WO2023033351A1 - Composé hétérocyclique, dispositif électroluminescent organique le comprenant et composition pour couche organique de dispositif électroluminescent organique - Google Patents

Composé hétérocyclique, dispositif électroluminescent organique le comprenant et composition pour couche organique de dispositif électroluminescent organique Download PDF

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WO2023033351A1
WO2023033351A1 PCT/KR2022/010212 KR2022010212W WO2023033351A1 WO 2023033351 A1 WO2023033351 A1 WO 2023033351A1 KR 2022010212 W KR2022010212 W KR 2022010212W WO 2023033351 A1 WO2023033351 A1 WO 2023033351A1
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heterocyclic compound
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박건유
노영석
김동준
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엘티소재주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D491/12—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
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D495/12—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 three hetero rings
    • C07D495/14—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
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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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

Definitions

  • the present invention relates to a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer of an organic light emitting device.
  • An organic light emitting device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as needed.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound capable of constituting the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant type light emitting layer may be used.
  • a compound capable of performing functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • Patent Document 1 US Patent No. 4,356,429
  • the present invention is to provide a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer of the organic light emitting device.
  • the present invention provides a heterocyclic compound represented by Formula 1 below:
  • R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of, wherein at least one of R1 to R12 is deuterium,
  • X1, X2 and X3 are the same as or different from each other, each independently represent NAr1, O, S or CR13R14, at least two or more of X1, X2 and X3 are NAr1, the plurality of Ar1s are different from each other, any of these One is a group represented by Formula 1-1 below,
  • Ar1 is each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; And it is selected from the group consisting of a group represented by Formula 1-1 below,
  • L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of
  • a and b are the same as or different from each other, and each independently represents an integer from 0 to 3;
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; is selected from the group consisting of.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound represented by Chemical Formula 1. do.
  • the present invention provides an organic light emitting device wherein the organic material layer further includes a heterocyclic compound represented by Chemical Formula 2:
  • R101 to R114 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of
  • L3 and L4 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • n and n are the same as or different from each other, and are each independently an integer of 0 to 3.
  • the present invention provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.
  • the heterocyclic compound according to an embodiment may be used as a material for an organic material layer of an organic light emitting device.
  • the compound may serve as a hole injection layer material, an electron blocking layer material, a hole transport layer material, an emission layer material, an electron transport layer material, a hole blocking layer material, and an electron injection layer material in an organic light emitting device.
  • the compound may be used as a material for a light emitting layer of an organic light emitting device.
  • the heterocyclic compound may be used as a light emitting material alone or in combination with a P-type host, and may be used as a host material or a dopant material of a light emitting layer.
  • the compound represented by Chemical Formula 1 is used in the organic material layer, the driving voltage of the organic light emitting device can be lowered, the light emitting efficiency can be improved, and the lifetime characteristics can be improved.
  • heterocyclic compound according to one embodiment when used as a light emitting layer, hole transport and electron transport characteristics are enhanced, and the band gap and triplet energy level (T1 level) value, improve hole transfer ability, increase molecular stability, lower driving voltage of organic light emitting device, improve light efficiency, and improve lifetime characteristics of organic light emitting device by improved thermal stability of compound can make it
  • FIGS. 1 to 3 are diagrams schematically illustrating a stacked structure of an organic light emitting device according to an exemplary embodiment of the present invention.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, the position where the substituent is substituted , When two or more substituents are substituted, two or more substituents may be the same as or different from each other.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically, 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 group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 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,
  • the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically, 2 to 20.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 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, etc., but is not limited thereto.
  • the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • the alkoxy group may be straight chain, branched chain or cyclic chain.
  • the number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like.
  • the number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, and the like.
  • the heterocycloalkyl group may have 2 to 60, specifically 2 to 40, and more specifically 3 to 20 carbon atoms.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents.
  • the polycyclic means a group in which an aryl group is directly connected or condensed with another cyclic group.
  • the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like.
  • the aryl group includes a spiro group.
  • the number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25.
  • aryl group examples include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, and a pyrene group.
  • Nyl group tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may bond to each other to form a ring.
  • the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like.
  • the heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 3 to 25 carbon atoms.
  • heteroaryl group examples include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, and a thiazolyl group.
  • the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine group; Diaryl amine group; Diheteroarylamine group; an alkyl arylamine group; Alkylheteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene
  • Examples include a ylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • the arylene group means that the aryl group has two bonding sites, that is, a divalent group.
  • the description of the aryl group described above can be applied except that each is a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The above description of the heteroaryl group may be applied except that each is a divalent group.
  • adjacent refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted.
  • two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as “adjacent” to each other.
  • "when no substituent is shown in the chemical formula or compound structure” may mean that all positions at which the substituent can occur are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be an isotope of deuterium, and in this case, the content of deuterium may be 0% to 100%.
  • deuterium is one of the isotopes of hydrogen and is an element having a deuteron composed of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.
  • isotopes which mean atoms having the same atomic number (Z) but different mass numbers (A), have the same number of protons, but have neutrons. It can also be interpreted as an element with a different number of neutrons.
  • the meaning of the content T% of a specific substituent is when the total number of substituents that a base compound can have is defined as T1, and the number of specific substituents among them is defined as T2.
  • the phenyl group represented by 20% of the deuterium content may mean that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium is 1 (T2 in the formula) . That is, it can be represented by the following structural formula that the content of deuterium in the phenyl group is 20%.
  • a phenyl group having a deuterium content of 0% it may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.
  • the C6 to C60 aromatic hydrocarbon ring means a compound containing an aromatic ring composed of C6 to C60 carbons and hydrogen, for example, phenyl, biphenyl, terphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. may be mentioned, but is not limited thereto, and an aromatic hydrocarbon ring compound known in the art as having the above number of carbon atoms may be used. All inclusive.
  • the present invention provides a heterocyclic compound represented by Formula 1 below:
  • R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of, wherein at least one of R1 to R12 is deuterium,
  • X1, X2 and X3 are the same as or different from each other, each independently represent NAr1, O, S or CR13R14, at least two or more of X1, X2 and X3 are NAr1, the plurality of Ar1s are different from each other, any of these One is a group represented by Formula 1-1 below,
  • Ar1 is each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; And it is selected from the group consisting of a group represented by Formula 1-1 below,
  • L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of
  • a and b are the same as or different from each other, and each independently represents an integer from 0 to 3;
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; is selected from the group consisting of.
  • X1 and X2 are NAr1, and X3 can be O, S or CR13R14.
  • X1 and X3 are NAr1 and X2 can be O, S or CR13R14.
  • the heterocyclic compound represented by Formula 1 may be any one of Formula 1-a and Formula 1-b, but is not limited to these examples:
  • X3 is O, S or CR13R14;
  • R1 to R14 and Ar1 are as defined in Formula 1 above,
  • Ar1' is the same as the definition of Ar1,
  • Ar1 and Ar1' are different from each other, and one of them is a group represented by Formula 1-1;
  • X2 is O, S or CR13R14;
  • R1 to R14 and Ar1 are as defined in Formula 1 above,
  • Ar1' is the same as the definition of Ar1,
  • Ar1 and Ar1' are different from each other, and either one of them is a group represented by Formula 1-1.
  • Ar1 is a group represented by Formula 1-1, and Ar1' is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar1 is a group represented by Formula 1-1, and Ar1' is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1' is a group represented by Formula 1-1, and Ar1 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1' is a group represented by Formula 1-1, and Ar1 is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1 is a group represented by Formula 1-1, and Ar1' is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar1 is a group represented by Formula 1-1, and Ar1' is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1' is a group represented by Formula 1-1, and Ar1 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar1' is a group represented by Formula 1-1, and Ar1 is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1 and Ar1' are each independently a group represented by Formula 1-1 and Formula 1-2-a to 1-2- It may be a heterocyclic compound which is any one of the groups represented by g:
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group,
  • L1, L2, a and b are as defined in Formula 1 above,
  • R21 to R60 are hydrogen or deuterium
  • X4 is O, S or CR61R62;
  • R61 and R62 are methyl groups
  • p, q and r are the same as or different from each other, and are each independently an integer of 3 to 5.
  • Ar2 and Ar3 may be a C6 to C30 aryl group substituted with deuterium or a C2 to C30 heteroaryl group substituted with deuterium.
  • R21 to R60 in Chemical Formulas 1-2-a to 1-2-g may be deuterium.
  • R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group; wherein at least one of R1 to R12 may be deuterium.
  • R1 to R12 are hydrogen or deuterium, and at least one of R1 to R12 may be deuterium.
  • R1 to R12 may be deuterium.
  • L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group, a and b may be the same as or different from each other, and each independently may be an integer of 0 to 3.
  • L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group, a and b may be the same as or different from each other, and each independently may be an integer of 0 to 3.
  • L1 and L2 may be the same as or different from each other, and may each independently have the following structures, but are not limited to these examples:
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently may have the following structure, but is not limited to these examples:
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C2 to C20 alkenyl group; A substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted C2 to C20 heterocycloalkyl group; A substituted or unsubstituted C6 to C20 aryl group; It may be selected from the group consisting of; and a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; and a substituted or unsubstituted C1 to C10 alkoxy group.
  • R13 and R14 are the same as or different from each other, and each independently may be a methyl group, an ethyl group, a propyl group, and the like.
  • the heterocyclic compound represented by Formula 1 may not contain deuterium as a substituent, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 1 may not contain deuterium as a substituent, or the content of deuterium may be 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 1 may not contain deuterium as a substituent, or the content of deuterium based on the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.
  • the heterocyclic compound represented by Formula 1 may not contain deuterium as a substituent, or the content of deuterium may be 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.
  • the content of deuterium in R1 to R12 may be 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.
  • the content of deuterium in R1 to R12 may be 5% to 95% based on the total number of hydrogen atoms and deuterium atoms.
  • the content of deuterium in R1 to R12 may be 10% to 90% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 1 does not contain deuterium as a substituent, or the content of deuterium in R1 to R12 is greater than 0%, 5% or more, or 10% based on the total number of hydrogen atoms and deuterium atoms. Can be greater than, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50%, 100% or less, 95% or less, 90% or less, 85 % or less, 80% or less, 75% or less, 70% or less, 65% or less or 60% or less.
  • Ar2 and Ar3 may be an aryl group or a heteroaryl group substituted with deuterium, and in this case, the content of deuterium based on the total number of hydrogen atoms and deuterium atoms is 1 % to 100%.
  • Ar2 and Ar3 may be an aryl group or a heteroaryl group substituted with deuterium, and in this case, the content of deuterium based on the total number of hydrogen atoms and deuterium atoms is 5 % to 95%.
  • Ar2 and Ar3 may be an aryl group or a heteroaryl group substituted with deuterium, and in this case, the content of deuterium based on the total number of hydrogen atoms and deuterium atoms is 10 % to 90%.
  • the substituents do not contain deuterium, or the content of deuterium in the substituent is based on the total number of hydrogen atoms and deuterium atoms can be greater than 0%, greater than 1%, greater than 5%, greater than 10%, greater than 15%, greater than 20%, greater than 25%, greater than 30%, greater than 35%, greater than 40%, greater than 45%, or greater than 50% 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less.
  • R21 to R60 do not contain deuterium, or the content of deuterium in R21 to R60 is based on the total number of hydrogen atoms and deuterium atoms. It may be 1% to 100%.
  • R21 to R60 do not contain deuterium, or the content of deuterium in R21 to R60 is based on the total number of hydrogen atoms and deuterium atoms. It may be 5% to 95%.
  • R21 to R60 do not contain deuterium, or the content of deuterium in R21 to R60 is based on the total number of hydrogen atoms and deuterium atoms. It may be 10% to 90%.
  • R21 to R60 do not contain deuterium, or the content of deuterium in R21 to R60 exceeds 0% based on the total number of hydrogen atoms and deuterium atoms; 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, and 100% or less , 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less.
  • the heterocyclic compound represented by Formula 1 may be any one selected from the group consisting of the following compounds:
  • substituents in the structure of Chemical Formula 1, compounds having unique characteristics of the introduced substituents can be synthesized.
  • a substituent mainly used in hole injection layer materials, hole transport layer materials, electron blocking layer materials, light emitting layer materials, electron transport layer materials, hole blocking layer materials, and electron injection layer materials used in the manufacture of organic light emitting devices is introduced into the core structure. By doing so, it is possible to synthesize a material that satisfies the conditions required by each organic layer.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light emitting device.
  • the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for an emission layer of the red organic light emitting device.
  • the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the green organic light emitting device.
  • the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the blue organic light emitting device.
  • the organic light emitting diode of the present invention may be manufactured by conventional organic light emitting diode manufacturing methods and materials, except for forming one or more organic material layers using the aforementioned heterocyclic compound.
  • the heterocyclic compound may form an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure or may have a multi-layer 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, a light emitting layer, an electron injection layer, an electron transport layer, a battery blocking layer, a hole blocking layer, and the like as organic material layers.
  • the structure of the organic light emitting diode is not limited thereto and may include a smaller number of organic material layers.
  • the organic light emitting device includes one layer or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. It may further include, and the one or more layers may include the heterocyclic compound.
  • the organic light emitting device may include one or more organic material layers, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound represented by Chemical Formula 1. there is.
  • the organic material layer may include a light emitting layer, the light emitting layer may include a host material, and the host material may include the heterocyclic compound.
  • the organic light emitting device may include a heterocyclic compound represented by Formula 1, and may further include a heterocyclic compound represented by Formula 2 below:
  • R101 to R114 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of
  • L3 and L4 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • n and n are the same as or different from each other, and are each independently an integer of 0 to 3.
  • R21 to R34 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; It may be selected from the group consisting of; and a substituted or unsubstituted C1 to C30 alkoxy group.
  • R101 to R114 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C2 to C10 alkenyl group; A substituted or unsubstituted C2 to C10 alkynyl group; It may be selected from the group consisting of; and a substituted or unsubstituted C1 to C30 alkoxy group.
  • R101 to R114 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; It may be selected from the group consisting of a halogen and a cyano group.
  • R101 to R114 are the same as or different from each other, and each independently may be hydrogen or deuterium.
  • L3 and L4 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group, m and n are the same as or different from each other, and each independently may be an integer of 0 to 3.
  • L3 and L4 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group, m and n are the same as or different from each other, and each independently may be an integer of 0 to 3.
  • the heterocyclic compound represented by Formula 2 may not contain deuterium as a substituent, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 2 may not contain deuterium as a substituent, or the content of deuterium may be 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 2 may not contain deuterium as a substituent, or the content of deuterium may be 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 2 may not contain deuterium as a substituent, or the content of deuterium may be 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.
  • the heterocyclic compound represented by Formula 2 does not contain deuterium as a substituent, or the content of deuterium is greater than 0%, 10% or more, 20% or more, or 30% based on the total number of hydrogen atoms and deuterium atoms. It may be more than, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.
  • the heterocyclic compound represented by Formula 2 may be any one selected from the group consisting of the following compounds:
  • the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be included.
  • the organic light emitting device of the present invention when the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are mixed and included, excellent driving voltage, luminous efficiency and lifetime of the organic light emitting device are obtained. can be improved This can be expected to occur when the two heterocyclic compounds are mixed and included at the same time.
  • the exciplex phenomenon is a phenomenon in which an energy difference between a HOMO energy level of a donor (p-host) and a LUMO energy level of an acceptor (n-host) is released by electron exchange between two molecules.
  • RISC reverse intersystem crossing
  • the internal quantum efficiency of fluorescence can be increased to 100%.
  • a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light emitting layer, holes are injected into the p-host and electrons are injected into the n-host. Since it is injected, the driving voltage can be lowered, thereby helping to improve the lifespan. That is, when the compound represented by Chemical Formula 1 is used as the acceptor and the compound represented by Chemical Formula 2 is used as the donor, excellent characteristics of the organic light emitting device are exhibited.
  • the organic light emitting device when the organic light emitting device includes a mixture of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compounds contain deuterium as a substituent. Alternatively, at least one of the heterocyclic compounds may have a deuterium content greater than 0% and less than or equal to 100%.
  • the organic light emitting device when the organic light emitting device includes a mixture of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compounds contain deuterium as a substituent. It may not contain, or at least one of the heterocyclic compounds may have a deuterium content of 10% to 100%.
  • the organic light emitting device when the organic light emitting device includes a mixture of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compounds contain deuterium as a substituent. It may not contain, or at least one of the heterocyclic compounds may have a deuterium content of 15% to 95%.
  • the organic light emitting device when the organic light emitting device includes a mixture of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compounds contain deuterium as a substituent. It may not contain, or at least one of the heterocyclic compounds may have a deuterium content of 20% to 80%.
  • the organic light-emitting device includes a mixture of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compounds do not contain deuterium as a substituent, or At least one of the heterocyclic compounds has a deuterium content of more than 0%, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more , or 50% or more, 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less.
  • one embodiment of the present invention provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 below.
  • the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition for the organic layer of the organic light emitting device is 1:10 to 10:1, 1:8 to 8:1, 1:6 to 6:1, 1:4 to 4:1, 1:3 to 3:1, or 1:2 to 2:1, but not limited thereto it is not going to be
  • composition for the organic material layer of the organic light emitting device can be used when forming the organic material layer of the organic light emitting device, and can be more preferably used when forming the host of the light emitting layer.
  • the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, and may be used together with a phosphorescent dopant.
  • phosphorescent dopant material those known in the art may be used.
  • phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M may be used, but the scope of the present invention is not limited by these examples.
  • the M may be iridium, platinum, osmium, or the like.
  • L is an anionic bidentate ligand coordinated to M by sp 2 carbon and a hetero atom
  • X may function to trap electrons or holes.
  • Non-limiting examples of L, L' and L" include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzo thiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc.
  • Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylate Silidene, picolinate, 8-hydroxyquinolinate and the like.
  • the organic material layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and may be used together with an iridium-based dopant.
  • Ir(ppy) 3 may be used as a green phosphorescent dopant as the iridium-based dopant.
  • the content of the dopant may have a content of 1% to 15%, preferably 2% to 10%, more preferably 3% to 7% based on the total weight of the light emitting layer. .
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer may include a heterocyclic compound represented by Chemical Formula 1.
  • the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer may include a heterocyclic compound represented by Chemical Formula 1. .
  • the organic material layer may include an electron transport layer, a light emitting layer, or a hole blocking layer, and the electron transport layer, the light emitting layer, or the hole blocking layer may include a heterocyclic compound represented by Chemical Formula 1.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a host material
  • the host material may include a heterocyclic compound represented by Chemical Formula 1 above.
  • the organic light emitting device may further include one layer or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. .
  • FIG. 1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an embodiment of the present invention.
  • the scope of the present application be limited by these drawings, and structures of organic light emitting devices known in the art may be applied to the present application as well.
  • an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown.
  • an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, an emission layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • an emission layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 a hole blocking layer 306.
  • the scope of the present application is not limited by such a laminated structure, and layers other than the light emitting layer may be omitted as necessary, and other necessary functional layers may be further added.
  • the forming of the organic material layer is performed by pre-mixing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and performing a thermal vacuum deposition method. It may be formed using.
  • the pre-mixing means that the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are first mixed and mixed in one source before depositing the heterocyclic compound represented by Chemical Formula 2 on the organic layer.
  • the premixed material may be referred to as a composition for an organic layer according to an exemplary embodiment of the present application.
  • the organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.
  • the organic material layer including both the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may further include other materials as needed.
  • materials other than the heterocyclic compound represented by Formula 1 or the heterocyclic compound represented by Formula 2 are exemplified below, but these are for illustrative purposes only. It is not intended to limit the scope of, and may be replaced with materials known in the art.
  • anode material Materials having a relatively high work function may be used as the anode material, and transparent conductive oxides, metals, or conductive polymers may be used.
  • the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material Materials having a relatively low work function may be used as the cathode material, and metals, metal oxides, or conductive polymers may be used.
  • Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO/Al, but are not limited thereto.
  • a known hole injection layer material may be used.
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a phthalocyanine compound disclosed in Advanced Material, 6, p.677 (1994).
  • Starburst amine derivatives described such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4′′-tri[phenyl(m-tolyl)amino]triphenylamine ( m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/camphor sulfonic acid, or Polyaniline/Poly(4-styrenesulfonate) or the like can be used.
  • TCTA tris(4-carbazoyl-9-
  • pyrazoline derivatives As the material for the hole transport layer, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low-molecular or high-molecular materials may also be used.
  • Materials for the electron transport layer include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, and fluorenone.
  • Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and high molecular materials as well as low molecular materials may be used.
  • LiF is typically used in the art, but the present application is not limited thereto.
  • a red, green or blue light emitting material may be used as a material for the light emitting layer, and if necessary, two or more light emitting materials may be mixed and used. At this time, two or more light emitting materials may be deposited and used as separate sources or may be pre-mixed and deposited as one source.
  • a fluorescent material may be used as a material for the light emitting layer, but it may also be used as a phosphorescent material.
  • As the material for the light emitting layer a single material that emits light by combining holes and electrons injected from the anode and the cathode may be used, but materials in which a host material and a dopant material are involved in light emission may also be used.
  • hosts of the same series may be mixed and used, or hosts of different series may be mixed and used.
  • two or more materials selected from among n-type host materials and p-type host materials may be selected and used as host materials for the light emitting layer.
  • An organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.
  • the heterocyclic compound according to an embodiment of the present invention may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
  • Dibenzo[b,d]furan-4-amine (9.5g, 51.9mM), 2-bromo-1-chloro-3-fluorobenzene (2- bromo-1-chloro-3-fluorobenzene) (13.0g, 62.3mM), Palladium (II) acetate (Pd(OAc) 2 ) (0.58g, 2.6mM), XantPhos (3g, 5.2 mM) and sodium tert-butoxide ( t -BuONa) (10.0g, 103.8mM) were dissolved in 1,4-dioxane (200mL) and refluxed for 12 hours.
  • the target compound was synthesized in the same manner as in the preparation of compounds 1-461-2, 1-461-1 and 1-461 in Preparation Example 3.
  • the target compound can be directly synthesized by adding 2 equivalents of Compound A in Preparation Example 12. That is, when compound A and compound A' are the same, preparation of compound 3-2-1 may be omitted.
  • the target compound can be directly synthesized by adding 2 equivalents of Compound B in Preparation Example 13. That is, when Compound B and Compound B' are the same, the preparation of Compound 3-26-1 may be omitted.
  • a glass substrate coated with a thin film of indium tin oxide (ITO) having a thickness of 1,500 ⁇ was washed with ultrasonic waves in distilled water. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, and after drying, UVO (Ultraviolet ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to increase the work function of ITO and remove residual films in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tin oxide
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • the light emitting layer was deposited with a thickness of 400 ⁇ of the compounds listed in Table 10 as a host, and using Ir(ppy) 3 as a green phosphorescent dopant, Ir(ppy) 3 was added to the host in an amount of 7 wt% of the deposition thickness of the light emitting layer. Deposited by doping.
  • bathocuproine BCP
  • BCP bathocuproine
  • an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • An organic light emitting device was manufactured by forming.
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with McSyers' M7000, and the standard luminance was 6,000 cd through the lifetime equipment measuring equipment (M6000) manufactured by McScience with the measurement result. / m 2 , the lifetime T 90 , which is the time to reach 90% of the initial luminance, was measured.
  • the results of measuring the driving voltage, luminous efficiency, color (EL color) and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 10.
  • the organic light emitting device using the heterocyclic compound of the present invention as a material for the light emitting layer had a lower driving voltage and significantly improved light emitting efficiency and lifetime compared to the organic light emitting devices of Comparative Examples 1 to 13.
  • the heterocyclic compound according to the present invention is a deuterium-substituted compound, and the compounds of Comparative Examples 1 to 13 are hydrogen-substituted or partially deuterium-substituted compounds.
  • Compounds substituted with deuterium, whose atomic mass is twice as large as hydrogen, have lower zero-point energy and lower vibrational energy than compounds substituted with hydrogen, resulting in lower energy in the ground state and reduced collisions due to intermolecular vibrations, turning the thin film into an amorphous state. Therefore, the lifetime of the organic light emitting device can be improved.
  • the compound substituted with deuterium has low ground state energy, thereby improving the stability of the compound, and high dissociation energy of the C-D bond, improving molecular stability, thereby improving the lifetime of the organic light emitting device.
  • the deuterium-substituted heterocyclic compound 1-184 according to the present invention is a comparative example compound substituted with hydrogen due to molecular stability and non-crystallinity Ref. It can be seen that the driving voltage and lifetime are improved compared to 1, 2, 3, 4, 6, 8, 9, 10, 11, 12 and 13, and the loss of energy due to the low vibration energy of the deuterium-substituted heterocyclic compound By minimizing and facilitating energy transfer to the dopant, it was possible to improve the luminous efficiency of the organic light emitting device.
  • the deuterium-substituted heterocyclic compound 1-549 according to the present invention is a comparative example compound Ref. 5, the compound 1-549 is different in that it is a compound in which R1 to R12 are substituted with deuterium in the compound of Formula 1 (hereinafter, referred to as a compound in which condensed carbazole is substituted with deuterium), and the present invention Heterocyclic compound 1-181 substituted with deuterium according to Comparative Example Compound Ref.
  • compounds 1-181 are compounds in which R1 to R12 are substituted with deuterium in the compound of Formula 1 (hereinafter, referred to as a compound in which condensed carbazole is substituted with deuterium) and Ar1 to R12 in the compound of Formula 1 It differs in that Ar3 is a compound substituted with deuterium (hereinafter, referred to as a compound having an aryl group substituted with deuterium).
  • the deuterium stabilizes the radical cation to improve the lifespan of the organic light emitting device.
  • the deuterium-substituted heterocyclic compounds 1-181 and 1-549 according to the present invention effectively stabilized the radical cation due to the deuterium substituted in the condensed carbazole, thereby effectively improving the lifespan of the organic light emitting device.
  • Comparative example compound Ref. 5 and 7 confirmed that the deuterium substituted only for the aryl group among the substituents did not contribute to the stabilization of the radical cation of the condensed carbazole. Therefore, it was confirmed that the lifespan of the organic light emitting device using compounds 1-181 and 1-549 in which condensed carbazole was substituted with deuterium was used as a material for the light emitting layer was improved.
  • heterocyclic compound 1-349 substituted with deuterium according to the present invention was able to improve the luminous efficiency of the organic light emitting device by reducing energy loss due to the low vibrational energy of the compound, and lowered the ground state energy of the organic light emitting device. lifespan could be improved.
  • compound 1-184 in which only condensed carbazole is substituted with deuterium, has an increased intermolecular interaction than compound 1-349, resulting in a smaller intermolecular distance and improved mobility, thereby improving the driving voltage of the organic light emitting device.
  • a glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 ⁇ was washed with ultrasonic waves in distilled water. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, and after drying, UVO (Ultraviolet ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to increase the work function of ITO and remove residual films in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tin oxide
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • the light emitting layer was pre-mixed with one (N-type) compound listed in Table 11 below and one (P-type) compound represented by Formula 2 as a host, and then 400 ⁇ from one source.
  • the host was doped with Ir(ppy) 3 in an amount of 7 wt% of the deposition thickness of the light emitting layer using Ir(ppy) 3 as a green phosphorescent dopant.
  • bathocuproine BCP
  • BCP bathocuproine
  • an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • An organic light emitting device was manufactured by forming.
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with McSyers' M7000, and the standard luminance was 6,000 cd through the lifetime equipment measuring equipment (M6000) manufactured by McScience with the measurement result. / m 2 , the lifetime T 90 , which is the time to reach 90% of the initial luminance, was measured.
  • the results of measuring the driving voltage, luminous efficiency, color (EL color) and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 11.
  • the exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of a donor (p-host) and the LUMO energy level of an acceptor (n-host) is released by electron exchange between two molecules.
  • RISC reverse intersystem crossing
  • the internal quantum efficiency of fluorescence can be increased to 100%.
  • a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light emitting layer, holes are injected into the p-host and electrons are injected into the n-host. Since it is injected into the organic light emitting diode, the driving voltage of the organic light emitting diode can be lowered, thereby helping to improve the lifetime of the organic light emitting diode.
  • the compound represented by Formula 2 it is a compound substituted with hydrogen or partially substituted with deuterium or total deuterium.
  • Compounds substituted with deuterium whose atomic mass is twice as large as hydrogen, have lower zero-point energy and lower vibrational energy than compounds substituted with hydrogen, resulting in lower energy in the ground state and reduced collisions due to intermolecular vibrations, resulting in thin films in an amorphous state. It can be made to improve the lifespan of the organic light emitting device.
  • the deuterium-substituted compound has low ground state energy, thereby improving the stability of the compound, and high dissociation energy of the C-D bond, improving molecular stability, thereby improving the lifetime of the organic light emitting device.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1, un dispositif électroluminescent organique le comprenant et une composition pour une couche organique d'un dispositif électroluminescent organique.
PCT/KR2022/010212 2021-08-31 2022-07-13 Composé hétérocyclique, dispositif électroluminescent organique le comprenant et composition pour couche organique de dispositif électroluminescent organique WO2023033351A1 (fr)

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KR20210062771A (ko) * 2019-11-21 2021-06-01 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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KR20140009838A (ko) * 2012-07-13 2014-01-23 덕산하이메탈(주) 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160028737A (ko) * 2014-09-04 2016-03-14 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20180042146A (ko) * 2015-08-28 2018-04-25 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자, 및 전자 기기
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