WO2022215864A1 - 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물 - Google Patents

헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물 Download PDF

Info

Publication number
WO2022215864A1
WO2022215864A1 PCT/KR2022/002683 KR2022002683W WO2022215864A1 WO 2022215864 A1 WO2022215864 A1 WO 2022215864A1 KR 2022002683 W KR2022002683 W KR 2022002683W WO 2022215864 A1 WO2022215864 A1 WO 2022215864A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
formula
same
Prior art date
Application number
PCT/KR2022/002683
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
이기백
모준태
김동준
Original Assignee
엘티소재주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 엘티소재주식회사 filed Critical 엘티소재주식회사
Publication of WO2022215864A1 publication Critical patent/WO2022215864A1/ko

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a heterocyclic compound, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.
  • the organic light emitting device is a type of self-emission type display device, and has 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 a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers, if necessary.
  • the material of the organic thin film may have a light emitting function if necessary.
  • a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used.
  • a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.
  • Patent Document 1 US Patent No. 4,356,429
  • An object of the present invention is to provide a heterocyclic compound, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.
  • the present invention provides a heterocyclic compound represented by the following formula (1).
  • X1 and X2 are the same as or different from each other, and each independently O; or S;
  • the N-Het is a substituted or unsubstituted, C2 to C60 monocyclic or polycyclic heterocyclic group containing one or more N.
  • the present invention is a first electrode
  • An organic light emitting device comprising a; at least one organic material layer provided between the first electrode and the second electrode,
  • At least one layer of the organic material layer provides an organic light emitting device comprising the heterocyclic compound represented by Formula 1 above.
  • the present invention provides an organic light emitting device wherein the organic material layer further comprises a heterocyclic compound represented by the following formula (6).
  • X21 and X22 are the same as or different from each other, and each independently O; or S;
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.
  • the present invention 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 6 above.
  • the present invention comprises the steps of preparing a substrate
  • It provides a method for manufacturing an organic light emitting device, wherein the step of forming the at least one organic layer includes forming at least one organic layer by using the composition for the organic layer of the organic light emitting device.
  • the compound described herein can be used as an organic material layer of an organic light emitting device.
  • the compound may serve as a hole injection layer material, an electron blocking layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, a hole blocking layer material, an electron injection layer material, etc. in the organic light emitting device.
  • the compound may be used as a material for the light emitting layer of the organic light emitting device.
  • the compound may be used alone or mixed with a P-type host as a light emitting material, and may be used as a host material or a dopant material of the light emitting layer.
  • the driving voltage of the organic light emitting device may be lowered, the luminous efficiency may be improved, and the lifespan characteristics may be improved.
  • the heterocyclic compound represented by Chemical Formula 1 of the present invention has high thermal stability and has a molecular weight and a band gap suitable for use in a light emitting layer of an organic light emitting device. This facilitates the formation of the emission layer of the organic light emitting device, and prevents loss of electrons and holes in the emission layer, thereby helping to form an effective recombination region.
  • the driving voltage can be lowered, and the luminous efficiency and lifespan characteristics can be improved.
  • 1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an embodiment of the present invention, respectively.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent is substitutable, is not limited. , When two or more substituents are substituted, two or more substituents may be the same as or different from each other.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group,
  • the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 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 are 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 carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
  • the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic refers to 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 be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • the number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic refers to 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 be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • the heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which an aryl group is directly connected to another ring group or condensed.
  • the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like.
  • the aryl group includes a spiro group.
  • the carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
  • aryl group examples include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.
  • the phosphine oxide group includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR101R102R103, R101 to R103 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; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.
  • the fluorenyl group may be substituted, and adjacent substituents may combine with 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 ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic refers to 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 be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
  • the heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.
  • heteroaryl group examples include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group , isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group, Thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolin
  • the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH 2 ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, 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, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.
  • "when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.
  • deuterium is an element having a deuteron consisting of one proton and one neutron as one of the isotopes of hydrogen as an atomic nucleus, hydrogen- It can be expressed as 2 , and the element symbol can also be written as D or 2H.
  • isotopes having the same atomic number (Z) but different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as elements with different numbers of (neutrons).
  • the 20% content of deuterium in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuterium is 1 (T2 in the formula). . That is, it can be represented by the following structural formula that the content of deuterium in the phenyl group is 20%.
  • a phenyl group having a deuterium content of 0% it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.
  • the content of deuterium in the heterocyclic compound represented by Formula 1 may be 0 to 100%, more preferably 30 to 100%.
  • C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring consisting of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., but are not limited thereto, and aromatic hydrocarbon ring compounds known in the art as satisfying the above carbon number include all
  • the present invention provides a heterocyclic compound represented by the following formula (1).
  • X1 and X2 are the same as or different from each other, and each independently O; or S;
  • the N-Het is a substituted or unsubstituted, C2 to C60 monocyclic or polycyclic heterocyclic group containing one or more N.
  • R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; Or it may be a group represented by -NR101R102.
  • R1 to R9 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 naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzocarbazolyl group; a substituted or unsubstituted triphenylamine group; a substituted or unsubstituted phenylcarbazolyl group; Alternatively, it may be a group represented by -NR101R102, wherein R101 and R102 are the same as or different from each other, and may be a substituted or unsubstituted C6 to C20 aryl group.
  • the N-Het may be a substituted or unsubstituted, C2 to C60 monocyclic or polycyclic heterocyclic group containing 1 or more and 3 or less N.
  • the N-Het may be a substituted or unsubstituted, C2 to C30 monocyclic or polycyclic heterocyclic group containing 1 or more and 3 or less N.
  • the N-Het may be a substituted or unsubstituted, C2 to C30 monocyclic or polycyclic heterocyclic group containing 2 or more and 3 or less N.
  • the N-Het may be a substituted or unsubstituted, C2 to C20 monocyclic or polycyclic heterocyclic group containing 2 or more and 3 or less N.
  • the content of deuterium based on the total number of hydrogen atoms and deuterium atoms in Formula 1 is 0% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more. and may be 100% or less, 90% or less, 80% or less, 70% or less, 60% or less.
  • the content of deuterium may be 30% to 100% based on the total number of hydrogen atoms and deuterium atoms in Formula 1 above.
  • the content of deuterium may be 30% to 80% based on the total number of hydrogen atoms and deuterium atoms in Formula 1 above.
  • the content of deuterium may be 50% to 60% based on the total number of hydrogen atoms and deuterium atoms in Formula 1 above.
  • N-Het may be a substituent represented by the following formula (2).
  • the X11 to X13 are the same as or different from each other, and each independently N; or CR13;
  • X11 to X13 are at least two or more N,
  • L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; Or it may be a group represented by -NR101R102.
  • L is a direct bond; a substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group.
  • L is a direct bond; a substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.
  • L is a direct bond; Or a substituted or unsubstituted phenylene group; Or it may be a substituted or unsubstituted naphthylene group.
  • Chemical Formula 2 may be represented by any one of Chemical Formulas 3 to 5 below.
  • L is the same as the definition in Formula 2 above.
  • R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group selected from the group consisting of, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 Heterocyclic rings may be formed.
  • R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R21 and R22 are the same as or different from each other, and 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 carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; Or it may be a substituted or unsubstituted dibenzothiophenyl group.
  • R26 to R28 are the same as or different from each other, and at least two of R26 to R28 are each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R26 to R28 are the same as or different from each other, and at least two of R26 to R28 are each independently a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R26 to R28 are the same as or different from each other, and at least two of R26 to R28 are each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R26 to R28 are the same as or different from each other, and at least two of R26 to R28 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; Or it may be a substituted or unsubstituted dibenzothiophenyl group.
  • Chemical Formula 4 may be represented by any one of the following Chemical Formulas 4-1 to 4-4.
  • the Y1 and Y2 are the same as or different from each other, and each independently O; or S;
  • L is the same as the definition in Formula 2 above.
  • R31 to R48 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R31 to R33 are the same as or different from each other, and at least two of R31 to R33 are each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R31 to R33 are the same as or different from each other, and at least two of R31 to R33 are each independently a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R31 to R33 are the same as or different from each other, and at least two of R31 to R33 are each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R31 to R33 are the same as or different from each other, and at least two of R31 to R33 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 carbazolyl group; Or it may be a substituted or unsubstituted dibenzofuranyl group.
  • any one of R34 to R38 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • any one of R34 to R38 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • any one of R34 to R38 is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • any one of R34 to R38 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; Or it may be a substituted or unsubstituted terphenyl group.
  • any one of R39 to R43 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • any one of R39 to R43 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • any one of R39 to R43 is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • any one of R39 to R43 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; Or it may be a substituted or unsubstituted terphenyl group.
  • any one of R44 to R48 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • any one of R44 to R48 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • any one of R44 to R48 is a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • any one of R44 to R48 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; Or it may be a substituted or unsubstituted terphenyl group.
  • Chemical Formula 1 may be a heterocyclic compound represented by any one of the following compounds.
  • substituents for example, a substituent mainly used for a hole injection layer material, an electron blocking layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, a hole blocking layer material, and a charge generating layer material used in manufacturing an organic light emitting device is introduced into the core structure.
  • a material that satisfies the conditions required by each organic material layer can be synthesized.
  • An organic light emitting device comprising a; at least one organic material layer provided between the first electrode and the second electrode,
  • At least one layer of the organic material layer relates to an organic light emitting device comprising the heterocyclic compound represented by Formula 1 above.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the red organic light emitting device.
  • the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the red organic light emitting device.
  • heterocyclic compound represented by Formula 1 Specific details of the heterocyclic compound represented by Formula 1 are the same as described above.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described 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 refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but 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, an electron blocking layer, a hole transport layer, a light emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, etc. as an organic material layer.
  • 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 including the heterocyclic compound represented by Formula 1 further includes a heterocyclic compound represented by the following Formula 6 It provides an organic light emitting device .
  • X21 and X22 are the same as or different from each other, and each independently O; or S;
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • L is the same as the definition in Formula 2 above.
  • R51 to R59 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; 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.
  • R51 to R59 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R51 to R59 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R51 to R59 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted isobutyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group may be a substituted or unsubstituted isochrysenyl group.
  • the exciplex phenomenon is a phenomenon in which energy having the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is emitted through electron exchange between two molecules.
  • RISC reverse intersystem crossing
  • a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts of the emission layer, holes are injected into the p-host and electrons are transferred to the n-host Since it is injected into That is, when the compound represented by Formula 1 is used as the acceptor and the compound represented by Formula 6 is used as the donor, excellent device characteristics are exhibited.
  • the heterocyclic compound represented by Formula 6 may be any one selected from the following compounds.
  • one embodiment of the present invention 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 6 above.
  • heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6 are the same as described above.
  • the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6 in the composition for an organic material layer of the organic light emitting device may be 1:10 to 10:1, and , 1: 8 to 8: 1, may be 1: 5 to 5: 1, may be 1: 2 to 2: 1, but is not limited thereto.
  • composition for the organic material layer of the organic light emitting device may be used when forming the organic material of the organic light emitting device, and in particular, it may be more preferably used when forming the host of the light emitting layer.
  • the organic material layer includes a heterocyclic compound represented by Formula 1, and a heterocyclic compound represented by Formula 6, and may be used together with a phosphorescent dopant.
  • phosphorescent dopant material those known in the art may be used.
  • phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M may be used, but the scope of the present invention is not limited by these examples.
  • M may be iridium, platinum, osmium, or the like.
  • the L is an anionic bidentate ligand coordinated to the M by sp 2 carbon and a hetero atom, and X may function to trap electrons or holes.
  • Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -benzoquinoline), (thiophenylpyridine), phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, tolylpyridine, and the like.
  • Non-limiting examples of X′ and X′′ include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.
  • the organic material layer includes the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6, and may be used together with an iridium-based dopant.
  • (piq) 2 (Ir)(acac) may be used as the red phosphorescent dopant.
  • the content of the dopant may have a content of 1% to 15%, preferably 2% to 10%, more preferably 3% to 7% based on the total weight of the light emitting layer. .
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport 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 the hole blocking layer may include the heterocyclic compound.
  • the organic material layer may include an electron transport layer, a light emitting layer, or a hole blocking layer, and the electron transport layer, the light emitting layer or the hole blocking layer may include the heterocyclic compound.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.
  • An organic light emitting device includes a light emitting layer, a hole injection layer, and a hole transport layer. It may further include one 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.
  • FIG. 1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an embodiment of the present invention.
  • the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.
  • 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 illustrated.
  • 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 diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting 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 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 .
  • the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.
  • the step of forming the at least one organic material layer is performed using the composition for an organic material layer according to an embodiment of the present invention. It provides a method of manufacturing an organic light emitting device comprising the step of forming one or more organic material layers.
  • the step of forming the organic material layer is a pre-mixed (pre-mixed) heterocyclic compound represented by the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6, thermal vacuum deposition method It may be formed using
  • the pre-mixed means, before depositing the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6 on the organic layer, first mixing the materials and putting them in one source and mixing.
  • the pre-mixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.
  • the organic material layer including the heterocyclic compound represented by Formula 1 may further include other materials as needed.
  • the organic material layer including the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 6 at the same time may further include other materials if necessary.
  • materials other than the heterocyclic compound represented by Formula 1 or the heterocyclic compound represented by Formula 6 are exemplified below, but these are for illustration only. It is not intended to limit the scope, and may be substituted with materials known in the art.
  • anode material Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used.
  • the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material Materials having a relatively low work function may be used as the cathode material, and a metal, metal oxide, conductive polymer, or the like may be used.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO2/Al, but is not limited thereto.
  • hole injection layer material a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994).
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994).
  • a pyrazoline derivative an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc.
  • a low molecular weight or high molecular material may be used.
  • Examples of the electron transport layer material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone.
  • Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.
  • the electron injection layer material for example, 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 layer material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as individual sources, or may be premixed and deposited as a single source for use.
  • a fluorescent material can be used as a light emitting layer material, it can also be used as a phosphorescent material.
  • As the light emitting layer material a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, may be used alone, but materials in which the host material and the dopant material together participate in light emission may be used.
  • a host of the light emitting layer material When a host of the light emitting layer material is mixed and used, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of n-type host material and p-type host material may be selected and used as the host material of the light emitting layer.
  • the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on a material used.
  • the heterocyclic compound according to an embodiment of the present invention may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
  • reaction solution was extracted with dichloromethane and distilled water, and moisture was removed using MgSO 4 . Then, it was separated by a silica gel column to obtain 25 g of compound 63-3 (yield 74%).
  • reaction solution was extracted with dichloromethane and distilled water, and moisture was removed using MgSO 4 . Then, it was separated by a silica gel column to obtain 9 g of compound 63 (yield 68%).
  • Tables 2 and 3 The synthesis results of the compounds described in Preparation Examples 1 to 2 and Table 1 are shown in Tables 2 and 3 below.
  • Table 2 below is a measurement value of 1 H NMR (CDCl 3 , 300Mz)
  • Table 3 below is a measurement value of an FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).
  • a glass substrate coated with a thin film of ITO to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO (Ultraviolet Ozone) treatment was performed for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and the substrate was transferred to a thermal deposition equipment for organic deposition.
  • PT plasma cleaner
  • NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
  • a light emitting layer was deposited thereon by thermal vacuum deposition as follows.
  • the compounds shown in Table 4 were deposited as a red host, and (piq) 2 (Ir)(acac) was doped to the host at 3 wt% using (piq) 2 (Ir)(acac) as a red phosphorescent dopant. and deposited to a thickness of 400 ⁇ .
  • Bphen was deposited to a thickness of 30 ⁇ as a hole blocking layer, and Alq 3 as an electron transport layer was deposited thereon to a thickness of 250 ⁇ .
  • lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then aluminum (Al) is deposited to a thickness of 1,200 ⁇ on the electron injection layer to form a cathode to form an organic electric field.
  • LiF lithium fluoride
  • Al aluminum
  • OLED Organic Light Emitting Device
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At /m 2 , T 90 was measured.
  • Table 4 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (CIE) and lifetime of the organic light emitting diode manufactured according to the present invention.
  • the T 90 denotes a lifetime (unit: time) that is 90% of the initial luminance.
  • Example 1 5 5.19 52.80 (0.680, 0.321) 119
  • Example 2 28 5.22 56.64 (0.679, 0.319) 123
  • Example 3 42 5.13 54.36 (0.678, 0.323) 130
  • Example 4 63 5.24 54.77 (0.681, 0.322) 108
  • Example 5 91 5.19 57.50 (0.678, 0.319)
  • Example 6 106 5.17 56.65 (0.682, 0.324) 137
  • Example 7 132 5.20 52.34 (0.677, 0.321)
  • Example 8 141 5.11 53.88 (0.680, 0.320) 128
  • Example 9 163 5.14 53.76 (0.681, 0.324) 115
  • Example 10 188 5.29 57.51 (0.683, 0.323) 138
  • Example 11 203 5.20 57.23 (0.683, 0.322) 128
  • Example 12 230 5.25 55.32 (0.679, 0.324)
  • An appropriate molecular weight facilitates the formation of the light emitting layer of the organic light emitting device, and an appropriate band gap prevents the loss of electrons and holes in the light emitting layer, thereby helping to form an effective recombination region.
  • the heterocyclic compound having an electron transport property substituted at an appropriate position can solve the hole blocking phenomenon occurring in the dopant than the compound substituted at another position. Therefore, as shown in Table 4, it can be seen that the heterocyclic compound of the present invention is superior to the results of Comparative Examples in all aspects of driving voltage, luminous efficiency and lifespan.
  • a glass substrate coated with a thin film of 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 a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO (Ultraviolet Ozone) treatment was performed for 5 minutes using UV in a UV washer. Thereafter, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal deposition equipment for organic deposition.
  • PT plasma cleaner
  • a light emitting layer was deposited thereon by thermal vacuum deposition as follows.
  • two types of compounds described in Table 5 below were deposited as a red host from a single source, and (piq) 2 (Ir)(acac) was used as a red phosphorescent dopant as a host (piq) 2 (Ir) (acac). ) was doped with 3 wt% and deposited to a thickness of 400 ⁇ .
  • the compound used as the p-Host is as follows.
  • Bphen was deposited to a thickness of 30 ⁇ as a hole blocking layer
  • TPBI was deposited to a thickness of 250 ⁇ as an electron transport layer thereon.
  • lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer
  • aluminum (Al) is deposited to a thickness of 1,200 ⁇ on the electron injection layer to form a cathode to form an organic electric field.
  • a light emitting device was manufactured.
  • OLED Organic Light Emitting Device
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At /m 2 , T 90 was measured. Table 5 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (CIE) and lifespan of the organic light emitting device manufactured according to the present invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
PCT/KR2022/002683 2021-04-07 2022-02-24 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물 WO2022215864A1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2021-0045392 2021-04-07
KR1020210045392A KR20220139504A (ko) 2021-04-07 2021-04-07 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물

Publications (1)

Publication Number Publication Date
WO2022215864A1 true WO2022215864A1 (ko) 2022-10-13

Family

ID=83546161

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2022/002683 WO2022215864A1 (ko) 2021-04-07 2022-02-24 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물

Country Status (3)

Country Link
KR (1) KR20220139504A (zh)
TW (1) TW202302596A (zh)
WO (1) WO2022215864A1 (zh)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130078438A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20170086277A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170086211A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20190106774A (ko) * 2018-03-09 2019-09-18 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN110903295A (zh) * 2018-09-18 2020-03-24 江苏三月光电科技有限公司 一种以苯并呋喃衍生物为核心的有机化合物及其应用
US20200270278A1 (en) * 2019-10-31 2020-08-27 Shanghai Tianma AM-OLED Co., Ltd. Compound, a display panel and an electronic device
KR20200134978A (ko) * 2019-05-24 2020-12-02 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130078438A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20170086277A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170086211A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20190106774A (ko) * 2018-03-09 2019-09-18 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN110903295A (zh) * 2018-09-18 2020-03-24 江苏三月光电科技有限公司 一种以苯并呋喃衍生物为核心的有机化合物及其应用
KR20200134978A (ko) * 2019-05-24 2020-12-02 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치
US20200270278A1 (en) * 2019-10-31 2020-08-27 Shanghai Tianma AM-OLED Co., Ltd. Compound, a display panel and an electronic device

Also Published As

Publication number Publication date
TW202302596A (zh) 2023-01-16
KR20220139504A (ko) 2022-10-17

Similar Documents

Publication Publication Date Title
WO2022065761A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 및 유기물층용 조성물
WO2021137565A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
WO2021133016A2 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법
WO2022075601A1 (ko) 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2021132984A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
WO2021241923A1 (ko) 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물
WO2022045606A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
WO2022131547A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
WO2022108141A1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
WO2021215742A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
WO2021132982A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
WO2023277446A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 및 유기물층용 조성물
WO2022244983A1 (ko) 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
WO2022186645A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
WO2022124594A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
WO2021071248A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법
WO2021101220A1 (ko) 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법
WO2022215864A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
WO2022211281A1 (ko) 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
WO2023033352A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
WO2023204694A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층용 조성물
WO2023214651A1 (ko) 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
WO2023214650A1 (ko) 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
WO2022139167A1 (ko) 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
WO2023106625A1 (ko) 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22784774

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22784774

Country of ref document: EP

Kind code of ref document: A1