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WO2018174678A1 - Composé hétérocyclique et élément électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et élément électroluminescent organique le comprenant Download PDF

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Publication number
WO2018174678A1
WO2018174678A1 PCT/KR2018/003532 KR2018003532W WO2018174678A1 WO 2018174678 A1 WO2018174678 A1 WO 2018174678A1 KR 2018003532 W KR2018003532 W KR 2018003532W WO 2018174678 A1 WO2018174678 A1 WO 2018174678A1
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Prior art keywords
group
substituted
unsubstituted
formula
light emitting
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PCT/KR2018/003532
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English (en)
Korean (ko)
Inventor
노영석
차주현
김동준
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LT Materials Co Ltd
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Heesung Material Ltd
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Priority claimed from KR1020180018782A external-priority patent/KR20180108426A/ko
Application filed by Heesung Material Ltd filed Critical Heesung Material Ltd
Priority to EP18772275.6A priority Critical patent/EP3604298B1/fr
Priority to US16/496,878 priority patent/US11527723B2/en
Priority to CN201880030210.1A priority patent/CN110621668A/zh
Priority to JP2019552245A priority patent/JP7298910B2/ja
Publication of WO2018174678A1 publication Critical patent/WO2018174678A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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 electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting element has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound which may itself constitute a light emitting layer may be used, or a compound that may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used.
  • a heterocyclic compound represented by Formula 1 is provided.
  • N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,
  • L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, a is an integer of 1 to 3, when a is 2 or more, L is the same as or different from each other,
  • R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, b and c each
  • the 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 a heterocyclic compound represented by Chemical Formula 1.
  • the compound described in this specification can be used as an organic material layer material of an organic light emitting element.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound can be used as the light emitting layer material of the organic light emitting device.
  • the compound may be used alone as a light emitting material, or may be used as a host material of the light emitting layer.
  • the N-containing ring is substituted at the carbon position of the dibenzofuran structure, and the carbazole structure is substituted for the benzene in which the N-containing ring is not substituted in the structure of the dibenzofuran structure, thereby providing a more electron stable structure. It is possible to improve the device life.
  • 1 to 3 are diagrams schematically showing a laminated structure of an organic light emitting device according to an exemplary embodiment of the present application.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same 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. Carbon number of 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, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 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, tert -Octyl
  • the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • Specific examples thereof include 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, and 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 and the like, 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 another substituent.
  • 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 linear, branched or cyclic. 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, i-propyloxy, 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 and the like It may be, but is not limited thereto.
  • the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number 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 means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic means a group in which an aryl group is directly connected or condensed with another ring group.
  • the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like.
  • the aryl group includes a spiro group. Carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
  • aryl group examples include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre Neyl group, tetrasenyl group, pentaxenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof Etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heteroaryl group includes S, O, 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 another substituent.
  • the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
  • Carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.
  • heteroaryl group examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl and thiazolyl Group, isothiazolyl group, triazolyl group, furazanyl group, oxdiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxyyl group, triazinyl group, tetragenyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenan
  • the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkyl heteroaryl amine group; And it may be selected from the group consisting of arylheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore And a phenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • an arylene group means one having two bonding positions, that is, a divalent group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • a heteroarylene group means having two bond positions, ie, a divalent group, in a heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.
  • the phosphine oxide group may be specifically substituted with an aryl group, and the aryl group described above may be applied.
  • the phosphine oxide group may include a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” groups.
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 5.
  • N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted and containing one or more N.
  • N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group, and containing one or more N.
  • N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorene group, a dibenzofuran group and a dibenzothiophene group, It is a monocyclic or polycyclic heterocycle containing one or more N.
  • N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorene group, a dibenzofuran group and a dibenzothiophene group, It is a monocyclic or polycyclic heterocycle containing 1 or more than 3 N.
  • N-Het is a monocyclic hetero ring which is substituted or unsubstituted and includes one or more N.
  • N-Het is a substituted or unsubstituted, bicyclic or more heterocyclic ring containing one or more N.
  • N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted and containing two or more N.
  • N-Het is a bicyclic or higher polycyclic heterocycle including two or more N's.
  • Chemical Formula 1 is represented by one of the following Chemical Formulas 6 to 8.
  • X1 is CR11 or N
  • X2 is CR12 or N
  • X3 is CR13 or N
  • X4 is CR14 or N
  • X5 is CR15 or N
  • R11 to R15 and R17 to R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.
  • R12, R14 and R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.
  • Chemical Formula 9 may be selected from the following structural formulas.
  • Chemical Formula 10 may be represented by the following Chemical Formula 13.
  • Chemical Formula 11 may be represented by the following Chemical Formula 14.
  • Substituents of Chemical Formula 14 are as defined in Chemical Formula 11.
  • Chemical Formula 10 may be represented by the following Chemical Formula 15.
  • R27 is the same as or different from each other, and hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And at least two groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring,
  • Chemical Formula 12 may be represented by the following Chemical Formula 16.
  • Substituents of Formula 16 are as defined in Formula 12.
  • L is a direct bond or an arylene group.
  • L is a direct bond or a phenylene group.
  • R9 and R10 are hydrogen; Or deuterium.
  • R9 and R10 are hydrogen.
  • R1 to R8 are hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group, an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • R1 to R8 are hydrogen; heavy hydrogen; Aryl group; Heteroaryl group; Or a heteroaryl group substituted with an aryl group.
  • R1 to R8 are hydrogen; heavy hydrogen; Phenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups; Or a carbazole group substituted with phenyl.
  • R1 to R8 are hydrogen; heavy hydrogen; Phenyl group; Dibenzofuran group; Or a carbazole group substituted with phenyl.
  • two adjacent substituents of R1 to R8 combine with each other to form a substituted or unsubstituted ring.
  • two adjacent substituents of R1 to R8 combine with each other to form a ring unsubstituted or substituted with an aryl group or an alkyl group.
  • two adjacent substituents of R1 to R8 combine with each other to form an aromatic hydrocarbon ring or a heterocyclic ring which is unsubstituted or substituted with an aryl group or an alkyl group.
  • two adjacent substituents of R1 to R8 combine with each other to form an aromatic hydrocarbon ring or a heterocyclic ring which is unsubstituted or substituted with a phenyl group or a methyl group.
  • two adjacent substituents of R1 to R8 are bonded to each other to form a benzene ring; Indole substituted or unsubstituted with a phenyl group; Benzothiophene ring; Benzofuran ring; Or a substituted or unsubstituted indene ring with a methyl group.
  • R1 to R4 are the same as defined in Formula 1,
  • Y is O, S, NR or CR'R "
  • R, R ', R ", R31 and R32 are the same as or different from each other, hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted Or an unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted phosphine oxide group And two or more groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, f is an
  • Chemical Formula 17 may be selected from the following structural formulas.
  • R18 to R21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.
  • R18 to R21 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  • R18 to R21 is hydrogen
  • R17 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.
  • R17 and R22 are the same as or different from each other, and each independently an aryl group; Or a heteroaryl group.
  • R17 and R22 are the same as or different from each other, and are each independently an aryl group.
  • R17 and R22 are phenyl groups.
  • R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group; Or a substituted or unsubstituted heteroaryl group.
  • R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group.
  • R11 to R15 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with a methyl group; Or a heteroaryl group.
  • R11 to R15 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenylyl group; Naphthyl group; Dimethyl fluorenyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • R12 and R14 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group.
  • R12 and R14 are the same as or different from each other, and each independently a phenyl group, a biphenylyl group, a naphthyl group, a dimethylfluorenyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.
  • R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group.
  • R23 to R26 are the same as or different from each other, and each independently hydrogen; Or an aryl group.
  • R23 to R26 are the same as or different from each other, and each independently hydrogen; Phenyl group; Or a biphenylyl group.
  • R27 is hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.
  • R27 is hydrogen; heavy hydrogen; Or an aryl group.
  • R27 is hydrogen; Or an aryl group.
  • R27 is hydrogen; Or a phenyl group.
  • Y is O or S.
  • Y is NR and R is an aryl group.
  • Y is NR and R is a phenyl group.
  • Y is CR'R ", and R 'and R" are alkyl groups.
  • Y is CR'R ", and R 'and R" are methyl groups.
  • R31 is hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.
  • R31 is hydrogen; heavy hydrogen; Or an aryl group.
  • R31 is hydrogen; Or a phenyl group.
  • R32 is hydrogen; Or deuterium.
  • R32 is hydrogen
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to Chemical Formula 1. to provide.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light emitting device may be a blue organic light emitting device
  • the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the blue organic light emitting device.
  • the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the green organic light emitting device.
  • the organic light emitting device may be a red organic light emitting device
  • the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the red organic light emitting device.
  • 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 that one or more organic material layers are formed using the heterocyclic compound described above.
  • the heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, 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 multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as 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 may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.
  • the organic material layer may include a light emitting layer, the light emitting layer may include a host material, and the host material may include the heterocyclic compound.
  • the organic material layer including the heterocyclic compound may include the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used together with an iridium-based dopant.
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.
  • the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
  • the organic light emitting device of the present invention is a light emitting layer, a hole injection layer, a hole transport layer. It may further include one or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.
  • FIG. 1 to 3 illustrate a lamination order of an electrode and an organic material layer of an organic light emitting diode according to an exemplary embodiment of the present application.
  • these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can 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.
  • the present invention is not limited thereto, and as illustrated in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 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 transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present application is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the organic material layer including the compound of Formula 1 may further include other materials as necessary.
  • the anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • hole injection material a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst amine derivatives such as tris (4-carbazoyl-9-ylphenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m-tolyl) amino] triphenylamine (m- MTDATA), 1,3,5-tris [4- (3-methylphenylphenylamino) phenyl] benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid, or poly (line) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Camphor sulfonic acid or polyaniline / Poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.
  • TCTA tri
  • pyrazoline derivatives arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.
  • Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthhraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.
  • LiF is representatively used in the art, but the present application is not limited thereto.
  • a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed. In this case, two or more light emitting materials may be deposited and used as separate sources, or premixed and deposited as one source.
  • a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material.
  • a material which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which both the host material and the dopant material are involved in light emission may be used.
  • a host of the same series may be mixed, or a host of another series may be mixed.
  • any two or more kinds of materials of n-type host material or P-type host material can 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 bottom emission type, or a double-sided emission type according to a material used.
  • the heterocyclic compound according to the exemplary embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
  • Compound C was synthesized in the same manner as in the preparation of Compound 1, except that A and B of the following [Table 1] to [Table 7] were used as intermediates in Preparation Example 1.
  • Compound F was synthesized in the same manner as in the preparation of Compound 129, except that D and E of the following [Table 8] to [Table 14] were used as intermediates in Preparation Example 2.
  • a glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then treated with UVO for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to an organic deposition thermal deposition apparatus.
  • PT plasma cleaner
  • the light emitting layer was thermally vacuum deposited on it as follows.
  • the light emitting layer was Ir (ppy) 3 as a compound and a green phosphorescent dopant described in [Table 17].
  • (tris (2-phenylpyridine) iridium) was used to dope 400 ⁇ of the host by irradiating Ir (ppy) 3 to 7% of the light emitting layer deposition thickness.
  • 60 ⁇ of BCP was deposited using the hole blocking layer, and Alq 3 was deposited on the electron transport layer.
  • Alq 3 was deposited on the electron transport layer.
  • LiF lithium fluoride
  • an aluminum (Al) cathode is deposited to a thickness of 1200 ⁇ on the electron injecting layer to form a cathode.
  • a light emitting device was manufactured.
  • the electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement result. T 90 was measured at cd / m 2 . Properties of the organic electroluminescent device of the present invention are shown in [Table 17].
  • the efficiency, particularly the life characteristics, of the heterocyclic compound of the present invention are excellent.
  • Long life is the most important factor for the commercialization of materials.
  • the strong electron donor nature of the oxygen of dibenzofuran can reduce the device life due to the increased electron instability of the LUMO site, and the N-containing ring at the carbon positions 2,4 of the dibenzofuran is particularly due to the Ortho and para orientation.
  • the compound according to the present invention can improve the life of the device by the N-containing ring is located on carbon number 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2018/003532 2017-03-24 2018-03-26 Composé hétérocyclique et élément électroluminescent organique le comprenant Ceased WO2018174678A1 (fr)

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EP18772275.6A EP3604298B1 (fr) 2017-03-24 2018-03-26 Composé hétérocyclique et élément électroluminescent organique le comprenant
US16/496,878 US11527723B2 (en) 2017-03-24 2018-03-26 Heterocyclic compound and organic light emitting element comprising same
CN201880030210.1A CN110621668A (zh) 2017-03-24 2018-03-26 杂环化合物与包含其的有机发光装置
JP2019552245A JP7298910B2 (ja) 2017-03-24 2018-03-26 ヘテロ環化合物およびこれを含む有機発光素子

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KR1020180018782A KR20180108426A (ko) 2017-03-24 2018-02-14 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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WO2020071778A1 (fr) 2018-10-02 2020-04-09 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, composition pour couche organique de diode électroluminescente organique, et procédé de fabrication de diode électroluminescente organique
WO2020169241A1 (fr) 2019-02-18 2020-08-27 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
CN112789747A (zh) * 2019-08-09 2021-05-11 株式会社Lg化学 有机发光器件
WO2021180614A1 (fr) 2020-03-11 2021-09-16 Merck Patent Gmbh Appareil électroluminescent organique
CN113795488A (zh) * 2019-12-19 2021-12-14 株式会社Lg化学 新型化合物及包含其的有机发光器件
US11618751B1 (en) 2022-03-25 2023-04-04 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives
WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045851A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045842A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045843A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025073675A1 (fr) 2023-10-04 2025-04-10 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US12281112B2 (en) 2021-04-07 2025-04-22 Ventus Therapeutics U.S., Inc. Compounds for inhibiting NLRP3 and uses thereof
WO2025104058A1 (fr) 2023-11-16 2025-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
US12312351B2 (en) 2022-10-31 2025-05-27 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
WO2025119821A1 (fr) 2023-12-05 2025-06-12 Merck Patent Gmbh Composition de matériau pour dispositifs électroluminescents organiques
WO2025168515A1 (fr) 2024-02-06 2025-08-14 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques
US12441728B2 (en) 2023-10-04 2025-10-14 Ventus Therapeutics U.S., Inc. Pyridazine compounds for inhibiting NLRP3

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JP2019069938A (ja) * 2017-10-05 2019-05-09 ユニバーサル ディスプレイ コーポレイション エレクトロルミネセンスデバイスのための有機ホスト材料
EP3862353A4 (fr) * 2018-10-02 2022-08-10 LT Materials Co., Ltd. Composé hétérocyclique, diode électroluminescente organique le comprenant, composition pour couche organique de diode électroluminescente organique, et procédé de fabrication de diode électroluminescente organique
WO2020071778A1 (fr) 2018-10-02 2020-04-09 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, composition pour couche organique de diode électroluminescente organique, et procédé de fabrication de diode électroluminescente organique
US12103934B2 (en) 2018-10-02 2024-10-01 Lt Materials Co., Ltd. Heterocyclic compound, organic light emitting diode comprising same, composition for organic layer of organic light emitting diode, and method for manufacturing organic light emitting diode
WO2020169241A1 (fr) 2019-02-18 2020-08-27 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
CN112789747A (zh) * 2019-08-09 2021-05-11 株式会社Lg化学 有机发光器件
CN113795488B (zh) * 2019-12-19 2024-08-02 株式会社Lg化学 化合物及包含其的有机发光器件
CN113795488A (zh) * 2019-12-19 2021-12-14 株式会社Lg化学 新型化合物及包含其的有机发光器件
WO2021180614A1 (fr) 2020-03-11 2021-09-16 Merck Patent Gmbh Appareil électroluminescent organique
US12312350B2 (en) 2021-04-07 2025-05-27 Ventus Therapeutics U.S., Inc. Compounds for inhibiting NLRP3 and uses thereof
US12410167B2 (en) 2021-04-07 2025-09-09 Ventus Therapeutics U.S., Inc. Pyridazine compounds for inhibiting NLRP3
US12351578B2 (en) 2021-04-07 2025-07-08 Ventus Therapeutics U.S., Inc. Compounds for inhibiting NLRP3 and uses thereof
US12281112B2 (en) 2021-04-07 2025-04-22 Ventus Therapeutics U.S., Inc. Compounds for inhibiting NLRP3 and uses thereof
US11618751B1 (en) 2022-03-25 2023-04-04 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives
US12168657B2 (en) 2022-03-25 2024-12-17 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives
US12195460B2 (en) 2022-03-25 2025-01-14 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
US12398136B2 (en) 2022-10-31 2025-08-26 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
US12331048B2 (en) 2022-10-31 2025-06-17 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
US12312351B2 (en) 2022-10-31 2025-05-27 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045843A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
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WO2025073675A1 (fr) 2023-10-04 2025-04-10 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US12441728B2 (en) 2023-10-04 2025-10-14 Ventus Therapeutics U.S., Inc. Pyridazine compounds for inhibiting NLRP3
WO2025104058A1 (fr) 2023-11-16 2025-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025119821A1 (fr) 2023-12-05 2025-06-12 Merck Patent Gmbh Composition de matériau pour dispositifs électroluminescents organiques
WO2025168515A1 (fr) 2024-02-06 2025-08-14 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques

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