WO2019221445A1 - Composé et diode électroluminescente organique le comprenant - Google Patents

Composé et diode électroluminescente organique le comprenant Download PDF

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WO2019221445A1
WO2019221445A1 PCT/KR2019/005554 KR2019005554W WO2019221445A1 WO 2019221445 A1 WO2019221445 A1 WO 2019221445A1 KR 2019005554 W KR2019005554 W KR 2019005554W WO 2019221445 A1 WO2019221445 A1 WO 2019221445A1
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formula
group
compound
layer
light emitting
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Korean (ko)
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김서연
박종호
서상덕
이동훈
박태윤
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주식회사 엘지화학
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention provides a compound represented by Formula 1 and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification is intended to provide an organic light emitting device having a low driving voltage, high luminous efficiency, good lifespan characteristics, or high color purity by including the compound represented by Chemical Formula 1 in an organic light emitting device.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • Adjacent two of Y1 to Y4 are carbon atoms respectively bonded to two '*' of Formula D, and one of two that does not bond to '*' of Formula D of Y1 to Y4 is N and the other is N or CR1,
  • R1 to R3, Rm, Rn, Rx, Ry and Rz are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group; Alkenyl groups; Alkynyl group; Halogen group; Hydroxyl group; An alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; Or a heteroaryl group or deuterium combined with an adjacent group; An alkyl group; Alkenyl groups; Alkynyl group; Halogen group; Hydroxyl group; An alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; And a ring unsubstituted or substituted with one or more substituents selected from the group consisting of heteroaryl groups,
  • a is an integer of 0-4, and when a is 2 or more, some R ⁇ 3> is the same or different from each other.
  • An exemplary embodiment of the present specification 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 the compound represented by Chemical Formula 1 is 1 It provides an organic light emitting device that is included in at least one layer of the organic material layer of the layer or more.
  • the efficiency of the device is improved, the driving voltage of the device is low, or the lifespan characteristics of the device are improved. Can be improved.
  • FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron transport layer 9, an electron injection and
  • An example of the organic light emitting element consisting of the transport layer 10 and the cathode 4 is shown.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent.
  • the position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent is substituted.
  • substituents are two or more, two or more substituents may be the same or different from each other.
  • an alkyl group means a straight or branched chain saturated hydrocarbon. Although carbon number of the said alkyl group is not specifically limited, It is preferable that it is 1-20. According to an exemplary embodiment, the alkyl group has 1 to 15 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chain or cyclic.
  • chain alkyl group examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl and isopentyl Neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like. It
  • carbon number of the said cyclic alkyl group is not specifically limited, It is preferable that it is 3-20. According to an exemplary embodiment, the cycloalkyl group has 3 to 16 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 12 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms.
  • cycloalkyl group examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethyl Cyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • the alkenyl group represents a hydrocarbon group having a carbon-carbon double bond, and the carbon number is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples of alkenyl groups include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl.
  • the alkynyl group represents a hydrocarbon group having a carbon-carbon triple bond, and the carbon number is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkynyl group has 2 to 20 carbon atoms. Specific examples of the alkynyl group include metainyl, ethynyl, 2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-pentynyl, and the like, but are not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkoxy group means a group in which an alkyl group is bonded to an oxygen atom, and the carbon number is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. Description of the aforementioned alkyl group may be applied to the alkyl group of the alkoxy group.
  • the aryloxy group means a group in which an aryl group is bonded to an oxygen atom.
  • Specific examples of the aryloxy group include, but are not limited to, phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, and the like. Description of the aryl group described below may be applied to the aryl group of the aryloxy group.
  • the silyl group may be represented by a chemical formula of -SiR 11 R 12 R 13 , wherein R 11 to R 13 are each independently hydrogen; An alkyl group; Or an aryl group.
  • the alkylsilyl group means a silyl group substituted with an alkyl group
  • the arylsilyl group means a silyl group substituted with an aryl group.
  • the silyl group includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.
  • an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, and the like.
  • polycyclic aryl group examples include naphthyl, anthracenyl, phenanthrenyl, perrylenyl, fluoranthenyl, triphenylenyl, penalenyl, pyrenyl, tetrasenyl, chrysenyl, pentansenyl, fluorenyl, indenyl, Acenaphthyl, benzofluorenyl, spirofluorenyl, and the like.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • substituted fluorenyl group , , , , , , And Etc., but is not limited thereto.
  • the heteroaryl group is a ring group containing one or more of N, O and S as heteroatoms, and carbon number is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms.
  • heteroaryl groups include thiophenyl, furanyl, imidazolyl, thiazolyl, oxazolyl, oxdiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, Acenaphthoquinoxalinyl, indenoquinazolinyl, indenoisoquinolinyl, indenoquinolinyl, pyridoindole, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthala Genyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl,
  • 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.
  • the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle, substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.
  • the hydrocarbon ring means a ring composed only of carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.
  • the heterocycle means a ring including at least one of heteroatoms, and the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms as a non-aromatic ring.
  • aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. It is not limited to this.
  • the aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms.
  • aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, penalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene and the like, but are not limited thereto.
  • the aliphatic heterocycle means an aliphatic ring containing at least one of heteroatoms.
  • Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxane, azocaine , Thiocaine and the like, but is not limited thereto.
  • the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, acridine, phenan Tridine, diazanaphthalene, deazaindene, indole, indolizin, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran,
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • adjacent two of Y1 to Y4 are Y1 and Y2; Y2 and Y3; Or Y3 and Y4.
  • R1 is hydrogen; heavy hydrogen; Or an alkyl group.
  • R1 is hydrogen; Or methyl.
  • R1 is hydrogen
  • R2 is hydrogen; Or an alkyl group having 1 to 10 carbon atoms.
  • R2 is hydrogen; Or an alkyl group having 1 to 8 carbon atoms.
  • R2 is hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • R2 is hydrogen; methyl; Or isopropyl.
  • R3 is hydrogen; heavy hydrogen; Or an alkyl group, or combine with an adjacent group to form a ring unsubstituted or substituted with one or more substituents of deuterium and an alkyl group.
  • R3 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms or combined with an adjacent group to form a benzene ring unsubstituted or substituted with one or more substituents among deuterium and an alkyl group having 1 to 10 carbon atoms.
  • R3 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms, or combine with an adjacent group to form a benzene ring unsubstituted or substituted with one or more substituents among deuterium and an alkyl group having 1 to 6 carbon atoms.
  • R3 is hydrogen; heavy hydrogen; methyl; Or t-butyl, or combine with adjacent groups to form a benzene ring.
  • the a is 2.
  • the a is 3.
  • Rm and Rn are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group.
  • Rm and Rm are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • Rm and Rn are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 3 carbon atoms.
  • Rm and Rn are the same as or different from each other, and each independently hydrogen; Or methyl.
  • Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 10 carbon atoms; Or a cycloalkyl group having 3 to 10 carbon atoms.
  • Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 8 carbon atoms; Or a cycloalkyl group having 3 to 8 carbon atoms.
  • Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 6 carbon atoms; Or a cycloalkyl group having 3 to 6 carbon atoms.
  • Rx and Rz are the same as or different from each other, and each independently methyl; Isopropyl; 1-ethylpropyl; t-butyl; Or cyclohexyl.
  • Ry is hydrogen
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • Adjacent two of Y2 to Y4 are carbon atoms respectively bonded to two '*' of Formula D, and one of Y2 to Y4 not bonded to '*' of Formula D is N or CR1,
  • Y3 and Y4 are each a carbon atom bonded to two '*' of Formula D, respectively, Y1 is N or CR1,
  • Y1 and Y2 are each a carbon atom bonded to two '*' of Formula D, and Y4 is N or CR1,
  • Adjacent two of Y1 to Y3 are carbon atoms respectively bonded to two '*' of Formula D, and one of Y1 to Y3 not bonded to '*' of Formula D is N or CR1,
  • R1, R3, Rx, Ry, Rz and a are the same as defined in the formula (1).
  • one of the Y2 to Y4 does not combine with '*' of the formula D is CR1.
  • Y1 is CR1.
  • Y4 is CR1.
  • one of Y1 to Y3 that does not combine with '*' of Chemical Formula D is CR1.
  • Chemical Formula 1 is represented by the following Chemical Formula 2-1 or Chemical Formula 2-2.
  • One of Y1 and Y2 is N, the other is N or CR1,
  • Chemical Formula 1 is represented by the following Chemical Formula 3-1 or Chemical Formula 3-2.
  • One of Y1 and Y4 is N, the other is N or CR1,
  • Chemical Formula 1 is represented by the following Chemical Formula 4-1 or Chemical Formula 4-2.
  • One of Y3 and Y4 is N, the other is N or CR1,
  • Chemical Formula 1 is represented by the following Chemical Formula 5.
  • R 4 is hydrogen; heavy hydrogen; An alkyl group; Alkenyl groups; Alkynyl group; Halogen group; Hydroxyl group; An alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; Or a heteroaryl group,
  • b is an integer of 0-6, and when b is 2 or more, some R ⁇ 4> is the same or different from each other.
  • R4 is hydrogen; heavy hydrogen; Or an alkyl group.
  • R4 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms.
  • R4 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • R4 is hydrogen; heavy hydrogen; methyl; Or t-butyl.
  • R3 is an alkyl group, a is 2, or (2) Formula 1 is represented by Formula 5.
  • the Is a group represented by the following formula 6-1 or 6-2.
  • R31 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group; Alkenyl groups; Alkynyl group; Halogen group; Hydroxyl group; An alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; Or a heteroaryl group,
  • c is an integer of 0 to 4, and when c is 2 or more, R 37 is the same as or different from each other.
  • At least two of the R31 to R34 are alkyl groups.
  • R31 and R33 are hydrogen.
  • R32 and R34 are the same as or different from each other, and each independently an alkyl group.
  • R32 and R34 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms.
  • R32 and R34 are the same as or different from each other, and are each independently methyl.
  • R35 is hydrogen
  • R37 is hydrogen
  • R36 is hydrogen; Or an alkyl group.
  • R36 is hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • R36 is hydrogen; Or t-butyl.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • the compound represented by Chemical Formula 2-1 may be prepared by the method of the following Formula 1.
  • Formula 1 is an example of a method of forming a compound represented by Formula 2-1, and a method of synthesizing the compound represented by Formula 2-1 is not limited to Formula 1, and some synthesis steps may be described in the art. It may be by a method known in the art.
  • the present specification provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • An exemplary embodiment of the present specification provides 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 the compound represented by Chemical Formula 1 is Provided is an organic light emitting device included in at least one layer of at least one organic material layer.
  • the organic light emitting diode of the present specification may include a single layer or a multilayer organic material layer between the first electrode and the second electrode.
  • the organic material layer included in the organic light emitting device of the present invention may include a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, and an electron transport layer. It may be at least one of the layers to be injected simultaneously.
  • the compound represented by Formula 1 is included in one or more layers of one or more light emitting layers.
  • the light emitting layer including the compound represented by Formula 1 is a red light emitting layer.
  • each light emitting layer may have a different color.
  • the organic light emitting device including the compound represented by Formula 1 is a red organic light emitting device.
  • the compound represented by Chemical Formula 1 is included in an amount of 1 part by weight to 10 parts by weight or less based on 100 parts by weight of the total amount of the light emitting layer including the compound.
  • the emission layer including the compound represented by Formula 1 further includes a host material.
  • the host material included in the emission layer including the compound represented by Chemical Formula 1 is a carbazole derivative compound or an aromatic polycyclic compound including N.
  • the light emitting layer including the compound represented by Chemical Formula 1 further includes a host compound represented by the following Chemical Formula H.
  • G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Silyl groups; Aryl group; Or a heteroaryl group, or combine with an adjacent group to form a ring,
  • G3 and G4 are the same as or different from each other, and each independently 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 alkyl group, an aryl group or a heteroaryl group,
  • b1 is an integer of 0 to 7, and when b1 is 2 or more, a plurality of G1s are the same as or different from each other,
  • b2 is an integer of 0-7, and when b2 is 2 or more, some G2 is same or different from each other.
  • G1 combines with an adjacent group to form a benzene ring.
  • G4 is a heteroaryl group which is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group and includes N.
  • G4 is a heteroaryl group which is unsubstituted or substituted with an alkyl group, an aryl group or a heteroaryl group, and includes a 6-membered ring including N.
  • Chemical Formula H is represented by the following Chemical Formula H-1.
  • G1 to G4 and b2 are the same as those defined in Formula H,
  • b3 is an integer of 0-9, and when b3 is two or more, some G1 is the same or different from each other.
  • the compound represented by Formula H is the following compound.
  • the compound represented by Chemical Formula 1 is included in at least one layer of a hole injection layer, a hole transport layer, a hole injection layer and a hole control layer at the same time.
  • the compound represented by Chemical Formula 1 is included in at least one layer of an electron injection layer, an electron transport layer, a layer simultaneously performing electron injection and transport, and an electron control layer.
  • the organic light emitting device may be an organic light emitting device having a normal structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • FIGS. 1 and 2 The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • an organic light emitting diode may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • the compound represented by Formula 1 is included in the organic material layer (3).
  • the organic light emitting diode includes a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, and a second hole transport layer 7. ), An emission layer 8, an electron transport layer 9, an electron injection and transport layer 10, and a cathode 4.
  • the compound represented by Formula 1 is included in the light emitting layer (8).
  • the structure of the organic light emitting diode according to the exemplary embodiment of the present specification is not limited to FIGS. 1 and 2, and may be any one of the following structures.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD, physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or an alloy thereof on the substrate It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • sputtering e-beam evaporation
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention 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); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes received from the electrode into the light emitting layer or an adjacent layer provided toward the light emitting layer.
  • the hole injection material has the ability to transport holes, has an effect of hole injection at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and transfers excitons generated from the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use the compound which prevents and is excellent in thin film formation ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene Organic, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together.
  • the hole control layer is a layer for preventing the flow of the electrons to the anode to the light emitting layer and to control the flow of holes flowing into the light emitting layer to control the performance of the entire device.
  • the hole control material a compound having the ability to prevent the inflow of electrons from the light emitting layer to the anode and to control the flow of holes injected to the light emitting layer or the light emitting material is preferable.
  • an arylamine-based organic material may be used as the hole control layer, but is not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material examples include a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include dibenzofuran derivatives, ladder type furan compounds, Pyrimidine derivatives, and the like.
  • the dopant material of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like.
  • aromatic amine derivative pyrene, anthracene, chrysene, periplanthene and the like having an arylamine group may be used as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group.
  • the styrylamine compound a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used.
  • styrylamine compound examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex may be an iridium complex, a platinum complex, or the like, but is not limited thereto.
  • the electron control layer is a layer that blocks the flow of holes from the light emitting layer to the cathode and controls the performance of the entire device by adjusting the electrons flowing into the light emitting layer.
  • the electron adjusting material a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control the electrons injected into the light emitting layer or the light emitting material is preferable.
  • the electron control material an appropriate material may be used according to the configuration of the organic material layer used in the device.
  • the electron control layer is positioned between the light emitting layer and the cathode, preferably provided in direct contact with the light emitting layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable.
  • Examples of the electron transporting material include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material, as used according to the prior art.
  • the negative electrode material includes a material having a low work function; And aluminum layers or silver layers. Examples of the material having a low work function include cesium, barium, calcium, ytterbium and samarium, and after forming a layer from the material, an aluminum layer or a silver layer may be formed on the layer.
  • the electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer.
  • the electron injecting material has an ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect on a light emitting layer or a light emitting material, and transfers excitons generated in the light emitting layer to a hole injection layer or a hole injection material. It is preferable to use a compound which prevents the addition and has excellent thin film forming ability.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like Derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • iridium chloride (30 g, 0.1 mol) and intermediate A1 (54 g, 0.26 mol) were added to 1500 ml of 2-ethoxyethanol and 500 ml of distilled water in a round-bottomed flask at 130 ° C for 24 hours. Was stirred under heating. The mixture was cooled to room temperature, filtered and washed with 2 L of ethanol to prepare solid Compound A2 (34.3 g, yield 53%).
  • the intermediate A4 was prepared by the same method as the method of preparing intermediate A2, except that intermediate A3 was used instead of intermediate A1. (31 g, yield 48%)
  • the intermediate A7 was prepared by the same method as the method of preparing intermediate A2, except that intermediate A6 was used instead of intermediate A1. (31 g, yield 48%)
  • the intermediate A8 was prepared by the same method as the method of preparing intermediate A5, except that ethanethioamide was used instead of acetamide. (37 g, 61% yield)
  • the intermediate A10 was prepared by the same method as the method of preparing intermediate A2, except that intermediate A9 was used instead of intermediate A1. (45 g, yield 50%)
  • the intermediate A13 was prepared by the same method as the method of preparing intermediate A2, except that intermediate A12 was used instead of intermediate A1. (33g, yield 46%)
  • Intermediate A16 was prepared by the same method as the method of preparing intermediate A1, except that naphthalen-2-ylboronic acid was used. (36 g, yield 88%)
  • the intermediate A21 was prepared by the same method as the method of preparing intermediate A2, except that intermediate A20 was used instead of intermediate A1. (24 g, yield 50%)
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 50 kPa on the thus prepared ITO transparent electrode to form a hole injection layer.
  • the following HT1 compound for transporting holes was vacuum deposited thereon, and the following HT2 compound was subsequently deposited to form a first (700 GPa) and a second hole transport layer (200 GPa).
  • the following H1 compound and compound 1 were vacuum-deposited to form a light emitting layer (300 ⁇ ) on the second hole transport layer so that Compound 1 contained 3 parts by weight based on 100 parts by weight of the total weight of the following H1 compound and Compound 1.
  • the following E0 compound was thermally vacuum deposited (300 kPa) sequentially with an electron injection and transport layer.
  • an organic light emitting device was manufactured.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the deposition rate of LiF was 0.2 ⁇ / sec
  • the deposition rate of aluminum was maintained at 3 ⁇ / sec to 7 ⁇ / sec.
  • the organic light emitting diodes of Examples 2 to 12 were prepared in the same manner as in Example 1, except that the compounds shown in Table 1 below were used as phosphorescent dopants, respectively, in forming the emission layer.
  • the organic light emitting diodes of Comparative Examples 1 to 3 were manufactured in the same manner as in Example 1, except that Compound 1, instead of Compound 1, was used as the phosphorescent dopant to form the EML.
  • T95 means the time taken for the luminance to decrease to 95% from the initial luminance.
  • ⁇ max means the maximum emission wavelength.
  • the organic light emitting device using the compound of the present invention exhibits high purity red light emission and has low voltage, high efficiency and long life characteristics.
  • the LUMO energy levels of the compounds of the present invention are mainly distributed in the ring containing pyridazine, pyrimidine, pyrazine and the like of the main ligand. Since the main ligand of the compound of the present invention includes a structure containing one or more nitrogen atoms having a high electronegativity in the pyridine ring, the main ligand is lower in LUMO level than the compound containing pyridine.
  • Examples 1 to 12 using the compound of the present invention showed a maximum emission wavelength in the longer wavelength region than the dopants of the oxazolopyridine, cyazolopyridine and cynopyrimidine structures of Comparative Examples 1 to 3.
  • red color with good color purity and high efficiency and long life In Example 6, the lifespan was increased by about 2 times compared to Comparative Example 1, and the low driving voltage and high efficiency were maintained.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/005554 2018-05-14 2019-05-14 Composé et diode électroluminescente organique le comprenant WO2019221445A1 (fr)

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