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WO2019164341A1 - Composé spiro et dispositif électroluminescent organique le comprenant - Google Patents

Composé spiro et dispositif électroluminescent organique le comprenant Download PDF

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WO2019164341A1
WO2019164341A1 PCT/KR2019/002225 KR2019002225W WO2019164341A1 WO 2019164341 A1 WO2019164341 A1 WO 2019164341A1 KR 2019002225 W KR2019002225 W KR 2019002225W WO 2019164341 A1 WO2019164341 A1 WO 2019164341A1
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group
substituted
unsubstituted
light emitting
compound
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Korean (ko)
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김진주
홍완표
서상덕
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LG Chem Ltd
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LG Chem Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
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    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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 a spiro compound and an organic light emitting device formed using the spiro compound.
  • 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 is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present specification provides a spiro compound and an organic light emitting device including the same.
  • R1 is a substituent represented by Formula 2 or 3
  • R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted Aryl group or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring,
  • L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • a, b and f are each an integer of 0 to 7,
  • c is an integer from 0 to 3
  • L is a substituted or unsubstituted heteroarylene group
  • d is an integer of 0 to 8
  • e is an integer from 0 to 3
  • R2 is the same as or different from each other
  • R3 is the same as or different from each other
  • R4 is the same as or different from each other
  • R5 is the same as or different from each other
  • R6 is the same as or different from each other.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the spiro compound.
  • the spiro compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device having thermal stability, and by using the same, the efficiency of the organic light emitting device may be improved, and the driving voltage and / or lifespan characteristics may be improved. Do.
  • the triplet energy is increased by fixing the substituent at the 4,4 'position, and P-type and N-type substituents are introduced at the substitution positions, respectively, to be applied as a bipolar host.
  • FIG. 1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • the present specification provides a spiro compound represented by Chemical Formula 1.
  • 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.
  • substituted or unsubstituted is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or one or two or more substituents selected from the group consisting of, or two or more substituents among the substituents exemplified above, or a substituent.
  • a substituent to which two or more substituents are linked may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • the halogen group may be a fluoro group, a chloro group, a bromo group, an iodo group, or the like.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • arylene group is the same as the definition of an aryl group except that it is divalent.
  • heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.
  • Chemical Formula 2 is represented by any one of the following Chemical Formulas 4 to 6.
  • R4 is as defined in Chemical Formula 1,
  • R7 to R9 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted Aryl group or substituted or unsubstituted heteroaryl group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted Aryl group or substituted or unsubstituted heteroaryl group,
  • d is an integer of 0 to 7
  • g is an integer from 0 to 8
  • h is an integer from 0 to 7
  • i is an integer from 0 to 10
  • R7 is the same as or different from each other
  • R8 is the same as or different from each other
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 7 to 9.
  • R2 to R6 and a to f are as defined in Formulas 1 to 3,
  • R9 is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted aryl group, or substituted or unsubstituted hetero An aryl group,
  • Ar3 is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted aryl group, or substituted or unsubstituted hetero An aryl group,
  • i is an integer from 0 to 10, and when i is plural, R9 are the same as or different from each other.
  • L is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
  • L is a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group containing N, O, or S having 3 to 20 carbon atoms.
  • L is a direct bond, a monocyclic arylene group having 6 to 20 carbon atoms, a polycyclic arylene group having 10 to 20 carbon atoms, or N, O, or S containing 3 to 20 carbon atoms Heteroarylene group.
  • L is a direct bond, a monocyclic arylene group having 6 to 20 carbon atoms, a polycyclic arylene group having 10 to 20 carbon atoms, or N, O, or S containing 3 to 20 carbon atoms Heteroarylene group.
  • L is a direct bond, a bivalent phenyl group, a bivalent biphenyl group, a bivalent terphenyl group, a bivalent naphthyl group, a bivalent fluorene group, a bivalent carbazole group, a divalent triazine group, A divalent pyrimidine group, a bivalent pyridine group, a bivalent dibenzothiophene group, or a bivalent dibenzofuran group.
  • L is a direct bond, a divalent phenyl group, or a divalent dibenzofuran group.
  • L is a substituted dibenzofuran group.
  • L is an unsubstituted dibenzofuran group.
  • R2 to R10 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or An unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring.
  • the R2 to R10 are the same as or different from each other, and each independently hydrogen; Nitrile group; Halogen group; An alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; Aryl groups having 6 to 20 carbon atoms; Or a substituted or unsubstituted N, O, or S-containing heteroaryl group having 3 to 10 carbon atoms.
  • the R2 to R10 are the same as or different from each other, and each independently hydrogen; Nitrile group; Halogen group; An alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; Aryl groups having 6 to 20 carbon atoms; Or an N, O, or S-containing heteroaryl group having 3 to 10 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
  • the R2 to R10 are the same as or different from each other, and each independently hydrogen; Nitrile group; F; Cl; Br; I; Methyl group; Ethyl group; Profile group; Isopropyl group; Butyl group; Terbutyl group; Pentyl group; Hexyl group; Heptyl group; Octyl group; Nonyl group; Decyl group; A silyl group unsubstituted or substituted with a methyl group; Methoxy group; Ethoxy group; Propoxy group; Butoxy group; Terbutoxy group; Pentoxy group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene groups; Phenanthrene group; Pyridine groups unsubstituted or substituted with a phenyl group, a naphthyl group, or a biphenyl group; Pyrimidine groups unsubstituted or substituted with
  • the R2 to R10 are the same as or different from each other, and each independently hydrogen; Or a carbazole group unsubstituted or substituted with a phenyl group, a naphthyl group, or a biphenyl group.
  • Ar1 to Ar3 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.
  • Ar1 to Ar3 are the same as or different from each other, and each independently contain a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted N, O, or S It is a C3-C20 heteroaryl group.
  • Ar1 to Ar3 are the same as or different from each other, and each independently a monocyclic aryl group having 6 to 20 carbon atoms, or a polycyclic aryl group having 10 to 20 carbon atoms.
  • Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, and a fluorene group. Pyrene group or triphenylene group.
  • Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a naphthyl group.
  • the spiro compound of Formula 1 may be represented by any one of the following structural formulas.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the spiro compound.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and one or more of the layers may include the compound.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
  • FIG. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 5, and a second electrode 4 are sequentially stacked on a substrate 1.
  • an organic material layer may be added between the first electrode, the light emitting layer, and the light emitting layer and the second electrode.
  • the organic material layer include, but are not limited to, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer.
  • 1 and 2 illustrate an organic light emitting diode and are not limited thereto.
  • the organic material layer including the spiro compound of Formula 1 includes a light emitting layer, and the light emitting layer includes the spiro compound of Formula 1.
  • the organic material layer including the spiro compound of Chemical Formula 1 includes a light emitting layer, and includes the spiro compound of Chemical Formula 1 as a host of the light emitting layer.
  • the dopant of the light emitting layer includes one or more compounds having a gap ⁇ E st ⁇ 0.2 eV between the lowest triplet state T1 and the first excited singlet state S1.
  • the UV-vis absorption spectrum was measured using V-730 manufactured by JASCO Corporation, and the photoluminescence spectrum in the film deposition state and the photoluminescence spectrum in the low-temperature state were Perkin Elmer. It was measured using LS-55 of the company, and the content of the compound 1 was measured in liquid N 1 -10 -5 M using HPLC grade THF as a solvent.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a host and a dopant in a weight ratio of 1:99 to 50:50.
  • the organic material layer includes a light emitting layer, and includes an organic compound or a metal complex compound as a dopant in the light emitting layer.
  • the light emitting layer includes a phosphorescent dopant.
  • the light emitting layer includes a phosphorescent host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the spiro compound of Formula 1 as a phosphorescent host of the light emitting layer.
  • the light emitting layer includes an iridium complex as a dopant.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes any one of the following compounds as a dopant.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate.
  • PVD metal vapor deposition
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an organic material layer including the spiro compound of Formula 1 thereon and then a material that can be used as a cathode thereon. It can be prepared by vapor deposition.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • 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); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), 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 material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.
  • 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.
  • 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 thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are 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, benzthiazole 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 is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include spiro compounds, dibenzofuran derivatives, and ladder furan compounds. Compounds, pyrimidine derivatives, and the like, but is not limited thereto.
  • 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 materials and methods known in the art, except that at least one layer of the organic material layer is formed using the spiro compound.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the present specification also provides a method of manufacturing an organic light emitting device formed using the spiro compound.
  • preparing a substrate Forming a cathode or anode on the substrate; Forming at least one organic layer on the cathode or anode; And forming an anode or a cathode on the organic material layer, wherein at least one layer of the organic material layer is formed using the spiro compound.
  • 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.
  • the organic light emitting device according to the present disclosure may synthesize all the compounds described in the specification by changing the type of substituents in the following Preparation Examples.
  • intermediate 6-1 (6.13 g, 16.34 mmol), 9H-carbazole (2.7 g, 16.34 mmol), and sodium t-butoxide (1.9 g, 19.61 mmol) were added to 45 ml of xylene, and then the temperature was increased and stirred. It was.
  • bis (tri-tert-butylphosphine) palladium (BIs (tri-tert-butylphosphine) palladium) (0.08 g, 0.16 mmol) was dissolved in xylene and slowly added dropwise. After 5 hours, the reaction was completed, the temperature was lowered to room temperature, silica filtration, concentration under reduced pressure, and column purification were performed to obtain compound 6 (5.0 g, 61% yield).
  • a glass substrate coated with a thickness of 1,000 kPa of ITO (indium tin oxide) was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • M-MTDATA 60nm) / TCTA (80nm) / Host + 10% Ir (ppy) 3 on the prepared ITO transparent electrode
  • a light emitting device was constructed in the order of (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm), and an organic EL device was manufactured using Compound 1 as the host.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 8 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that Comparative Compound 1 was used instead of Compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that Comparative Compound 2 was used instead of Compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that Comparative Compound 3 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured by using Compound 1 as a host of the light emitting material layer.
  • a glass substrate with an ITO (including reflector) electrode having a thickness of 40 mm ⁇ 40 mm ⁇ 0.5 mm was subjected to ultrasonic cleaning for 5 minutes with isopropyl alcohol, acetone, and DI water, and then dried at 100 ° C. Oven.
  • the organic layer was deposited in the following order by evaporation from a heating boat under about 10 ⁇ 7 Torr vacuum. At this time, the deposition rate of the organic material was set to 1 dl / s.
  • Hole injection layer HIL; HAT-CN, 70 kPa
  • hole transport layer HTL; NPB, 780 kPa
  • electron blocking layer EBL; mCBP, 150 kPa
  • light emitting material layer EML; compound 1
  • HBL hole blocking layer
  • ETL electron transport layer
  • EIL Cathode
  • Al Al
  • CPL capping layer
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 2 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 3 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 4 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 5 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 6 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 7 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 8 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that Comparative Compound 1 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that Comparative Compound 2 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that Comparative Compound 3 was used instead of Compound 1 in Experimental Example 2-1.
  • the driving voltage is lower and external quantum is lower than that of Comparative Compounds 1 to 3 of Comparative Examples 2-1 to 2-3 as a host.
  • the efficiency (EQE) is improved.
  • the organic compound of the present invention was applied to the organic light emitting layer to lower the driving voltage of the light emitting diode, improve the light emission efficiency, and improve the color purity.
  • the organic light emitting diode may be utilized in a light emitting device such as an organic light emitting diode display device and / or a lighting device which lowers power consumption and improves luminous efficiency and device life.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé spiro de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/002225 2018-02-23 2019-02-22 Composé spiro et dispositif électroluminescent organique le comprenant Ceased WO2019164341A1 (fr)

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EP4647476A1 (fr) * 2024-05-09 2025-11-12 Canon Kabushiki Kaisha Composé organique et élément électroluminescent organique

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