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WO2023096225A1 - Composé hétérocyclique, et dispositif électroluminescent organique et composition pour former une couche de matériau organique, comprenant celui-ci - Google Patents

Composé hétérocyclique, et dispositif électroluminescent organique et composition pour former une couche de matériau organique, comprenant celui-ci Download PDF

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WO2023096225A1
WO2023096225A1 PCT/KR2022/017694 KR2022017694W WO2023096225A1 WO 2023096225 A1 WO2023096225 A1 WO 2023096225A1 KR 2022017694 W KR2022017694 W KR 2022017694W WO 2023096225 A1 WO2023096225 A1 WO 2023096225A1
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이용희
모준태
김동준
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LT Materials Co Ltd
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • 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
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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
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Definitions

  • the present specification relates to a heterocyclic compound, an organic light emitting device including the heterocyclic compound, and a composition for forming an organic material layer.
  • the electroluminescent 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 roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • the present specification is to provide a heterocyclic compound, an organic light emitting device including the same, and a composition for forming an organic material layer.
  • a heterocyclic compound represented by Formula 1 is provided.
  • X is O; S; or NR;
  • R and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -Si(R101)(R102)(R103); -N(R104)(R105); A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or two or more groups adjacent to each other combine to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
  • R101 to R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • At least one of R1 to R10 is -(L1)m-(N-Het),
  • At least one of the remaining R1 to R10 is -(L2)n-Z,
  • L1 and L2 are 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,
  • n and n are each independently an integer of 0 to 3, and when 2 or more, the substituents in parentheses are the same or different,
  • N-Het is a substituted or unsubstituted heteroaryl group containing 2 or more N
  • Z is -N(R104')(R105'); 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,
  • R104' and R105' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • the first electrode a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes at least one kind of the heterocyclic compound.
  • composition for forming an organic material layer including the heterocyclic compound is provided.
  • benzoxanthene, benzothioxanthene, or benzoacridine has at least two substituents, in particular, a heteroaryl group containing two or more N (nitrogen) atoms as a substituent. characterized by
  • the heterocyclic compound of Formula 1 having the above characteristics has high thermal stability, has an appropriate molecular weight and band gap, and an appropriate band gap of the light emitting layer has good electron transport ability, prevents loss of holes, and helps to form an effective recombination zone. . Therefore, when used in an organic light emitting device, the performance of the device is improved and, in particular, excellent performance is provided in terms of driving voltage and luminous efficiency.
  • 1 to 4 are views each exemplarily illustrating a stacked structure of an organic light emitting device according to an exemplary embodiment of the present specification.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with 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, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
  • "when no substituent is indicated in the chemical formula or compound structure” may mean that all possible positions of the substituent 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%.
  • the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents explicitly exclude deuterium such as hydrogen. If not, hydrogen and deuterium may be mixed and used in the compound.
  • 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 2 H.
  • 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 deuterium content of 20% can be represented by the following structural formula.
  • a phenyl group having a deuterium content of 0% it may mean a phenyl group without deuterium atoms, that is, having 5 hydrogen atoms.
  • 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group
  • the alkenyl group includes a straight chain 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 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.
  • a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples thereof include -CF 3 , -CF 2 CF 3 , but are not limited thereto.
  • the alkoxy group is represented by -O(R101), and examples of the above-described alkyl group may be applied to R101.
  • the aryloxy group is represented by -O(R102), and examples of the above-described aryl group may be applied to R102.
  • alkylthioxy group is represented by -S(R103), and examples of the above-described alkyl group may be applied to R103.
  • the arylthiooxy group is represented by -S(R104), and examples of the above-described aryl group may be applied to R104.
  • the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted with 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, 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 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 group 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 terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, and a phenalenyl group.
  • a condensed ring group may be included, but is not limited thereto.
  • terphenyl group may be selected from the following structures.
  • 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 pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, Triazole group, furazine group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxin group, triazine group, tetrazine group, quinoline group, Isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthridine group, imidazole
  • the substituent when the substituent is a carbazole group, it means bonding to nitrogen or carbon of carbazole.
  • benzocarbazole group may have any one of the following structures.
  • the dibenzocarbazole group may have any one of the following structures.
  • the naphthobenzofuran group may have any one of the following structures.
  • the naphthobenzothiophene group may have any one of the following structures.
  • the silyl group is a substituent that includes Si and the Si atom is directly connected as a radical, and is represented by -Si(R107)(R108)(R109), R107 to R109 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group.
  • Specific examples of the silyl group include the following structures, but are not limited thereto.
  • the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.
  • the amine group is represented by -N(R112)(R113), R112 and R113 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group.
  • the amine group is -NH 2 ; monoalkylamine group; monoarylamine group; Monoheteroarylamine group; 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.
  • heteroaryl group examples of the above-described heteroaryl group may be applied, except that the heteroarylene group 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.
  • Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles and aromatic heterocycles, except that the rings are not monovalent, respectively, the above-mentioned cycloalkyl groups, aryl Structures exemplified by groups, heterocycloalkyl groups and heteroaryl groups can be applied.
  • An exemplary embodiment of the present specification provides a heterocyclic compound represented by Chemical Formula 1.
  • X is O; S; or NR, R is hydrogen; heavy hydrogen; halogen group; cyano group; -Si(R101)(R102)(R103); -N(R104)(R105); A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or bonded to an adjacent group among R1 to R10 to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.
  • X may be O.
  • X may be S.
  • X is NR
  • R is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • X is NR
  • R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • X is NR
  • R is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted dibenzothiophene group.
  • X is NR
  • R is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; Or it may be a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.
  • X is NR
  • R is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; Or it may be a dibenzothiophene group unsubstituted or substituted with deuterium.
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -Si(R101)(R102)(R103); -N(R104)(R105); A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or two or more groups adjacent to each other combine to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, and R101 to R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -Si(R101)(R102)(R103); -N(R104)(R105); A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R101 to R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -N(R104)(R105); 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, and R104 and R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -N(R104)(R105); A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R104 and R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; -N(R104)(R105); A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R104 and R105 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • At least one of R1 to R10 is -(L1)m-(N-Het), and at least one of the remaining R1 to R10 is -(L2)n-Z.
  • any one of R1 to R10 is -(L1)m-(N-Het), and any one of the remaining R1 to R10 is -(L2)n-Z.
  • the rest other than -(L1)m-(N-Het) or -(L2)n-Z among R1 to R10 are hydrogen; or deuterium.
  • any one of R1 to R10 is -(L1)m-(N-Het), and any one of the other R1 to R10 is -(L2)n-Z, and the others are hydrogen; or deuterium.
  • R3 may be -(L1)m-(N-Het) or -(L2)n-Z.
  • R1, R2 and R4 to R6 are each independently hydrogen; or deuterium.
  • L1 and L2 are 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.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.
  • L1 and L2 are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L1 and L2 are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 and L2 are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenylene group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.
  • n and n are each independently an integer of 0 to 3, and when 2 or more, the substituents in parentheses are the same or different.
  • N-Het is a substituted or unsubstituted heteroaryl group containing two or more N atoms.
  • N-Het is a substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted quinoxaline group; A substituted or unsubstituted benzofuropyrimidine group; A substituted or unsubstituted benzothienopyrimidine group; Or it may be a substituted or unsubstituted naphthopuropyrimidine group.
  • N-Het may be any one of Formulas A to C below.
  • X1 to X3 are N or C (R31), at least two are N,
  • R21 to R24 and R31 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • R25 and R26 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms; or forming a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms;
  • r23 is an integer from 0 to 5, and when it is 2 or more, R23 is the same or different.
  • X1 to X3 are N or C (R31), R31 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, and at least two of X1 to X3 are N.
  • X1 and X2 are N, and X3 is C (R31).
  • X1 and X3 are N, and X2 is C(R31).
  • X1 to X3 are N.
  • R31 is hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • R31 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R31 is hydrogen; or deuterium.
  • R21 and R22 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • R21 and R22 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • R21 and R22 are 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.
  • R21 and R22 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R21 and R22 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R21 and R22 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted naphthobenzothiophene group; A substituted or unsubstituted benzoxanthene group; Or a substituted or unsubstituted carbazole group.
  • R21 and R22 are each independently a phenyl group unsubstituted or substituted with one or more substituents among deuterium and an aryl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A triphenylene group unsubstituted or substituted with heavy hydrogen; a naphthyl group unsubstituted or substituted with one or more substituents among deuterium and aryl groups unsubstituted or substituted with deuterium; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; A naphthobenzofuran group unsubstituted or substituted with heavy hydrogen; Naphthobenzothiophene group unsubstituted or substituted or substituted;
  • R23 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or two or more adjacent groups combine to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.
  • R23 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • R23 is hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • R23 is hydrogen; heavy hydrogen; 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.
  • R23 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R23 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R23 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; or a substituted or unsubstituted naphthobenzothiophene group.
  • R23 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; A naphthobenzofuran group unsubstituted or substituted with heavy hydrogen; or a naphthobenzothiophene group unsubstituted or substituted with deuterium.
  • R24 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • R24 is hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • R24 is 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.
  • R24 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R24 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R24 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; or a substituted or unsubstituted naphthobenzothiophene group.
  • R24 is a phenyl group unsubstituted or substituted with one or more substituents among deuterium and an aryl group substituted or unsubstituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; A naphthobenzofuran group unsubstituted or substituted with heavy hydrogen; or a naphthobenzothiophene group unsubstituted or substituted with deuterium.
  • R25 and R26 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.
  • R25 and R26 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.
  • R25 and R26 are bonded to each other to form a substituted or unsubstituted benzene ring; A substituted or unsubstituted benzofuran ring; A substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted naphthopuran ring; Or it forms a substituted or unsubstituted naphthothiophene ring.
  • R25 and R26 are bonded to each other to form a benzene ring unsubstituted or substituted with deuterium; A benzofuran ring unsubstituted or substituted with heavy hydrogen; A benzothiophene ring unsubstituted or substituted with deuterium; Naphthofuran ring unsubstituted or substituted with deuterium; Or it forms a naphthothiophene ring unsubstituted or substituted with deuterium.
  • N-Het may have any one of the following structures, Is a position that binds to L1, and the following structural formula is deuterium; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be further substituted with a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Z is -N (R104') (R105'); 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, and R104' and R105' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • Z is -N (R104') (R105'); A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z is -N (R104') (R105'), and R104' and R105' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Z is -N (R104') (R105'), and R104' and R105' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z is -N(R104')(R105'), and R104' and R105' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z is -N(R104')(R105'), and R104' and R105' are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted carbazole group.
  • Z is -N(R104')(R105'), and R104' and R105' are each independently a phenyl group unsubstituted or substituted with at least one substituent selected from deuterium and an arylamine group; A biphenyl group unsubstituted or substituted with heavy hydrogen; A dimethylfluorenyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; Or it may be a carbazole group unsubstituted or substituted with one or more substituents among deuterium and aryl groups unsubstituted or substituted with deuterium.
  • Z may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Z is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or it may be a substituted or unsubstituted triphenylene group.
  • Z is a phenyl group unsubstituted or substituted with one or more substituents among deuterium and an aryl group substituted or unsubstituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; Or it may be a triphenylene group unsubstituted or substituted with deuterium.
  • Z may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z is a substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted naphthobenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzocarbazole group; Or it may be any one of the following structures.
  • Ar11 in the above structure is hydrogen; heavy hydrogen; 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, and the above structures are deuterium; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be further substituted with a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Z is a dibenzofuran group unsubstituted or substituted with deuterium; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; A naphthobenzofuran group unsubstituted or substituted with heavy hydrogen; Naphthobenzothiophene group unsubstituted or substituted with heavy hydrogen; a carbazole group unsubstituted or substituted with one or more substituents among deuterium and aryl groups unsubstituted or substituted with deuterium; a benzocarbazole group unsubstituted or substituted with one or more substituents among deuterium and aryl groups unsubstituted or substituted with deuterium; a dibenzocarbazole group unsubstituted or substituted with one or more substituents among deuterium and aryl groups unsubstituted or substituted with deuterium; Or it may be any one of the following structures.
  • Formula 1 may be represented by Formula 1-1 or 1-2 below.
  • L1, L2, N-Het, Z, m and n are the same as those in Formula 1,
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • r11 is an integer from 0 to 5, and when it is 2 or more, R11 is the same or different,
  • r12 is an integer from 0 to 3, and when it is 2 or more, R12 is the same or different.
  • Chemical Formula 1 may be represented by Chemical Formula 1-1-1 or 1-2-1.
  • L1, L2, N-Het, Z, m and n are the same as those in Formula 1,
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • r11 is an integer from 0 to 5, and when it is 2 or more, R11 is the same or different,
  • r12 is an integer from 0 to 3, and when it is 2 or more, R12 is the same or different.
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R11 and R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R11 and R12 are each independently hydrogen; or deuterium.
  • the deuterium content of Chemical Formula 1 may be 0% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0%.
  • the deuterium content of Chemical Formula 1 may be greater than 0% and less than or equal to 100%.
  • the deuterium content of Chemical Formula 1 may be 5% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 1% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 5% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 10% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 30% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 50% to 100%.
  • the deuterium content of Chemical Formula 1 may be 0% or 70% to 100%.
  • Formula 1 may be represented by any one of the following compounds.
  • the first electrode a second 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 at least one heterocyclic compound represented by Chemical Formula 1.
  • the organic material layer may include one or two kinds of the heterocyclic compound.
  • the organic material layer may include a hole transport layer, and the hole transport layer may include one or more types of the heterocyclic compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include one or more kinds of the heterocyclic compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include one kind of the heterocyclic compound.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a host
  • the host may include one or more kinds of the heterocyclic compound.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a host
  • the host may include one kind of the heterocyclic compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include the heterocyclic compound as an N-type host.
  • the organic material layer including the heterocyclic compound may further include a compound represented by Formula 2 below.
  • R41 to R50 is -(L11)o-N(Ar1)(Ar2),
  • R41 to R50 is -(L12)p-Ar3,
  • R41 to R50 are hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or two or more groups adjacent to each other combine to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
  • L11 and L12 are 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,
  • Ar1 to Ar3 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • o and p are integers from 0 to 3;
  • the organic material layer including the heterocyclic compound may include the compound of Formula 2 as a P-type host.
  • the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 are used in combination in one organic material layer, particularly the light emitting layer, the heterocyclic compound of Chemical Formula 1 serves as an acceptor due to its good electron transport ability, and the compound of Chemical Formula 2 By acting as a donor (p-host) with good hole transport ability, electron and hole injection is improved, and efficiency and lifetime are improved through the formation of an effective recombination zone.
  • any one of R41 to R50 is -(L11)o-N(Ar1)(Ar2), and any one of the remaining R41 to R50 is -(L12)p-Ar3.
  • L11 and L12 are 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 30 carbon atoms.
  • L11 and L12 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L11 and L12 are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L11 and L12 are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • Ar1 and Ar2 are 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.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 and Ar2 are each independently a phenyl group unsubstituted or substituted with one or more substituents selected from deuterium, an aryl group, and a heteroaryl group; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with at least one substituent selected from deuterium and aryl groups; A fluorenyl group unsubstituted or substituted with at least one substituent selected from deuterium, an alkyl group and an aryl group; A substituted or unsubstituted spirobifluorenyl group with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; or a dibenzothiophene group unsubstituted or substituted with deuterium.
  • Ar3 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • Ar3 is a halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • Ar3 is 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.
  • Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
  • Ar3 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A fluorenyl group unsubstituted or substituted with at least one substituent selected from deuterium, an alkyl group and an aryl group; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; or a dibenzothiophene group unsubstituted or substituted with deuterium.
  • the rest other than -(L11)o-N(Ar1)(Ar2) or -(L12)p-Ar3 among R41 to R50 are hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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, or two or more adjacent groups combine to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.
  • the rest other than -(L11)o-N(Ar1)(Ar2) or -(L12)p-Ar3 among R41 to R50 are hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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.
  • the rest other than -(L11)o-N(Ar1)(Ar2) or -(L12)p-Ar3 among R41 to R50 are hydrogen; heavy hydrogen; halogen group; cyano group; 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.
  • the rest other than -(L11)o-N(Ar1)(Ar2) or -(L12)p-Ar3 among R41 to R50 are hydrogen; heavy hydrogen; 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.
  • the rest other than -(L11)o-N(Ar1)(Ar2) or -(L12)p-Ar3 among R41 to R50 are hydrogen; or deuterium.
  • o and p are integers from 0 to 3, and when o and p are each 2 or more, the substituents in parentheses are the same or different.
  • Formula 2 may be represented by Formula 2-1 or 2-2 below.
  • L11, L12, Ar1, Ar2, Ar3, o and p are the same as those in Formula 2,
  • R51 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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,
  • q is an integer from 0 to 8, and when it is 2 or more, R51 is the same or different.
  • the deuterium content of Chemical Formula 2 may be 0% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0%.
  • the deuterium content of Chemical Formula 2 may be greater than 0% and less than or equal to 100%.
  • the deuterium content of Chemical Formula 2 may be 5% to 100%.
  • the deuterium content of Chemical Formula 2 may be 10% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 1% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 5% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 10% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 30% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 50% to 100%.
  • the deuterium content of Chemical Formula 2 may be 0% or 70% to 100%.
  • Formula 2 may be represented by any one of the following compounds.
  • 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 transport layer, an electron injection layer, and the like as organic material layers.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the first electrode may be an anode and the second electrode may be a cathode.
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • An organic light emitting device may be manufactured by a conventional organic light emitting device manufacturing method and material, except for forming one or more organic material layers using the heterocyclic compound of Formula 1 described above. there is.
  • the heterocyclic compound of Chemical Formula 1 may be formed as 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 light emitting device may be a blue organic light emitting device
  • the heterocyclic compound of Chemical Formula 1 may be used as a material for the blue organic light emitting device.
  • the heterocyclic compound of Chemical Formula 1 may be included in a light emitting layer of a blue organic light emitting device.
  • the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the green organic light emitting device.
  • the heterocyclic compound of Chemical Formula 1 may be included in a light emitting layer of a green organic light emitting device.
  • the organic light emitting device may be a red organic light emitting device
  • the heterocyclic compound of Chemical Formula 1 may be used as a material for the red organic light emitting device.
  • the heterocyclic compound of Chemical Formula 1 may be included in an emission layer of a red organic light emitting device.
  • the organic light emitting device of the present invention may further include at least one layer 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, an electron blocking layer, and a hole blocking layer.
  • 1 to 4 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification.
  • 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, a light emitting layer 304, a hole blocking layer 305, an electron transport layer 306 and an electron injection layer 307
  • the organic light emitting device according to 4 includes a hole injection layer 301, a hole transport layer 302, an electron blocking layer 303, a light emitting layer 304, a hole blocking layer 305, an electron transport layer 306, and an electron injection layer 307.
  • 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 organic material layer including the heterocyclic compound of Chemical Formula 1 may further include other materials as needed.
  • materials other than the heterocyclic compound of Chemical Formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application. may be substituted with known materials.
  • 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 SnO 2 :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 2 /Al, but are not limited thereto.
  • a known hole injection material may be used.
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in [Advanced Material, 6, p.677 (1994)] starburst amine derivatives, 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-st
  • hole transport material pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular weight or high molecular weight materials may also be used.
  • Examples of the electron transport material 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 the light emitting material, 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 can be used as a light emitting material, but it can also be used as a phosphorescent material.
  • As the light emitting material a material that emits light by combining holes and electrons respectively injected from an anode and a 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.
  • at least two materials selected from among N-type host materials and P-type host materials may be 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 materials used.
  • the heterocyclic compound according to an exemplary embodiment of the present specification 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.
  • composition for forming an organic material layer containing the heterocyclic compound is provided.
  • composition for forming the organic material layer may further include the compound of Chemical Formula 2.
  • the composition for forming the organic layer may include the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:10 to 10:1.
  • the forming of the organic material layer is formed using a thermal vacuum deposition method by pre-mixing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2. It provides a method for manufacturing an organic light emitting device that is to do.
  • the pre-mixing means that the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are first mixed and mixed in one park before depositing the compound represented by Chemical Formula 2 on the organic material layer.
  • the premixed material may be referred to as a composition for forming an organic material layer according to an exemplary embodiment of the present specification.
  • 1,8-dibromonaphthalene 20.0g (69.9mM), (4-chloro-2-methoxyphenyl)boronic acid 13.0g (69.9 mM), Pd (PPh 3 ) 4 (tetrakis (triphenylphosphine) palladium (0)) 4.0 g (3.5 mM) and NaOH 5.6 g (139.8 mM) were mixed with 1,4-dioxane (1,4 -dioxane) / H 2 O (200ml / 40ml) and then refluxed for 1 hour. The reaction product was purified by column chromatography (DCM: Hex 1: 4) to obtain 22.3 g of Compound 2-B (yield: 91.7%).
  • DCM dichloromethane and Hex is hexane.
  • the target compound shown in Table 1 was prepared in the same manner as in Preparation Example 1, except that Intermediate A in Table 1 was used instead of (4-chloro-2-methoxyphenyl)boronic acid in Preparation Example 1.
  • 1,8-dibromonaphthalene 20g (69.9mM), 2-chlorobenzenethiol 10.1g (69.9mM), CuI 13.3g (69.9mM), cyclohexane-1,2-diamine 1,2-diamine) 8.0g (69.9mM) and K 3 PO 4 29.7g (139.8mM) were dissolved in 1,4-dioxane (200ml) and refluxed for 1 hour.
  • the target compounds in Table 4 were prepared in the same manner as in Preparation Example 5, except that Intermediate A in Table 4 was used instead of Compound 1-26 in Preparation Example 5.
  • the target compound shown in Table 7 was prepared in the same manner as in Preparation Example 8, except that Intermediate A in Table 7 was used instead of 3-bromo-1,1'-biphenyl in Preparation Example 8.
  • the target compound shown in Table 12 was prepared in the same manner as in Preparation Example 14, except that Intermediate A in Table 12 was used instead of Compound 3-49 in Preparation Example 14.
  • N- (4-bromophenyl) -N-phenyl- [1,1'-biphenyl] -4-amine N- (4-bromophenyl) -N-phenyl- [1,1'-biphenyl] -4 -amine
  • triflic acid 48.8g 325.0mM
  • the mixture was neutralized with an aqueous solution of K 3 PO 4 at room temperature and extracted with DCM/H 2 O.
  • 5-chloro-2-nitrophenyl)boronic acid ((5-chloro-2-nitrophenyl)boronic acid) 21.1g (104.9mM)
  • Pd (PPh) 3 ) After dissolving 6.1g (5.2mM) of 4 and 8.4g (209.8mM) of NaOH in 1,4-dioxane/H 2 O (300ml/60ml), the mixture was refluxed for 3 hours.
  • Table 14 is a measurement value of 1 H NMR (CDCl 3 , 400 Mz)
  • Table 15 is a measurement value of FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).
  • a glass substrate coated with ITO thin film to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, it was ultrasonically washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated for ITO surface treatment and residual film removal in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • PT plasma cleaner
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • one or two compounds listed in Table 16 were deposited from one source as a red host, and (piq) 2 (Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% of an Ir compound. 400 ⁇ deposited. Thereafter, 30 ⁇ of Bphen was deposited as a hole blocking layer, and 250 ⁇ of Alq3 was deposited thereon as an electron transport layer.
  • lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode is deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • An electroluminescent device was manufactured.
  • the electroluminescence (EL) characteristics of the organic light emitting devices of Examples 1-1 to 1-74 and Comparative Examples 1-1 to 1-8 prepared as described above were measured with McScience's M7000, respectively, and the measurement results When the standard luminance is 6,000 cd / m 2 through the life measurement equipment (M6000) manufactured by McScience, the lifetime T 90 , which is the time to become 90% of the initial luminance, was measured, and the results are shown in Table 16 and It was like
  • the heterocyclic compound represented by Chemical Formula 1 of the present invention has high thermal stability and an appropriate molecular weight and band gap.
  • An appropriate bandgap of the light emitting layer has good electron transport ability, prevents loss of holes, and helps to form an effective recombination zone. Therefore, as can be seen from the device evaluation above, it can be seen that the examples using the compounds of the present invention have improved performance than the comparative examples.
  • Example 1-194 using the compound 1-194 of the present invention in which the biphenyl group is further substituted has a low driving voltage, 1.7 times higher efficiency, and 2 times higher lifespan.
  • compounds C, D, G, and H used in Comparative Examples 1-3 and 1-4 have the core structure of Formula 1 of the present invention and have two substituents, but do not contain substituents containing two or more N.
  • a glass substrate coated with ITO thin film to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, it was ultrasonically washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • PT plasma cleaner
  • Hole injection layer 2-TNATA (4,4', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine), which is a common layer on the ITO transparent electrode (anode), hole transport layer NPB (N, N'-Di (1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) and electron blocking TAPC (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] formed
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • one or two of the compounds listed in Table 17 below were deposited from one source as a red host, and (piq) 2 (Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% of an Ir compound. 400 ⁇ deposited. Thereafter, 30 ⁇ of Bphen was deposited as a hole blocking layer, and 250 ⁇ of TPBI was deposited thereon as an electron transport layer.
  • lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode is deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • An electroluminescent device was manufactured.
  • the electroluminescence (EL) characteristics of the organic light emitting devices of Examples 2-1 to 2-15 and Comparative Examples 2-1 to 2-3 prepared as described above were measured with McScience's M7000, respectively, and the measurement results When the standard luminance is 6,000 cd / m 2 through the life measurement equipment (M6000) manufactured by McScience, the lifetime T 90 , which is the time to become 90% of the initial luminance, was measured, and the results are shown in Table 17 and It was like

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Abstract

La présente invention concerne un composé hétérocyclique de formule chimique 1, et un dispositif électroluminescent organique et une composition pour former une couche de matériau organique, comprenant celui-ci.
PCT/KR2022/017694 2021-11-29 2022-11-11 Composé hétérocyclique, et dispositif électroluminescent organique et composition pour former une couche de matériau organique, comprenant celui-ci Ceased WO2023096225A1 (fr)

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WO2025047371A1 (fr) * 2023-08-25 2025-03-06 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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WO2025047371A1 (fr) * 2023-08-25 2025-03-06 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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