WO2018174679A1 - Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique - Google Patents

Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique Download PDF

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WO2018174679A1
WO2018174679A1 PCT/KR2018/003534 KR2018003534W WO2018174679A1 WO 2018174679 A1 WO2018174679 A1 WO 2018174679A1 KR 2018003534 W KR2018003534 W KR 2018003534W WO 2018174679 A1 WO2018174679 A1 WO 2018174679A1
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group
substituted
unsubstituted
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light emitting
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PCT/KR2018/003534
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English (en)
Korean (ko)
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노영석
차주현
김동준
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희성소재(주)
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Priority claimed from KR1020180018786A external-priority patent/KR101943428B1/ko
Application filed by 희성소재(주) filed Critical 희성소재(주)
Priority to US16/496,712 priority Critical patent/US11515487B2/en
Priority to EP18770573.6A priority patent/EP3604296B1/fr
Priority to CN201880024904.4A priority patent/CN110506042A/zh
Priority to JP2019552108A priority patent/JP7062305B2/ja
Publication of WO2018174679A1 publication Critical patent/WO2018174679A1/fr

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    • 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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to an organic light emitting device and a composition for an organic material layer of the organic light emitting device.
  • 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.
  • An exemplary embodiment of the present application is an organic light emitting device including a first electrode, a second electrode and at least one organic material layer provided between the first electrode and the second electrode,
  • an organic light emitting device in which at least one layer of the organic material layer simultaneously contains a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 below.
  • 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,
  • R a and R b are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R10, R c and R d 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 silyl 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 unsub
  • another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device, wherein the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are simultaneously included.
  • one embodiment of the present application preparing a substrate; Forming a first electrode on the substrate; Forming at least one organic material layer on the first electrode; And forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application.
  • forming the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application.
  • Provided is a method of manufacturing an organic light emitting device.
  • the heterocyclic compound according to the exemplary embodiment of the present application may be used as an organic material layer material of the organic light emitting device.
  • the heterocyclic compound may be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a charge generating layer, etc. in an organic light emitting device.
  • the heterocyclic compound represented by Formula 1, and the compound represented by Formula 2 may be used simultaneously as a material of the light emitting layer of the organic light emitting device.
  • the driving voltage of the device is lowered, the light efficiency is improved, and the compound is thermally stabilized. Lifespan characteristics can be improved.
  • an N-containing ring is substituted at carbon number 1 of the dibenzofuran structure, and a carbazole structure is substituted in the benzene in which the N-containing ring is not substituted in the dibenzofuran structure.
  • the structure has a more electronic stability structure, thereby improving 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.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR 104 R 105 R 106 , R 104 to R 106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.
  • 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.
  • An exemplary embodiment of the present application is an organic light emitting device including a first electrode, a second electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is represented by Chemical Formula 1 It provides an organic light emitting device comprising a heterocyclic compound represented by, and a heterocyclic compound represented by the formula (2) at the same time.
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 3 to 6.
  • 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 7 to 9.
  • 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 10 may be selected from the following structural formulas.
  • 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 12 may be represented by the following Chemical Formula 15.
  • Chemical Formula 11 may be represented by the following Chemical Formula 16.
  • 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 13 may be represented by the following Chemical Formula 17.
  • Substituents of Formula 17 are as defined in Formula 13.
  • 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 18 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
  • R c and R d in Chemical Formula 2 may be hydrogen.
  • R a and R b in Formula 2 may be the same as or different from each other, and each independently a substituted or unsubstituted aryl group.
  • R a and R b in Formula 2 may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group.
  • R a and R b in Formula 2 may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group.
  • R a and R b in Formula 2 are the same as or different from each other, and each independently C1 to C40 alkyl group, C6 to C40 aryl group, -CN and -SiR 101 R 102 R 103 It may be a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of.
  • R a and R b of Chemical Formula 2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, -CN, or -SiR 101 R 102 R 103 ; A biphenyl group unsubstituted or substituted with a phenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Spirobifluorene group; Or a triphenylene group.
  • R 101, R 102, and R 103 in Formula 2 may be a phenyl group.
  • the exciplex phenomenon is a phenomenon in which energy of a HOMO level of a donor (p-host) and an acceptor (n-host) LUMO level are emitted by electron exchange between two molecules.
  • RISC Reverse Intersystem Crossing
  • a donor (p-host) with good hole transporting capacity and an acceptor (n-host) with good electron transporting capacity are used as a host of the light emitting layer, holes are injected into the p-host, and electrons are injected into the n-host. Can be lowered, thereby improving the lifespan.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto.
  • the heterocyclic compound has a high glass transition temperature (Tg) is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.
  • the heterocyclic compound according to one embodiment of the present application may be prepared by a multistage chemical reaction. Some intermediate compounds may be prepared first, and compounds of formula 1 or 2 may be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application may be prepared based on the preparation examples described below.
  • another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device, wherein the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are simultaneously included.
  • the weight ratio of the heterocyclic compound represented by Formula 1 in the composition: the compound represented by Formula 2 may be 1:10 to 10: 1, 1: 8 to 8: 1, and 1: 5 to 5 : 1, and 1: 2 to 2: 1, but is not limited thereto.
  • the composition may be used when forming the organic material of the organic light emitting device, and particularly preferably used when forming the host of the light emitting layer.
  • the composition may be a form in which two or more compounds are simply mixed, and may be mixed with a powder material before forming an organic material layer of the organic light emitting device, or may be mixed with a compound that is in a liquid state at an appropriate temperature or more.
  • the composition is in a solid state below the melting point of each material, and can be maintained in the liquid phase by adjusting the temperature.
  • composition may further include materials known in the art such as solvents, additives, and the like.
  • An organic light emitting device is a conventional organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2. It can be produced by a method and a material for manufacturing a light emitting device.
  • the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an 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 light emitting device includes a first electrode, a second electrode and one or more organic material layers provided between the first electrode and the second electrode, one or more of the organic material layers It includes a heterocyclic compound represented by the formula (1), and a heterocyclic compound represented by the formula (2).
  • 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, and the heterocyclic compound according to Formula 1 and the heterocyclic compound according to Formula 2 may be used as a material of the blue organic light emitting device. .
  • the organic light emitting device may be a green organic light emitting device, the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be used as a material of the green organic light emitting device. .
  • the organic light emitting device may be a red organic light emitting device
  • the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be used as a material of the red organic light emitting device.
  • 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.
  • the organic material layer includes at least one layer of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one layer of the hole blocking layer, the electron injection layer, and the electron transport layer is represented by Chemical Formula 1
  • Chemical Formula 1 Provided is an organic light emitting device comprising a heterocyclic compound represented, and a heterocyclic compound represented by the formula (2) at the same time.
  • the organic material layer includes an emission layer
  • the emission layer includes an organic light emitting device including a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 at the same time. to provide.
  • the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material is a heterocyclic compound represented by Chemical Formula 1, and a heterocyclic compound represented by Chemical Formula 2 It provides an organic light emitting device comprising at the same time.
  • 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.
  • forming the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application.
  • the forming of the organic material layer may be performed by pre-mixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 by using a thermal vacuum deposition method. It provides a method for producing a phosphorus organic light emitting device.
  • the pre-mixed means that the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 are first mixed with each other in a single park before being deposited on the organic material layer.
  • the premixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.
  • 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 sulfonicacid or polyaniline / poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.
  • TCTA
  • 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 may be pre-mixed and deposited as one source after premixing.
  • 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 n-type host materials or p-type host materials may be selected and used as the host material of the light emitting layer.
  • the organic light emitting device may be a top emission type, a 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 washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated 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 deposited with a compound of Formula 1 and a compound of Formula 2 at 400 kV from each individual source as a host and the green phosphorescent dopant was deposited by 7% doping of Ir (ppy) 3 .
  • 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.
  • lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 ⁇ thick.
  • an aluminum (Al) cathode is deposited to a thickness of 1,200 ⁇ on the electron injecting layer to form a cathode.
  • An electroluminescent device was manufactured.
  • 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 washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated 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 pre-mixed with a compound of Formula 1 and a compound of Formula 2 as a host, and deposited 400 kPa in one park, and a green phosphorescent dopant was deposited by doping Ir (ppy) 3 with 7%.
  • 60 B of BCP was deposited as the hole blocking layer, and 200 ⁇ of Alq 3 was deposited thereon as the electron transport layer.
  • lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 ⁇ thick.
  • an aluminum (Al) cathode is deposited to a thickness of 1,200 ⁇ on the electron injecting layer to form a cathode.
  • An electroluminescent device was manufactured.
  • the electroluminescent (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 results. T 90 was measured at cd / m 2 .
  • Table 19 shows an example of simultaneously depositing two host compounds of Experimental Example 1 as a separate source
  • Table 20 shows an example of pre-mixing two light emitting layer compounds of Experimental Example 2 and depositing them as one source after premixing.
  • Table 18 is an example of applying a single host material in Experimental Example 1.
  • Example 39 1: 1 3.41 118.6 (0.275, 0.676) 507
  • the exciplex phenomenon is a phenomenon in which energy of a HOMO level of a donor (p-host) and an acceptor (n-host) LUMO level are emitted by electron exchange between two molecules.
  • RISC Reverse Intersystem Crossing
  • a donor (p-host) with good hole transporting capacity and an acceptor (n-host) with good electron transporting capacity are used as a host of the light emitting layer, holes are injected into the p-host, and electrons are injected into the n-host. Can be lowered, thereby improving the lifespan.

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Abstract

La présente invention concerne un élément électroluminescent organique comprenant une première électrode, une seconde électrode et une ou plusieurs couches de matériau organique disposées entre la première électrode et la seconde électrode, au moins une couche des couches de matériau organique contenant à la fois un composé hétérocyclique représenté par la formule chimique 1 et un composé hétérocyclique représenté par la formule chimique 2, et une composition pour une couche de matériau organique dans l'élément électroluminescent organique.
PCT/KR2018/003534 2017-03-24 2018-03-26 Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique WO2018174679A1 (fr)

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US16/496,712 US11515487B2 (en) 2017-03-24 2018-03-26 Organic light emitting element and composition for organic material layer in organic light emitting element
EP18770573.6A EP3604296B1 (fr) 2017-03-24 2018-03-26 Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique
CN201880024904.4A CN110506042A (zh) 2017-03-24 2018-03-26 有机发光装置以及用于有机发光装置中的有机材料层的组成物
JP2019552108A JP7062305B2 (ja) 2017-03-24 2018-03-26 有機発光素子および有機発光素子の有機物層用組成物

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CN114096535A (zh) * 2019-11-21 2022-02-25 Lt素材株式会社 杂环化合物、包括其的有机发光元件、用于有机发光元件的有机层的组成物及有机发光元件制造方法
JP2023500759A (ja) * 2019-11-21 2023-01-11 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法
WO2021180614A1 (fr) 2020-03-11 2021-09-16 Merck Patent Gmbh Appareil électroluminescent organique
WO2021180625A1 (fr) 2020-03-11 2021-09-16 Merck Patent Gmbh Appareil électroluminescent organique
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

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