WO2021261856A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2021261856A1
WO2021261856A1 PCT/KR2021/007746 KR2021007746W WO2021261856A1 WO 2021261856 A1 WO2021261856 A1 WO 2021261856A1 KR 2021007746 W KR2021007746 W KR 2021007746W WO 2021261856 A1 WO2021261856 A1 WO 2021261856A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
layer
unsubstituted
formula
Prior art date
Application number
PCT/KR2021/007746
Other languages
English (en)
Korean (ko)
Inventor
허동욱
홍성길
한미연
윤정민
윤희경
Original Assignee
주식회사 엘지화학
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 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202180035677.7A priority Critical patent/CN115667249A/zh
Publication of WO2021261856A1 publication Critical patent/WO2021261856A1/fr

Links

Images

Classifications

    • 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
    • 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
    • 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
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
  • 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.
  • hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into
  • the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used.
  • an electron injection material or an electron transport material an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used.
  • the light emitting layer material a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed.
  • a material with high luminous efficiency that converts it into light when it is formed is preferable.
  • the present specification provides a heterocyclic compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a heterocyclic compound represented by the following formula (1).
  • Z is O or S
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R3 to R6 are each independently hydrogen, or combine with each other to form a hydrocarbon ring
  • L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • a is an integer of 1 to 3, and when a is 2 or more, L of 2 or more are the same as or different from each other,
  • b is an integer of 1 to 4, and when b is 2 or more, the structures in parentheses are the same as or different from each other,
  • Ar1 is any one selected from the group consisting of
  • c is an integer of 1 to 5, and when c is 2 or more, 2 or more G15 are the same as or different from each other,
  • d is an integer of 1 to 4, and when d is 2 or more, 2 or more G16 are the same as or different from each other,
  • X1 to X4 are the same as or different from each other, and each independently represents N or CR10, provided that at least two of X1 to X4 are N;
  • R10 and G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Another embodiment of the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound.
  • the heterocyclic compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
  • 1 to 4 illustrate an organic light emitting diode according to an exemplary embodiment of the present specification.
  • the present specification provides a heterocyclic compound represented by the following formula (1).
  • Z is O or S
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R3 to R6 are each independently hydrogen, or combine with each other to form a hydrocarbon ring
  • L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • a is an integer of 1 to 3, and when a is 2 or more, L of 2 or more are the same as or different from each other,
  • b is an integer of 1 to 4, and when b is 2 or more, the structures in parentheses are the same as or different from each other,
  • Ar1 is any one selected from the group consisting of
  • c is an integer of 1 to 5, and when c is 2 or more, 2 or more G15 are the same as or different from each other,
  • d is an integer of 1 to 4, and when d is 2 or more, 2 or more G16 are the same as or different from each other,
  • X1 to X4 are the same as or different from each other, and each independently represents N or CR10, provided that at least two of X1 to X4 are N;
  • R10 and G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • the compound represented by Formula 1 of the present invention is polarized by including only one substituent in the xanthene group, thioxanthene group, benzoxanthene group, or benzothioxanthene group in which Z is O or S. As a result, the dipole moment is improved and the lifespan is improved.
  • the compound represented by Formula 1 of the present invention includes a polycyclic aryl group as R1 and R2; or a heterocyclic group to enhance polarization.
  • the compound exhibits the effect of improving the electron transfer characteristics by substituting Ar1 on one side of the xanthene group, thereby improving the efficiency of the organic light emitting device.
  • 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 position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; cyano group (-CN); ester group; imid; amine group; alkoxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the aryl group is not particularly limited, but preferably has 6 to 50 carbon atoms, such as 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a fluoranthene group, etc.
  • the present invention is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, S and P, and the like.
  • the number of carbon atoms is not particularly limited, but preferably has 1 to 50 carbon atoms, further preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • the heterocyclic group may be an aromatic ring, an aliphatic ring, or a ring condensed therewith.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazoly
  • the description of the above-mentioned heterocyclic group may be cited except that the divalent heterocyclic group is divalent.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto it is not
  • the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of an aromatic and an aliphatic group, and may be selected from examples of the cycloalkyl group or the aryl group.
  • 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-C30. 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 and the like may be used, but is not limited thereto.
  • the amine group is -NH 2 ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 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, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • diphenylamine group diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • L is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 divalent heterocyclic group.
  • L is a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 30 carbon atoms; a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 divalent heterocyclic group.
  • L is a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 30 carbon atoms; a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms; or a substituted or unsubstituted divalent N-containing heterocyclic group having 2 to 30 carbon atoms.
  • L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent pyridine group.
  • L is a direct bond; an arylene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group; or direct bonding; It is a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group.
  • L is a direct bond; an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group; or a divalent heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group.
  • L is a direct bond; a phenylene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group; a biphenylene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group; a naphthylene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group and an aryl group; or a divalent pyridine group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group.
  • L is a direct bond; an arylene group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group; It is a divalent heterocyclic group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group.
  • L is a direct bond; a phenylene group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group; a biphenylene group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group; a naphthylene group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group; or a divalent pyridine group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, or an aryl group.
  • L is a direct bond; a phenylene group unsubstituted or substituted with a cyano group or an alkyl group; a biphenylene group unsubstituted or substituted with a cyano group or an alkyl group; a naphthylene group unsubstituted or substituted with a cyano group or an alkyl group; or a divalent pyridine group unsubstituted or substituted with a cyano group or an alkyl group.
  • L is a direct bond; phenylene group; a biphenylene group unsubstituted or substituted with a cyano group; naphthylene group; or a divalent pyridine group.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 N-containing heterocyclic group.
  • R1 and R2 are the same as or different from each other, and each independently a monocyclic aryl group having 6 to 30 carbon atoms; a polycyclic aryl group having 10 to 30 carbon atoms; or an N-containing heterocyclic group having 2 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted pyridine group.
  • R1 and R2 are the same as or different from each other, and each independently a phenyl group; naphthyl group; or a pyridine group.
  • Ar1 is any one of the following structures.
  • c is an integer of 1 to 5, and when c is 2 or more, 2 or more G15 are the same as or different from each other,
  • d is an integer of 1 to 4, and when d is 2 or more, 2 or more G16 are the same as or different from each other,
  • X1 to X4 are the same as or different from each other, and each independently represents N or CR10, provided that at least two of X1 to X4 are N;
  • R10 and G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar1 is any one of the following structures.
  • two of X1 to X4 are N, the other two are CR10, and R10 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • two of X1 to X4 are N, the other two are CR10, and R10 is hydrogen.
  • X2 and X3 are N
  • X1 and X4 are CR10
  • R10 is hydrogen
  • heavy hydrogen a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • X2 and X3 are N
  • X1 and X4 are CR10
  • R10 is hydrogen
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or an aryl group unsubstituted or substituted with deuterium, a cyano group, an alkyl group, an aryl group, or a heterocyclic group.
  • G1 to G16 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; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluoranthene group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofuran group.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; or a substituted or unsubstituted phenyl group.
  • G1 to G16 are the same as or different from each other, and each independently hydrogen; or a phenyl group unsubstituted or substituted with a cyano group or a pyridine group.
  • b is an integer of 1 to 3.
  • b is 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • Chemical Formula 1 is represented by Chemical Formula 1-1.
  • Chemical Formula 1 is represented by Chemical Formula 1-2.
  • Chemical Formula 1 is represented by Chemical Formula 1-3.
  • Chemical Formula 1 is represented by Chemical Formula 1-4.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-5 to 1-7.
  • R1 to R6, L, a, b, and Ar1 are the same as defined in Formula 1 above.
  • Chemical Formula 1 is represented by Chemical Formula 1-5.
  • Chemical Formula 1 is represented by Chemical Formula 1-6.
  • Chemical Formula 1 is represented by Chemical Formula 1-7.
  • the heterocyclic compound of Formula 1 has any one of the following structures.
  • the core structure of Chemical Formula 1 according to an exemplary embodiment of the present specification may be prepared as shown in the following reaction scheme, the substituents may be combined by methods known in the art, and the type, position or number of the substituents may be determined in the art. It can be changed according to the known technique.
  • A is Cl or Br.
  • An exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer of the organic material layer provides an organic light-emitting device including the above-described heterocyclic compound.
  • the organic light emitting device of the present specification is prepared by manufacturing methods and materials known in the art, except that at least one layer of the organic material layer contains the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by Formula 1 above. can be manufactured.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to It can be manufactured by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing the second electrode material, the organic material layer, and the first electrode material on the substrate.
  • the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layers may be formed of the same material or different materials.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, etc.
  • the present invention is not limited thereto and may have a single-layer structure.
  • the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
  • the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons and the heterocyclic compound.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.
  • the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the structure of the organic light emitting diode of the present specification may have the structure shown in FIGS. 1 to 4 , but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 2 , a light emitting layer 3 , and a second electrode 4 are sequentially stacked on a substrate 1 .
  • 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • 2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, an electron injection layer 8 and a second electrode ( 4)
  • the structure of the organic light emitting device stacked in this order is exemplified. 2 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.
  • 3 shows a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light emitting layer 3, an electron injection and
  • the structure of the organic light emitting device in which the transport layer 9 and the second electrode 4 are sequentially stacked is illustrated.
  • 3 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.
  • 4 shows a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light emitting layer 3, and a hole blocking layer on the substrate 1 (10).
  • the structure of the organic light emitting device in which the electron injection and transport layer 9 and the second electrode 4 are sequentially stacked is illustrated. 4 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.
  • the organic light emitting device may have, for example, the following stacked structure in addition to the structure specified in the drawings, but is not limited thereto.
  • the hole transport layer may have a multilayer structure.
  • it may be composed of a first hole transport layer and a second hole transport layer comprising different materials.
  • the anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and 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 is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO2/Al, but is not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer.
  • the hole injection material holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material.
  • Organic materials carbazole-based organic materials, fluorene-based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, etc., but are not limited thereto.
  • a compound including a substituted or unsubstituted carbazole and a substituted or unsubstituted fluorene may be used, but is not limited thereto.
  • the hole injection layer may have a thickness of 1 nm to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.
  • the hole transport layer may serve to facilitate hole transport.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable.
  • the hole transport material include an arylamine-based organic material, a carbazole-based organic material, a quinoxaline-based organic material, a fluorene-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. is not limited to Specifically, the hole transport material includes, but is not limited to, a quinoxazoline-based compound and an arylamine-based compound.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and a hole injection or transport material known in the art may be included.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron-blocking layer the above-described compound or a material known in the art may be used.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compound, dimerized styryl compound, BAlq, 10-hydroxybenzoquinoline-metal compound, benzoxazole-based compound, benz There are thiazole-based compounds, benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene and rubrene, etc., but are limited to these no.
  • the light emitting layer includes a host and a dopant.
  • the host may include the above-mentioned compounds, condensed aromatic ring derivatives, heterocyclic-containing compounds, and the like.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • phosphorescent material or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • the present invention is not limited thereto.
  • the light emitting layer emits blue light
  • 4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer , PPV-based, pyrene-based, arylamine-based compounds, etc. may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used for the hole blocking layer.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline , a complex including Alq 3 , an organic radical compound, an anthracene-based compound, an imidazole-based compound, and a hydroxyflavone-metal complex.
  • the electron transport layer may have a thickness of 1 nm to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons.
  • the electron injection layer may serve to facilitate electron injection.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, anthracene, imidazole and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and lithium quinolate (LiQ), but is not limited thereto.
  • the organic material layer including the heterocyclic compound of Formula 1 is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer or the electron injection and The layer that simultaneously transports electrons further includes a metal complex.
  • examples of the metal complex include , but are not limited to, Al complex of 8-hydroxyquinoline (Alq 3 ), LiQ, and a metal complex compound.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium,
  • the present invention is not limited thereto.
  • the heterocyclic compound of Formula 1 and the metal complex in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons may be included in a mass ratio of 0.5:1.5 to 1.5:0.5. .
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP and aluminum complexes, but is not limited thereto.
  • An exemplary embodiment of the present specification is a compound represented by Formula 1; And it provides a composition comprising a metal complex.
  • metal complex included in the composition is the same as described above in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons.
  • the heterocyclic compound of Formula 1 and the metal complex in the composition may be included in a mass ratio of 0.5:1.5 to 1.5:0.5.
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • E1-A (20 g, 43.4 mmol) and E1-B (10.5 g, 43.4 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.3 mmol) was dissolved in 18 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E10 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E13 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E14 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E15 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • a first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 ⁇ of the HAT compound and 60 ⁇ of the HT-A compound on the hole injection layer.
  • the following BH compound and BD compound were vacuum-deposited in a weight ratio of 25:1 to a thickness of 20 nm on the second hole transport layer to form a light emitting layer.
  • the compound E1 prepared in Preparation Example 1-1 and the following LiQ compound were vacuum deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 350 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was By maintaining 1 ⁇ 10 -7 torr to 5 ⁇ 10 -5 torr, an organic light emitting device was manufactured.
  • Example 1-2 to 1-15 Example 1-2 to 1-15.
  • An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds E2 to E15 of Table 1 were used instead of compound E1 of Example 1-1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds ET-A to ET-M shown in Table 1 were used instead of Compound E1 of Example 1-1.
  • the compound represented by Formula 1 according to the present specification may be used in an organic material layer that simultaneously injects and transports electrons of an organic light emitting device.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • a first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 ⁇ of the HAT compound and 60 ⁇ of the HT-A compound on the hole injection layer.
  • the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to a thickness of 20 nm on the second hole transport layer to form a light emitting layer.
  • the compound E1 prepared in Preparation Example 1-1 was vacuum deposited to a thickness of 50 ⁇ to form a hole blocking layer, and ET-N and the following LiQ compound were vacuum deposited in a weight ratio of 1:1 to a thickness of 300 ⁇ .
  • An electron injection and transport layer was formed.
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was By maintaining 1 ⁇ 10 -7 torr to 5 ⁇ 10 -5 torr, an organic light emitting device was manufactured.
  • An organic light emitting device was prepared in the same manner as in Example 2-1, except that compounds E2 to E8, E10 to E12, E14 and E15 described in Table 2 below were used instead of compound E1 of Example 2-1. prepared.
  • Example 2-1 The same method as in Example 2-1, except that compounds ET-A to ET-H and ET-J to ET-L described in Table 2 below were used instead of Compound E1 in Example 2-1 to manufacture an organic light emitting device.
  • Example 2-1 E1 4.35 5.09 (0.140, 0.092) 126
  • Example 2-2 E2 4.44 4.99 (0.140, 0.093) 138
  • Example 2-3 E3 4.26 5.25 (0.140, 0.093) 114
  • Example 2-4 E4 4.39 5.09 (0.141, 0.092) 128
  • Example 2-5 E5 4.26 5.22 (0.140, 0.092)
  • Example 2-6 E6 4.48 4.89 (0.140, 0.093)
  • Example 2-7 E7 4.31 5.12 (0.140, 0.093) 122
  • Examples 2-8 E8 4.40 5.04 (0.141, 0.092) 146
  • Examples 2-9 E10 4.31 5.19 (0.140, 0.093) 121
  • Example 2-10 E11 4.14 5.17 (0.140, 0.093) 117
  • the compound represented by Chemical Formula 1 according to the present specification may be used in the organic material layer for blocking holes of the organic light emitting device.
  • the organic light emitting device to which the heterocyclic compound of Formula 1 according to the present specification is applied is a compound in which both sides of the xanthene group include a substituent It was confirmed that it showed significantly superior characteristics in terms of efficiency and lifespan compared to organic light emitting devices to which .

Abstract

La présente invention concerne un composé hétérocyclique et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/007746 2020-06-26 2021-06-21 Composé hétérocyclique et dispositif électroluminescent organique le comprenant WO2021261856A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202180035677.7A CN115667249A (zh) 2020-06-26 2021-06-21 杂环化合物及包含其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020200078172A KR102605828B1 (ko) 2020-06-26 2020-06-26 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR10-2020-0078172 2020-06-26

Publications (1)

Publication Number Publication Date
WO2021261856A1 true WO2021261856A1 (fr) 2021-12-30

Family

ID=79281476

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/007746 WO2021261856A1 (fr) 2020-06-26 2021-06-21 Composé hétérocyclique et dispositif électroluminescent organique le comprenant

Country Status (3)

Country Link
KR (1) KR102605828B1 (fr)
CN (1) CN115667249A (fr)
WO (1) WO2021261856A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102560362B1 (ko) * 2020-06-26 2023-07-27 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012049828A1 (fr) * 2010-10-12 2012-04-19 出光興産株式会社 Dérivé hétérocyclique aromatique, et élément électroluminescent organique le comprenant
KR20160047670A (ko) * 2014-10-22 2016-05-03 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20170121691A (ko) * 2016-04-25 2017-11-02 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20200020582A (ko) * 2018-08-17 2020-02-26 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN111100072A (zh) * 2019-11-28 2020-05-05 吉林奥来德光电材料股份有限公司 一种有机光电化合物、其合成方法及有机电致发光器件

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6370568B2 (ja) 2014-03-14 2018-08-08 出光興産株式会社 インク組成物、インク組成物を用いた有機エレクトロルミネッセンス素子、及び電子機器

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012049828A1 (fr) * 2010-10-12 2012-04-19 出光興産株式会社 Dérivé hétérocyclique aromatique, et élément électroluminescent organique le comprenant
KR20160047670A (ko) * 2014-10-22 2016-05-03 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20170121691A (ko) * 2016-04-25 2017-11-02 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20200020582A (ko) * 2018-08-17 2020-02-26 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN111100072A (zh) * 2019-11-28 2020-05-05 吉林奥来德光电材料股份有限公司 一种有机光电化合物、其合成方法及有机电致发光器件

Also Published As

Publication number Publication date
CN115667249A (zh) 2023-01-31
KR20220001019A (ko) 2022-01-05
KR102605828B1 (ko) 2023-11-24

Similar Documents

Publication Publication Date Title
WO2017204594A1 (fr) Elément électroluminescent organique
WO2019235873A1 (fr) Dispositif électroluminescent organique
WO2019143151A1 (fr) Diode électroluminescente organique
WO2014081168A1 (fr) Composé de fluoranthène et dispositif électronique organique comprenant celui-ci
WO2017119792A1 (fr) Composé et élément électronique organique le comprenant
WO2019151733A1 (fr) Diode électroluminescente organique
WO2019182402A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019160315A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2019147077A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2017146522A1 (fr) Composé hétérocyclique et diode électroluminescente organique contenant ce composé
WO2018030786A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2021125813A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019164301A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2017164614A1 (fr) Composé hétérocyclique et élément électroluminescent organique comprenant ledit composé
WO2022154283A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2016068478A2 (fr) Composé cyclique et élément électroluminescent organique comprenant celui-ci
WO2020055059A1 (fr) Diode électroluminescente organique
WO2019194594A1 (fr) Composé et dispositif électronique organique le comprenant
WO2019177393A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019143223A9 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2019151615A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2020262861A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020222433A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2021261856A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2018070840A1 (fr) Dispositif électroluminescent organique

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: 21830145

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: 21830145

Country of ref document: EP

Kind code of ref document: A1