WO2023277446A1 - 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 및 유기물층용 조성물 - Google Patents

헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 및 유기물층용 조성물 Download PDF

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WO2023277446A1
WO2023277446A1 PCT/KR2022/008933 KR2022008933W WO2023277446A1 WO 2023277446 A1 WO2023277446 A1 WO 2023277446A1 KR 2022008933 W KR2022008933 W KR 2022008933W WO 2023277446 A1 WO2023277446 A1 WO 2023277446A1
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substituted
unsubstituted
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light emitting
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French (fr)
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모준태
이기백
김동준
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엘티소재주식회사
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    • 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
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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
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    • C07D495/04—Ortho-condensed systems
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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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • 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
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    • Y02E10/549—Organic PV cells

Definitions

  • the present specification relates to a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer.
  • the organic 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 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 application relates to a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer.
  • a heterocyclic compound represented by Formula 1 is provided.
  • X1 and X2 are the same as or different from each other, and are each independently O; S; or CRaRb;
  • At least one of R1 to R6 is represented by -N-Hetlene-L1-Z1,
  • L1 is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • Z1 is a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 heteroaryl group; Or a substituted or unsubstituted amine group,
  • Ra, Rb, R, R' and R" are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted It is a C2 to C60 heteroaryl group.
  • the 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.
  • an exemplary embodiment of the present application provides an organic light emitting device in which the organic material layer including the heterocyclic compound of Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula A.
  • L2 is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • R, R' and R" are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group,
  • a1 is an integer from 0 to 4.
  • r and s are integers from 0 to 7;
  • another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A.
  • an exemplary embodiment of the present application includes preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer includes forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application.
  • a method for manufacturing an organic light emitting device is provided.
  • the compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, or the like in an organic light emitting device.
  • the compound can be used as a hole transport material, light emitting material or electron blocking material of an organic light emitting device.
  • heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A may be simultaneously used as materials for an emission layer of an organic light emitting device.
  • the driving voltage of the device is lowered, the light efficiency is improved, and the lifespan of the device is improved due to the thermal stability of the compound. can improve
  • 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 application.
  • 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.
  • silyl group is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is 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.
  • a heterocyclic compound represented by Formula 1 is provided.
  • the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or more and 100% or less.
  • the deuterium content of the heterocyclic compound represented by Formula 1 may be 0% or more and 100% or less, 1% or more and 100% or less, 10% or more and 100% or less, or 20% or more and 100% or less. there is.
  • the deuterium content of the heterocyclic compound represented by Formula 1 is 0%; 1% or more and 20% or less; or 100%.
  • Formula 1 may be represented by any one of Formulas 2 to 7 below.
  • X1 and X2 are the same as or different from each other, and are each independently O; S; or CRaRb.
  • X1 may be O
  • X2 may be O
  • X1 may be O and X2 may be S.
  • X1 may be O
  • X2 may be CRaRb.
  • X1 may be S and X2 may be O.
  • X1 may be S and X2 may be S.
  • X1 may be S and X2 may be CRaRb.
  • X1 may be CRaRb and X2 may be O.
  • X1 may be CRaRb and X2 may be S.
  • X1 may be CRaRb and X2 may be CRaRb.
  • Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
  • Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; Or a substituted or unsubstituted C6 to C40 aryl group.
  • Ra and Rb are the same as or different from each other, and each independently a C1 to C40 alkyl group; Or an aryl group of C6 to C40.
  • Ra and Rb are the same as or different from each other, and each independently represents a C1 to C40 alkyl group.
  • Ra and Rb are the same as or different from each other, and each independently represents a C1 to C20 alkyl group.
  • Ra and Rb are the same as or different from each other, and each independently a linear C1 to C20 alkyl group; or a branched C3 to C20 alkyl group.
  • Ra and Rb may be methyl groups.
  • Ra and Rb may be substituted again with deuterium.
  • Formula 1 may be represented by Formula 8 or Formula 9 below.
  • R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • a is an integer from 0 to 3, and when a is 2 or more, the substituents in parentheses are the same as or different from each other.
  • Chemical Formula 8 may be represented by any one of Chemical Formulas 8-1 to 8-4.
  • Formula 9 may be represented by any one of Formulas 9-1 to 9-4 below.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C40 aryl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a C6 to C40 aryl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a C6 to C20 aryl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a monocyclic C6 to C10 aryl group; or a polycyclic C10 to C20 aryl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.
  • R7 to R10 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R1 to R6 may be represented by -N-Hetlene -L1-Z1.
  • one of R1 to R6 may be represented by -N-Hetlene-L1-Z1.
  • one of R1 to R6 is represented by -N-Hetlene-L1-Z1, and the others may be the same as the definitions of R7 to R10 above.
  • R1 is represented by -N-Hetlene-L1-Z1, and R2 to R6 may be the same as the definitions of R7 to R10 above.
  • R2 is represented by -N-Hetlene-L1-Z1, and R1 and R3 to R6 may be the same as the definitions of R7 to R10 above.
  • R3 is represented by -N-Hetlene-L1-Z1, and R1, R2, and R4 to R6 may be the same as the definitions of R7 to R10 above.
  • R4 is represented by -N-Hetlene-L1-Z1, and R1 to R3, R5 and R6 may be the same as the definitions of R7 to R10 above.
  • R5 is represented by -N-Hetlene-L1-Z1, and R1 to R4 and R6 may be the same as the definitions of R7 to R10 above.
  • R6 is represented by -N-Hetlene-L1-Z1, and R1 to R5 may be the same as the definitions of R7 to R10 above.
  • L1 is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • L1 is a direct bond; Or it may be a substituted or unsubstituted C6 to C60 arylene group.
  • L1 is a direct bond; Or it may be a substituted or unsubstituted C6 to C40 arylene group.
  • L1 is a direct bond; Or it may be a substituted or unsubstituted C6 to C20 arylene group.
  • L1 is a direct bond; Or it may be a C6 to C20 arylene group.
  • L1 is a direct bond; phenylene group; Biphenylene group; Or it may be a naphthalene group.
  • L1 is a direct bond; Or it may be a phenylene group.
  • L1 may be substituted again with deuterium.
  • N-Hetlene is a substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted divalent quinoxaline group; A substituted or unsubstituted divalent benzofuro[3,2-d]pyrimidine group; or a substituted or unsubstituted divalent benzo[4,5]thieno[3,2-d]pyrimidine group.
  • N-Hetlene is a divalent pyridine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group;
  • a divalent pyrimidine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group;
  • a divalent triazine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group;
  • N-Hetlene may be substituted with deuterium again.
  • the N-Hettlene may be represented by any one of Chemical Formulas 1-1 to 1-3.
  • Y is O; or S,
  • X1 to X3 are N; Or CRc, at least one of X1 to X3 is N,
  • One of X4 and X5 , and the remainder is N; or CRc;
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; Or a substituted or unsubstituted C6 to C60 aryl group.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; Or a substituted or unsubstituted C6 to C60 aryl group.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C40 aryl group.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group of C6 to C40.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group of C6 to C20.
  • Rc, R21 and R61 to R64 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.
  • Z1 is a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 heteroaryl group; Or it may be a substituted or unsubstituted amine group.
  • Z1 is a substituted or unsubstituted C2 to C60 heteroaryl group; Or it may be a substituted or unsubstituted amine group.
  • Z1 is a C2 to C60 heteroaryl group including a substituted or unsubstituted N; Or it may be a substituted or unsubstituted amine group.
  • Z1 is a C2 to C40 heteroaryl group including a substituted or unsubstituted N; Or it may be a substituted or unsubstituted amine group.
  • Z1 is a C2 to C20 heteroaryl group including a substituted or unsubstituted N; Or it may be a substituted or unsubstituted amine group.
  • Z1 is a C2 to C20 heteroaryl group including N unsubstituted or substituted with a C1 to C20 alkyl group or a C6 to C20 aryl group; Or it may be an amine group unsubstituted or substituted with a C6 to C20 aryl group.
  • Z1 may be substituted again with deuterium.
  • Z1 may be a substituted or unsubstituted amine group, or may be represented by one of the following Chemical Formulas 2-1 to 2-5.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 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 it is selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group,
  • X10 is O; S; NRd; or CReRf;
  • Rd, Re and Rf are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; Or a substituted or unsubstituted C6 to C60 aryl group.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 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.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C6 to C20 aryl group; And it may be selected from the group consisting of a C2 to C20 heteroaryl group.
  • R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.
  • Rd, Re, and Rf are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group.
  • Rd, Re and Rf are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; Or a substituted or unsubstituted C6 to C60 aryl group.
  • Rd, Re and Rf are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; Or a substituted or unsubstituted C6 to C40 aryl group.
  • Rd, Re and Rf are the same as or different from each other, and each independently a C1 to C40 alkyl group; Or an aryl group of C6 to C40.
  • Rd, Re and Rf are the same as or different from each other, and each independently a C1 to C20 alkyl group; Or an aryl group of C6 to C20.
  • Rd, Re and Rf are the same as or different from each other, and each independently a methyl group; or a phenyl group.
  • Z1 is represented by one of Formulas 2-1 to 2-5, or is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a dimethylfluorenyl group. It may be an amine group.
  • R, R' and R" are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or It may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R, R' and R" are the same as or different from each other, and each independently may be a substituted or unsubstituted C6 to C60 aryl group.
  • R, R' and R" are the same as or different from each other, and each independently may be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.
  • R, R' and R" are the same as or different from each other, and each independently may be a substituted or unsubstituted C6 to C40 monocyclic aryl group.
  • R, R' and R" are the same as or different from each other, and each independently may be a C6 to C20 monocyclic aryl group.
  • R, R' and R" may be a phenyl group.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • the 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 according to Chemical Formula 1. to provide.
  • the 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 at least one heterocyclic compound according to Chemical Formula 1. provide a small
  • the 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 two kinds of heterocyclic compounds according to Chemical Formula 1. provide a small
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic light emitting device may be a blue organic light emitting device
  • the heterocyclic compound according to Chemical Formula 1 may be used as a material for the blue organic light emitting device.
  • the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a blue light emitting layer of a blue organic light emitting device.
  • the organic light emitting device may be a green organic light emitting device
  • the heterocyclic compound according to Chemical Formula 1 may be used as a material for the green organic light emitting device.
  • the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a green 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 according to Chemical Formula 1 may be used as a material for the red organic light emitting device.
  • the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a red light emitting layer of a red organic light emitting device.
  • the organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the aforementioned heterocyclic compound.
  • the heterocyclic compound 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 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 organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.
  • the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include the heterocyclic compound.
  • the organic material layer including the heterocyclic compound may include the heterocyclic compound represented by Chemical Formula 1 as a host and may be used together with an iridium-based dopant.
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or electron injection layer may include the heterocyclic compound.
  • 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 the heterocyclic compound.
  • the organic material layer may include a hole transport layer, and the hole transport layer may include the heterocyclic compound.
  • the organic light emitting device of the present invention includes a light emitting layer, a hole injection layer, and a hole transport layer.
  • One layer or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer may be further included.
  • the organic material layer including the heterocyclic compound represented by Formula 1 provides an organic light emitting device that further includes a heterocyclic compound represented by the following Formula A .
  • L2 is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • R, R' and R" are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group,
  • a1 is an integer from 0 to 4.
  • r and s are integers from 0 to 7;
  • L2 is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • L2 is a direct bond; A substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.
  • L2 is a direct bond; C6 to C40 arylene group; Or it may be a C2 to C40 heteroarylene group.
  • L2 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted divalent dibenzothiophene group; Or it may be a substituted or unsubstituted divalent dibenzofuran group.
  • L2 is a direct bond; phenylene group; Biphenylene group; naphthalene group; Divalent dibenzothiophene group; A divalent dimethylfluorene group; Or it may be a divalent dibenzofuran group.
  • the L2 may be substituted with deuterium.
  • Rb1 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Rb1 may be a C1 to C40 alkyl group, -CN, SiRR'R" or a C6 to C60 aryl group unsubstituted or substituted with a C6 to C40 aryl group.
  • Rb1 may be a C6 to C40 aryl group unsubstituted or substituted with a C1 to C40 alkyl group, -CN, SiRR'R" or a C6 to C40 aryl group.
  • Rb1 is a phenyl group unsubstituted or substituted with -CN or SiRR'R"; a biphenyl group substituted or unsubstituted with a phenyl group; a naphthyl group; a terphenyl group; a phenynthrenyl group; or dimethylfluorenyl. it can be
  • the Ra1 and Rb1 may be substituted with deuterium.
  • -(L2)a-Ra1 and Rb1 of Formula A may be different from each other.
  • -(L2)a-Ra1 and Rb1 of Chemical Formula A may be identical to each other.
  • R, R', and R" may be a substituted or unsubstituted phenyl group.
  • R, R', and R" may be a phenyl group.
  • the deuterium content of Formula A may be 0% or more and 100% or less.
  • the deuterium content of Chemical Formula A may be 10% or more and 100% or less.
  • the deuterium content of Formula A may be 0%, 100%, or 10% to 80%.
  • Rc1 and Rd1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group; it may be.
  • Rc1 and Rd1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; biphenyl group; Or a naphthyl group; it may be.
  • r may be 7, and Rc1 may be hydrogen.
  • r is 7, and Rc1 may be deuterium.
  • r is 7, and Rc1 is hydrogen; or deuterium.
  • s may be 7, and Rd1 may be hydrogen.
  • s is 7, and Rd1 may be deuterium.
  • s is 7, and Rd1 is hydrogen; or deuterium.
  • the exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released through electron exchange between two molecules.
  • a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport capability 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. can be lowered, thereby helping to improve the lifespan.
  • heterocyclic compound of Formula A may be represented by any one of the following compounds.
  • another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A.
  • heterocyclic compound represented by Formula 1 Details of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A are the same as described above.
  • the weight ratio of the heterocyclic compound represented by Formula 1 in the composition to the heterocyclic compound represented by Formula A may be 1: 10 to 10: 1, 1: 8 to 8: 1, or 1: 5 to 5:1, or 1:2 to 2:1, but is not limited thereto.
  • the composition can be used when forming an organic material of an organic light emitting device, and can be more preferably used when forming a host of a light emitting layer.
  • the composition is in the form of simple mixing of two or more compounds, and powder materials may be mixed before forming the organic material layer of the organic light emitting device, or liquid compounds may be mixed at an appropriate temperature or higher.
  • the composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.
  • composition may further include materials known in the art, such as solvents and additives.
  • the organic light emitting device uses a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula A, except that one or more organic material layers are formed. It can be manufactured by the manufacturing method and material of the light emitting element.
  • the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method during manufacturing of 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 transport layer, and an electron injection layer 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 organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Formula 1 and the heterocyclic compound according to Formula A may be used as materials for the blue organic light emitting device. .
  • the organic light emitting device may be a green organic light emitting device, and the compound represented by Formula 1 and the heterocyclic compound represented by Formula A may be used as materials for the green organic light emitting device. .
  • the organic light emitting device may be a red organic light emitting device, and the compound represented by Formula 1 and the heterocyclic compound represented by Formula A may be used as materials for the red organic light emitting device. .
  • 1 to 3 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 application.
  • 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 formed by pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula A using a thermal vacuum deposition method.
  • a method for manufacturing a phosphorus organic light emitting device is provided.
  • the pre-mixing means that the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A are first mixed and mixed in one park before depositing 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 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.
  • 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 materials used.
  • the heterocyclic compound according to an exemplary embodiment of the present application 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.
  • Heterocyclic compounds corresponding to Formula 1 and Formula A other than the compounds described in Preparation Example 1, Preparation Example 2, Table 1 and Table 2 were also prepared in the same manner as described in Preparation Example.
  • Table 3 is a measurement value of 1 H NMR (CDCl 3 , 200 Mz)
  • Table 4 is a measurement value of FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).
  • a glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. 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 remove the ITO work function and residual film in a vacuum state, and 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 single species of the compound listed in Table 5 as a red host from one source, and using (piq) 2 (Ir) (acac) as a red phosphorescent dopant, the host was doped with 3 wt% of an Ir compound and deposited at 400 ⁇ . did Thereafter, 30 ⁇ of Bphen was deposited as a hole blocking layer, and 250 ⁇ of Alq 3 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.
  • Example 1 5 5.0 53.1 (0.68, 0.32) 124 Example 2 7 5.1 52.0 (0.68, 0.32) 120 Example 3 29 5.0 52.4 (0.68, 0.32) 122 Example 4 52 5.0 53.2 (0.68, 0.32) 130 Example 5 78 5.3 50.0 (0.68, 0.32) 105 Example 6 86 5.0 52.7 (0.68, 0.32) 129 Example 7 102 5.3 50.5 (0.68, 0.32) 102 Example 8 138 5.0 52.1 (0.68, 0.32) 133 Example 9 147 5.1 52.6 (0.68, 0.32) 122 Example 10 167 5.0 53.8 (0.68, 0.32) 136 Example 11 183 5.3 50.7 (0.68, 0.32) 104 Example 12 217 5.0 52.4 (0.68, 0.32) 132 Example 13 226 5.0 53.6 (0.68, 0.32) 120 Example 14 244 5.3 50.3 (0.68, V) 5.0 53.1 (0.68, 0.32) 124 Example 2 7 5.1 52.0 (0.68, 0.3
  • the heterocyclic compound according to the present application has a molecular weight and a band gap suitable for use in a light emitting layer of an organic light emitting device while having high thermal stability. Appropriate molecular weight makes it easy to form the light emitting layer of the organic light emitting device, and an appropriate band gap prevents loss of electrons and holes in the light emitting layer, helping to form an effective recombination region.
  • heterocyclic compound having electron transport characteristics substituted at an appropriate position resolves the hole blocking phenomenon occurring in the dopant more than the compound substituted at another position, and as can be seen from the above device evaluation, the compound of the present invention is driven, It is judged to have brought excellence in all aspects of efficiency and lifespan.
  • a glass substrate coated with a thin film of indium tinoxide (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 remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • the 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), the hole transport layer NPB (N, N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) and the electron blocking layer TAPC (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] or exciton
  • a block layer TCTA Tris(4-carbazoyl-9-ylphenyl)amine
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • the light emitting layer was deposited from one source using two types of compounds listed in Table 6 as a red host, and using (piq)2(Ir)(acac) as a red phosphorescent dopant, the host was doped with 3 wt% of an Ir compound and deposited at 400 ⁇ . did 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.
  • Example 30 PH3:5 1:3 4.8 53.8 (0.68, 0.32) 174 Example 33 PH3:5 1:2 4.8 54.1 (0.68, 0.32) 175 Example 34 PH3:5 1:1 4.7 54.2 (0.68, 0.32) 178 Example 35 PH3:5 2:1 4.7 53.1 (0.68, 0.32) 163 Example 36 PH3:5 3:1 4.8 52.9 (0.68, 0.32) 150 Example 37 PH3:7 1:1 4.8 53.5 (0.68, 0.32) 177 Example 38 PH3:29 1:1 4.7 55.0 (0.68, 0.32) 186 Example 39 PH3:52 1:1 4.7 54.8 (0.68, 0.32) 180 Example 40 PH22:78 1:1 5.0 51.6 (0.68, 0.32) 149 Example 41 PH22:86 1:1 4.8 53.1 (0.68, 0.32) 165 Example 42 PH22:102 1:1 5.0 5.0
  • the heterocyclic compound of the present invention when used as an N-type host and mixed with a P-type host for deposition, it was confirmed that the driving, efficiency, and lifespan of the organic light emitting device are improved.
  • 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 transferred to the p-host due to the exciplex phenomenon of the N+P compound. Since the electrons are injected into the n-host, the charge balance in the device can be adjusted. It was found that the combination of an N-type host compound having appropriate electron transport characteristics and a P-type host compound having appropriate hole transport characteristics in an appropriate ratio can help improve driving efficiency and lifespan.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/KR2022/008933 2021-07-02 2022-06-23 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 및 유기물층용 조성물 WO2023277446A1 (ko)

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