WO2018004318A2 - Heterocyclic compound and organic light emitting element comprising same - Google Patents

Heterocyclic compound and organic light emitting element comprising same Download PDF

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WO2018004318A2
WO2018004318A2 PCT/KR2017/007032 KR2017007032W WO2018004318A2 WO 2018004318 A2 WO2018004318 A2 WO 2018004318A2 KR 2017007032 W KR2017007032 W KR 2017007032W WO 2018004318 A2 WO2018004318 A2 WO 2018004318A2
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group
substituted
unsubstituted
same
light emitting
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Korean (ko)
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WO2018004318A3 (en
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구기동
정현석
이기곤
이형진
김동헌
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주식회사 엘지화학
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Priority to CN201780041280.2A priority Critical patent/CN109415376B/en
Priority to JP2018565344A priority patent/JP6716854B2/en
Publication of WO2018004318A2 publication Critical patent/WO2018004318A2/en
Publication of WO2018004318A3 publication Critical patent/WO2018004318A3/en

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    • H—ELECTRICITY
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    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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    • 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

Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
  • the principle of the organic light emitting phenomenon is as follows. When the organic material layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall back to the ground to shine.
  • An organic light emitting device using this principle may be generally composed of an organic material layer including a cathode and an anode and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a heterocyclic compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsub
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 is a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
  • R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and b are each an integer of 0 to 4,
  • c and d are integers from 0 to 3
  • n1 and n2 are each 0 or 1
  • n1 and n2 are integers 1,
  • X1 and X2 are hydrogen or directly bond to each other.
  • an exemplary embodiment of the present specification includes a first electrode, a second electrode and one or more organic material layers disposed between the first electrode and the second electrode, one or more of the organic material layers includes the heterocyclic compound.
  • An organic light emitting device is provided.
  • the heterocyclic compound described herein can be used as a material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4. It is.
  • 5 is a diagram showing a mass data of the compound 10.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsub
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 is a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
  • R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and b are each an integer of 0 to 4,
  • c and d are integers from 0 to 3
  • n1 and n2 are each 0 or 1
  • n1 and n2 are integers 1,
  • X1 and X2 are hydrogen or directly bond to each other.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent may be substituted, and two or more. When substituted, two or more substituents may be the same or different from one another.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. Do not.
  • the boron group may be represented by a chemical formula of -BR a R b , wherein R and R b are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • the alkyl group may be linear or branched, the carbon number is not particularly limited, but may be 1 to 50, according to one embodiment, the carbon number may be 1 to 30. According to another exemplary embodiment, the carbon number may be 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n
  • the cycloalkyl group is not particularly limited, but may be 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group may have 3 to 30 carbon atoms, and according to another embodiment, 3 to 20 carbon atoms.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , Benzyloxy group, p-methylbenzyloxy group and the like, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
  • the alkenyl group may be linear or branched, the carbon number is not particularly limited, but may be 2 to 40, according to one embodiment may be 2 to 20.
  • Specific examples thereof include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, and 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the alkylamine group is not particularly limited, but may be 1 to 40, according to one embodiment may be 1 to 20.
  • Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups and the like, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, and triphenyl amine group, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group, may be a polycyclic heteroaryl group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.
  • examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
  • the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but may be 6 to 60 carbon atoms, 6 to 30 according to one embodiment, and 6 to 20 according to another embodiment.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It may have 10 to 60 carbon atoms, according to one embodiment may be 6 to 30, it may be 6 to 20.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but may be 2 to 60 carbon atoms, and according to one embodiment may be 2 to 30 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzoquinolinyl group, benzopyridazinyl group, benzothiazole group, benzocarbazole group, benzothiophene group,
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
  • the hydrocarbon ring may be an aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, and may be selected from examples of the cycloalkyl group or aryl group, except that they are not monovalent.
  • the heterocyclic group may be an aliphatic, aromatic or a condensed ring of aliphatic and aromatic, and may be selected from examples of the heterocyclic group, except that it is not a monovalent group.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
  • the description of one aryl group may apply.
  • the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
  • heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the aralkenyl group and the arylalkenyl group may be applied to the description of the alkenyl group described above.
  • alkyl group of the arylalkyl group and the thioalkyl group may be described with respect to the alkyl group described above.
  • heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • X1 and X2 are both hydrogen.
  • X1 and X2 directly bond with each other to form a pentagonal ring.
  • n1 and n2 are 0 or 1, and at least one of n1 and n2 is an integer of 1.
  • n1 and n2 are integers of 1.
  • Ar1 is a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 is a substituted or unsubstituted hydrocarbon ring having 3 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar1-L2-NR3R4 is one of the following structures.
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkyl sulfoxy group; an aryl sulfoxy group; Silyl groups; boron groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted aralkyl groups; substituted or unsubstituted Alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Sub
  • the structures may be further substituted.
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; halogen; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted Cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; substituted Or an unsubstituted arylheteroarylamine group, or a substituted or unsubstituted heteroring group.
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl Or a substituted or unsubstituted heterocyclic group.
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted carbon group having 3 to 60 carbon atoms Or a cycloalkyl group of D, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon atom 3 to 30 Or a cycloalkyl group of C, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
  • R 'and R are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R ′ and R ′′ are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted tert-butyl group .
  • R 'and R are the same as or different from each other, and are each independently a methyl group, an ethyl group, or a tert-butyl group.
  • the heterocyclic compound represented by Formula 1 may be any one selected from the following Formula 1-A to 1-F.
  • X1, X2, R1 to R8, L1, L2, n1 and n2 are the same as defined in Formula 1,
  • W1 to W6 are the same as or different from each other, and are each independently O, S, SiT1T2, or CT3T4,
  • T1 to T4 and R101 to R106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • s1 and s3 are each an integer of 0 to 5
  • s2 and s4 are each an integer of 0 to 7,
  • s5 and s6 are each an integer of 0 to 4,
  • s1 is 0 or 1.
  • s2 is 0 or 1.
  • s3 is 0 or 1.
  • s4 is 0 or 1.
  • s5 is 0 or 1.
  • s6 is 0 or 1.
  • the T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • the T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • the T1 to T4 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted t-butyl group.
  • T1 to T4 are methyl groups.
  • R101 to R106 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the R101 to R106 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R101 to R106 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R101 to R106 are hydrogen.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
  • the R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted dibenzofuran group.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; Naphthylene group; Or a dibenzofuran group.
  • R5 and R8 are the same as or different from each other, and are each independently hydrogen or a tert-butyl group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted pyrrole group; Substituted or unsubstituted dibenzofuranylene group;
  • L1 and L2 are the same as or different from each other, and each independently a phenylene group; Biphenylylene group; Terphenylene group; Naphthalene group; 9,9-diphenyl fluorenyl group; 9,9-dimethyl fluorenyl group; Phenanthrenylene group; Anthracenylene group; Triphenylenyl group; Thiophenylene group; Furanylene group; Pyrrolene group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzofuranylene group; Dibenzothiophenylene group; Carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or one of the following structures.
  • L1 and L2 are direct bonds.
  • R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • the R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthryl group; Substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluoranthenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted indenofluorenyl group; Substit
  • R1 to R4 are the same as or different from each other, and each independently may be any one selected from the structures described below.
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Silyl groups; Boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a1, a6, a10, a23 and a25 are each an integer of 0 to 5
  • a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
  • a3 and a22 are each an integer of 0 to 7
  • a4, a7, a12, a15. a19, a26 and a27 are each an integer of 0 to 3,
  • a11 is an integer of 0 to 9
  • a13, a20 and a24 are each an integer of 0 to 6
  • a18, b5, b10, b14 and b16 are each an integer of 0 to 2
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • the R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups substituted with methyl groups; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted t-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.
  • R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Methyl group; t-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group.
  • the a1 to a35 and b1 to b32 are each an integer of 0 to 2.
  • heterocyclic compound of Formula 1 may be any one selected from the following compounds.
  • heterocyclic compound according to one embodiment of the present specification may be prepared by the manufacturing method described below.
  • the heterocyclic compound of Formula 1 may have a core structure as in Preparation Example.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • the first electrode, the second electrode and one or more organic material layers disposed between the first electrode and the second electrode, one or more of the organic material layer is one embodiment of the present specification It provides an organic light emitting device comprising the heterocyclic compound according to.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron transport layer 7.
  • the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes a heterocyclic compound represented by Formula 1 above. .
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer
  • the organic material layer includes a heterocyclic compound represented by Formula 1
  • the light emitting layer further includes a compound represented by Formula 2 below.
  • R9 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group;
  • p is an integer from 0 to 6
  • L3 to L6 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R9 is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
  • R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
  • R9 is hydrogen
  • p is 0 or 1.
  • L3 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • L3 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
  • the L3 to L6 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted dibenzothiophenylene group; Substituted or unsubstituted dibenzofurany
  • L3 to L6 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
  • the L3 to L6 are the same as or different from each other, and each independently a direct bond; Or the following structures.
  • L3 is a direct bond.
  • L4 is a phenylene group.
  • L5 and L6 is a direct bond.
  • Ar2 to Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; A C6-C60 aryl group unsubstituted or substituted with a C6-C60 aryl group or a C2-C60 heteroaryl group; Or a C2-C60 heteroaryl group unsubstituted or substituted with a C6-60 aryl group or a C2-C60 heteroaryl group.
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or unsubsti
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; Furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbamate; benzyl
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; Furan group unsubstituted or substituted with a phenyl group
  • Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Or the following structures.
  • the organic material layer includes a light emitting layer
  • the organic material layer includes a heterocyclic compound represented by Chemical Formula 1
  • the light emitting layer further includes a compound represented by Chemical Formula 3 below.
  • R10 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group;
  • q is an integer from 0 to 7
  • L7 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar6 to Ar8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R10 is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
  • R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
  • R10 is hydrogen
  • q is 0 or 1.
  • L7 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • L7 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
  • the L7 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted dibenzothiophenylene group; Substituted or unsubstituted dibenzofurany
  • L7 to L9 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
  • the L7 to L9 are the same as or different from each other, and each independently a direct bond; Or the following structures.
  • L7 to L9 are direct bonds.
  • Ar6 to Ar8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar6 to Ar8 are the same as or different from each other, and each independently an aryl having 6 to 60 carbon atoms substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms. group; Or a C2-C60 heteroaryl group unsubstituted or substituted with a C6-60 aryl group or a C2-C60 heteroaryl group.
  • Ar6 to Ar8 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or
  • Ar6 to Ar8 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; Furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbamate; Triphenylene
  • Ar6 to Ar8 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; Furan group unsubstituted or substituted with a phenyl group
  • Ar6 to Ar8 are the same as or different from each other, and each independently may be selected from the following structures.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 as a host of the light emitting layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, and the compound represented by Formula 2 or Formula 3 of the light emitting layer Include as host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, and the compound represented by Formula 2 or Formula 3 of the light emitting layer Included as a host, it can be doped with a heterocyclic compound represented by Formula 1 to 2 to 10wt%.
  • the organic material layer includes a hole blocking layer, an electron transport layer or an electron injection layer, and the hole blocking layer, an electron transport layer or an electron injection layer includes a heterocyclic compound represented by Formula 1 above. .
  • the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • an organic light emitting device the first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1.
  • the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer may further include a host including a heterocyclic compound represented by Chemical Formula 1 as a dopant.
  • the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer further includes a heterocyclic compound represented by Chemical Formula 1 as a dopant, and may further include a host. It may be a compound represented by 2 or 3.
  • the organic light emitting device may further include one or more organic material layers selected from a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer.
  • the structure of the organic light emitting device is not limited thereto.
  • the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, and may include one or more organic material layers selected from a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and the second electrode and the light emitting layer. At least one organic material layer selected from among the electron transport layer and the electron injection layer may be included.
  • the structure of the organic light emitting device of the present invention is not limited thereto.
  • the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Formula 1 as a host, and a hole injection layer and a hole transport layer between the first electrode and the light emitting layer. It may include one or more organic material layer selected from among, and may include one or more organic material layer selected from the electron transport layer and the electron injection layer between the second electrode and the light emitting layer.
  • the structure of the organic light emitting device of the present invention is not limited thereto.
  • the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1 as a dopant, and the compound represented by Chemical Formula 2 or 3 as a host of the light emitting layer. And at least one organic material layer selected from a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and at least one organic material layer selected from an electron transport layer and an electron injection layer between the second electrode and the light emitting layer. It may include. However, the structure of the organic light emitting device of the present invention is not limited thereto.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by Chemical Formula 1 above. Can be.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition PVD: physical vapor deposition
  • PVD physical vapor deposition
  • sputtering e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof on the substrate
  • It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, Mg / Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a hetero ring-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and at least one substituent selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • ⁇ Intermediate 1-3> (9.50 g, 31.2 mmol) was added to 300 mL of dichloromethane, stirred, and then slowly added dropwise 9.97 g (62.3 mmol) of bromine diluted in 50 mL of dichloromethane. Stir at room temperature for 48 hours. Subsequent replacements were washed with dichloromethane and normal hexane after filtration. The solid was recrystallized from toluene and normal hexane to obtain ⁇ Intermediate 1-4> (7.0 g, 59% yield).
  • ⁇ Intermediate 1-5> (7.60 g, 12.1 mmol), acetic acid (100 mL) and 2 drops of sulfuric acid were added to a 0.25 L flask, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the solid was filtered and washed with water and ethanol and recrystallized with ethyl acetate and normal hexane to give ⁇ Intermediate 1-6> (7.04 g, 95% yield).
  • Compound 1 was synthesized according to the following scheme.
  • Compound 2 was synthesized according to the following scheme.
  • Compound 8 was synthesized according to the following scheme.
  • Compound 8 was synthesized according to Synthesis Example 8 using ⁇ Intermediate 1-6> and ⁇ Intermediate 2-4>.
  • Compound 13 was synthesized according to the following scheme.
  • Compound 13 was synthesized according to Synthesis Example 8 using ⁇ Intermediate 1-6> and ⁇ Intermediate 2-5>.
  • Compound 15 was synthesized according to the following scheme.
  • Compound 15 was synthesized according to Synthesis Example 8 using ⁇ Intermediate 1-6> and ⁇ Intermediate 2-6>.
  • ⁇ Intermediate 3-1> (32.0g, 0.153mol) and potassium carbonate (63.4g, 0.459mol) were added to a 1L flask, and the mixture was diluted with dimethylacetamide (400mL) and stirred under reflux for 3 hours. After distilling the reaction solvent under reduced pressure, the organic layer obtained by extraction with ethyl acetate and water was filtered and concentrated over anhydrous magnesium sulfate, and recrystallized with ethyl acetate and ethanol to obtain ⁇ Intermediate 4-2> (33.0 g, Yield 85%).
  • Compound 25 was synthesized according to the following scheme.
  • Compound 18 was synthesized according to the following scheme.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • the HAT was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the HT-A 1000 Pa was vacuum deposited on the hole transport layer, and HT-B was subsequently deposited to a thickness of 100 Pa.
  • the light emitting layer was doped with H-A and Compound 1 at 2 to 10 wt% as a host, and was vacuum deposited to a thickness of 200 ⁇ .
  • ET-A and Liq were deposited at 300 ⁇ s in a 1: 1 ratio, and 150 ⁇ m thick Ag (Ag) 10% doped magnesium (Mg) and 1,000 ⁇ m thick aluminum were deposited to form a cathode.
  • An organic light emitting device was manufactured.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • LiF was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 7 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 13 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 28 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 29 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 30 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using H-B instead of compound H-A.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 7 was used instead of Compound 1 in Example 7.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 13 was used instead of Compound 1 in Example 7.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 28 was used instead of Compound 1 in Example 7.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 29 was used instead of Compound 1 in Example 7.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 30 was used instead of Compound 1 in Example 7.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using H-C instead of H-A.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 7 was used instead of Compound 1 in Example 13.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 13 was used instead of Compound 1 in Example 13.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 28 was used instead of Compound 1 in Example 13.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 29 was used instead of Compound 1 in Example 13.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 30 was used instead of Compound 1 in Example 13.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-1 instead of compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that D-2 was used instead of Compound 1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-3 instead of compound 1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-1 instead of compound 1 in Example 7.
  • An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-2 instead of compound 1 in Example 7.
  • An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-3 instead of compound 1 in Example 7.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that D-1 was used instead of Compound 1 in Example 13.
  • An organic light-emitting device was manufactured in the same manner as in Example 13, except that D-2 was used instead of Compound 1 in Example 13.
  • An organic light emitting diode was manufactured according to the same method as Example 13 except for using D-3 instead of compound 1 in Example 13.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes of Examples 1 to 18 and Comparative Examples 1 to 9 were measured at a current density of 10 mA / cm, and the time became 95% of the initial luminance at a current density of 20 mA / cm. (LT95) was measured.
  • the results are shown in Table 1 below.
  • the electron density distribution of HOMO is generally distributed in the spiro indolo acridine moiety containing nitrogen, which is known to have a stable cation state. Therefore, it was confirmed that the efficiency and lifespan characteristics were superior to those of the organic light emitting devices manufactured in Comparative Examples 1 to 9 including pyrene-based or fluorene-based compounds.

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Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting element comprising the same.

Description

헤테로고리 화합물 및 이를 포함하는 유기 발광 소자Heterocyclic compound and organic light emitting device comprising the same
본 출원은 2016년 07월 01일 한국 특허청에 제출된 한국 특허 출원 제10-2016-0083728호의 출원일 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of Korean Patent Application No. 10-2016-0083728, filed July 1, 2016 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a heterocyclic compound and an organic light emitting device including the same.
유기 발광 현상은 특정 유기 분자의 내부 프로세스에 의하여 전류가 가시광으로 전환되는 예의 하나이다. 유기 발광 현상의 원리는 다음과 같다. 양극과 음극 사이에 유기물층을 위치시켰을 때, 두 전극 사이에 전압을 걸어주게 되면 음극과 양극으로부터 각각 전자와 정공이 유기물 층으로 주입된다. 유기물층으로 주입된 전자와 정공은 재결합하여 엑시톤(exciton)을 형성하고, 이 엑시톤이 다시 바닥 상태로 떨어지면서 빛이 나게 된다. 이러한 원리를 이용하는 유기 발광 소자는 일반적으로 음극과 양극 및 그 사이에 위치한 유기물층, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 유기물층으로 구성될 수 있다.The organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule. The principle of the organic light emitting phenomenon is as follows. When the organic material layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall back to the ground to shine. An organic light emitting device using this principle may be generally composed of an organic material layer including a cathode and an anode and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
유기발광소자의 성능, 수명 또는 효율을 향상시키기 위하여, 유기박막의 재료의 개발이 지속적으로 요구되고 있다. In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of the material of the organic thin film is continuously required.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a heterocyclic compound and an organic light emitting device including the same.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 헤테로고리 화합물을 제공한다.An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2017007032-appb-I000001
Figure PCTKR2017007032-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1은 치환 또는 비치환된 탄화수소고리기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 is a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a 및 b는 각각 0 내지 4의 정수이고,a and b are each an integer of 0 to 4,
c 및 d는 0 내지 3의 정수이며,c and d are integers from 0 to 3,
a 내지 d가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 동일하거나 상이하며,when a to d are each 2 or more, the substituents in parentheses are the same as or different from each other,
n1 및 n2는 각각 0 또는 1이고,n1 and n2 are each 0 or 1,
n1 및 n2 중 1 이상은 1의 정수이며,at least one of n1 and n2 is an integer of 1,
X1 및 X2는 수소이거나, 서로 직접결합한다.X1 and X2 are hydrogen or directly bond to each other.
또한, 본 명세서의 일 실시상태는 제1 전극, 제2 전극 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 상기 헤테로고리 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification includes a first electrode, a second electrode and one or more organic material layers disposed between the first electrode and the second electrode, one or more of the organic material layers includes the heterocyclic compound. An organic light emitting device is provided.
본 명세서에 기재된 헤테로고리 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자억제, 발광, 정공억제, 전자수송, 또는 전자주입 재료로 사용될 수 있다. The heterocyclic compound described herein can be used as a material of the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. The compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
도 1은 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판(1), 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(3), 전자 수송층(7) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4. It is.
도 3은 화합물 1의 NMR data를 나타낸 도이다.3 is a diagram showing NMR data of compound 1.
도 4는 화합물 2의 NMR data를 나타낸 도이다.4 is a diagram showing NMR data of compound 2.
도 5는 화합물 10의 Mass data를 나타낸 도이다.5 is a diagram showing a mass data of the compound 10.
1: 기판1: substrate
2: 양극2: anode
3: 발광층3: light emitting layer
4: 음극4: cathode
5: 정공 주입층5: hole injection layer
6: 정공 수송층6: hole transport layer
7: 전자 수송층7: electron transport layer
이하에서 본 명세서를 보다 상세히 설명한다.The present specification is described in more detail below.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
Figure PCTKR2017007032-appb-I000002
Figure PCTKR2017007032-appb-I000002
상기 화학식 1에 있어서,In Chemical Formula 1,
R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1은 치환 또는 비치환된 탄화수소고리기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 is a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a 및 b는 각각 0 내지 4의 정수이고,a and b are each an integer of 0 to 4,
c 및 d는 0 내지 3의 정수이며,c and d are integers from 0 to 3,
a 내지 d가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 동일하거나 상이하며,when a to d are each 2 or more, the substituents in parentheses are the same as or different from each other,
n1 및 n2는 각각 0 또는 1이고,n1 and n2 are each 0 or 1,
n1 및 n2 중 1 이상은 1의 정수이며,at least one of n1 and n2 is an integer of 1,
X1 및 X2는 수소이거나, 서로 직접결합한다.X1 and X2 are hydrogen or directly bond to each other.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents are described below, but are not limited thereto.
본 명세서에서 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.As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent may be substituted, and two or more. When substituted, two or more substituents may be the same or different from one another.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 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 아릴기로 치환된 아릴기, 헤테로아릴기로 치환된 아릴기, 아릴기로 치환된 헤테로고리기, 알킬기로 치환된 아릴기 등일 수 있다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한"기로 해석될 수 있다.In the present specification, "adjacent" The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
본 명세서에 있어서, "
Figure PCTKR2017007032-appb-I000003
" 및 "
Figure PCTKR2017007032-appb-I000004
"는 결합되는 부위를 의미한다.In the present specification, "
Figure PCTKR2017007032-appb-I000003
"And"
Figure PCTKR2017007032-appb-I000004
"Means the site to be bound.
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, 실릴기는 -SiRaRbRc의 화학식으로 표시될 수 있고, 상기 Ra, Rb 및 Rc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. Do not.
본 명세서에 있어서, 붕소기는 -BRaRb의 화학식으로 표시될 수 있고, 상기 R 및 Rb는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be represented by a chemical formula of -BR a R b , wherein R and R b are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50일 수 있고, 일 실시예에 따르면, 탄소수는 1 내지 30일 수 있다. 또 하나의 일 실시상태에 따르면, 탄소수는 1 내지 20일 수 있다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥실메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched, the carbon number is not particularly limited, but may be 1 to 50, according to one embodiment, the carbon number may be 1 to 30. According to another exemplary embodiment, the carbon number may be 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but is not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60일 수 있다. 일 실시예에 따르면 상기 시클로알킬기의 탄소수는 3 내지 30일 수 있으며, 또 하나의 실시예에 따르면 3 내지 20일 수 있다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기 3-메틸시클로펜틸기, 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but may be 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group may have 3 to 30 carbon atoms, and according to another embodiment, 3 to 20 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3 -Dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , Benzyloxy group, p-methylbenzyloxy group and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-아릴알킬아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, N-페닐나프틸아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40일 수 있고, 일 실시예에 따르면 2 내지 20일 수 있다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched, the carbon number is not particularly limited, but may be 2 to 40, according to one embodiment may be 2 to 20. Specific examples thereof include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, and 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like, but are not limited thereto.
본 명세서에 있어서, 알킬아민기는 탄소수는 특별히 한정되지 않으나, 1 내지 40일 수 있고, 일 실시예에 따르면 1 내지 20일 수 있다. 알킬아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 트리페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the alkylamine group is not particularly limited, but may be 1 to 40, according to one embodiment may be 1 to 20. Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups and the like, but are not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 2 이상의 아릴기를 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다. In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐 나프틸 아민기, 디톨릴 아민기, 페닐 톨릴 아민기 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, and triphenyl amine group, but are not limited thereto.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 치환 또는 비치환된 디헤테로아릴아민기, 또는 치환 또는 비치환된 트리헤테로아릴아민기가 있다. 상기 헤테로아릴아민기 중의 헤테로아릴기는 단환식 헤테로아릴기일 수 있고, 다환식 헤테로아릴기일 수 있다. 상기 2 이상의 헤테로아릴기를 포함하는 헤테로아릴아민기는 단환식 헤테아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group, may be a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
본 명세서에 있어서, 아릴헤테로아릴아민기는 아릴기 및 헤테로아릴기로 치환된 아민기를 의미한다.In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.
본 명세서에 있어서, 아릴포스핀기의 예로는 치환 또는 비치환된 모노아릴포스핀기, 치환 또는 비치환된 디아릴포스핀기, 또는 치환 또는 비치환된 트리아릴포스핀기가 있다. 상기 아릴포스핀기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴포스핀기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 60일 수 있고, 일 실시예에 따르면 6 내지 30일 수 있으며, 또 하나의 실시예에 따르면 6 내지 20일 수 있다. 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, carbon number is not particularly limited, but may be 6 to 60 carbon atoms, 6 to 30 according to one embodiment, and 6 to 20 according to another embodiment. have. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 60일 수 있고, 일 실시예에 따르면 6 내지 30일 수 있으며, 6 내지 20일 수 있다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It may have 10 to 60 carbon atoms, according to one embodiment may be 6 to 30, it may be 6 to 20. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
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 PCTKR2017007032-appb-I000005
,
Figure PCTKR2017007032-appb-I000006
,
Figure PCTKR2017007032-appb-I000007
,
Figure PCTKR2017007032-appb-I000008
,
Figure PCTKR2017007032-appb-I000009
,
Figure PCTKR2017007032-appb-I000010
,
Figure PCTKR2017007032-appb-I000011
,
Figure PCTKR2017007032-appb-I000012
및
Figure PCTKR2017007032-appb-I000013
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2017007032-appb-I000005
,
Figure PCTKR2017007032-appb-I000006
,
Figure PCTKR2017007032-appb-I000007
,
Figure PCTKR2017007032-appb-I000008
,
Figure PCTKR2017007032-appb-I000009
,
Figure PCTKR2017007032-appb-I000010
,
Figure PCTKR2017007032-appb-I000011
,
Figure PCTKR2017007032-appb-I000012
And
Figure PCTKR2017007032-appb-I000013
And so on. However, 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 60일 수 있고, 일 실시예에 따르면 탄소수 2 내지 30일 수 있다. 헤테로 고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조퀴놀리닐기, 벤조피리다지닐기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기, 벤조이미다조나프틸리닌기, 페난트로이미다졸기, 벤조이미다조페난트리딘기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but may be 2 to 60 carbon atoms, and according to one embodiment may be 2 to 30 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzoquinolinyl group, benzopyridazinyl group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrroline group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group, benzoimidazone naphthyllinine group, phenanthromidazole group, Benzoimidazophenanthridine groups and the like, but only It is not decided.
상기 헤테로고리기는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있다.The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
본 명세서에서 상기 탄화수소고리는 지방족, 방향족 또는 지방족과 방향족의 축합고리일 수 있으며, 1가기가 아닌 것을 제외하고, 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다. 상기 헤테로고리기는 지방족, 방향족 또는 지방족과 방향족의 축합고리일 수 있으며, 1가기가 아닌 것을 제외하고, 상기 헤테로고리기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, and may be selected from examples of the cycloalkyl group or aryl group, except that they are not monovalent. The heterocyclic group may be an aliphatic, aromatic or a condensed ring of aliphatic and aromatic, and may be selected from examples of the heterocyclic group, except that it is not a monovalent group.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, 아릴포스핀기, 아르알킬기, 아랄킬아민기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴헤테로아릴아민기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above. The description of one aryl group may apply.
본 명세서에 있어서, 알킬티옥시기, 알킬술폭시기, 아르알킬기, 아랄킬아민기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다. In the present specification, the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
본 명세서에 있어서, 헤테로아릴기, 헤테로아릴아민기, 아릴헤테로아릴아민기 중 헤테로아릴기는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, a heteroaryl group, a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
본 명세서에 있어서, 아르알케닐기, 아릴알케닐기 중 알케닐기는 전술한 알케닐기에 관한 설명이 적용될 수 있다. In the present specification, the alkenyl group of the aralkenyl group and the arylalkenyl group may be applied to the description of the alkenyl group described above.
본 명세서에 있어서, 아릴알킬기, 티오알킬기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the alkyl group of the arylalkyl group and the thioalkyl group may be described with respect to the alkyl group described above.
본 명세서에 있어서, 헤테로아릴렌기는 2가기인 것을 제외하고는 전술한 헤테로아릴기에 관한 설명이 적용될 수 있다. In the present specification, the description about the heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X2는 모두 수소이다.In one embodiment of the present specification, X1 and X2 are both hydrogen.
또 하나의 일 실시상태에 있어서, 상기 X1 및 X2는 서로 직접결합하여 5각 고리를 형성한다.In another exemplary embodiment, X1 and X2 directly bond with each other to form a pentagonal ring.
본 명세서의 일 실시상태에 있어서, 상기 n1 및 n2는 0 또는 1이고, n1 및 n2 중 1 이상은 1의 정수이다.In one embodiment of the present specification, n1 and n2 are 0 or 1, and at least one of n1 and n2 is an integer of 1.
또 하나의 일 실시상태에 따르면, 상기 n1 및 n2는 1의 정수이다.According to another exemplary embodiment, n1 and n2 are integers of 1.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 치환 또는 비치환된 탄소수 3 내지 60의 탄화수소고리기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 Ar1은 치환 또는 비치환된 탄소수 3 내지 40의 탄화수소고리기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로고리기이다.In another exemplary embodiment, Ar1 is a substituted or unsubstituted hydrocarbon ring having 3 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar1-L2-NR3R4는 하기 구조들 중 하나이다.In one embodiment of the present specification, Ar1-L2-NR3R4 is one of the following structures.
Figure PCTKR2017007032-appb-I000014
Figure PCTKR2017007032-appb-I000014
Figure PCTKR2017007032-appb-I000015
Figure PCTKR2017007032-appb-I000015
Figure PCTKR2017007032-appb-I000016
Figure PCTKR2017007032-appb-I000016
상기 구조들에 있어서, In the above structures,
L2, R3 및 R4의 정의는 상기 화학식 1에서의 정의와 같고,Definitions of L2, R3 and R4 are the same as the definition in Formula 1,
R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이며,R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkyl sulfoxy group; an aryl sulfoxy group; Silyl groups; boron groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted aralkyl groups; substituted or unsubstituted Alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl A phosphine group or a substituted or unsubstituted heterocyclic group,
상기 구조들은 추가로 치환될 수 있다.The structures may be further substituted.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; halogen; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted Cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; substituted Or an unsubstituted arylheteroarylamine group, or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted carbon group having 3 to 60 carbon atoms Or a cycloalkyl group of D, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon atom 3 to 30 Or a cycloalkyl group of C, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이다.In another exemplary embodiment, R 'and R "are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 R' 및 R"는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 또는 치환 또는 비치환된 tert-부틸기이다.According to another exemplary embodiment, R ′ and R ″ are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted tert-butyl group .
또 하나의 일 실시상태에 있어서, 상기 R' 및 R"는 서로 동일하거나 상이하고, 각각 독립적으로 메틸기, 에틸기 또는 tert-부틸기이다.In another exemplary embodiment, R 'and R "are the same as or different from each other, and are each independently a methyl group, an ethyl group, or a tert-butyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 헤테로고리 화합물은 하기 화학식 1-A 내지 1-F 에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present specification, the heterocyclic compound represented by Formula 1 may be any one selected from the following Formula 1-A to 1-F.
[화학식 1-A][Formula 1-A]
Figure PCTKR2017007032-appb-I000017
Figure PCTKR2017007032-appb-I000017
[화학식 1-B][Formula 1-B]
Figure PCTKR2017007032-appb-I000018
Figure PCTKR2017007032-appb-I000018
[화학식 1-C][Formula 1-C]
Figure PCTKR2017007032-appb-I000019
Figure PCTKR2017007032-appb-I000019
[화학식 1-D][Formula 1-D]
Figure PCTKR2017007032-appb-I000020
Figure PCTKR2017007032-appb-I000020
[화학식 1-E][Formula 1-E]
Figure PCTKR2017007032-appb-I000021
Figure PCTKR2017007032-appb-I000021
[화학식 1-F][Formula 1-F]
Figure PCTKR2017007032-appb-I000022
Figure PCTKR2017007032-appb-I000022
상기 화학식 1-A 내지 1-F에 있어서,In Chemical Formulas 1-A to 1-F,
X1, X2, R1 내지 R8, L1, L2, n1 및 n2는 상기 화학식 1에서의 정의와 같고,X1, X2, R1 to R8, L1, L2, n1 and n2 are the same as defined in Formula 1,
W1 내지 W6은 서로 동일하거나 상이하고, 각각 독립적으로 O, S, SiT1T2 또는 CT3T4이며,W1 to W6 are the same as or different from each other, and are each independently O, S, SiT1T2, or CT3T4,
T1 내지 T4, R101 내지 R106은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,T1 to T4 and R101 to R106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
s1 및 s3는 각각 0 내지 5의 정수이며,s1 and s3 are each an integer of 0 to 5,
s2 및 s4는 각각 0 내지 7의 정수이고,s2 and s4 are each an integer of 0 to 7,
s5 및 s6은 각각 0 내지 4의 정수이고,s5 and s6 are each an integer of 0 to 4,
s1 내지 s6이 각각 2 이상의 정수인 경우, 괄호 내의 치환기는 서로 동일하거나 상이하다.When s1 to s6 are each an integer of 2 or more, the substituents in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 s1은 0 또는 1이다.According to an exemplary embodiment of the present specification, s1 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 s2는 0 또는 1이다.According to an exemplary embodiment of the present specification, s2 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 s3은 0 또는 1이다.According to an exemplary embodiment of the present specification, s3 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 s4는 0 또는 1이다.According to an exemplary embodiment of the present specification, s4 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 s5는 0 또는 1이다.According to an exemplary embodiment of the present specification, s5 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 s6는 0 또는 1이다.According to an exemplary embodiment of the present specification, s6 is 0 or 1.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 알킬기이다.According to an exemplary embodiment of the present specification, the T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
또 하나의 일 실시상태에 있어서, 상기 T1 내지 T4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 알킬기이다.In another exemplary embodiment, T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
또 하나의 일 실시상태에 따르면, 상기 T1 내지 T4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 탄소수 1 내지 40의 알킬기이다.According to another exemplary embodiment, the T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 T1 내지 T4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이다.In another exemplary embodiment, T1 to T4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 T1 내지 T4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 또는 치환 또는 비치환된 t-부틸기이다.According to another exemplary embodiment, the T1 to T4 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted t-butyl group.
또 하나의 일 실시상태에 있어서, 상기 T1 내지 T4는 메틸기이다.In another exemplary embodiment, T1 to T4 are methyl groups.
본 명세서의 일 실시상태에 있어서, 상기 R101 내지 R106은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, R101 to R106 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
또 하나의 일 실시상태에 따르면, 상기 R101 내지 R106은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 40의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.According to another exemplary embodiment, the R101 to R106 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R101 내지 R106은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In another exemplary embodiment, R101 to R106 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 R101 내지 R106은 수소이다.According to another exemplary embodiment, R101 to R106 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 tert-부틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환되 바이페닐기; 치환 또는 비치환된 나프틸렌기; 또는 치환 또는 비치환된 디벤조퓨란기이다.According to another exemplary embodiment, the R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted dibenzofuran group.
또 하나의 일 실시상태에 있어서, 상기 R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 메틸기; 에틸기; tert-부틸기; 페닐기; 바이페닐기; 나프틸렌기; 또는 디벤조퓨란기이다.In another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; Naphthylene group; Or a dibenzofuran group.
또 하나의 일 실시상태에 따르면, 상기 R5 및 R8은 서로 같거나 상이하고, 각각 독립적으로 수소 또는 tert-부틸기이다.According to another exemplary embodiment, R5 and R8 are the same as or different from each other, and are each independently hydrogen or a tert-butyl group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 2가의 헤테로고리기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프탈렌기; 치환 또는 비치환된 플루오레닐렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 티오페닐렌기; 치환 또는 비치환된 퓨라닐렌기; 치환 또는 비치환된 피롤렌기; 치환 또는 비치환된 디벤조퓨라닐렌기; 치환 또는 비치환된 디벤조티오페닐렌기; 또는 치환 또는 비치환된 카바졸릴렌기이다.In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted pyrrole group; Substituted or unsubstituted dibenzofuranylene group; Substituted or unsubstituted dibenzothiophenylene group; Or a substituted or unsubstituted carbazolylene group.
또 하나의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 페닐렌기; 바이페닐릴렌기; 터페닐렌기; 나프탈렌기; 9,9-디페닐플루오레닐기; 9,9-디메틸플루오레닐기; 페난트레닐렌기; 안트라세닐렌기; 트리페닐레닐기; 티오페닐렌기; 퓨라닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 피롤렌기; 디벤조퓨라닐렌기; 디벤조티오페닐렌기; 에틸기 또는 페닐기로 치환 또는 비치환된 카바졸릴렌기이다.According to another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a phenylene group; Biphenylylene group; Terphenylene group; Naphthalene group; 9,9-diphenyl fluorenyl group; 9,9-dimethyl fluorenyl group; Phenanthrenylene group; Anthracenylene group; Triphenylenyl group; Thiophenylene group; Furanylene group; Pyrrolene group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzofuranylene group; Dibenzothiophenylene group; Carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 또는 하기 구조들 중 하나이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or one of the following structures.
Figure PCTKR2017007032-appb-I000023
Figure PCTKR2017007032-appb-I000023
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 직접결합이다.In one embodiment of the present specification, L1 and L2 are direct bonds.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로고리기이다. 또 하나의 일 실시상태에 따르면, 상기 R1 내지 R4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트릴기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 플루오란테닐기; 치환 또는 비치환된 크라이세닐기; 치환 또는 비치환된 피레닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 인데노플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 피라지닐기; 치환 또는 비치환된 피리다지닐기; 치환 또는 비치환된 피리미디닐기; 치환 또는 비치환된 퀴놀리닐기; 치환 또는 비치환된 퀴녹살리닐기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 나프토벤조티오펜기; 치환 또는 비치환된 벤조퓨란기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 벤조이미다졸기; 치환 또는 비치환된 벤즈옥사졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 플루오레노벤조퓨란기; 또는 치환 또는 비치환된 벤조퓨라노디벤조퓨란기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms. According to another exemplary embodiment, the R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthryl group; Substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluoranthenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted indenofluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrazinyl group; Substituted or unsubstituted pyridazinyl group; Substituted or unsubstituted pyrimidinyl group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted quinoxalinyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted naphthobenzothiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted benzoimidazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; A substituted or unsubstituted fluorenobenzofuran group; Or a substituted or unsubstituted benzofuranodibenzofuran group.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 동일하거나 상이하고, 각각 독립적으로 하기 기재된 구조들로부터 선택되는 어느 하나일 수 있다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently may be any one selected from the structures described below.
Figure PCTKR2017007032-appb-I000024
Figure PCTKR2017007032-appb-I000024
Figure PCTKR2017007032-appb-I000025
Figure PCTKR2017007032-appb-I000025
Figure PCTKR2017007032-appb-I000026
Figure PCTKR2017007032-appb-I000026
Figure PCTKR2017007032-appb-I000027
Figure PCTKR2017007032-appb-I000027
Figure PCTKR2017007032-appb-I000028
Figure PCTKR2017007032-appb-I000028
상기 구조들에 있어서,In the above structures,
R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 실릴기; 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Silyl groups; Boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a1, a6, a10, a23 및 a25는 각각 0 내지 5의 정수이며,a1, a6, a10, a23 and a25 are each an integer of 0 to 5,
a2, a5, a8, a9, a14, a16, a17, a21, a28 내지 a35, b1 내지 b4, b6 내지 b9, b11 내지 b13, b15 및 b17 내지 b32는 각각 0 내지 4의 정수이고,a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
a3 및 a22는 각각 0 내지 7의 정수이며,a3 and a22 are each an integer of 0 to 7,
a4, a7, a12, a15. a19, a26 및 a27은 각각 0 내지 3의 정수이고,a4, a7, a12, a15. a19, a26 and a27 are each an integer of 0 to 3,
a11은 0 내지 9의 정수이며,a11 is an integer of 0 to 9,
a13, a20 및 a24은 각각 0 내지 6의 정수이고,a13, a20 and a24 are each an integer of 0 to 6,
a18, b5, b10, b14 및 b16은 각각 0 내지 2의 정수이며,a18, b5, b10, b14 and b16 are each an integer of 0 to 2,
a18, b5, b10, b14 및 b16이 2 인 경우, 괄호 내의 치환기는 서로 상이하고,when a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other,
a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 내지 a35, b1 내지 b4, b6 내지 b9, b11 내지 b13, b15, b17 내지 b32, a3, a22, a4, a7, a12, a15. a19, a26, a27, a11, a13, a20 및 a24가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하다.a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15, b17 to b32, a3, a22, a4, a7, a12, a15. When a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in parentheses are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
또 하나의 일 실시상태에 있어서, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 실릴기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In another exemplary embodiment, R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In another exemplary embodiment, R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 알킬기로 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In another exemplary embodiment, R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 메틸기로 치환된 실릴기; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 t-부틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 시클로펜틸기; 또는 치환 또는 비치환된 시클로헥실기이다.According to another exemplary embodiment, the R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups substituted with methyl groups; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted t-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.
또 하나의 일 실시상태에 있어서, 상기 R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 트리메틸실릴기; 메틸기; t-부틸기; 페닐기; 바이페닐기; 또는 나프틸기이다.In another exemplary embodiment, R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Methyl group; t-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 a1 내지 a35 및 b1 내지 b32는 각각 0 내지 2의 정수이다.In one embodiment of the present specification, the a1 to a35 and b1 to b32 are each an integer of 0 to 2.
또 명세서의 일 실시상태에 따르면, 상기 화학식 1의 헤테로고리 화합물은 하기 화합물들 중에서 선택된 어느 하나일 수 있다.In addition, according to an exemplary embodiment of the specification, the heterocyclic compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2017007032-appb-I000029
Figure PCTKR2017007032-appb-I000029
Figure PCTKR2017007032-appb-I000030
Figure PCTKR2017007032-appb-I000030
Figure PCTKR2017007032-appb-I000031
Figure PCTKR2017007032-appb-I000031
본 명세서의 일 실시상태에 따른 헤테로고리 화합물은 후술하는 제조 방법으로 제조될 수 있다. 예컨대 상기 화학식 1의 헤테로고리 화합물은 하기 제조예와 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.The heterocyclic compound according to one embodiment of the present specification may be prepared by the manufacturing method described below. For example, the heterocyclic compound of Formula 1 may have a core structure as in Preparation Example. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
본 명세서의 일 실시상태에 따르면, 제1 전극, 제2 전극 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 본 명세서의 일 실시상태에 따른 상기 헤테로고리 화합물을 포함하는 것인 유기 발광 소자를 제공한다.According to an exemplary embodiment of the present specification, the first electrode, the second electrode and one or more organic material layers disposed between the first electrode and the second electrode, one or more of the organic material layer is one embodiment of the present specification It provides an organic light emitting device comprising the heterocyclic compound according to.
본 명세서의 일 실시상태에 따르면, 본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 전자차단층, 발광층, 정공차단층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적거나 많은 수의 유기층을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
도 1에는 기판(1) 위에 양극(2), 발광층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다.1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer (3).
도 2에는 기판(1) 위에 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(3), 전자 수송층(7) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층(5), 정공 수송층(6), 발광층(3) 또는 전자 수송층(7)에 포함될 수 있다.2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked on a substrate 1. The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron transport layer 7.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공주입층, 정공수송층 또는 전자차단층을 포함하고, 상기 정공주입층, 정공수송층 또는 전자차단층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes a heterocyclic compound represented by Formula 1 above. .
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 유기물층 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함하며, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 더 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the organic material layer includes a heterocyclic compound represented by Formula 1, and the light emitting layer further includes a compound represented by Formula 2 below.
[화학식 2][Formula 2]
Figure PCTKR2017007032-appb-I000032
Figure PCTKR2017007032-appb-I000032
상기 화학식 2에 있어서,In Chemical Formula 2,
R9은 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R9 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
p는 0 내지 6의 정수이며,p is an integer from 0 to 6,
p가 2 이상인 경우 괄호 내의 치환기는 서로 동일하거나 상이하고,when p is 2 or more, the substituents in parentheses are the same as or different from each other,
L3 내지 L6은 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L3 to L6 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar2 내지 Ar5는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 R9는 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present disclosure, wherein R9 is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 R9는 수소이다.According to another exemplary embodiment, R9 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 p는 0 또는 1이다.In one embodiment of the present specification, p is 0 or 1.
본 명세서의 일 실시상태에 있어서, 상기 L3 내지 L6는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴렌기이다.In one embodiment of the present specification, L3 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L3 내지 L6는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 40의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로아릴렌기이다.In one embodiment of the present specification, L3 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 L3 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐릴렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 티오페닐렌기; 치환 또는 비치환된 퓨라닐렌기; 치환 또는 비치환된 디벤조티오페닐렌기; 치환 또는 비치환된 디벤조퓨라닐렌기; 또는 치환 또는 비치환된 카바졸릴렌기이다.According to another exemplary embodiment, the L3 to L6 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted dibenzothiophenylene group; Substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.
또 하나의 일 실시상태에 있어서, 상기 L3 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐릴렌기; 터페닐렌기; 나프틸렌기; 안트라세닐렌기; 페난트레닐렌기; 트리페닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 티오페닐렌기; 퓨라닐렌기; 디벤조티오페닐렌기; 디벤조퓨라닐렌기; 또는 에틸기 또는 페닐기로 치환 또는 비치환된 카바졸릴렌기이다.In another exemplary embodiment, L3 to L6 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
또 하나의 일 실시상태에 따르면, 상기 L3 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택될 수 있다.According to another exemplary embodiment, the L3 to L6 are the same as or different from each other, and each independently a direct bond; Or the following structures.
Figure PCTKR2017007032-appb-I000033
Figure PCTKR2017007032-appb-I000033
본 명세서의 일 실시상태에 따르면, L3은 직접결합이다.According to an exemplary embodiment of the present disclosure, L3 is a direct bond.
본 명세서의 일 실시상태에 따르면, L4는 페닐렌기이다.According to an exemplary embodiment of the present specification, L4 is a phenylene group.
본 명세서의 일 실시상태에 따르면, L5 및 L6은 직접결합이다.According to an exemplary embodiment of the present disclosure, L5 and L6 is a direct bond.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 내지 Ar5는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.In one embodiment of the present specification, Ar2 to Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 Ar2 내지 Ar5는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 탄소수 6 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 탄소수 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to another exemplary embodiment, Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; A C6-C60 aryl group unsubstituted or substituted with a C6-C60 aryl group or a C2-C60 heteroaryl group; Or a C2-C60 heteroaryl group unsubstituted or substituted with a C6-60 aryl group or a C2-C60 heteroaryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar2 내지 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 벤조퓨란기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 인돌카바졸기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 이소퀴놀릴기; 치환 또는 비치환된 퀴놀릴기; 치환 또는 비치환된 퀴나졸릴기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 벤즈이미다졸기; 치환 또는 비치환된 벤조옥사졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 다이하이드로아크리딘기; 치환 또는 비치환된 크산텐기; 또는 치환 또는 비치환된 디벤조실롤기이다.In another exemplary embodiment, Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted indole carbazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted isoquinolyl group; Substituted or unsubstituted quinolyl group; Substituted or unsubstituted quinazolyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; Substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.
또 하나의 일 실시상태에 따르면, 상기 Ar2 내지 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 아릴기로 치환 또는 비치환된 디벤조티오펜기; 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 아릴기로 치환 또는 비치환된 티오펜기; 아릴기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 피리딜기; 아릴기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 아릴기로 치환 또는 비치환된 퀴나졸릴기; 아릴기로 치환 또는 비치환된 트리아진기; 아릴기로 치환 또는 비치환된 벤즈이미다졸기; 아릴기로 치환 또는 비치환된 벤조옥사졸기; 아릴기로 치환 또는 비치환된 벤조티아졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 다이하이드로아크리딘기; 알킬기, 또는 아릴기로 치환 또는 비치환된 크산텐기; 또는 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조실롤기이다.According to another exemplary embodiment, Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; Furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole groups; Pyridyl group; Isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; Triazine group unsubstituted or substituted with an aryl group; Benzimidazole groups unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted by an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted by an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar2 내지 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 메틸기, 에틸기, 또는 페닐기로 치환 또는 비치환된 카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 페닐기로 치환 또는 비치환된 티오펜기; 페닐기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 페닐기 또는 나프틸기로 치환 또는 비치환된 피리딜기; 페닐기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 페닐기로 치환 또는 비치환된 퀴나졸릴기; 페닐기로 치환 또는 비치환된 트리아진기; 페닐기로 치환 또는 비치환된 벤즈이미다졸기; 페닐기로 치환 또는 비치환된 벤조옥사졸기; 페닐기로 치환 또는 비치환된 벤조티아졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 다이하이드로아크리딘기; 메틸기, 또는 페닐기로 치환 또는 비치환된 크산텐기; 또는 메틸기, 또는 페닐기로 치환 또는 비치환된 디벤조실롤기이다.In another exemplary embodiment, Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; Furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole groups; Pyridyl groups unsubstituted or substituted with a phenyl group or a naphthyl group; Isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Benzimidazole groups unsubstituted or substituted with a phenyl group; Benzoxazole group unsubstituted or substituted by a phenyl group; Benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; Xanthene group unsubstituted or substituted by the methyl group or the phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 내지 Ar5는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택될 수 있다.In one embodiment of the present specification, Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Or the following structures.
Figure PCTKR2017007032-appb-I000034
Figure PCTKR2017007032-appb-I000034
Figure PCTKR2017007032-appb-I000035
Figure PCTKR2017007032-appb-I000035
Figure PCTKR2017007032-appb-I000036
Figure PCTKR2017007032-appb-I000036
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 유기물층 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함하며, 상기 발광층은 하기 화학식 3으로 표시되는 화합물을 더 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1, and the light emitting layer further includes a compound represented by Chemical Formula 3 below.
[화학식 3][Formula 3]
Figure PCTKR2017007032-appb-I000037
Figure PCTKR2017007032-appb-I000037
상기 화학식 3에 있어서,In Chemical Formula 3,
R10은 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R10 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
q는 0 내지 7의 정수이며,q is an integer from 0 to 7,
q가 2 이상인 경우 괄호 내의 치환기는 서로 동일하거나 상이하고,when q is 2 or more, the substituents in parentheses are the same as or different from each other,
L7 내지 L9는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L7 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar6 to Ar8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 R10은 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R10 is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R10은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R10은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R10은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, R10 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 R10은 수소이다.In another exemplary embodiment, R10 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 q는 0 또는 1이다.In one embodiment of the present specification, q is 0 or 1.
본 명세서의 일 실시상태에 있어서, 상기 L7 내지 L9는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴렌기이다.In one embodiment of the present specification, L7 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L7 내지 L9는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 40의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로아릴렌기이다.In one embodiment of the present specification, L7 to L9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 L7 내지 L9는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐릴렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 티오페닐렌기; 치환 또는 비치환된 퓨라닐렌기; 치환 또는 비치환된 디벤조티오페닐렌기; 치환 또는 비치환된 디벤조퓨라닐렌기; 또는 치환 또는 비치환된 카바졸릴렌기이다.According to another exemplary embodiment, the L7 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted thiophenylene group; Substituted or unsubstituted furanylene group; Substituted or unsubstituted dibenzothiophenylene group; Substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.
또 하나의 일 실시상태에 있어서, 상기 L7 내지 L9는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐릴렌기; 터페닐렌기; 나프틸렌기; 안트라세닐렌기; 페난트레닐렌기; 트리페닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 티오페닐렌기; 퓨라닐렌기; 디벤조티오페닐렌기; 디벤조퓨라닐렌기; 또는 에틸기 또는 페닐기로 치환 또는 비치환된 카바졸릴렌기이다.In another exemplary embodiment, L7 to L9 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.
또 하나의 일 실시상태에 따르면, 상기 L7 내지 L9는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택될 수 있다.According to another exemplary embodiment, the L7 to L9 are the same as or different from each other, and each independently a direct bond; Or the following structures.
Figure PCTKR2017007032-appb-I000038
Figure PCTKR2017007032-appb-I000038
본 명세서의 일 실시상태에 있어서, 상기 L7 내지 L9는 직접결합이다.In one embodiment of the present specification, L7 to L9 are direct bonds.
본 명세서의 일 실시상태에 있어서, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.In one embodiment of the present specification, Ar6 to Ar8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하며, 각각 독립적으로 탄소수 6 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 탄소수 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to another exemplary embodiment, Ar6 to Ar8 are the same as or different from each other, and each independently an aryl having 6 to 60 carbon atoms substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms. group; Or a C2-C60 heteroaryl group unsubstituted or substituted with a C6-60 aryl group or a C2-C60 heteroaryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 벤조퓨란기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 인돌카바졸기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 이소퀴놀릴기; 치환 또는 비치환된 퀴놀릴기; 치환 또는 비치환된 퀴나졸릴기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 벤즈이미다졸기; 치환 또는 비치환된 벤조옥사졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 다이하이드로아크리딘기; 치환 또는 비치환된 크산텐기; 또는 치환 또는 비치환된 디벤조실롤기이다.In another exemplary embodiment, Ar6 to Ar8 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted indole carbazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted isoquinolyl group; Substituted or unsubstituted quinolyl group; Substituted or unsubstituted quinazolyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; Substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.
또 하나의 일 실시상태에 따르면, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 아릴기로 치환 또는 비치환된 디벤조티오펜기; 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 아릴기로 치환 또는 비치환된 티오펜기; 아릴기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 피리딜기; 아릴기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 아릴기로 치환 또는 비치환된 퀴나졸릴기; 아릴기로 치환 또는 비치환된 트리아진기; 아릴기로 치환 또는 비치환된 벤즈이미다졸기; 아릴기로 치환 또는 비치환된 벤조옥사졸기; 아릴기로 치환 또는 비치환된 벤조티아졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 다이하이드로아크리딘기; 알킬기, 또는 아릴기로 치환 또는 비치환된 크산텐기; 또는 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조실롤기이다.According to another exemplary embodiment, Ar6 to Ar8 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; Furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole groups; Pyridyl group; Isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; Triazine group unsubstituted or substituted with an aryl group; Benzimidazole groups unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted by an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted by an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 메틸기, 에틸기, 또는 페닐기로 치환 또는 비치환된 카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 페닐기로 치환 또는 비치환된 티오펜기; 페닐기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 페닐기 또는 나프틸기로 치환 또는 비치환된 피리딜기; 페닐기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 페닐기로 치환 또는 비치환된 퀴나졸릴기; 페닐기로 치환 또는 비치환된 트리아진기; 페닐기로 치환 또는 비치환된 벤즈이미다졸기; 페닐기로 치환 또는 비치환된 벤조옥사졸기; 페닐기로 치환 또는 비치환된 벤조티아졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 다이하이드로아크리딘기; 메틸기, 또는 페닐기로 치환 또는 비치환된 크산텐기; 또는 메틸기, 또는 페닐기로 치환 또는 비치환된 디벤조실롤기이다.In another exemplary embodiment, Ar6 to Ar8 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; Furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole groups; Pyridyl groups unsubstituted or substituted with a phenyl group or a naphthyl group; Isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Benzimidazole groups unsubstituted or substituted with a phenyl group; Benzoxazole group unsubstituted or substituted by a phenyl group; Benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; Xanthene group unsubstituted or substituted by the methyl group or the phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조들 중 선택될 수 있다.In one embodiment of the present specification, Ar6 to Ar8 are the same as or different from each other, and each independently may be selected from the following structures.
Figure PCTKR2017007032-appb-I000039
Figure PCTKR2017007032-appb-I000039
Figure PCTKR2017007032-appb-I000040
Figure PCTKR2017007032-appb-I000040
Figure PCTKR2017007032-appb-I000041
Figure PCTKR2017007032-appb-I000041
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 발광층의 호스트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 as a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 발광층의 도펀트로서 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 발광층의 도펀트로서 포함하며, 상기 화학식 2 또는 화학식 3으로 표시되는 화합물을 발광층의 호스트로서 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, and the compound represented by Formula 2 or Formula 3 of the light emitting layer Include as host.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 발광층의 도펀트로 포함하며, 상기 화학식 2 또는 화학식 3으로 표시되는 화합물을 발광층의 호스트로 포함하며, 상기 화학식 1로 표시되는 헤테로고리 화합물을 2 내지 10wt%로 도핑할 수 있다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, and the compound represented by Formula 2 or Formula 3 of the light emitting layer Included as a host, it can be doped with a heterocyclic compound represented by Formula 1 to 2 to 10wt%.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공차단층, 전자수송층 또는 전자주입층을 포함하고, 상기 정공차단층, 전자수송층 또는 전자주입층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, an electron transport layer or an electron injection layer, and the hole blocking layer, an electron transport layer or an electron injection layer includes a heterocyclic compound represented by Formula 1 above. .
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택되는 1층 이상을 더 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
본 명세서의 일 실시상태에 따른 유기 발광 소자는, 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함한다.An organic light emitting device according to an exemplary embodiment of the present specification, the first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1.
또 하나의 일 실시상태에 따르면, 본 발명의 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 도펀트로서 포함하고, 호스트를 더 포함할 수 있다. According to another exemplary embodiment, the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer may further include a host including a heterocyclic compound represented by Chemical Formula 1 as a dopant.
또 하나의 일 실시상태에 있어서, 본 발명의 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 도펀트로서 포함하고, 호스트를 더 포함할 수 있으며, 상기 호스트는 상기 화학식 2 또는 3으로 표시되는 화합물일 수 있다. 상기 유기 발광 소자는 발광층 외에 정공 수송층, 정공 주입층, 전자 수송층 및 전자 주입층 중 선택되는 1 이상의 유기물층을 더 포함할 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않는다.In another exemplary embodiment, the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer further includes a heterocyclic compound represented by Chemical Formula 1 as a dopant, and may further include a host. It may be a compound represented by 2 or 3. The organic light emitting device may further include one or more organic material layers selected from a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer. However, the structure of the organic light emitting device is not limited thereto.
또 하나의 일 실시상태에 따르면, 본 발명의 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 발광층을 포함하고, 상기 제1 전극과 발광층 사이에 정공 주입층 및 정공 수송층 중 선택되는 1 이상의 유기물층을 포함할 수 있으며, 상기 제2 전극과 발광층 사이에 전자 수송층 및 전자 주입층 중 선택되는 1 이상의 유기물층을 포함할 수 있다. 다만, 본 발명의 유기 발광 소자의 구조는 이에 한정되지 않는다.According to another exemplary embodiment, the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, and may include one or more organic material layers selected from a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and the second electrode and the light emitting layer. At least one organic material layer selected from among the electron transport layer and the electron injection layer may be included. However, the structure of the organic light emitting device of the present invention is not limited thereto.
또 하나의 일 실시상태에 있어서, 본 발명의 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 호스트로서 포함하고, 상기 제1 전극과 발광층 사이에 정공 주입층 및 정공 수송층 중 선택되는 1 이상의 유기물층을 포함할 수 있으며, 상기 제2 전극과 발광층 사이에 전자 수송층 및 전자 주입층 중 선택되는 1 이상의 유기물층을 포함할 수 있다. 다만, 본 발명의 유기 발광 소자의 구조는 이에 한정되지 않는다.In another exemplary embodiment, the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Formula 1 as a host, and a hole injection layer and a hole transport layer between the first electrode and the light emitting layer. It may include one or more organic material layer selected from among, and may include one or more organic material layer selected from the electron transport layer and the electron injection layer between the second electrode and the light emitting layer. However, the structure of the organic light emitting device of the present invention is not limited thereto.
또 하나의 일 실시상태에 따르면, 본 발명의 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 헤테로고리 화합물을 도펀트로서 포함하고, 상기 화학식 2 또는 3으로 표시되는 화합물을 발광층의 호스트로서 포함하며, 상기 제1 전극과 발광층 사이에 정공 주입층 및 정공 수송층 중 선택되는 1 이상의 유기물층을 포함할 수 있으며, 상기 제2 전극과 발광층 사이에 전자 수송층 및 전자 주입층 중 선택되는 1 이상의 유기물층을 포함할 수 있다. 다만, 본 발명의 유기 발광 소자의 구조는 이에 한정되지 않는다.According to another exemplary embodiment, the organic light emitting diode of the present invention includes a first electrode; Second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1 as a dopant, and the compound represented by Chemical Formula 2 or 3 as a host of the light emitting layer. And at least one organic material layer selected from a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and at least one organic material layer selected from an electron transport layer and an electron injection layer between the second electrode and the light emitting layer. It may include. However, the structure of the organic light emitting device of the present invention is not limited thereto.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 본 명세서의 헤테로고리 화합물, 즉, 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by Chemical Formula 1 above. Can be.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리 증착 방법(PVD: physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 제1 전극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 제2 전극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 제2 전극 물질부터 유기물층, 제1 전극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 상기 화학식 1로 표시되는 헤테로고리 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD: physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or an alloy thereof on the substrate It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. According to one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
본 명세서의 또 하나의 실시상태에 따르면, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. According to another exemplary embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.
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 usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
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/Al, Mg/Ag과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, Mg / Ag, and the like, but are not limited thereto.
상기 정공주입층은 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 injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 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 transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광층의 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; 벤즈옥사졸, 벤조티아졸 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 of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; 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 헤테로 고리 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로 고리 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 hetero ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 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 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and at least one substituent selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
상기 전자수송층의 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.A layer for receiving electrons from the electron injection layer of the electron transport layer and transporting electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
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 that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
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 specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
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 with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present disclosure is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.
<< 합성예Synthesis Example >>
합성예Synthesis Example 1. 중간체 1-1의 합성 1. Synthesis of Intermediate 1-1
하기 반응식에 따라 중간체 1-1을 합성하였다.Intermediate 1-1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000042
Figure PCTKR2017007032-appb-I000042
질소 분위기에서 1 L 플라스크에 2-브로모-5-클로로벤즈알데히드 (30.0g, 137 mmol), 4-디벤조퓨라닐보로닉산 (31.9 g, 150 mmol)을 테트라하이드로퓨란 375 mL에 완전히 녹인 후 탄산칼륨 (56.7 g, 410 mmol) 수용액 125 mL을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐 (3.16 g, 2.73 mmol)을 첨가한 후 24 시간 동안 환류하여 교반하였다. 반응 완료 후 상온으로 온도를 낮춘 다음 물과 에칠 아세테이트로 추출하여 유기층을 분리하였다. 유기층은 무수황산마그네슘으로 처리 후 여과 감압 농축하였다. 고체는 에틸 아세테이트로 재결정하여 <중간체 1-1> (32.3 g, 수율77 %)를 얻었다.In a nitrogen atmosphere, 2-bromo-5-chlorobenzaldehyde (30.0 g, 137 mmol) and 4-dibenzofuranyl boronic acid (31.9 g, 150 mmol) were completely dissolved in 375 mL of tetrahydrofuran in a 1 L flask. 125 mL of an aqueous potassium (56.7 g, 410 mmol) solution was added, tetrakis- (triphenylphosphine) palladium (3.16 g, 2.73 mmol) was added and then refluxed and stirred for 24 h. After the reaction was completed, the temperature was lowered to room temperature, followed by extraction with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate and concentrated under reduced pressure with filtration. The solid was recrystallized from ethyl acetate to give <Intermediate 1-1> (32.3 g, yield 77%).
Mass [M+1] = 307Mass [M + 1] = 307
합성예Synthesis Example 2. 중간체 1-2의 합성 2. Synthesis of Intermediate 1-2
하기 반응식에 따라 중간체 1-2를 합성하였다.Intermediate 1-2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000043
Figure PCTKR2017007032-appb-I000043
1L 플라스크에 <중간체 1-1> (32.0 g, 104 mmol)을 테트라하이드로퓨란 450 mL 에 녹인 다음 아염소산나트륨 (14.2 g, 115 mmol), 설파믹산 (20.3 g, 209 mmol)을 물 (각 75 mL) 에 희석하여 첨가해 주고 4 시간 동안 가열 교반해 주었다. 반응 완료 후 상온으로 온도를 낮춘 다음 물과 에칠아세테이트로 추출하여 유기층을 분리하였다. 유기층은 무수황산마그네슘으로 처리 후 여과 감압 농축하였다. 고체는 에틸 아세테이트와 노르말헥산으로 재결정하여 <중간체 1-2> (28.3 g, 수율 84 %)를 얻었다.In a 1 L flask, <Intermediate 1-1> (32.0 g, 104 mmol) was dissolved in 450 mL of tetrahydrofuran, followed by sodium chlorite (14.2 g, 115 mmol) and sulfamic acid (20.3 g, 209 mmol) in water (75 each). mL) was added and stirred for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, followed by extraction with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate and concentrated under reduced pressure with filtration. The solid was recrystallized from ethyl acetate and normal hexane to give <Intermediate 1-2> (28.3 g, 84% yield).
TLC와 HPLC로 확인하였음Confirmed by TLC and HPLC
합성예Synthesis Example 3. 중간체 1-3의 합성 3. Synthesis of Intermediate 1-3
하기 반응식에 따라 중간체 1-3을 합성하였다. Intermediate 1-3 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000044
Figure PCTKR2017007032-appb-I000044
0.5L 플라스크에 <중간체 1-2> (28 g, 86.8 mmol), 메탄설폰산 350mL 를 넣고 80℃로 9 시간 동안 가열 교반하였다. 반응 완료 후 상온으로 온도를 낮춘 다음 물에 천천히 적가하여 고체를 생성하였다. 생성된 고체는 물과 에탄올로 씻어주어 <중간체 1-3> (24.3 g, 수율 92 %)을 얻었다.<Intermediate 1-2> (28 g, 86.8 mmol) and 350 mL of methanesulfonic acid were added to a 0.5 L flask, and the mixture was heated and stirred at 80 ° C. for 9 hours. After the reaction was completed, the temperature was lowered to room temperature, and then slowly added dropwise to water to form a solid. The resulting solid was washed with water and ethanol to obtain <Intermediate 1-3> (24.3 g, yield 92%).
Mass [M+1] = 305Mass [M + 1] = 305
합성예Synthesis Example 4. 중간체 1-4의 합성 4. Synthesis of Intermediate 1-4
하기 반응식에 따라 중간체 1-4를 합성하였다.Intermediate 1-4 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000045
Figure PCTKR2017007032-appb-I000045
질소 분위기에서 0.5L 플라스크에 <중간체 1-3> (9.50 g, 31.2 mmol)을 디클로로메탄 300 mL에 넣고 교반한 다음 디클로로메탄 50 mL에 희석한 브로민 9.97 g (62.3 mmol)을 천천히 적가한 후 48시간 동안 상온에서 교반하였다. 이후 생성된 교체는 여과 후 디클로로메탄 및 노르말헥산으로 씻어주었다. 고체는 톨루엔과 노르말헥산으로 재결정하여 <중간체 1-4> (7.0 g, 수율 59 %)를 얻었다.In an atmosphere of nitrogen, <Intermediate 1-3> (9.50 g, 31.2 mmol) was added to 300 mL of dichloromethane, stirred, and then slowly added dropwise 9.97 g (62.3 mmol) of bromine diluted in 50 mL of dichloromethane. Stir at room temperature for 48 hours. Subsequent replacements were washed with dichloromethane and normal hexane after filtration. The solid was recrystallized from toluene and normal hexane to obtain <Intermediate 1-4> (7.0 g, 59% yield).
Mass [M+1] = 383Mass [M + 1] = 383
합성예Synthesis Example 5. 중간체 1-5의 합성 5. Synthesis of Intermediates 1-5
하기 반응식에 따라 중간체 1-5를 합성하였다.Intermediate 1-5 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000046
Figure PCTKR2017007032-appb-I000046
질소분위기에서 0.5L 플라스크에 9-(2-브로모페닐)-9H-카바졸(7.53 g, 23.4 mmol)과 테트라하이드로퓨란 180 mL을 넣고 -78℃로 냉각 하였다. 냉각된 반응 용액에 노말부틸리튬 (10.8 mL, 27.0 mmol)을 적가 한 후 1시간 동안 교반하였다. 이후 <중간체 1-4>를 넣고 상온에서 교반하였다. 반응 완료 후 포화 탄산수소나트륨을 넣어 반응을 종결 한 후 에칠아세테이트와 물로 추출하였다. 유기층은 무수황산마그네슘으로 처리 후 여과 감압 농축하였다. 고체는 에칠아세테이트와 노르말헥산으로 재결정하여 <중간체 1-5> (7.60 g, 수율 67 %)를 얻었다.In a nitrogen atmosphere, 9- (2-bromophenyl) -9H-carbazole (7.53 g, 23.4 mmol) and 180 mL of tetrahydrofuran were added to a 0.5 L flask and cooled to -78 ° C. Normal butyllithium (10.8 mL, 27.0 mmol) was added dropwise to the cooled reaction solution, followed by stirring for 1 hour. Then <Intermediate 1-4> was added and stirred at room temperature. After completion of the reaction, saturated sodium bicarbonate was added to terminate the reaction, and the mixture was extracted with ethyl acetate and water. The organic layer was treated with anhydrous magnesium sulfate and concentrated under reduced pressure with filtration. The solid was recrystallized from ethyl acetate and normal hexane to obtain <Intermediate 1-5> (7.60 g, yield 67%).
Mass [M+1] = 626Mass [M + 1] = 626
합성예Synthesis Example 6. 중간체 1-6의 합성 6. Synthesis of Intermediates 1-6
하기 반응식에 따라 중간체 1-6을 합성하였다.Intermediates 1-6 were synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000047
Figure PCTKR2017007032-appb-I000047
0.25L 플라스크에 <중간체 1-5> (7.60 g, 12.1 mmol)과 아세트산(100 mL), 황산 2 방울을 넣고 3 시간 동안 가열 교반하였다. 반응 완료 후 고체를 여과 후 물과 에탄올로 씻어준 다음 에틸 아세테이트와 노르말헥산으로 재결정하여 <중간체 1-6> (7.04 g, 수율 95 %)을 얻었다.<Intermediate 1-5> (7.60 g, 12.1 mmol), acetic acid (100 mL) and 2 drops of sulfuric acid were added to a 0.25 L flask, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the solid was filtered and washed with water and ethanol and recrystallized with ethyl acetate and normal hexane to give <Intermediate 1-6> (7.04 g, 95% yield).
Mass [M+1] = 608Mass [M + 1] = 608
합성예Synthesis Example 7. 중간체 2-1의 합성 7. Synthesis of Intermediate 2-1
하기 반응식에 따라 중간체 2-1을 합성하였다.Intermediate 2-1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000048
Figure PCTKR2017007032-appb-I000048
질소분위기하에서 1L 플라스크에 2-(4-브로모페닐)나프탈렌 (23.0g, 0.081mol), 4-티부틸아닐린(13.3g, 0.089mol), 소듐터트부톡사이드 (23.4g, 0.244mol), 비스(트리-터트-부틸포스핀)팔라듐(0) (1.25g, 2.44mmol)을 톨루엔 350mL에 넣고 환류하여 교반하였다. 반응이 종료되면 상온으로 식힌 다음 톨루엔과 물로 추출하고 물 층을 제거하였다. 무수황산마그네슘으로 처리 후 여과 감압 농축하였다. 생성물은 컬럼 크로마토그래피로 법으로 분리 정제한 후 톨루엔과 노르말헥산으로 재결정하여 <중간체 2-1> (15.2g, 수율 53%)을 얻었다.2- (4-bromophenyl) naphthalene (23.0 g, 0.081 mol), 4-tibutylaniline (13.3 g, 0.089 mol), sodium tert-butoxide (23.4 g, 0.244 mol), bis in a 1 L flask under nitrogen atmosphere (Tri-tert-butylphosphine) palladium (0) (1.25 g, 2.44 mmol) was added to 350 mL of toluene and refluxed and stirred. After the reaction was completed, the mixture was cooled to room temperature, extracted with toluene and water, and the water layer was removed. After treatment with anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure by filtration. The product was separated and purified by column chromatography, and recrystallized with toluene and normal hexane to obtain <Intermediate 2-1> (15.2g, 53% yield).
Mass [M+1] = 352Mass [M + 1] = 352
합성예Synthesis Example 8. 화합물 1의 합성 8. Synthesis of Compound 1
하기 반응식에 따라 화합물 1을 합성하였다. Compound 1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000049
Figure PCTKR2017007032-appb-I000049
질소분위기하에서 0.25L 플라스크에 <중간체 1-6> (5.0 g, 8.21 mmol), <중간체 1-7> (6.36 g, 18.1 mmol), 소듐티부톡사이드(3.9g, 41 mmol), 비스(트리티부틸포스핀)팔라듐(0) (210 mg, 0.41 mmol)을 톨루엔 80mL 에 넣고 환류하여 교반하였다. 반응이 종료되면 상온으로 식힌 다음 톨루엔과 물로 추출하고 물 층을 제거하였다. 무수황산마그네슘으로 처리 후 여과 감압 농축하였다. 생성물은 컬럼 크로마토그래피로 법으로 분리 정제한 후 톨루엔과 노르말헥산으로 재결정하여 화합물 1 (4.3 g, 수율 43 %)을 얻었다. 상기 화합물 1의 NMR data를 하기 도 3에 나타내었다.In a 0.25L flask under nitrogen atmosphere, <Intermediate 1-6> (5.0 g, 8.21 mmol), <Intermediate 1-7> (6.36 g, 18.1 mmol), Sodium Tibutoxide (3.9 g, 41 mmol), Bis (Tree) Thibutylphosphine) palladium (0) (210 mg, 0.41 mmol) was added to 80 mL of toluene and refluxed and stirred. After the reaction was completed, the mixture was cooled to room temperature, extracted with toluene and water, and the water layer was removed. After treatment with anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure by filtration. The product was separated and purified by column chromatography, and recrystallized with toluene and normal hexane to obtain compound 1 (4.3 g, yield 43%). NMR data of the compound 1 is shown in FIG. 3.
Mass [M+1] = 1195 Mass [M + 1] = 1195
합성예Synthesis Example 9: 중간체 3-1의 합성  9: Synthesis of Intermediate 3-1
하기 반응식에 따라 중간체 3-1을 합성하였다.Intermediate 3-1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000050
Figure PCTKR2017007032-appb-I000050
<중간체 1-4>를 이용하여 상기 합성예 5와 동일하게 실험하여, <중간체 3-1>을 합성하였다.<Intermediate 3-1> was synthesized in the same manner as in Synthesis Example 5 using <Intermediate 1-4>.
Mass [M+1] = 628Mass [M + 1] = 628
합성예Synthesis Example 10: 중간체 3-2의 합성 10: Synthesis of Intermediate 3-2
하기 반응식에 따라 중간체 3-2를 합성하였다.Intermediate 3-2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000051
Figure PCTKR2017007032-appb-I000051
<중간체 3-1>을 이용하여 상기 합성예 6과 동일하게 실험하여, <중간체 3-2>를 합성하였다.<Intermediate 3-2> was synthesized in the same manner as in Synthesis Example 6 using <Intermediate 3-1>.
Mass [M+1] = 610Mass [M + 1] = 610
합성예Synthesis Example 11: 중간체 2-2의 합성 11: Synthesis of Intermediate 2-2
하기 반응식에 따라 중간체 2-2를 합성하였다.Intermediate 2-2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000052
Figure PCTKR2017007032-appb-I000052
4-티부틸아닐린과 4-티부틸브로모벤젠을 이용하여 상기 합성예 7과 동일하게 실시하여, <중간체 2-2>를 합성하였다.<Intermediate 2-2> was synthesized in the same manner as in Synthesis Example 7 using 4-thibutylaniline and 4-tibutylbromobenzene.
Mass [M+1] = 282Mass [M + 1] = 282
합성예Synthesis Example 12. 화합물 2의 합성 12. Synthesis of Compound 2
하기 반응식에 따라 화합물 2를 합성하였다.Compound 2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000053
Figure PCTKR2017007032-appb-I000053
<중간체 3-2>와 <중간체 2-2>를 이용해 합성예 8을 따라 화합물 2를 합성하였다. 상기 화합물 2의 NMR data를 하기 도 3에 나타내었다.Compound 2 was synthesized according to Synthesis Example 8 using <Intermediate 3-2> and <Intermediate 2-2>. NMR data of the compound 2 is shown in FIG. 3.
Mass [M+1] = 1057Mass [M + 1] = 1057
합성예Synthesis Example 13: 중간체 2-3의 합성 13: Synthesis of Intermediate 2-3
하기 반응식에 따라 중간체 2-3을 합성하였다.Intermediate 2-3 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000054
Figure PCTKR2017007032-appb-I000054
4-티부틸아닐린과 4-티부틸브로모벤젠을 이용하여 상기 합성예 7과 동일하게 실시하여, <중간체 2-3>을 합성하였다.<Intermediate 2-3> was synthesized in the same manner as in Synthesis Example 7 using 4-thibutylaniline and 4-tibutylbromobenzene.
Mass [M+1] = 316Mass [M + 1] = 316
합성예Synthesis Example 14. 화합물 3의 합성 14. Synthesis of Compound 3
하기 반응식에 따라 화합물 3을 합성하였다. Compound 3 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000055
Figure PCTKR2017007032-appb-I000055
<중간체 1-6>과 <중간체 2-3>을 이용해 합성예 8을 따라 화합물 3을 합성하였다. Compound 3 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-3>.
Mass [M+1] = 1123Mass [M + 1] = 1123
합성예Synthesis Example 15: 중간체 2-4의 합성 15: Synthesis of Intermediate 2-4
하기 반응식에 따라 중간체 2-4를 합성하였다.Intermediate 2-4 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000056
Figure PCTKR2017007032-appb-I000056
4-티부틸아닐린과 3-브로모나프토{2,3-b}벤조퓨란을 이용하여 상기 합성예 7과 동일하게 실시하여, <중간체 2-4>를 합성하였다.<Intermediate 2-4> was synthesized in the same manner as in Synthesis Example 7 using 4-thibutylaniline and 3-bromonaphtho {2,3-b} benzofuran.
Mass [M+1] = 366Mass [M + 1] = 366
합성예Synthesis Example 16. 화합물 8의 합성 16. Synthesis of Compound 8
하기 반응식에 따라 화합물 8을 합성하였다.Compound 8 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000057
Figure PCTKR2017007032-appb-I000057
<중간체 1-6>과 <중간체 2-4>를 이용해 합성예 8을 따라 화합물 8을 합성하였다.Compound 8 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-4>.
Mass [M+1] = 1223Mass [M + 1] = 1223
합성예Synthesis Example 17: 중간체 2-5의 합성 17: Synthesis of Intermediate 2-5
하기 반응식에 따라 중간체 2-5를 합성하였다.Intermediate 2-5 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000058
Figure PCTKR2017007032-appb-I000058
2-브로모-9,9-디메틸-9H-플루오렌과 9,9-디메틸-9H-플루오렌-2-아민을 이용하여 상기 합성예 7과 동일하게 실시하여, <중간체 2-5>를 합성하였다.<Intermediate 2-5> was carried out in the same manner as in Synthesis Example 7 using 2-bromo-9,9-dimethyl-9H-fluorene and 9,9-dimethyl-9H-fluorene-2-amine. Synthesized.
Mass [M+1] = 366Mass [M + 1] = 366
합성예Synthesis Example 18. 화합물 13의 합성 18. Synthesis of Compound 13
하기 반응식에 따라 화합물 13을 합성하였다. Compound 13 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000059
Figure PCTKR2017007032-appb-I000059
<중간체 1-6>과 <중간체 2-5>를 이용해 합성예 8을 따라 화합물 13을 합성하였다. Compound 13 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-5>.
Mass [M+1] = 1223Mass [M + 1] = 1223
합성예Synthesis Example 19: 중간체 2-6의 합성 19: Synthesis of Intermediate 2-6
하기 반응식에 따라 중간체 2-6을 합성하였다.Intermediate 2-6 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000060
Figure PCTKR2017007032-appb-I000060
2-브로모-9,9-디메틸-9H-플루오렌과 9,9-디메틸-9H-플루오렌-2-아민을 이용하여 상기 합성예 7과 동일하게 실시하여, <중간체 2-6>을 합성하였다.<Intermediate 2-6> was carried out in the same manner as in Synthesis Example 7 using 2-bromo-9,9-dimethyl-9H-fluorene and 9,9-dimethyl-9H-fluorene-2-amine. Synthesized.
Mass [M+1] = 402Mass [M + 1] = 402
합성예Synthesis Example 20. 화합물 15의 합성 20. Synthesis of Compound 15
하기 반응식에 따라 화합물 15를 합성하였다.Compound 15 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000061
Figure PCTKR2017007032-appb-I000061
<중간체 1-6>과 <중간체 2-6>을 이용해 합성예 8을 따라 화합물 15를 합성하였다.Compound 15 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-6>.
Mass [M+1] = 1295Mass [M + 1] = 1295
합성예Synthesis Example 21. 중간체 4-1의 합성 21. Synthesis of Intermediate 4-1
하기 반응식에 따라 중간체 4-1을 합성하였다.Intermediate 4-1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000062
Figure PCTKR2017007032-appb-I000062
3-브로모나프탈렌-2-올과 (2-클로로-6-플루오로페닐)보론산을 이용하여 상기 합성예 1과 동일하게 실험하여, <중간체 4-1>을 합성하였다.<Intermediate 4-1> was synthesized in the same manner as in Synthesis Example 1 using 3-bromonaphthalen-2-ol and (2-chloro-6-fluorophenyl) boronic acid.
Mass [M+1] = 273Mass [M + 1] = 273
합성예Synthesis Example 22: 중간체 4-2의 합성  22: Synthesis of Intermediate 4-2
하기 반응식에 따라 중간체 4-2를 합성하였다.Intermediate 4-2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000063
Figure PCTKR2017007032-appb-I000063
1L 플라스크에 <중간체 3-1> (32.0g, 0.153mol)과 포타슘카보네이트 (63.4g, 0.459mol)을 투입 후 디메틸아세트아미드(400mL)로 묽히고 환류교반하여 3시간 반응 후 종료하였다. 반응용매를 감압증류한 이후 에칠아세데이트와 물로 추출하여 얻어진 유기층을 무수황산마그네슘 처리 후 여과 농축하여 에칠아세테이트, 에탄올용매로 재결정하여 <중간체 4-2> (33.0g, 수율 85%)를 얻었다. <Intermediate 3-1> (32.0g, 0.153mol) and potassium carbonate (63.4g, 0.459mol) were added to a 1L flask, and the mixture was diluted with dimethylacetamide (400mL) and stirred under reflux for 3 hours. After distilling the reaction solvent under reduced pressure, the organic layer obtained by extraction with ethyl acetate and water was filtered and concentrated over anhydrous magnesium sulfate, and recrystallized with ethyl acetate and ethanol to obtain <Intermediate 4-2> (33.0 g, Yield 85%).
Mass [M+1] = 253 Mass [M + 1] = 253
합성예Synthesis Example 23: 중간체 4-3의 합성  23: Synthesis of Intermediate 4-3
하기 반응식에 따라 중간체 4-3을 합성하였다.Intermediate 4-3 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000064
Figure PCTKR2017007032-appb-I000064
0.5L 플라스크에 <중간체 3-2> (17.0g, 0.067mol)과 테트라하히드로퓨란 (180mL)을 넣고 아세톤-드라이아이스 중탕으로 내부 온도를 넣고 -78℃로 냉각 내린후 2.5M 노르말부틸리튬 (30.9mL, 0.077mol)을 서서히 적하한 후 한 시간 교반하였다. 이후 트리메틸보레이트 (9.0mL, 0.081mol)을 서서히 적가한 후 30분더 교반하여주었다. 이후 16h 후 반응을 종료하고 물로 처리 후 에칠아세데이트와 소금물로 추출하여 얻어진 유기층을 무수황산마그네슘 처리 후 여과 농축하여 에틸아세테이트, 노르말헥산으로 재결정하여 <중간체 4-3> (11.7g, 수율 59%)을 얻었다. Place intermediate 3-2 (17.0 g, 0.067 mol) and tetrahahydrofuran (180 mL) in a 0.5 L flask, add the internal temperature with acetone-dry ice bath, cool down to -78 ° C, and remove 2.5M normal butyllithium ( 30.9 mL, 0.077 mol) was slowly added dropwise and the mixture was stirred for one hour. After trimethyl borate (9.0mL, 0.081mol) was slowly added dropwise and stirred for 30 minutes. After 16 h, the reaction was terminated, treated with water, extracted with ethyl acetate and brine, and the organic layer obtained was treated with anhydrous magnesium sulfate, concentrated by filtration, and recrystallized with ethyl acetate and normal hexane to give <Intermediate 4-3> (11.7 g, yield 59%). )
TLC와 HPLC로 확인하였음Confirmed by TLC and HPLC
합성예Synthesis Example 24. 중간체 4-4의 합성 24. Synthesis of Intermediate 4-4
하기 반응식에 따라 중간체 4-4를 합성하였다.Intermediate 4-4 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000065
Figure PCTKR2017007032-appb-I000065
<중간체 4-3>을 이용하여 상기 합성예 1과 동일하게 실험하여, <중간체 4-4>를 합성하였다.<Intermediate 4-4> was synthesized in the same manner as in Synthesis Example 1 using <Intermediate 4-3>.
Mass [M+1] = 391Mass [M + 1] = 391
합성예Synthesis Example 25: 중간체 4-5의 합성  25: Synthesis of Intermediate 4-5
하기 반응식에 따라 중간체 4-5를 합성하였다.Intermediate 4-5 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000066
Figure PCTKR2017007032-appb-I000066
<중간체 4-4>를 이용하여 상기 합성예 2와 동일하게 실험하여, <중간체 4-5>를 합성하였다.<Intermediate 4-5> was synthesized in the same manner as in Synthesis Example 2 using <Intermediate 4-4>.
TLC와 HPLC로 확인하였음Confirmed by TLC and HPLC
합성예Synthesis Example 26: 중간체 4-6의 합성  26: Synthesis of Intermediate 4-6
하기 반응식에 따라 중간체 4-6을 합성하였다.Intermediate 4-6 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000067
Figure PCTKR2017007032-appb-I000067
<중간체 4-5>를 이용하여 상기 합성예 3과 동일하게 실험하여, <중간체 4-6>을 합성하였다.<Intermediate 4-6> was synthesized in the same manner as in Synthesis Example 3 using <Intermediate 4-5>.
Mass [M+1] = 389Mass [M + 1] = 389
합성예Synthesis Example 27: 중간체 4-7의 합성  27: Synthesis of Intermediate 4-7
하기 반응식에 따라 중간체 4-7을 합성하였다.Intermediate 4-7 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000068
Figure PCTKR2017007032-appb-I000068
<중간체 4-6>을 이용하여 상기 합성예 5와 동일하게 실험하여, <중간체 4-7>을 합성하였다.Using <Intermediate 4-6>, the experiment was carried out in the same manner as in Synthesis Example 5 to synthesize <Intermediate 4-7>.
Mass [M+1] = 632Mass [M + 1] = 632
합성예Synthesis Example 28: 중간체 4-8의 합성 28: Synthesis of Intermediate 4-8
하기 반응식에 따라 중간체 4-8을 합성하였다.Intermediate 4-8 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000069
Figure PCTKR2017007032-appb-I000069
<중간체 4-7>를 이용하여 상기 합성예 6과 동일하게 실험하여, <중간체 4-8>을 합성하였다.<Intermediate 4-8> was synthesized in the same manner as in Synthesis Example 6 using <Intermediate 4-7>.
Mass [M+1] = 614Mass [M + 1] = 614
합성예Synthesis Example 29: 화합물 25의 합성 29: Synthesis of Compound 25
하기 반응식에 따라 화합물 25를 합성하였다.Compound 25 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000070
Figure PCTKR2017007032-appb-I000070
<중간체 4-8>과 <중간체 2-2>를 이용하여 상기 합성예 8과 동일하게 실험하여, <화합물 25>를 합성하였다.Using <Intermediate 4-8> and <Intermediate 2-2>, the same experiment as in Synthesis Example 8 was conducted to synthesize <Compound 25>.
Mass [M+1] = 1105Mass [M + 1] = 1105
합성예Synthesis Example 30. 중간체 5-1의 합성 30. Synthesis of Intermediate 5-1
하기 반응식에 따라 중간체 5-1을 합성하였다.Intermediate 5-1 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000071
Figure PCTKR2017007032-appb-I000071
디벤조[b,d]티오펜-1-일 보론산을 이용하여 상기 합성예 1과 동일하게 실험하여, <중간체 5-1>을 합성하였다.<Intermediate 5-1> was synthesized in the same manner as in Synthesis Example 1 using dibenzo [b, d] thiophen-1-yl boronic acid.
Mass [M+1] = 323Mass [M + 1] = 323
합성예Synthesis Example 31: 중간체 5-2의 합성  31: Synthesis of Intermediate 5-2
하기 반응식에 따라 중간체 5-2를 합성하였다.Intermediate 5-2 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000072
Figure PCTKR2017007032-appb-I000072
<중간체 5-1>을 이용하여 상기 합성예 3과 동일하게 실험하여, <중간체 5-2>를 합성하였다.<Intermediate 5-2> was synthesized in the same manner as in Synthesis Example 3 using <Intermediate 5-1>.
TLC와 HPLC로 확인하였음Confirmed by TLC and HPLC
합성예Synthesis Example 32: 중간체 5-3의 합성  32: Synthesis of Intermediate 5-3
하기 반응식에 따라 중간체 5-3을 합성하였다.Intermediate 5-3 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000073
Figure PCTKR2017007032-appb-I000073
<중간체 5-2>를 이용하여 상기 합성예 3과 동일하게 실험하여, <중간체 5-3>을 합성하였다.<Intermediate 5-3> was synthesized in the same manner as in Synthesis Example 3 using <Intermediate 5-2>.
Mass [M+1] = 321Mass [M + 1] = 321
합성예Synthesis Example 33: 중간체 5-4의 합성  33: Synthesis of Intermediate 5-4
하기 반응식에 따라 중간체 5-4를 합성하였다.Intermediate 5-4 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000074
Figure PCTKR2017007032-appb-I000074
<중간체 5-3>을 이용하여 상기 합성예 4와 동일하게 실험하여, <중간체 5-4>를 합성하였다.<Intermediate 5-4> was synthesized in the same manner as in Synthesis Example 4 using <Intermediate 5-3>.
Mass [M+1] = 321Mass [M + 1] = 321
합성예Synthesis Example 34: 중간체 5-5의 합성  34: Synthesis of Intermediate 5-5
하기 반응식에 따라 중간체 5-5를 합성하였다.Intermediate 5-5 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000075
Figure PCTKR2017007032-appb-I000075
<중간체 5-4>를 이용하여 상기 합성예 5와 동일하게 실험하여, <중간체 5-5>를 합성하였다.<Intermediate 5-5> was synthesized in the same manner as in Synthesis Example 5 using <Intermediate 5-4>.
Mass [M+1] = 642Mass [M + 1] = 642
합성예Synthesis Example 35: 중간체 5-6의 합성 35: Synthesis of Intermediate 5-6
하기 반응식에 따라 중간체 5-6을 합성하였다.Intermediate 5-6 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000076
Figure PCTKR2017007032-appb-I000076
<중간체 5-5>를 이용하여 상기 합성예 6과 동일하게 실험하여, <중간체 5-6>을 합성하였다.<Intermediate 5-6> was synthesized in the same manner as in Synthesis Example 6 using <Intermediate 5-5>.
Mass [M+1] = 624Mass [M + 1] = 624
합성예Synthesis Example 36: 화합물 18의 합성 36: Synthesis of Compound 18
하기 반응식에 따라 화합물 18을 합성하였다.Compound 18 was synthesized according to the following scheme.
Figure PCTKR2017007032-appb-I000077
Figure PCTKR2017007032-appb-I000077
<중간체 5-6>과 <중간체 2-3>을 이용하여 상기 합성예 8과 동일하게 실험하여, <화합물 18>을 합성하였다.Using <Intermediate 5-6> and <Intermediate 2-3>, the same experiment as in Synthesis Example 8 was conducted to synthesize <Compound 18>.
Mass [M+1] = 1138Mass [M + 1] = 1138
상기 합성예에 기재된 합성방법과 같은 방법을 통하여, 상기 합성예에서 합성된 화합물 외에 본원 화학식 1에 해당하는 화합물을 합성할 수 있다. 상기 화합물 10의 Mass data를 하기 도 5에 나타내었다.Through the same method as the synthesis method described in the synthesis example, it is possible to synthesize a compound corresponding to the general formula (1) in addition to the compound synthesized in the synthesis example. Mass data of the compound 10 is shown in FIG. 5.
<실시예><Example>
Figure PCTKR2017007032-appb-I000078
Figure PCTKR2017007032-appb-I000078
Figure PCTKR2017007032-appb-I000079
Figure PCTKR2017007032-appb-I000079
실시예 1.Example 1.
ITO(인듐 주석 산화물)가 1,000Å 두께로 박막 코팅된 유리 기판(corning 7059 glass)을, 분산제를 녹인 증류수 에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
이렇게 준비된 ITO 투명 전극 위에 상기 HAT를 50Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공수송층으로 상기 HT-A 1000Å을 진공 증착하고, 연이어 HT-B를 100 Å두께로 증착하였다. 발광층에는 호스트로 H-A와 화합물 1을 2 ~ 10 wt%로 도핑하여, 200Å두께로 진공 증착하였다. 그 다음에 ET-A 와 Liq를 1:1 비율로 300Å을 증착하였고 이 위에 순차적으로 150Å 두께의 은(Ag) 10% 도핑된 마그네슘(Mg) 그리고 1,000Å 두께의 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다. The HAT was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The HT-A 1000 Pa was vacuum deposited on the hole transport layer, and HT-B was subsequently deposited to a thickness of 100 Pa. The light emitting layer was doped with H-A and Compound 1 at 2 to 10 wt% as a host, and was vacuum deposited to a thickness of 200 Å. Next, ET-A and Liq were deposited at 300 μs in a 1: 1 ratio, and 150 μm thick Ag (Ag) 10% doped magnesium (Mg) and 1,000 μm thick aluminum were deposited to form a cathode. , An organic light emitting device was manufactured.
상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였고, LiF는 0.2 Å/sec, 알루미늄은 3Å/sec 내지 7Å/sec의 증착속도를 유지하였다. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was 0.2 Å / sec, and the aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.
실시예 2.Example 2.
상기 실시예 1에서, 화합물 1 대신 화합물 7을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 7 instead of Compound 1.
실시예 3.Example 3.
상기 실시예 1에서, 화합물 1 대신 화합물 13을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 13 instead of Compound 1.
실시예 4.Example 4.
상기 실시예 1에서, 화합물 1 대신 화합물 28을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 28 instead of Compound 1.
실시예 5.Example 5.
상기 실시예 1에서, 화합물 1 대신 화합물 29를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 29 instead of Compound 1.
실시예 6.Example 6.
상기 실시예 1에서, 화합물 1 대신 화합물 30을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 30 instead of Compound 1.
실시예 7.Example 7.
상기 실시예 1에서, 화합물 H-A 대신 H-B를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using H-B instead of compound H-A.
실시예 8.Example 8.
상기 실시예 7에서 화합물 1 대신 화합물 7을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 7 was used instead of Compound 1 in Example 7.
실시예 9.Example 9.
상기 실시예 7에서 화합물 1 대신 화합물 13을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 13 was used instead of Compound 1 in Example 7.
실시예 10.Example 10.
상기 실시예 7에서 화합물 1 대신 화합물 28을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 28 was used instead of Compound 1 in Example 7.
실시예 11.Example 11.
상기 실시예 7에서 화합물 1 대신 화합물 29를 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 29 was used instead of Compound 1 in Example 7.
실시예 12.Example 12.
상기 실시예 7에서 화합물 1 대신 화합물 30을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 30 was used instead of Compound 1 in Example 7.
실시예 13.Example 13.
상기 실시예 1에서, H-A 대신 H-C를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using H-C instead of H-A.
실시예 14.Example 14.
상기 실시예 13에서 화합물 1 대신 화합물 7을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 7 was used instead of Compound 1 in Example 13.
실시예 15.Example 15.
상기 실시예 13에서 화합물 1 대신 화합물 13을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 13 was used instead of Compound 1 in Example 13.
실시예 16.Example 16.
상기 실시예 13에서 화합물 1 대신 화합물 28을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 28 was used instead of Compound 1 in Example 13.
실시예 17.Example 17.
상기 실시예 13에서 화합물 1 대신 화합물 29를 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 29 was used instead of Compound 1 in Example 13.
실시예 18.Example 18.
상기 실시예 13에서 화합물 1 대신 화합물 30을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that Compound 30 was used instead of Compound 1 in Example 13.
비교예 1.Comparative Example 1.
상기 실시예 1에서 화합물 1 대신 D-1을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-1 instead of compound 1 in Example 1.
비교예 2.Comparative Example 2.
상기 실시예 1에서 화합물 1 대신 D-2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that D-2 was used instead of Compound 1 in Example 1.
비교예 3.Comparative Example 3.
상기 실시예 1에서 화합물 1 대신 D-3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-3 instead of compound 1 in Example 1.
비교예 4.Comparative Example 4.
상기 실시예 7에서 화합물 1 대신 D-1을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-1 instead of compound 1 in Example 7.
비교예 5.Comparative Example 5.
상기 실시예 7에서 화합물 1 대신 D-2를 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-2 instead of compound 1 in Example 7.
비교예 6.Comparative Example 6.
상기 실시예 7에서 화합물 1 대신 D-3을 사용한 것을 제외하고는 실시예 7과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 7 except for using D-3 instead of compound 1 in Example 7.
비교예 7.Comparative Example 7.
상기 실시예 13에서 화합물 1 대신 D-1을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that D-1 was used instead of Compound 1 in Example 13.
비교예 8.Comparative Example 8.
상기 실시예 13에서 화합물 1 대신 D-2를 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 13, except that D-2 was used instead of Compound 1 in Example 13.
비교예 9.Comparative Example 9.
상기 실시예 13에서 화합물 1 대신 D-3을 사용한 것을 제외하고는 실시예 13과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Example 13 except for using D-3 instead of compound 1 in Example 13.
상기 실시예 1 내지 18 및 비교예 1 내지 비교예 9의 유기 발광 소자를 10mA/cm의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20mA/cm의 전류밀도에서 초기 휘도 대비 95%가 되는 시간(LT95)을 측정하였다. 그 결과를 하기 표 1에 나타내었다.The driving voltage and the luminous efficiency of the organic light emitting diodes of Examples 1 to 18 and Comparative Examples 1 to 9 were measured at a current density of 10 mA / cm, and the time became 95% of the initial luminance at a current density of 20 mA / cm. (LT95) was measured. The results are shown in Table 1 below.
실시예Example 호스트Host 도펀트Dopant @ 10 mA/cm2 @ 10 mA / cm 2 @ 20 mA/cm2 @ 20 mA / cm 2
전압(V)Voltage (V) 효율(cd/A)Efficiency (cd / A) CIE (x,y)CIE (x, y) 수명(hr)Life (hr)
실시예 1Example 1 H-AH-A 화합물 1Compound 1 4.14.1 6.226.22 (0.143,0.041)(0.143,0.041) 130130
실시예 2Example 2 H-AH-A 화합물 7Compound 7 4.24.2 6.526.52 (0.142,0.043)(0.142,0.043) 125125
실시예 3Example 3 H-AH-A 화합물 13Compound 13 4.24.2 6.306.30 (0.142,0.043)(0.142,0.043) 110110
실시예 4Example 4 H-AH-A 화합물 28Compound 28 4.34.3 6.126.12 (0.143,0.042)(0.143,0.042) 120120
실시예 5Example 5 H-AH-A 화합물 29Compound 29 4.24.2 6.606.60 (0.142,0.044)(0.142,0.044) 115115
실시예 6Example 6 H-AH-A 화합물 30Compound 30 4.44.4 6.426.42 (0.142,0.045)(0.142,0.045) 105105
실시예 7Example 7 H-BH-B 화합물 1Compound 1 3.93.9 6.106.10 (0.142,0.041)(0.142,0.041) 140140
실시예 8Example 8 H-BH-B 화합물 7Compound 7 4.04.0 6.306.30 (0.141,0.043)(0.141,0.043) 150150
실시예 9Example 9 H-BH-B 화합물 13Compound 13 4.14.1 6.026.02 (0.141,0.045)(0.141,0.045) 135135
실시예 10Example 10 H-BH-B 화합물 28Compound 28 4.04.0 5.955.95 (0.143,0.044)(0.143,0.044) 135135
실시예 11Example 11 H-BH-B 화합물 29Compound 29 4.14.1 6.256.25 (0.141,0.043)(0.141,0.043) 125125
실시예 12Example 12 H-BH-B 화합물 30Compound 30 4.14.1 6.126.12 (0.142,0.044)(0.142,0.044) 130130
실시예 13Example 13 H-CH-C 화합물 1Compound 1 4.04.0 5.805.80 (0.143,0.041)(0.143,0.041) 145145
실시예 14Example 14 H-CH-C 화합물 7Compound 7 3.83.8 5.955.95 (0.142,0.043)(0.142,0.043) 155155
실시예 15Example 15 H-CH-C 화합물 13Compound 13 3.93.9 6.106.10 (0.142,0.046)(0.142,0.046) 145145
실시예 16Example 16 H-CH-C 화합물 28Compound 28 4.14.1 6.306.30 (0.144,0.045)(0.144,0.045) 135135
실시예 17Example 17 H-CH-C 화합물 29Compound 29 4.04.0 6.256.25 (0.142,0.045)(0.142,0.045) 145145
실시예 18Example 18 H-CH-C 화합물 30Compound 30 3.93.9 5.985.98 (0.142,0.046)(0.142,0.046) 130130
비교예 1Comparative Example 1 H-AH-A D-1D-1 4.44.4 5.135.13 (0.143,0.042)(0.143,0.042) 7575
비교예 2Comparative Example 2 H-AH-A D-2D-2 4.44.4 3.503.50 (0.141,0.045)(0.141,0.045) 5050
비교예 3Comparative Example 3 H-AH-A D-3D-3 4.34.3 5.125.12 (0.142,0.044)(0.142,0.044) 8585
비교예 4Comparative Example 4 H-BH-B D-1D-1 4.34.3 5.035.03 (0.143,0.042)(0.143,0.042) 8080
비교예 5Comparative Example 5 H-BH-B D-2D-2 4.24.2 3.613.61 (0.142,0.044)(0.142,0.044) 5050
비교예 6Comparative Example 6 H-BH-B D-3D-3 4.34.3 5.225.22 (0.142,0.045)(0.142,0.045) 7070
비교예 7Comparative Example 7 H-CH-C D-1D-1 4.14.1 4.984.98 (0.144,0.045)(0.144,0.045) 8080
비교예 8Comparative Example 8 H-CH-C D-2D-2 4.24.2 3.663.66 (0.141,0.044)(0.141,0.044) 6060
비교예 9Comparative Example 9 H-CH-C D-3D-3 4.24.2 5.125.12 (0.142,0.046)(0.142,0.046) 9090
상기 표 1의 실시예 1 내지 18 및 비교예 1 내지 9를 비교하면, 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함시켜 제조된 유기 발광 소자의 경우 3차원적 구조로 인해 분자간 조밀한 쌓임으로 인한 분자간 형광 감쇄를 막아 우수한 성능을 보인다. 또한 전자를 하나 잃어버린 상태에서 (cation condition) HOMO 의 전자밀도 분포가 일반적으로 안정한 양이온 상태를 가지고 있다고 알려진 질소를 포함한 스파이로 인돌로 아크리딘 부분에 분포하여 소자 수명의 개선을 가져 왔다. 따라서 파이렌계 또는 플루오렌계 화합물을 포함하는 비교예 1 내지 9에서 제조된 유기 발광 소자보다 효율 및 수명 특성이 우수함을 확인할 수 있었다.Comparing Examples 1 to 18 and Comparative Examples 1 to 9 of Table 1, in the case of an organic light emitting device manufactured by including the heterocyclic compound represented by Chemical Formula 1, due to the three-dimensional structure, It shows excellent performance by preventing intermolecular fluorescence attenuation. In addition, the electron density distribution of HOMO is generally distributed in the spiro indolo acridine moiety containing nitrogen, which is known to have a stable cation state. Therefore, it was confirmed that the efficiency and lifespan characteristics were superior to those of the organic light emitting devices manufactured in Comparative Examples 1 to 9 including pyrene-based or fluorene-based compounds.

Claims (17)

  1. 하기 화학식 1로 표시되는 것인 헤테로고리 화합물:Heterocyclic compound represented by the formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2017007032-appb-I000080
    Figure PCTKR2017007032-appb-I000080
    상기 화학식 1에 있어서,In Chemical Formula 1,
    R5 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
    L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
    Ar1은 치환 또는 비치환된 탄화수소고리기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 is a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
    R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    a 및 b는 각각 0 내지 4의 정수이고,a and b are each an integer of 0 to 4,
    c 및 d는 0 내지 3의 정수이며,c and d are integers from 0 to 3,
    a 내지 d가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 동일하거나 상이하며,when a to d are each 2 or more, the substituents in parentheses are the same as or different from each other,
    n1 및 n2는 각각 0 또는 1이고,n1 and n2 are each 0 or 1,
    n1 및 n2 중 1 이상은 1의 정수이며,at least one of n1 and n2 is an integer of 1,
    X1 및 X2는 수소이거나, 서로 직접결합한다.X1 and X2 are hydrogen or directly bond to each other.
  2. 청구항 1에 있어서,The method according to claim 1,
    Ar1-L2-NR3R4는 하기 구조들 중 하나인 것인 헤테로고리 화합물:Wherein Ar 1 -L 2 -NR 3 R 4 is one of the following structures:
    Figure PCTKR2017007032-appb-I000081
    Figure PCTKR2017007032-appb-I000081
    Figure PCTKR2017007032-appb-I000082
    Figure PCTKR2017007032-appb-I000082
    Figure PCTKR2017007032-appb-I000083
    Figure PCTKR2017007032-appb-I000083
    상기 구조들에 있어서,In the above structures,
    L2, R3 및 R4의 정의는 상기 화학식 1에서의 정의와 같고,Definitions of L2, R3 and R4 are the same as the definition in Formula 1,
    R' 및 R"는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이이며,R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; halogen; nitrile; nitro; hydroxy; aryloxy; alkylthioxy; arylthioxy; alkylsulphoxy; Silyl groups; boron groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted aralkyl groups; substituted or unsubstituted Alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl A phosphine group or a substituted or unsubstituted heterocyclic group,
    상기 구조들은 추가로 치환된 수 있다.The structures may be further substituted.
  3. 청구항 1에 있어서, The method according to claim 1,
    L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 2가의 헤테로고리기인 것인 헤테로고리 화합물.L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  4. 청구항 1에 있어서,The method according to claim 1,
    L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 또는 하기에 기재되어 있는 치환기 중 하나인 것인 헤테로고리 화합물:L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a heterocyclic compound, which is one of the substituents described below:
    Figure PCTKR2017007032-appb-I000084
    .
    Figure PCTKR2017007032-appb-I000084
    .
  5. 청구항 1에 있어서,The method according to claim 1,
    R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기인 것인 헤테로고리 화합물.R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  6. 청구항 1에 있어서,The method according to claim 1,
    R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 하기 구조들 중 어느 하나인 것인 헤테로고리 화합물:R 1 to R 4 are the same as or different from each other, and each independently a heterocyclic compound having any one of the following structures:
    Figure PCTKR2017007032-appb-I000085
    Figure PCTKR2017007032-appb-I000085
    Figure PCTKR2017007032-appb-I000086
    Figure PCTKR2017007032-appb-I000086
    Figure PCTKR2017007032-appb-I000087
    Figure PCTKR2017007032-appb-I000087
    Figure PCTKR2017007032-appb-I000088
    Figure PCTKR2017007032-appb-I000088
    Figure PCTKR2017007032-appb-I000089
    Figure PCTKR2017007032-appb-I000089
    상기 구조들에 있어서,In the above structures,
    R201 내지 R297은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 실릴기; 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R201 to R297 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Silyl groups; Boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    a1, a6, a10, a23 및 a25는 각각 0 내지 5의 정수이며,a1, a6, a10, a23 and a25 are each an integer of 0 to 5,
    a2, a5, a8, a9, a14, a16, a17, a21, a28 내지 a35, b1 내지 b4, b6 내지 b9, b11 내지 b13, b15 및 b17 내지 b32는 각각 0 내지 4의 정수이고,a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
    a3 및 a22는 각각 0 내지 7의 정수이며,a3 and a22 are each an integer of 0 to 7,
    a4, a7, a12, a15. a19, a26 및 a27은 각각 0 내지 3의 정수이고,a4, a7, a12, a15. a19, a26 and a27 are each an integer of 0 to 3,
    a11은 0 내지 9의 정수이며,a11 is an integer of 0 to 9,
    a13, a20 및 a24은 각각 0 내지 6의 정수이고,a13, a20 and a24 are each an integer of 0 to 6,
    a18, b5, b10, b14 및 b16은 각각 0 내지 2의 정수이며,a18, b5, b10, b14 and b16 are each an integer of 0 to 2,
    a18, b5, b10, b14 및 b16이 2 인 경우, 괄호 내의 치환기는 서로 상이하고,when a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other,
    a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 내지 a35, b1 내지 b4, b6 내지 b9, b11 내지 b13, b15, b17 내지 b32, a3, a22, a4, a7, a12, a15. a19, a26, a27, a11, a13, a20 및 a24가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하다.a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15, b17 to b32, a3, a22, a4, a7, a12, a15. When a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in parentheses are the same as or different from each other.
  7. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1은 하기 화합물들로부터 선택되는 것인 헤테로고리 화합물:Formula 1 is a heterocyclic compound selected from the following compounds:
    Figure PCTKR2017007032-appb-I000090
    Figure PCTKR2017007032-appb-I000090
    Figure PCTKR2017007032-appb-I000091
    Figure PCTKR2017007032-appb-I000091
    Figure PCTKR2017007032-appb-I000092
    .
    Figure PCTKR2017007032-appb-I000092
    .
  8. 제1 전극, 제2 전극 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 청구항 1 내지 7 중 어느 하나의 항에 따른 헤테로고리 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자.A first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layer is a heterocyclic compound according to any one of claims 1 to 7 An organic light emitting device comprising a.
  9. 청구항 8에 있어서,The method according to claim 8,
    상기 유기물층은 정공주입층 또는 정공수송층을 포함하고,The organic material layer includes a hole injection layer or a hole transport layer,
    상기 정공주입층 또는 정공수송층은 상기 화학식 1의 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.The hole injection layer or the hole transport layer is an organic light emitting device comprising the heterocyclic compound of Formula 1.
  10. 청구항 8에 있어서,The method according to claim 8,
    상기 유기물층은 전자수송층 또는 전자주입층을 포함하고,The organic material layer includes an electron transport layer or an electron injection layer,
    상기 전자수송층 또는 전자주입층은 상기 화학식 1의 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.The electron transport layer or the electron injection layer is an organic light emitting device comprising the heterocyclic compound of Formula 1.
  11. 청구항 8에 있어서, The method according to claim 8,
    상기 유기물층은 발광층을 포함하고, The organic material layer includes a light emitting layer,
    상기 발광층은 상기 화학식 1의 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.The light emitting layer is an organic light emitting device comprising the heterocyclic compound of Formula 1.
  12. 청구항 11에 있어서, The method according to claim 11,
    상기 발광층은 하기 화학식 2의 화합물을 더 포함하는 유기 발광 소자.The light emitting layer is an organic light emitting device further comprising a compound of formula (2).
    [화학식 2][Formula 2]
    Figure PCTKR2017007032-appb-I000093
    Figure PCTKR2017007032-appb-I000093
    상기 화학식 2에 있어서,In Chemical Formula 2,
    R9은 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R9 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
    p는 0 내지 6의 정수이며,p is an integer from 0 to 6,
    p가 2 이상인 경우 괄호 내의 치환기는 서로 동일하거나 상이하고,when p is 2 or more, the substituents in parentheses are the same as or different from each other,
    L3 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L3 to L6 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar2 내지 Ar5는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  13. 청구항 12에 있어서,The method according to claim 12,
    상기 L3 내지 L6은 서로 동일하거나, 상이하고 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:L3 to L6 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device selected from the following structures:
    Figure PCTKR2017007032-appb-I000094
    .
    Figure PCTKR2017007032-appb-I000094
    .
  14. 청구항 12에 있어서,The method according to claim 12,
    상기 Ar2 내지 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:Ar2 to Ar5 are the same as or different from each other, and each independently hydrogen; Or an organic light emitting device selected from the following structures:
    Figure PCTKR2017007032-appb-I000095
    Figure PCTKR2017007032-appb-I000095
    Figure PCTKR2017007032-appb-I000096
    Figure PCTKR2017007032-appb-I000096
    Figure PCTKR2017007032-appb-I000097
    .
    Figure PCTKR2017007032-appb-I000097
    .
  15. 청구항 11에 있어서, The method according to claim 11,
    상기 발광층은 하기 화학식 3의 화합물을 더 포함하는 유기 발광 소자.The light emitting layer is an organic light emitting device further comprising a compound of formula (3).
    [화학식 3][Formula 3]
    Figure PCTKR2017007032-appb-I000098
    Figure PCTKR2017007032-appb-I000098
    상기 화학식 3에 있어서,In Chemical Formula 3,
    R10은 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 또는 치환 또는 비치환된 헤테로고리기이고,R10 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Or a substituted or unsubstituted heterocyclic group,
    q는 0 내지 7의 정수이며,q is an integer from 0 to 7,
    q가 2 이상인 경우 괄호 내의 치환기는 서로 동일하거나 상이하고,when q is 2 or more, the substituents in parentheses are the same as or different from each other,
    L7 내지 L9는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L7 to L9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar6 to Ar8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  16. 청구항 15에 있어서,The method according to claim 15,
    상기 L7 내지 L9는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:L7 to L9 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device selected from the following structures:
    Figure PCTKR2017007032-appb-I000099
    .
    Figure PCTKR2017007032-appb-I000099
    .
  17. 청구항 15에 있어서,The method according to claim 15,
    상기 Ar6 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조들 중 선택되는 것인 유기 발광 소자:Wherein Ar6 to Ar8 are the same as or different from each other, and are each independently selected from the following structures:
    Figure PCTKR2017007032-appb-I000100
    Figure PCTKR2017007032-appb-I000100
    Figure PCTKR2017007032-appb-I000101
    Figure PCTKR2017007032-appb-I000101
    Figure PCTKR2017007032-appb-I000102
    .
    Figure PCTKR2017007032-appb-I000102
    .
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