WO2018004318A2 - Composé hétérocyclique et élément électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et élément électroluminescent organique le comprenant 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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WO2018004318A3 (fr
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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/zh
Priority to JP2018565344A priority patent/JP6716854B2/ja
Publication of WO2018004318A2 publication Critical patent/WO2018004318A2/fr
Publication of WO2018004318A3 publication Critical patent/WO2018004318A3/fr

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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
    • C07D491/02—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
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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
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    • 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
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    • H10K50/17—Carrier injection layers
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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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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    • 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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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne un composé hétérocyclique de formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2017/007032 2016-07-01 2017-07-03 Composé hétérocyclique et élément électroluminescent organique le comprenant WO2018004318A2 (fr)

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