기 발광 소자에 관한 것이다.This application relates to an organic light emitting device.
본 출원은 2018년 1월 17일 한국특허청에 제출된 한국특허출원 제10-2018-0005890호의 출원일의 이익을 주장하며, 그 내용은 전부 명세서에 포함된다.The present application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0005890 filed with the Korean Intellectual Property Office on January 17, 2018, the entire contents of which are incorporated herein by reference.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, 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. Here, in order to increase the efficiency and stability of the organic light emitting device, 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. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다. Development of new materials for such organic light emitting devices has been continuously required.
본 출원은 유기 발광 소자를 제공하는 것이다.The present application provides an organic light emitting device.
본 발명은 양극; 상기 양극에 대향하여 구비된 음극; 및 상기 양극과 상기 음극 사이의 유기물층을 포함하는 유기 발광 소자로서, 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,
상기 유기물층은 발광층을 포함하고, Wherein the organic layer includes a light emitting layer,
상기 양극과 발광층 사이에 구비된 제1 유기물층; 상기 제1 유기물층과 발광층 사이에 발광층과 접하는 제2 유기물층을 포함하고,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,
상기 제1 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고, Wherein the first organic layer comprises a compound represented by the following formula (1)
상기 제2 유기물층은 하기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다. And the second organic compound layer comprises a compound represented by the following general formula (2).
[화학식 1][Chemical Formula 1]
Figure PCTKR2019000703-appb-I000001
Figure PCTKR2019000703-appb-I000001
[화학식 2](2)
Figure PCTKR2019000703-appb-I000002
Figure PCTKR2019000703-appb-I000002
상기 화학식 1 및 2에 있어서, In the above formulas (1) and (2)
Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group,
상기 Ar1 내지 Ar4 중 적어도 하나는 치환 또는 비치환된 다환의 아릴기이고, At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며, 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 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, 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,
n은 0 내지 8 내지의 정수이고, R은 수소이거나, n이 2 이상일때, 인접한 R은 서로 결합하여 고리를 형성하며, n is an integer of 0 to 8, and R is hydrogen or when n is 2 or more, adjacent Rs are bonded to each other to form a ring,
단, Ar1 및 Ar2 중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기이고, 나머지 Ar1 내지 Ar4가 비치환된 페닐기인 경우는 제외된다.Provided that 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.
본 출원의 일 실시상태에 따른 유기발광소자는 구동전압이 낮고, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다. The organic light emitting device according to one embodiment of the present application has a low driving voltage and can improve the lifetime characteristics of the device by the thermal stability of the compound.
화학식 1로 표시되는 화합물은 정공수송층에 적용하는 경우 저전압, 고효율 특성을 갖으며, 화학식 2로 표시되는 화합물을 전자차단층에 적용하는 경우 장수명의 특성을 갖는다. 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.
화학식 1의 화합물은 바이페닐 양쪽에 아릴아민기가 결합하며, 아릴아민기는 아릴기 중 적어도 하나는 다환의 아릴기이며, 아릴아민에 결합하는 화합물이 모두 단환의 아릴이거나, 1-나프틸기이고 비치환된 페닐기인 경우의 화합물과 비교하여 유리전이 온도가 높아서 안정성이 향상된다. 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.
특히, 화학식 2의 화합물과 바이페닐과 아릴아민기가 파라(para)로 결합하고, 바이페닐과 카바졸이 파라(para) 또는 메타(meta)로 결합하는 화합물을 비교하면 본 발명의 화학식 2의 화합물이 고효율 및 장수명효과가 있다.Particularly, when compounds of formula (2), biphenyl and arylamine groups are bonded in para, and compounds in which biphenyl and carbazole are bonded in para or meta, the compound of formula This has high efficiency and long life effect.
도 1 내지 3은 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다. 1 to 3 show examples of an organic light emitting device according to one embodiment of the present invention.
[부호의 설명][Description of Symbols]
101 : 기판101: substrate
201 : 양극201: anode
301 : 제1 유기물층301: first organic layer
401 : 제2 유기물층401: second organic layer
501 : 발광층501: light emitting layer
601 : 음극601: cathode
701 : 제3 유기물층701: Third organic layer
302 : 정공주입층 302: Hole injection layer
303 : 정공수송층303: Hole transport layer
402: 전자차단층402: electron blocking layer
702: 정공차단층702: hole blocking layer
703: 전자 주입 및 수송층703: electron injection and transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.
본 명세서는 양극; 상기 양극에 대향하여 구비된 음극; 및 상기 양극과 상기 음극 사이에서 유기물층을 유기 발광 소자로서, 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,
상기 유기물층은 발광층을 포함하고, Wherein the organic layer includes a light emitting layer,
상기 양극과 발광층 사이에는 양극과 접하는 제1 유기물층; 발광층과 접하는 제2 유기물층을 포함하고, A first organic material layer in contact with the anode, between the anode and the light emitting layer; And a second organic material layer in contact with the light emitting layer,
상기 제1 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하고, Wherein the first organic material layer comprises the compound represented by Formula 1,
상기 제2 유기물층은 상기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다. And the second organic compound layer includes a compound represented by Formula 2. [Formula 2] < EMI ID = 2.0 >
본 명세서에 있어서, 상기 화학식 1로 표시되는 화합물은 Ar1 내지 Ar4에 분자량이 큰 다환의 아릴기가 결합하여, 유리전이온도를 높혀 유기 전자 소자에서의 수명에서 우수한 효과를 갖는다. Ar1 및 Ar2 중 어느 하나; 및 Ar3 및 Ar4 중 어느 하나가 1-나프틸기인 경우, 나머지 Ar1 내지 Ar4가 다환의 아릴기이거나, 치환된 페닐기가 되어, 높은 전류효율을 갖는다.In the present specification, 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. 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 a polycyclic aryl group or a substituted phenyl group, and have high current efficiency.
또한, 전류효율 및 수명면에서 우수한 효과가 있는 본원 화학식 1의 화합물을 정공수송층에 사용하고, 본원 화학식 2의 화합물을 전자차단층에 사용하는 경우, 유기 발광 소자에서 전류 효율 및 수명을 동시에 향상시킬 수 있다. In addition, when the compound of Formula 1 is used in the hole transport layer and the compound of Formula 2 is used in the electron blocking layer, the current efficiency and lifetime of the organic light emitting device are simultaneously improved .
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알케닐기; 알콕시기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. As used herein, the term " 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. For example, "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.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, 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-methylhexyl and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다. In the present specification, 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.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, when 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.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When 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.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2019000703-appb-I000003
,
Figure PCTKR2019000703-appb-I000004
및
Figure PCTKR2019000703-appb-I000005
등이 될 수 있으나, 이에 한정되는 것은 아니다. When the fluorenyl group is substituted,
Figure PCTKR2019000703-appb-I000003
,
Figure PCTKR2019000703-appb-I000004
And
Figure PCTKR2019000703-appb-I000005
And the like, but the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 헤테로고리기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오페닐기, 퓨라닐기, 피롤기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 트리아졸릴기, 피리딜기, 비피리딜기, 피리미딜기, 트리아지닐기, 아크리딜기, 하이드로아크리딜기(예컨대,
Figure PCTKR2019000703-appb-I000006
), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기; 벤조실롤기; 디벤조실롤기; 페난트롤리닐기(phenanthrolinyl group), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대,
Figure PCTKR2019000703-appb-I000007
등이 있다.In the present specification, 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. Examples of the heterocyclic group 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.,
Figure PCTKR2019000703-appb-I000006
), 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 benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, A furanyl group; Benzosyl group; Dibenzosilyl groups; A phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and condensation structures thereof , But are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,
Figure PCTKR2019000703-appb-I000007
.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 터페닐기이고, In one embodiment of the present invention, 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,
상기 Ar1 내지 Ar4 중 적어도 하나는 치환 또는 비치환된 다환의 아릴기이며,At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group,
단, Ar1 및 Ar2 중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기이고, 나머지 Ar1 내지 Ar4가 비치환된 페닐기인 경우는 제외된다. Provided that 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 터페닐기이고, In one embodiment of the present invention, 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,
상기 Ar1 내지 Ar4 중 적어도 하나는 치환 또는 비치환된 다환의 아릴기이며,At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group,
단, Ar1 및 Ar2 중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기인 경우, 나머지 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 아릴기로 치환된 단환의 아릴기; 또는 아릴기로 치환 또는 비치환된 아릴기로 치환 또는 비치환된 다환의 아릴기이다. Provided 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 monocyclic aryl group substituted with an aryl group; Or a polycyclic aryl group substituted or unsubstituted with an aryl group substituted or unsubstituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이고, 상기 Ar1 내지 Ar4 중 적어도 하나는 아릴기로 치환 또는 비치환된 다환의 아릴기이며, 단, Ar1 및 Ar2중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기인 경우, 나머지 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 아릴기로 치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이고, 상기 Ar1 내지 Ar4 중 적어도 하나는 나프틸기; 페난쓰렌기; 또는 트리페닐렌기이며, 단, Ar1 및 Ar2중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기인 경우, 나머지 Ar1 내지 Ar4은 서로 같거나 상이하고, 각각 독립적으로 페닐기, 나프틸기, 또는 페난쓰렌기로 치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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 Ar4 is a naphthyl group; Phenanthrene; Or a triphenylene group, provided 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 independently a phenyl group, a naphthyl group, or a phenyl group 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 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4 중 적어도 하나는 다환의 아릴기이다.In one embodiment of the present invention, at least one of Ar1 to Ar4 is a polycyclic aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4 중 적어도 하나는 나프틸기; 페난쓰렌기; 또는 트리페닐렌기이다.In one embodiment of the present invention, at least one of Ar1 to Ar4 represents a naphthyl group; Phenanthrene; Or a triphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4 중 적어도 하나는 나프틸기; 페난쓰렌기; 또는 트리페닐렌기이다. In one embodiment of the present invention, at least one of Ar1 to Ar4 represents a naphthyl group; Phenanthrene; Or a triphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하며, Ar1 및 Ar4는 다환의 아릴기이다. In one embodiment of the present invention, Ar1 to Ar4 are the same as each other, and Ar1 and Ar4 are each a polycyclic aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하며, Ar1 내지 Ar4는 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하며, Ar1 내지 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar3은 서로 동일하며, 상기 Ar4와 상이하고, 상기 Ar1 내지 Ar3은 다환의 아릴기이며, 상기 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar3은 서로 동일하며, 상기 Ar4와 상이하고, 상기 Ar1 내지 Ar3은 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌이고, 상기 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar3은 서로 동일하며, 상기 Ar4와 상이하고, 상기 Ar1 내지 Ar3은 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar2는 상기 A3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 다환의 아릴기이며, 상기 Ar3 및 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이다. 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar2는 상기 A3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar3 및 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar2는 상기 A3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기이고,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,
상기 Ar3 및 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다.  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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 다환의 아릴기이며, 상기 Ar2 및 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이고, 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,
Ar1 및 Ar3이 1-나프틸기인 경우, Ar2 및 Ar4는 아릴기로 치환된 단환의 아릴기; 또는 다환의 아릴기이다.When 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar2 및 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이고, 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,
Ar1 및 Ar3이 1-나프틸기인 경우, Ar2 및 Ar4는 아릴기로 치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이고, 상기 Ar2 및 Ar4는 아릴기로 치환 또는 비치환된 페닐기이다. When 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 동일하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 이고, 상기 Ar2 및 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이고, Ar1 및 Ar3이 1-나프틸기인 경우, Ar2 및 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다.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 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; when Ar 1 and Ar 3 are 1-naphthyl groups, Ar 2 and Ar 4 are phenyl groups substituted with a phenyl group, a naphthyl group or 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar2는 상기 Ar3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 다환의 아릴기이며, 상기 Ar3 및 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar2는 상기 Ar3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 이고, 상기 Ar3 및 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 동일하고, Ar3 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar2는 상기 Ar3 및 Ar4와 상이하고, 상기 Ar1 및 Ar2는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 이고, 상기 Ar3 및 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다. 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 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 다환의 아릴기이며, 상기 Ar2 및 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar2 및 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하고, Ar2 및 Ar4는 서로 상이하고, 상기 Ar1 및 Ar3은 상기 Ar2 및 Ar4와 상이하고, 상기 Ar1 및 Ar3은 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar2 및 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 내지 Ar4는 서로 상이하고, 상기 Ar1은 상기 Ar2 내지 Ar4와 상이하고, 상기 Ar1은 다환의 아릴기이며, 상기 Ar2 내지 Ar4는 아릴기로 치환 또는 비치환된 단환의 아릴기; 또는 다환의 아릴기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 내지 Ar4는 서로 상이하고, 상기 Ar1은 상기 Ar2 내지 Ar4와 상이하고, 상기 Ar1은 아릴기로 치환 또는 비치환된 나프틸기; 또는 아릴기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar2 내지 Ar4는 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 아릴기로 치환 또는 비치환된 바이페닐기; 또는 아릴기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 내지 Ar4는 서로 상이하고, 상기 Ar1은 상기 Ar2 내지 Ar4와 상이하고, 상기 Ar1은 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기이고, 상기 Ar2 내지 Ar4는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 페난쓰렌기; 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 바이페닐기; 또는 페닐기, 나프틸기, 또는 페난쓰렌기로 치환 또는 비치환된 터페닐기이다. In one embodiment of the present invention, 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; 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.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2는 하기 화학식 2-1 내지 2-1 내지 2-3 중 어느 하나로 표시된다. In one embodiment of the present invention, the formula (2) is represented by any one of the following formulas (2-1) to (2-1) to (2-3).
[화학식 2-1][Formula 2-1]
Figure PCTKR2019000703-appb-I000008
Figure PCTKR2019000703-appb-I000008
[화학식 2-2][Formula 2-2]
Figure PCTKR2019000703-appb-I000009
Figure PCTKR2019000703-appb-I000009
[화학식 2-3][Formula 2-3]
Figure PCTKR2019000703-appb-I000010
Figure PCTKR2019000703-appb-I000010
상기 화학식 2-1 내지 2-3에 있어서, L1, L2, Ar5 및 Ar6은 화학식 2에서의 정의와 같다. In Formulas (2-1) to (2-3), L1, L2, Ar5 and Ar6 are as defined in Formula (2).
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기 이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 나프틸기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 터페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 트리페닐렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오레닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조퓨란기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기이다. In one embodiment of the present invention, 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 dibenzofurane group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or a dibenzothiophene group substituted or unsubstituted with a deuterium, an alkyl group, or an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 페닐기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 나프틸기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 페난쓰렌기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 바이페닐기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 터페닐기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 트리페닐렌기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 플루오레닐기; 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 디벤조퓨란기; 또는 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 페난쓰렌기, 또는 디메틸플루오렌기로 치환 또는 비치환된 디벤조티오펜기이다. In one embodiment of the present invention, 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 ; A naphthyl 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; A phenanthrene group substituted or unsubstituted by deuterium, a methyl group, a butyl group, a phenyl group, a naphthyl group, a phenanthrene group, or a dimethylfluorene group; A biphenyl 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; A terphenyl 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; A triphenylene 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; A fluorenyl group substituted or unsubstituted by deuterium, a methyl group, a butyl group, a phenyl group, a naphthyl group, a phenanthrene group, or a dimethylfluorene group; A dibenzofurane group substituted or unsubstituted by deuterium, a methyl group, a butyl group, a phenyl group, a naphthyl group, a phenanthrene group, or a dimethylfluorene group; Or a dibenzothiophene 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 중수소, 메틸기, 부틸기, 페닐기, 나프틸기, 또는 디메틸플루오렌기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기로 치환 또는 비치환된 나프틸기; 페난쓰렌기; 바이페닐기; 터페닐기; 트리페닐렌기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 디벤조퓨란기; 또는 디벤조티오펜기이다. In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar6 은 서로 같거나 상이하고, 각각 독립적으로 하기 구조식들 중에서 선택된다. In one embodiment of the present specification, Ar1 to Ar6 are the same or different from each other, and each independently selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000011
Figure PCTKR2019000703-appb-I000011
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기이다. In one embodiment of the present invention, L 1 and L 2 are the same or different from each other, and are each independently a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 직접결합이다. In one embodiment of the present disclosure, L1 is a direct bond.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합, 또는 페닐렌기이다. In one embodiment of the present invention, L2 is a direct bond or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 직접결합, 또는 para-페닐렌기이다. In one embodiment of the present invention, L2 is a direct bond or a para-phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 구조식들 중에서 선택된다. In one embodiment of the present invention, the compound represented by Formula 1 is selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000012
Figure PCTKR2019000703-appb-I000012
Figure PCTKR2019000703-appb-I000013
Figure PCTKR2019000703-appb-I000013
본 명세서의 일 실시상태에 있어서, 상기 화학식 2로 표시되는 화합물은 하기 구조식들 중에서 선택된다. In one embodiment of the present invention, the compound represented by Formula 2 is selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000014
Figure PCTKR2019000703-appb-I000014
Figure PCTKR2019000703-appb-I000015
Figure PCTKR2019000703-appb-I000015
Figure PCTKR2019000703-appb-I000016
Figure PCTKR2019000703-appb-I000016
Figure PCTKR2019000703-appb-I000017
Figure PCTKR2019000703-appb-I000017
Figure PCTKR2019000703-appb-I000018
Figure PCTKR2019000703-appb-I000018
Figure PCTKR2019000703-appb-I000019
Figure PCTKR2019000703-appb-I000019
본 명세서의 일 실시상태에 있어서, 상기 제1 유기물층은 정공수송층이다. In one embodiment of the present invention, the first organic layer is a hole transporting layer.
본 명세서의 일 실시상태에 있어서, 상기 정공수송층의 HOMO 값은 5.3 eV 내지 5.7 eV이다.In one embodiment of the present disclosure, the HOMO value of the hole transport layer is 5.3 eV to 5.7 eV.
본 명세서의 일 실시상태에 있어서, 상기 제2 유기물층은 전자차단층이다.In one embodiment of the present invention, the second organic layer is an electron blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 제1 유기물층의 두께는 100 Å 내지 2000 Å이다.According to an embodiment of the present invention, the thickness of the first organic layer is 100 to 2000 ANGSTROM.
본 명세서의 일 실시상태에 따르면, 상기 제1 유기물층의 두께는 100 Å 내지 1500 Å이다.According to one embodiment of the present invention, the thickness of the first organic material layer is 100 to 1500 ANGSTROM.
본 명세서의 일 실시상태에 따르면, 상기 제1 유기물층은 정공수송층이고, 상기 정공수송층의 두께는 300Å 내지 2000Å이다. According to an embodiment of the present invention, the first organic layer is a hole transporting layer, and the thickness of the hole transporting layer is 300 ANGSTROM to 2000 ANGSTROM.
본 명세서의 일 실시상태에 따르면, 상기 제2 유기물층의 두께는 30Å 내지 400Å이다. According to an embodiment of the present invention, the thickness of the second organic layer is 30 to 400 ANGSTROM.
본 명세서의 일 실시상태에 따르면, 상기 제2 유기물층은 전자차단층이고, 상기 전자차단층의 두께는 30Å 내지 200Å이다. According to an embodiment of the present invention, the second organic layer is an electron blocking layer, and the thickness of the electron blocking layer is 30 ANGSTROM to 200 ANGSTROM.
본 명세서의 일 실시상태에 있어서, 상기 정공수송층과 제2 유기물층은 접한다. In one embodiment of the present invention, the hole transport layer and the second organic material layer are in contact with each other.
본 명세서의 일 실시상태에 있어서, 상기 제1 유기물층과 제2 유기물층은 접한다. In one embodiment of the present invention, the first organic material layer and the second organic material layer are in contact with each other.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자의 음극과 발광층 사이에 제3 유기물층을 포함하고, 상기 제3 유기물층은 하기 화학식 3로 표시되는 화합물을 포함한다.In one embodiment of the present invention, 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).
[화학식 3](3)
Figure PCTKR2019000703-appb-I000020
Figure PCTKR2019000703-appb-I000020
상기 화학식 3에 있어서, In Formula 3,
L3 및 L4는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, L3 and L4 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, Ar7 to Ar10 are the same or different and each independently represents a substituted or unsubstituted aryl group,
X1 내지 X3 중 적어도 하나와 X4 내지 X6 중 적어도 하나는 N이고, 나머지는 CH이다. At least one of X1 to X3 and at least one of X4 to X6 is N and the others are CH.
본 명세서의 일 실시상태에 있어서, 상기 제3 유기물층은 전자 주입 및 수송층이다. In one embodiment of the present disclosure, the third organic layer is an electron injection and transport layer.
본 명세서의 일 실시상태에 있어서, 상기 제3 유기물층은 전자주입층이다.In one embodiment of the present invention, the third organic compound layer is an electron injection layer.
본 명세서의 일 실시상태에 있어서, 상기 제3 유기물층은 전자수송층이다.In one embodiment of the present invention, the third organic material layer is an electron transporting layer.
본 명세서의 일 실시상태에 있어서, 상기 화학식 3은 하기 화학식 3-1 내지 3-8 중 어느 하나로 표시된다. In one embodiment of the present invention, the formula (3) is represented by any one of the following formulas (3-1) to (3-8).
[화학식 3-1][Formula 3-1]
Figure PCTKR2019000703-appb-I000021
Figure PCTKR2019000703-appb-I000021
[화학식 3-2][Formula 3-2]
Figure PCTKR2019000703-appb-I000022
Figure PCTKR2019000703-appb-I000022
[화학식 3-3][Formula 3-3]
Figure PCTKR2019000703-appb-I000023
Figure PCTKR2019000703-appb-I000023
[화학식 3-4][Chemical Formula 3-4]
Figure PCTKR2019000703-appb-I000024
Figure PCTKR2019000703-appb-I000024
[화학식 3-5][Formula 3-5]
Figure PCTKR2019000703-appb-I000025
Figure PCTKR2019000703-appb-I000025
[화학식 3-6][Chemical Formula 3-6]
Figure PCTKR2019000703-appb-I000026
Figure PCTKR2019000703-appb-I000026
[화학식 3-7][Chemical Formula 3-7]
Figure PCTKR2019000703-appb-I000027
Figure PCTKR2019000703-appb-I000027
[화학식 3-8][Chemical Formula 3-8]
Figure PCTKR2019000703-appb-I000028
Figure PCTKR2019000703-appb-I000028
상기 화학식 3-1 내지 3-8에 있어서, L3, L4, Ar7 내지 Ar10 및 X1 내지 X6의 정의는 화학식 3에서와 같다. In the above Formulas (3-1) to (3-8), the definitions of L3, L4, Ar7 to Ar10 and X1 to X6 are as shown in Formula (3).
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 적어도 하나와 X4 내지 X6 중 적어도 하나는 N이고, 나머지는 CH이다. In one embodiment of the present specification, at least one of X1 to X3 and at least one of X4 to X6 is N and the others are CH.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3; 및 X4 내지 X6은 N이다. In one embodiment of the present disclosure, X1 to X3; And X4 to X6 are N;
본 명세서의 일 실시상태에 있어서, 상기 L3 및 L4는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 페닐렌기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 L3 및 L4는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기이다.In one embodiment of the present invention, L3 and L4 are the same or different from each other and are each independently a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3 및 L4는 서로 같거나 상이하고, 각각 독립적으로 직접결합; para-페닐렌기; 또는 meta-페닐렌기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 트리페닐렌기; 또는 치환 또는 비치환된 플루오레닐기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 바이페닐기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 페닐기; 또는 바이페닐기이다.In one embodiment of the present specification, Ar7 to Ar10 are the same or different from each other and are each independently a phenyl group; Or a biphenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 하기 구조식들 중에서 선택된다. In one embodiment of the present specification, Ar7 to Ar10 are the same or different from each other, and each independently selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000029
Figure PCTKR2019000703-appb-I000029
본 명세서의 일 실시상태에 있어서, 상기 화학식 3으로 표시되는 화합물은 하기 구조식들 중에서 선택된다. In one embodiment of the present invention, the compound represented by Formula 3 is selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000030
Figure PCTKR2019000703-appb-I000030
Figure PCTKR2019000703-appb-I000031
Figure PCTKR2019000703-appb-I000031
본 명세서의 일 실시상태에 있어서, 상기 발광층은 하기 화학식 4로 표시되는 화합물을 포함한다.In one embodiment of the present invention, the light emitting layer includes a compound represented by the following general formula (4).
[화학식 4][Chemical Formula 4]
Figure PCTKR2019000703-appb-I000032
Figure PCTKR2019000703-appb-I000032
상기 화학식 4에 있어서, Ar11 및 Ar12는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. In 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar11 및 Ar12는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 하기 화학식 5로 표시되는 화합물을 포함한다. In one embodiment of the present invention, the light emitting layer comprises a compound represented by the following general formula (5).
[화학식 5] [Chemical Formula 5]
Figure PCTKR2019000703-appb-I000033
Figure PCTKR2019000703-appb-I000033
상기 화학식 5에 있어서, In Formula 5,
Ar11은 치환 또는 비치환된 아릴기이고, Ar11 is a substituted or unsubstituted aryl group,
Y는 O 또는 S이고, Y is O or S,
R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기이다. 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar11은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 또는 치환 또는 비치환된 바이페닐기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar11은 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난쓰렌기; 또는 아릴기로 치환 또는 비치환된 바이페닐기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar11은 페닐기 또는 나프틸기로 치환 또는 비치환된 페닐기; 페닐기 또는 나프틸기로 치환 또는 비치환된 나프틸기; 페닐기 또는 나프틸기로 치환 또는 비치환된 페난쓰렌기; 또는 페닐기 또는 나프틸기로 치환 또는 비치환된 바이페닐기이다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Y는 O이다. In one embodiment of the present disclosure, Y is O.
본 명세서의 일 실시상태에 있어서, 상기 Y는 S이다. In one embodiment of the present disclosure, Y is S.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 수소이다. In one embodiment of the present specification, R1 to R4 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 화학식 4로 표시되는 화합물은 하기 구조식들 중에서 선택된다.In one embodiment of the present invention, the compound represented by Formula 4 is selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000034
Figure PCTKR2019000703-appb-I000034
Figure PCTKR2019000703-appb-I000035
Figure PCTKR2019000703-appb-I000035
Figure PCTKR2019000703-appb-I000036
Figure PCTKR2019000703-appb-I000036
Figure PCTKR2019000703-appb-I000037
Figure PCTKR2019000703-appb-I000037
본 명세서의 일 실시상태에 있어서, 상기 화학식 5로 표시되는 화합물은 하기 구조식들 중에서 선택된다. In one embodiment of the present invention, the compound represented by Formula 5 is selected from the following structural formulas.
Figure PCTKR2019000703-appb-I000038
Figure PCTKR2019000703-appb-I000038
Figure PCTKR2019000703-appb-I000039
Figure PCTKR2019000703-appb-I000039
Figure PCTKR2019000703-appb-I000040
Figure PCTKR2019000703-appb-I000040
Figure PCTKR2019000703-appb-I000041
Figure PCTKR2019000703-appb-I000041
본 명세서의 유기 발광 소자는 제1 유기물층 및 제2 유기물층을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 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.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 애노드, 유기물층 및 캐소드를 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공 주입층, 정공 수송층, 전자차단층, 발광층, 정공차단층, 및 전자 주입 및 수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질부터 유기물층, 애노드 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, 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. At this time, 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 . In addition to such a method, 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.
본 명세서의 유기 발광 소자의 유기물층은 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 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.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공주입층, 전자수송층, 전자주입층, 및 정공저지층으로 이루어진 군에서 선택되는 1 층 또는 2 층 이상을 더 포함할 수 있다. In one embodiment of the present invention, 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.
예컨대, 본 명세서의 유기 발광 소자의 구조는 도 1에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.For example, 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.
도 1에는 기판(101) 위에 양극(201), 제1 유기물층(301), 제2 유기물층(401), 발광층(501), 및 음극(601) 이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 1은 본 명세서의 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있고, 상기 제1 유기물층은 상기 화학식 1의 화합물을 포함할 수 있고, 제2 유기물층은 상기 화학식 2의 화합물을 포함할 수 있으나 이에 한정되지 않는다.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.
도 2에는 기판(101) 위에 양극(201), 제1 유기물층(301), 제2 유기물층(401), 발광층(501), 제3 유기물층(701), 및 음극(601) 이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 1은 본 명세서의 실시상태에 따른 예시적인 구조이며, 제1 유기물층은 상기 화학식 1의 화합물을 포함할 수 있고, 제2 유기물층은 상기 화학식 2의 화합물을 포함할 수 있으며, 제3 유기물층은 상기 화학식 3의 화합물을 포함할 수 있고, 상기 발광층은 상기 화학식 4 또는 5의 화합물을 포함할 수 있으나, 이에 한정되지 않는다. 도 3에는 기판(101) 위에 양극(201), 정공주입층(302), 정공수송층(303), 전자차단층(402) 발광층(501), 정공차단층(702), 전자 주입 및 수송층(703) 및 음극(601) 이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있고, 상기 정공수송층은 상기 화학식 1의 화합물을 포함할 수 있고, 전자차단층은 상기 화학식 2의 화합물을 포함할 수 있으며, 전자 주입 및 수송층은 상기 화학식 3의 화합물을 포함할 수 있고, 상기 발광층은 상기 화학식 4 또는 5의 화합물을 포함할 수 있으나, 이에 한정되지 않는다. 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.2 shows an organic EL device in which an anode 201, a first organic layer 301, a second organic layer 401, a light emitting layer 501, a third organic layer 701 and a cathode 601 are sequentially stacked on a substrate 101 The structure of the light emitting device is illustrated. 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. 3 shows an example of a structure in which an anode 201, a hole injection layer 302, a hole transport layer 303, an electron blocking layer 402, a light emitting layer 501, a hole blocking layer 702, an electron injection and transport layer 703 ) And a cathode 601 are successively laminated on a substrate 100. 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, and the light emitting layer may include the compound of Formula 4 or 5, but is not limited thereto. When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 정공 주입 층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. 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. Specific examples of 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.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 본 명세서의 제1 유기물층 이외의 층일 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 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. As the hole transporting material, 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.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 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.
도펀트 재료로는 유기 화합물, 금속 또는 금속 화합물이 있다. The dopant material includes an organic compound, a metal, or a metal compound.
도펀트 재료로서의 유기 화합물로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 또는 금속 화합물로는 일반적인 금속 또는 금속 화합물을 사용할 수 있으며, 구체적으로 금속 착체를 사용할 수 있다. 상기 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.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. Examples of the styrylamine compound 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. As 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.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. 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.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.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.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다. 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.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.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.
또한, 본 명세서에 따른 유기 발광 소자는 하부 전극이 애노드이고 상부전극이 캐소드인 정구조(normal type)일 수 있고, 하부전극이 캐소드이고 상부전극이 애노드인 역구조(inverted type)일 수도 있다.In addition, 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.
본 명세서의 일 실시상태에 따른 구조는 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다.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.
본 명세서의 일 실시상태에 따른 화학식 1로 표시되는 화합물의 코어 구조는 종래의 기술을 통하여 제조할 수 있다. The core structure of the compound represented by formula (1) according to one embodiment of the present invention can be prepared by conventional techniques.
본 명세서의 일 실시상태에 따른 화학식 2로 표시되는 화합물의 코어 구조는 하기와 같은 반응식 1을 통하여 제조될 수 있으나, 이에 한정되는 것은 아니다.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.
[반응식 1][Reaction Scheme 1]
Figure PCTKR2019000703-appb-I000042
Figure PCTKR2019000703-appb-I000042
상기 반응식 1에 있어서, L1, L2, Ar5, Ar6, R 및 n은 화학식 1에서 정의한 바와 동일하다. In the above Reaction Scheme 1, L1, L2, Ar5, Ar6, R and n are the same as defined in Formula (1).
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.
<< 실시예Example >>
<< 제조예Manufacturing example 1> - 화합물 2-1의 합성 1 > - Synthesis of Compound 2-1
Figure PCTKR2019000703-appb-I000043
Figure PCTKR2019000703-appb-I000043
질소 분위기에서 500ml 둥근 바닥 플라스크에 상기 화합물 A, 2-브로모-1,1'-비페닐을 자일렌(Xylene)에 완전히 녹인 후 소듐-tert-부톡사이드를 첨가하고, 비스(트리-tert-부틸포스핀)팔라듐을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기(base)를 제거한 후에, 자일렌(Xylene)을 감압농축 시키고 에틸아세테이트로 재결정하여 상기 화합물 2-1을 제조하였다. MS[M+H]+=715The compound A, 2-bromo-1,1'-biphenyl was completely dissolved in xylene in a 500 ml round-bottomed flask in a nitrogen atmosphere, sodium-tert-butoxide was added, and bis (tri- Butylphosphine) palladium, and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate to give Compound 2-1. MS [M + H] &lt; + &gt; = 715
<< 제조예Manufacturing example 2> - 화합물 2-2의 합성 2> - Synthesis of Compound 2-2
Figure PCTKR2019000703-appb-I000044
Figure PCTKR2019000703-appb-I000044
질소 분위기에서 500ml 둥근 바닥 플라스크에 상기 화합물 A, 4-브로모-1,1'-비페닐을 자일렌(Xylene)에 완전히 녹인 후 소듐-tert-부톡사이드를 첨가하고, 비스(트리-tert-부틸포스핀)팔라듐을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기(base)를 제거한 후, 자일렌(Xylene)을 감압농축 시키고 에틸아세테이트으로 재결정하여 상기 화합물 2-2를 제조하였다. MS[M+H]+=715The compound A, 4-bromo-1,1'-biphenyl was completely dissolved in xylene in a 500 ml round bottom flask in a nitrogen atmosphere, sodium tert-butoxide was added, and bis (tri- Butylphosphine) palladium, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate to give Compound 2-2. MS [M + H] &lt; + &gt; = 715
<< 제조예Manufacturing example 3> - 화합물 2-3의 합성 3> - Synthesis of Compound 2-3
Figure PCTKR2019000703-appb-I000045
Figure PCTKR2019000703-appb-I000045
질소 분위기에서 500ml 둥근 바닥 플라스크에 상기 화합물 B, 2-브로모-9,9-디페닐-9H-플루오렌을 자일렌(Xylene)에 완전히 녹인 후 소듐-tert-부톡사이드를 첨가하고, 비스(트리-tert-부틸포스핀)팔라듐을 넣은 후 2 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기(base)를 제거한 후에, 자일렌(Xylene)을 감압농축 시키고 에틸아세테이트으로 재결정하여 상기 화합물 2-3을 제조하였다. MS[M+H]+= 803The compound B, 2-bromo-9,9-diphenyl-9H-fluorene was completely dissolved in xylene in a 500 ml round-bottomed flask in a nitrogen atmosphere, sodium-tert-butoxide was added, Tri-tert-butylphosphine) palladium, and the mixture was heated with stirring for 2 hours. After lowering the temperature to room temperature and removing the base by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain the compound 2-3. MS [M + H] &lt; + &gt; = 803
<< 제조예Manufacturing example 4> - 화합물 2-4의 합성 4> - Synthesis of Compound 2-4
Figure PCTKR2019000703-appb-I000046
Figure PCTKR2019000703-appb-I000046
질소 분위기에서 500ml 둥근 바닥 플라스크에 상기 화합물 B, 2-브로모-9,9-디메틸-9H-플루오렌을 자일렌(Xylene)에 완전히 녹인 후 소듐-tert-부톡사이드를 첨가하고, 비스(트리-tert-부틸포스핀)팔라듐을 넣은 후 2 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기(base)를 제거한 후에, 자일렌(Xylene)을 감압농축 시키고 에틸아세테이트으로 재결정하여 상기 화합물 2-4를 제조하였다. MS[M+H]+= 679The compound B, 2-bromo-9,9-dimethyl-9H-fluorene was completely dissolved in xylene in a 500 ml round-bottomed flask in a nitrogen atmosphere, sodium-tert-butoxide was added, -tert-butylphosphine) palladium, and the mixture was heated with stirring for 2 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from ethyl acetate to give Compound 2-4. MS [M + H] &lt; + &gt; = 679
<< 비교예Comparative Example 1-1> 1-1>
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and 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.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 [HI-1] 및 하기 화합물 [HI-2]의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다.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 Å so as to have a molar ratio of 98: 2 on the prepared ITO transparent electrode.
Figure PCTKR2019000703-appb-I000047
Figure PCTKR2019000703-appb-I000047
상기 정공주입층 위에 정공을 수송하는 물질인 하기 화합물 [HT-1] (1150Å)를 진공 증착하여 정공수송층을 형성하였다.[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.
Figure PCTKR2019000703-appb-I000048
Figure PCTKR2019000703-appb-I000048
이어서, 상기 정공수송층 위에 막 두께 50Å으로 하기 화합물 [EB-1]을 진공 증착하여 전자차단층을 형성하였다.Subsequently, the following compound [EB-1] was vacuum deposited on the hole transport layer to a thickness of 50 ANGSTROM to form an electron blocking layer.
Figure PCTKR2019000703-appb-I000049
Figure PCTKR2019000703-appb-I000049
이어서, 상기 전자차단층 위에 막 두께 200Å으로 아래와 같은 화합물 [BH]와 화합물 [BD]를 50:1의 중량비로 진공증착하여 발광층을 형성하였다.Subsequently, the following compound [BH] and compound [BD] were vacuum deposited on the electron blocking layer to a thickness of 200 ANGSTROM at a weight ratio of 50: 1 to form a light emitting layer.
[BH] [BH]
Figure PCTKR2019000703-appb-I000050
Figure PCTKR2019000703-appb-I000050
[BD][BD]
Figure PCTKR2019000703-appb-I000051
Figure PCTKR2019000703-appb-I000051
[HB-1] [HB-1]
Figure PCTKR2019000703-appb-I000052
Figure PCTKR2019000703-appb-I000052
[ET-1][ET-1]
Figure PCTKR2019000703-appb-I000053
Figure PCTKR2019000703-appb-I000053
[LiQ][LiQ]
Figure PCTKR2019000703-appb-I000054
Figure PCTKR2019000703-appb-I000054
상기 발광층 위에 상기 정공 수송층 위에 막 두께 50Å으로 상기 화합물 [HB-1]를 진공 증착하여 정공 차단층을 형성하였다.The compound [HB-1] was vacuum deposited on the hole transporting layer to a thickness of 50 ANGSTROM to form a hole blocking layer.
이어서, 상기 정공 차단층 위에 화합물 [ET-1]과 상기 화합물 [LiQ](Lithium Quinolate)를 1:1의 중량비로 진공증착하여 310Å의 두께로 전자 주입 및 수송을 동시에 하는 층을 형성하였다.Subsequently, the compound [ET-1] and the compound [LiQ] (Lithium Quinolate) 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 Å.
상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다.Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 Х10-7 ~5 Х10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition Х10 2 -7 To 5 x 10 &lt; -6 &gt; torr. Thus, an organic light emitting device was fabricated.
Figure PCTKR2019000703-appb-I000055
Figure PCTKR2019000703-appb-I000055
<< 비교예Comparative Example 1-2> 1-2>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-3> 1-3>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-2를 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-4> 1-4>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-3을 사용한 것을 제외는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-5> 1-5>
상기 비교예 1-1에서 화합물 [EB-1] 대신 상기 화합물 2-1을 사용한 것을 제외는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-6> 1-6>
상기 비교예 1-1에서 화합물 [EB-1] 대신 상기 화합물 2-2를 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-7> 1-7>
상기 비교예 1-1에서 화합물 [EB-1] 대신 상기 화합물 2-3을 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-8> 1-8>
상기 비교예 1-1에서 화합물 [EB-1] 대신 상기 화합물 2-4를 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-9> 1-9>
상기 비교예 1-1에서 화합물 [ET-1] 대신 상기 화합물 3-1를 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic luminescent device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 3-1 was used in place of Compound [ET-1] in Comparative Example 1-1.
<< 비교예Comparative Example 1-10> 1-10>
상기 비교예 1-1에서 화합물 [BH] 대신 상기 화합물 4-1을 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-11> 1-11>
상기 비교예 1-1에서 화합물 [BH] 대신 상기 화합물 4-2를 사용한 것을 제외하고는 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-1> 1-1>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-1의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-2> 1-2>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-3> 1-3>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-3의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.Except that the above compound 1-1 was used in place of the compound [HT-1] in the above 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.
<< 실시예Example 1-4> 1-4>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-4의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-5> 1-5>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-2를 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-1의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-6> 1-6>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-2를 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-7> 1-7>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-2를 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-3의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-8> 1-8>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-2를 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-4의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-9> 1-9>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-3을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-1의 화합물을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-10> 1-10>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-3을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The same procedure as in Comparative Example 1-1 was repeated except that the compound 1-3 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-2 was used in place of the compound [EB-1] To prepare an organic light emitting device.
<< 실시예Example 1-11> 1-11>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-3을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-3을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The same procedure as in Comparative Example 1-1 was repeated except that the compound 1-3 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-3 was used in place of the compound [EB-1] To prepare an organic light emitting device.
<< 실시예Example 1-12> 1-12>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-3을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-4를 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The same procedure as in Comparative Example 1-1 was repeated except that the compound 1-3 was used in place of the compound [HT-1] in Comparative Example 1-1 and the compound 2-4 was used in place of the compound [EB-1] To prepare an organic light emitting device.
<< 실시예Example 1-13> 1-13>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2를 사용하고, 화합물 [BH] 대신 상기 화합물 4-1을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-14> 1-14>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2을 사용하고, 화합물 [BH] 대신 상기 화합물 4-2를 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-15> 1-15>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2를 사용하고, 화합물 [ET-1] 대신 상기 화합물 3-1을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 실시예Example 1-16> 1-16>
상기 비교예 1-1에서 화합물 [HT-1] 대신 상기 화합물 1-1을 사용하고, 화합물 [EB-1] 대신 상기 화합물 2-2를 사용하고, 화합물 [ET-1] 대신 상기 화합물 3-1을 사용하고, 화합물 [BH] 대신 상기 화합물 4-1을 사용한 것을 제외하고는 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-12> 1-12>
상기 실시예 1-2에서 화합물 1-1 대신 화합물 HT-2를 사용한 것을 제외하고는 상기 실시예 1-2과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-13> 1-13>
상기 실시예 1-2에서 화합물 2-2 대신 화합물 EB-2를 사용한 것을 제외하고는 상기 실시예 1-2과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
<< 비교예Comparative Example 1-14> 1-14>
상기 실시예 1-2에서 화합물 2-2 대신 화합물 EB-3을 사용한 것을 제외하고는 상기 실시예 1-2과 동일한 방법으로 유기 발광 소자를 제작하였다.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.
정공수송층Hole transport layer 전자차단층The electron blocking layer 전자 주입 및수송층Electron injection and transport layer 발광층The light- 전압(V)Voltage (V) 휘도(CD/A)Brightness (CD / A) T95(hr)T95 (hr)
비교예 1-1Comparative Example 1-1 [HT-1][HT-1] [EB-1][EB-1] [ET-1][ET-1] [BH][BH] 4.514.51 5.845.84 235235
비교예 1-2Comparative Example 1-2 1-11-1 [EB-1][EB-1] [ET-1][ET-1] [BH][BH] 4.124.12 6.066.06 260260
비교예 1-3Comparative Example 1-3 1-21-2 [EB-1][EB-1] [ET-1][ET-1] [BH][BH] 4.144.14 6.076.07 250250
비교예 1-4Comparative Example 1-4 1-31-3 [EB-1][EB-1] [ET-1][ET-1] [BH][BH] 4.134.13 6.086.08 265265
비교예 1-5Comparative Example 1-5 [HT-1][HT-1] 2-12-1 [ET-1][ET-1] [BH][BH] 4.054.05 6.256.25 315315
비교예 1-6Comparative Example 1-6 [HT-1][HT-1] 2-22-2 [ET-1][ET-1] [BH][BH] 4.464.46 6.056.05 290290
비교예 1-7Comparative Example 1-7 [HT-1][HT-1] 2-32-3 [ET-1][ET-1] [BH][BH] 4.064.06 6.296.29 315315
비교예 1-8Comparative Example 1-8 [HT-1][HT-1] 2-42-4 [ET-1][ET-1] [BH][BH] 4.084.08 6.276.27 310310
비교예 1-9Comparative Example 1-9 [HT-1][HT-1] [EB-1][EB-1] 3-13-1 [BH][BH] 4.294.29 5.955.95 275275
비교예 1-10Comparative Example 1-10 [HT-1][HT-1] [EB-1][EB-1] [ET-1][ET-1] 4-14-1 4.254.25 6.176.17 280280
비교예 1-11Comparative Example 1-11 [HT-1][HT-1] [EB-1][EB-1] [ET-1][ET-1] 4-24-2 4.274.27 6.156.15 270270
비교예 1-12Comparative Example 1-12 [HT-2][HT-2] 2-22-2 [ET-1][ET-1] [BH][BH] 4.324.32 6.166.16 310310
비교예 1-13Comparative Example 1-13 1-11-1 [EB-2][EB-2] [ET-1][ET-1] [BH][BH] 4.054.05 6.216.21 210210
비교예 1-14Comparative Example 1-14 1-11-1 [EB-3][EB-3] [ET-1][ET-1] [BH][BH] 5.265.26 5.575.57 8080
실시예 1-1Example 1-1 1-11-1 2-12-1 [ET-1][ET-1] [BH][BH] 3.553.55 6.416.41 340340
실시예 1-2Examples 1-2 1-11-1 2-22-2 [ET-1][ET-1] [BH][BH] 3.543.54 6.436.43 365365
실시예 1-3Example 1-3 1-11-1 2-32-3 [ET-1][ET-1] [BH][BH] 3.533.53 6.466.46 340340
실시예 1-4Examples 1-4 1-11-1 2-42-4 [ET-1][ET-1] [BH][BH] 3.543.54 6.416.41 345345
실시예 1-5Examples 1-5 1-21-2 2-12-1 [ET-1][ET-1] [BH][BH] 3.653.65 6.496.49 335335
실시예 1-6Examples 1-6 1-21-2 2-22-2 [ET-1][ET-1] [BH][BH] 3.673.67 6.476.47 365365
실시예 1-7Examples 1-7 1-21-2 2-32-3 [ET-1][ET-1] [BH][BH] 3.683.68 6.436.43 340340
실시예 1-8Examples 1-8 1-21-2 2-42-4 [ET-1][ET-1] [BH][BH] 3.693.69 6.406.40 345345
실시예 1-9Examples 1-9 1-31-3 2-12-1 [ET-1][ET-1] [BH][BH] 3.653.65 6.456.45 335335
실시예 1-10Example 1-10 1-31-3 2-22-2 [ET-1][ET-1] [BH][BH] 3.653.65 6.446.44 360360
실시예 1-11Example 1-11 1-31-3 2-32-3 [ET-1][ET-1] [BH][BH] 3.653.65 6.426.42 340340
실시예 1-12Examples 1-12 1-31-3 2-42-4 [ET-1][ET-1] [BH][BH] 3.623.62 6.416.41 340340
실시예 1-13Examples 1-13 1-11-1 2-22-2 [ET-1][ET-1] 4-14-1 3.753.75 6.646.64 405405
실시예 1-14Examples 1-14 1-11-1 2-22-2 [ET-1][ET-1] 4-24-2 370370 6.586.58 385385
실시예 1-15Examples 1-15 1-11-1 2-22-2 3-13-1 [BH][BH] 3.803.80 6.376.37 410410
실시예 1-16Examples 1-16 1-11-1 2-22-2 3-13-1 4-14-1 3.713.71 6.636.63 425425
실시예 1-1 내지 1-16 및 비교예 1-1 내지 1-14에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 상기 표 1의 결과를 얻었다. 상기 비교예 1-1의 청색 유기 발광 소자는 종래 널리 사용되고 있는 물질을 사용하였으며, 정공 수송층으로 화합물 [HT-1], 전자 차단층으로 화합물 [EB-1], 전자 주입 및 수송층으로 화합물 [ET-1], 청색발광층으로 화합물 [BH] 을 사용하는 구조이다.When current was applied to the organic light-emitting devices manufactured in Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-14, the results shown in Table 1 were obtained. 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.
상기 표 1에 따르면, 비교예 1-2 내지 1-4는 종래의 정공 수송층으로 사용되는 화합물 [HT-1] 대신 본 명세서의 일 실시상태에 따른 화학식 1의 화합물을 사용하였고, 비교예 1-5 내지 1-8은 종래의 전자차단층으로 사용되는 화합물 [EB-1] 대신 본 명세서의 일 실시상태에 따른 화학식 2의 화합물을 사용하였으며, 비교예 1-9 는 종래의 전자수송층으로 사용되는 화합물 [ET-1] 대신 본 명세서의 일 실시상태에 따른 화학식 3-1의 화합물을 사용하였으며, 비교예 1-10 및 1-11은 종래의 청색발광층으로 사용되는 화합물 [BH] 대신 본 명세서의 일 실시상태에 따른 화학식 4-1의 화합물을 사용하여 화학식 1, 화학식 2, 화학식 3 및 화학식 4의 화합물을 각각 포함하는 유기 발광 소자를 제조하였다.According to Table 1, 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. In 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.
화학식 1을 정공 수송층으로 사용하였을 때 구동전압은 8~10% 낮아지는 저전압 특성을 보이며, 화학식 2를 전자 차단층으로 사용하였을 때 발광효율은 8% 높아지고 수명이 30% 이상 증가하는 고효율, 장수명의 결과를 얻었다.When the compound of formula (1) is used as a hole transport layer, the driving voltage is lowered by 8 to 10%, and when 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.
화학식 3을 전자 주입 및 수송층으로 사용하였을 때 수명이 10~20% 증가하는 장수명 특성을 보이며, 화학식 4를 청색발광층으로 사용하였을 때 저전압 및 고효율 특성 뿐만 아니라 수명도 10~20% 증가하는 결과를 얻었다.When the compound of Formula 3 was used as an electron injecting and transporting layer, the lifetime was increased by 10 to 20%, and when 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 .
실시예 1-1 내지 1-12는 본 명세서의 화학식 1을 정공수송층으로 사용하고, 본 명세서의 화학식 2을 전자차단층으로 사용하는 유기 발광 소자이며, 상기 실시예 1-1 내지 1-12의 유기 발광 소자는 본 명세서의 화학식 1, 화학식 2를 각각 포함하는 유기 발광 소자 보다 전체적으로 구동전압은 8~10% 낮아지는 발광효율은 8% 높아지고 수명이 30% 이상 증가하는 특성을 나타낸다.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. In Examples 1-1 to 1-12, 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.
특히, 정공수송층으로 화합물 1-1을 사용하고, 전자차단층으로 본 명세서의 화학식 2의 화합물인 화합물 2-1 내지 2-4를 사용한 실시예 1-1 내지 1-4의 유기 발광 소자의 구동 전압이 가장 낮았고, 정공수송층으로 본 명세서의 화학식 1의 화합물인 화합물 1-1 내지 1-3을 사용하고, 전자차단층으로 화합물 2-2를 사용한 실시예 1-2, 1-6 및 1-10의 유기 발광 소자의 수명이 가장 길게 측정되었다.Particularly, when 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 &lt; / RTI &gt;
실시예 1-13 내지 1-16는 실시예 1-2의 유기 발광 소자에서 전자 주입 및 수송층 및 청색발광층을 각각 화합물 3-1 및 화합물 4-1을 사용하거나 동시에 포함하는 소자로 전압은 약간 상승하지만, 대신 가장 좋은 수명 특성을 보였다.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.
비교예 1-12 에서 종래에 널리 쓰이는 [HT-2] 물질을 정공수송층으로 사용하고 본원 발명의 화합물 2-2을 [EB-1] 대신 사용하였을 때 전압이 10% 이상 크게 증가하는 결과를 얻었다.When the [HT-2] material conventionally used in Comparative Example 1-12 was used as the hole transport layer and the compound 2-2 of the present invention was used instead of [EB-1], the voltage was significantly increased by 10% or more .
비교예 1-13는 본 명세서의 화학식 2의 치환기인 바이페닐과 카바졸이 ortho 방향이 아닌 meta 방향으로 연결된 화합물 [EB-2]를 전자차단층으로 사용하는 유기 발광 소자로 소자 효율이 10% 이상 감소하며, 수명 또한 20% 이상 감소하는 결과를 얻었다. 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.
비교예 1-14는 본 명세서의 화학식 2의 치환기인 바이페닐에 추가의 아민 치환기가 결합한 화합물 [EB-3]을 전자수송층으로 사용한 유기 발광 소자로 밸런스(Balance)가 무너져서 소자의 수명이 크게 감소하는 결과를 얻었다. 그 이유는 아민기가 3개 포함하는 화합물 [EB-3]는 HOMO 값이 너무 낮아서 인접한 발광층과 베리어(barrier)가 크게 높아지게 되기 때문이다.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.
정공수송층으로 HT-2를 사용한 비교예 1-12와 본원 발명의 화합물 1-3을 사용한 실시예 1-10을 비교하면, 비교적으로 낮은 유리 전이 온도를 갖는 HT-2 (98℃)을 사용하는 경우, 효율이 약 4% 감소하는 것을 확인하였으며, 소자의 수명을 약 16% 줄어드는 것을 확인하였습니다. Comparing Comparative Example 1-12 using HT-2 as the hole transporting layer with Example 1-10 using the Compound 1-3 of the present invention, it was found that using HT-2 (98 ° C) having a relatively low glass transition temperature , We have confirmed that the efficiency is reduced by about 4%, and that the lifetime of the device is reduced by about 16%.
반면, 정공수송층으로 유리 전이 온도가 높은 HT-1 (120℃ 이상)을 사용한 비교예 1-5 내지 1-8과 본원 발명의 화합물 1-1, 1-2 및 1-3을 사용한 실시예 1-1 내지 1-12와 비교하면 전류 효율이 크게 줄어드는 것을 확인하였습니다. On the other hand, in Comparative Examples 1-5 to 1-8 in which HT-1 (120 占 폚 or more) having a high glass transition temperature was used as the hole transport layer and Example 1 Compared with -1 to 1-12, we have found that the current efficiency is greatly reduced.
따라서, 본원 화학식 1을 만족하는 화합물은 Ar1 내지 Ar4의 치환기를 조절하여 유리 전이 온도를 상승시켜 수명을 보완하고, 1-나프틸기가 결합하는 경우에서는 효율을 보완하여 정공수송층에 사용하고, 동시에 화학식 2를 만족하는 화합물을 전자차단층으로 사용하여 유기 발광 소자에서의 전류효율 및 수명을 최적화하였다. 이를 통하여 본원 발명의 화학식 1(다환의 아릴기를 하나 이상 포함하는 benzidine type 구조)을 정공수송층 재료(HTL)로 사용하고, 화학식 2(치환기인 바이페닐과 카바졸이 ortho 방향으로 연결된 monoamine 구조)을 전자차단층 재료(EBL)로 조합하여 만들어지는 청색 유기 발광 소자의 구동전압 및 발광효율, 특히 수명 특성을 개선할 수 있다는 것을 확인할 수 있다. 또한 전자 주입 및 수송층 및 청색발광층으로 화학식 3 및 화학식 4 또는 5의 화합물들을 적용하면 전압을 조금 상승하더라도 가장 좋은 수명 특성을 갖는 유기 발광 소자를 만들 수 있다는 것을 알게 되었다.Therefore, 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. (1) (benzidine type structure containing at least one aryl group of a polycyclic group) is used as a hole transport layer material (HTL), and Formula 2 (monoamine structure in which a substituent biphenyl and carbazole are connected in an ortho direction) It can be confirmed that the driving voltage and the luminous efficiency, in particular the lifetime characteristics, of the blue organic light emitting device formed by combining with the electron blocking layer material (EBL) can be improved. Further, it has been found that applying the compounds of the formulas (3) and (4) or (5) to the electron injecting and transporting layer and the blue emitting layer can produce an organic light emitting device having the best lifespan characteristics even when the voltage is slightly increased.

Claims (9)

  1. 양극; 상기 양극에 대향하여 구비된 음극; 및 상기 양극과 상기 음극 사이의 유기물층을 포함하는 유기 발광 소자로서, anode; A negative electrode opposed to the positive electrode; And an organic layer between the anode and the cathode,
    상기 유기물층은 발광층을 포함하고, Wherein the organic layer includes a light emitting layer,
    상기 양극과 발광층 사이에 구비된 제1 유기물층; 상기 제1 유기물층과 발광층 사이에 발광층과 접하는 제2 유기물층을 포함하고,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,
    상기 제1 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고, Wherein the first organic layer comprises a compound represented by the following formula (1)
    상기 제2 유기물층은 하기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자:Wherein the second organic compound layer comprises a compound represented by Formula 2:
    [화학식 1][Chemical Formula 1]
    Figure PCTKR2019000703-appb-I000056
    Figure PCTKR2019000703-appb-I000056
    [화학식 2](2)
    Figure PCTKR2019000703-appb-I000057
    Figure PCTKR2019000703-appb-I000057
    상기 화학식 1 및 2에 있어서, In the above formulas (1) and (2)
    Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group,
    상기 Ar1 내지 Ar4 중 적어도 하나는 치환 또는 비치환된 다환의 아릴기이며, At least one of Ar1 to Ar4 is a substituted or unsubstituted polycyclic aryl group,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며, 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 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, 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,
    n은 0 내지 8 내지의 정수이고, R은 수소이거나, n이 2 이상일 때, 인접한 R은 서로 결합하여 고리를 형성하며, n is an integer of 0 to 8, and R is hydrogen or when n is 2 or more, adjacent Rs are bonded to each other to form a ring,
    단, Ar1 및 Ar2 중 어느 하나; 및 Ar3 및 Ar4중 어느 하나가 1-나프틸기이고, 나머지 Ar1 내지 Ar4가 비치환된 페닐기인 경우는 제외된다. Provided that 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.
  2. 청구항 1에 있어서, 상기 Ar1 내지 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 터페닐기인 것인 유기 발광 소자.[4] The compound according to claim 1, wherein 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.
  3. 청구항 1에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 트리페닐렌기; 또는 치환 또는 비치환된 플루오레닐기인 것인 유기 발광 소자. 2. The compound according to claim 1, wherein Ar5 and Ar6 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.
  4. 청구항 1에 있어서, 상기 제1 유기물층은 정공수송층인 것인 유기 발광 소자.The organic light emitting device according to claim 1, wherein the first organic material layer is a hole transporting layer.
  5. 청구항 1에 있어서, 상기 제2 유기물층은 전자차단층인 것인 유기 발광 소자.The organic light emitting device according to claim 1, wherein the second organic material layer is an electron blocking layer.
  6. 청구항 1에 있어서, 상기 유기 발광 소자의 음극과 발광층 사이에 제3 유기물층을 포함하고, 상기 제3 유기물층은 하기 화학식 3로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic electroluminescent device of claim 1, further comprising a third organic compound layer between the cathode of the organic light emitting device and the light emitting layer, and the third organic compound layer comprises a compound represented by Formula 3:
    [화학식 3](3)
    Figure PCTKR2019000703-appb-I000058
    Figure PCTKR2019000703-appb-I000058
    상기 화학식 3에 있어서, In Formula 3,
    L3 및 L4는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, L3 and L4 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
    Ar7 내지 Ar10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, Ar7 to Ar10 are the same or different and each independently represents a substituted or unsubstituted aryl group,
    X1 내지 X3 중 적어도 하나와 X4 내지 X6 중 적어도 하나는 N이고, 나머지는 CH이다. At least one of X1 to X3 and at least one of X4 to X6 is N and the others are CH.
  7. 청구항 6에 있어서, 상기 화학식 3은 하기 화학식 3-1 내지 3-8 중 어느 하나로 표시되는 것인 유기 발광 소자:The organic electroluminescent device according to claim 6, wherein the formula (3) is represented by any one of the following formulas (3-1) to (3-8)
    [화학식 3-1][Formula 3-1]
    Figure PCTKR2019000703-appb-I000059
    Figure PCTKR2019000703-appb-I000059
    [화학식 3-2][Formula 3-2]
    Figure PCTKR2019000703-appb-I000060
    Figure PCTKR2019000703-appb-I000060
    [화학식 3-3][Formula 3-3]
    Figure PCTKR2019000703-appb-I000061
    Figure PCTKR2019000703-appb-I000061
    [화학식 3-4][Chemical Formula 3-4]
    Figure PCTKR2019000703-appb-I000062
    Figure PCTKR2019000703-appb-I000062
    [화학식 3-5][Formula 3-5]
    Figure PCTKR2019000703-appb-I000063
    Figure PCTKR2019000703-appb-I000063
    [화학식 3-6][Chemical Formula 3-6]
    Figure PCTKR2019000703-appb-I000064
    Figure PCTKR2019000703-appb-I000064
    [화학식 3-7][Chemical Formula 3-7]
    Figure PCTKR2019000703-appb-I000065
    Figure PCTKR2019000703-appb-I000065
    [화학식 3-8][Chemical Formula 3-8]
    Figure PCTKR2019000703-appb-I000066
    Figure PCTKR2019000703-appb-I000066
    상기 화학식 3-1 내지 3-8에 있어서, L3, L4, Ar7 내지 Ar10 및 X1 내지 X6의 정의는 화학식 3에서와 같다. In the above Formulas (3-1) to (3-8), the definitions of L3, L4, Ar7 to Ar10 and X1 to X6 are as shown in Formula (3).
  8. 청구항 1에 있어서, 상기 발광층은 하기 화학식 4로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic electroluminescent device according to claim 1, wherein the light emitting layer comprises a compound represented by Formula 4:
    [화학식 4][Chemical Formula 4]
    Figure PCTKR2019000703-appb-I000067
    Figure PCTKR2019000703-appb-I000067
    상기 화학식 4에 있어서, Ar11 및 Ar12는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In 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.
  9. 청구항 1에 있어서, 상기 발광층은 하기 화학식 5로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic electroluminescent device according to claim 1, wherein the light emitting layer comprises a compound represented by Formula 5:
    [화학식 5] [Chemical Formula 5]
    Figure PCTKR2019000703-appb-I000068
    Figure PCTKR2019000703-appb-I000068
    상기 화학식 5에 있어서, In Formula 5,
    Ar11은 치환 또는 비치환된 아릴기이고, Ar11 is a substituted or unsubstituted aryl group,
    Y는 O 또는 S이고, Y is O or S,
    R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기이다. 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.
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