WO2020122451A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2020122451A1
WO2020122451A1 PCT/KR2019/016002 KR2019016002W WO2020122451A1 WO 2020122451 A1 WO2020122451 A1 WO 2020122451A1 KR 2019016002 W KR2019016002 W KR 2019016002W WO 2020122451 A1 WO2020122451 A1 WO 2020122451A1
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group
compound
light emitting
layer
emitting device
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Korean (ko)
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김진주
김형석
이상우
홍완표
윤홍식
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주식회사 엘지화학
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Priority to CN201980075686.1A priority Critical patent/CN113166120B/zh
Publication of WO2020122451A1 publication Critical patent/WO2020122451A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—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

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon that converts 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 and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of 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 provides a compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by Formula 1 below.
  • X and Y are the same as or different from each other, and each independently S or O,
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted An alkylaryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a ring,
  • R 3 and R 4 are the same as or different from each other, and each independently a hydrogen or nitrile group,
  • R 5 and R 6 are the same as or different from each other, and each independently hydrogen, a nitrile group, or a substituted or unsubstituted aryl group,
  • a, b and c are each an integer from 0 to 4,
  • d, e and f are each an integer from 0 to 3
  • the first electrode A second electrode provided opposite to the first electrode; And it provides an organic light-emitting device comprising one or more layers of an organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound.
  • the compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using this, it is possible to improve efficiency, improve low driving voltage and/or life characteristics in the organic light emitting device.
  • FIG. 1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting diode according to another exemplary embodiment of the present specification.
  • substitution means that the hydrogen atom bonded to the 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 the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group consisting of substituted or unsubstituted substituents, or having no substituents.
  • the "substituent to which two or more substituents are connected" 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 alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms.
  • Specific examples include methyl groups; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethyl butyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-oct
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms.
  • the amine group is -NH 2 ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluoren
  • the silyl group may be represented by the formula of —SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms.
  • the aryl group may be monocyclic or polycyclic.
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms.
  • a monocyclic aryl group includes a phenyl group; Biphenyl group; It may be a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited.
  • a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group, and the like, but is not limited thereto.
  • the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • 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 or a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group can be selected from the examples of the aryl group described above.
  • the heteroaryl group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the number of carbon atoms is not particularly limited, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heteroaryl group examples include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Ph
  • Chemical Formula 1 is represented by Chemical Formula 2.
  • X, Y, R 1 to R 6 , a to d and f are as defined in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 and 1-2.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 and 2-2.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3 to 1-10.
  • X and Y are O.
  • X and Y are S.
  • X is O and Y is S.
  • X is S and Y is O.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a hydrogen, nitrile group, alkyl group, or aryl group.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon number 6 It is an aryl group of 30 to 30.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, a nitrile group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, pentyl group , Hexyl group, phenyl group, biphenyl group, terphenyl group, quarterphenyl group, anthracenyl group, phenanthrenyl group, naphthyl group, pyrenyl group, triphenylenyl group, or fluorenyl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a hydrogen, nitrile group, methyl group, or phenyl group.
  • R 3 and R 4 are the same as or different from each other, and each independently a hydrogen or nitrile group.
  • R 3 and R 4 are hydrogen.
  • R 5 and R 6 are the same as or different from each other, and each independently a hydrogen, a nitrile group, or an aryl group having 6 to 30 carbon atoms.
  • R 5 and R 6 are the same as or different from each other, and each independently hydrogen, nitrile group, phenyl group, biphenyl group, naphthyl group, terphenyl group, quarterphenyl group, pyrenyl group, tri It is a phenylenyl group, anthracenyl group, phenanthrenyl group, or fluorenyl group.
  • R 5 and R 6 are the same as or different from each other, and each independently a hydrogen, nitrile group, or phenyl group.
  • R 5 is hydrogen, a nitrile group, or a phenyl group
  • R 6 is hydrogen
  • Chemical Formula 1 is any one selected from the following compounds.
  • the organic light emitting device of the present invention also includes a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 a structure of an organic light emitting device in which the first electrode 2, the organic material layer 3, and the second electrode 4 are sequentially stacked on the substrate 1 is illustrated.
  • FIG 1 illustrates an organic light emitting device and is not limited thereto.
  • FIG. 2 the structure of the organic light emitting device in which the first electrode 2, the first organic material layer 5, the light emitting layer 6, the second organic material layer 7 and the second electrode 4 are sequentially stacked on the substrate 1 is shown. Is illustrated.
  • the first organic material layer and the second organic material layer may be a hole transport region and an electron transport region, respectively.
  • the hole transport region means an organic material layer between the anode and the light emitting layer, for example, includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer
  • the electron transport region means an organic material layer between the cathode and the light emitting layer, for example, at least one of an electron injection layer, an electron transport layer and a hole blocking layer is included.
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 above.
  • the light emitting layer includes the compound as a host.
  • the light-emitting layer includes the compound as a phosphorescent host.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 1:99.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 10:90.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 50:50.
  • the light emitting layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a host, and a thermally activated delayed fluorescent compound as a dopant.
  • the thermally activated delayed fluorescence compound refers to fluorescence by generating reverse energy transfer from the lowest excited triplet state (T 1 ) to the lowest excited singlet state (S 1 ) by thermal activation. It means a compound that exhibits a phenomenon leading to luminescence.
  • delayed fluorescence refers to fluorescence in which triplet excitons emit light by performing reverse-intersystem crossing with singlet excitons.
  • the lowest excited triplet state (T 1 ) is the energy of the triplet state having the lowest energy.
  • a triplet state means a state in which the sum of the quantum numbers of the spin angular momentum of the entire electron is 1.
  • the lowest excited singlet state (S 1 ) is the energy of the singlet state having the lowest energy.
  • a singlet state means a state in which the sum of the quantum numbers of the spin angular momentum of the entire electron is zero.
  • the energy of the lowest excited triplet state (T 1 ) and the lowest excited singlet state (S 1 ) is determined by quantum chemical calculation.
  • the photoluminescence spectrum in the solid state (energy level in the lowest singlet state) and the photoluminescence spectrum in the low temperature state (the energy level in the lowest triplet state) are measured, and the photoluminescence spectrum in the solid state is manufactured by Perkin Elmer. It was measured using LS-55, and the emission spectrum at an excitation wavelength of 370 nm was 400 nm to 660 nm, HPLC grade THF was used as a solvent, and the content of the compound was 1 ⁇ 10 -6 M. The photoluminescence spectrum at low temperature was measured using LS-55 of Perkin Elmer, and the emission spectrum at an excitation wavelength of 445 nm is 400 nm to 700 nm. HPLC grade THF was used as the solvent, and it was measured under liquid nitrogen.
  • the difference ( ⁇ E st ) between the lowest excited triplet state (T 1 ) and the lowest excited singlet state (S 1 ) of the thermally activated delayed fluorescence compound is preferably greater than 0 eV and less than 0.2 eV.
  • the singlet exciton emits light as it is. (Ie, fluorescence), and triplet excitons are reversed-intersystem crossing with singlet excitons (ie, delayed fluorescence). Accordingly, since the delayed fluorescence mechanism is added to light emission by the fluorescence mechanism, it may be possible to increase the internal quantum efficiency to 100%.
  • the energy (Eg S ) in the singlet state of the thermally activated delayed fluorescent compound and the energy (Eg 77K ) in 77K can be expressed by the following equation.
  • Eg S and Eg 77K are values that can be measured through the energy level measurement methods of the singlet state and triplet state described above, respectively. When the difference is small and the above equation is satisfied, transitions between inverses are smooth and natural. Fluorescence is generated.
  • the mixture of the compound represented by Chemical Formula 1 and the thermally activated delayed fluorescent compound is represented by ⁇ HOMO(Host) ⁇ > ⁇ HOMO(TADF) ⁇ in order to prevent the exciplex formation of the light emitting layer, It is preferable that S 1 (Host)>2.8 eV and HOMO (Host) ⁇ 5.8 eV.
  • the exciplex of the light emitting layer refers to a complex formed by a combination of excited and ground molecules between two different molecules.
  • the content of the heat activated delayed fluorescent compound may be 1 to 60 parts by weight based on 100 parts by weight of the host.
  • the content of the compound of Formula 1 based on 100 parts by weight of the host may be 99 to 40 parts by weight.
  • the thermally activated delayed fluorescent compound may be any one selected from the following compounds, but is not limited thereto.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer includes the compound of Formula 1 Can be.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer
  • the electron injection layer, electron transport layer, or electron injection and transport layer includes the compound of Formula 1 Can be.
  • the organic material layer includes an electron blocking layer, or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the compound of Formula 1 above.
  • the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and then form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer containing the compound of Formula 1, and deposit a material that can be used as a cathode thereon. It can be prepared by.
  • an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection material is a material that can be easily injected holes from the positive electrode at a low voltage, and it is preferable that the hole injection material's HOMO (highest occupied molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable as a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene; Rubrene, and the like, but are not limited to these.
  • Alq3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Poly(p-phenylenevinylene) (PPV
  • 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 compound.
  • the present specification also provides a method for manufacturing an organic light emitting device formed using the compound.
  • the dopant material examples include aromatic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanene, etc.
  • styrylamine compound having an arylamino group, and substituted or unsubstituted as a styrylamine compound
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
  • examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the electron blocking layer is a layer that prevents electrons from reaching the anode, and a material known in the art may be used as the material.
  • the hole blocking layer is a layer that prevents the cathode from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
  • the organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described compound.
  • Ra and Rb are the same as the definitions of R1 and R2 in Chemical Formula 1,
  • Rc and Rd are the same as the definitions of R3 and R4 in Formula 1, respectively.
  • Rf and Rg are the same as the definitions of R5 and R6 in Formula 1, respectively.
  • l, m and n are each an integer from 0 to 4,
  • o, p and q are each an integer from 0 to 3
  • Ra and Rb are the same as the definitions of R1 and R2 in Formula 1, respectively.
  • Rc and Rd are the same as the definitions of R3 and R4 in Formula 1, respectively.
  • Rf and Rg are the same as the definitions of R5 and R6 in Formula 1, respectively.
  • l, m and n are each an integer from 0 to 4,
  • o, p and q are each an integer from 0 to 3
  • a glass substrate coated with a thin film of ITO (ndium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • Each layer of the organic light emitting device was deposited in the following order by evaporation from a heating boat under a vacuum of about 10 -7 Torr. At this time, the deposition rate of the organic or inorganic material was set to 1 ⁇ /s.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 11 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 1 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 2 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 3 was used instead of Compound 1 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 4 was used instead of Compound 1 in Experimental Example 1-1.
  • the green organic light emitting devices of Experimental Examples 1-1 to 1-11 using the compounds represented by Compounds 1 to 11 according to the present invention as the host material of the light emitting layer are Comparative Examples 1 using the conventional green host (GH) It showed better performance in terms of current efficiency and driving voltage than green organic light emitting devices of -1 to 1-4.
  • An organic light emitting device in which Compound 1 is applied as a host of a light emitting material layer was manufactured.
  • a 40 mm ⁇ 40 mm ⁇ 0.5 mm thick ITO (including reflective plate) electrode-equipped glass substrate was subjected to ultrasonic cleaning for 5 minutes with isopropyl alcohol, acetone, and DI Water, and then dried in an oven at 100°C.
  • the plasma was treated with O 2 for 2 minutes in vacuum and transferred to a deposition chamber to deposit other layers on top.
  • Each layer of the organic light emitting device was deposited in the following order by evaporation from a heating boat under a vacuum of about 10 -7 Torr. At this time, the deposition rate of the organic or inorganic material was set to 1 ⁇ /s.
  • a hole injection layer HIL; HAT-CN, 70 (), a hole transport layer (HTL; NPB, 780 ⁇ ), an electron blocking layer (EBL; mCBP, 150 ⁇ ), a light emitting material Layer (EML; Compound 1 as host and BDpyInCz doped with 30% by weight as a delayed fluorescent material, 350 ⁇ ), hole blocking layer (HBL; B3PYMPM; 100 ⁇ ), electron transport layer (ETL: TPBi, 250 ⁇ ) and electrons
  • An organic light emitting device was manufactured in the order of the injection layer (EIL; LiF, 8 kHz) and the cathode (Al; 1000 kHz).
  • HAT-CN NPB
  • mCBP BDpyInCz
  • B3PYMPM TPBi
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 11 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that GH 1 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that GH 2 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that GH 3 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that GH 4 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic compound synthesized according to the present invention When the organic compound synthesized according to the present invention is used as a host for a delayed fluorescent material layer, the driving voltage is lowered and the external quantum is lower than when using GH 1 to GH 4 of Comparative Examples 2-1 to 2-4 as a host. Efficiency (EQE) was improved. As a result, it was confirmed that 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, to improve luminous efficiency and to improve color purity. Therefore, by using the organic light emitting device to which the organic compound of the present invention is applied, it can be utilized in a light emitting device such as an organic light emitting device display device and/or a lighting device with reduced power consumption and improved light emission efficiency and device life.
  • a light emitting device such as an organic light emitting device display device and/or a lighting device with reduced power consumption and improved light emission efficiency and device life.

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

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/016002 2018-12-10 2019-11-21 Composé et dispositif électroluminescent organique le comprenant WO2020122451A1 (fr)

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CN112409240A (zh) * 2020-11-20 2021-02-26 清华大学 一种有机化合物及其应用及采用该化合物的有机电致发光器
CN114105956A (zh) * 2020-09-01 2022-03-01 江苏三月科技股份有限公司 一种以三嗪衍生物为核心的化合物及包含其的有机电致发光器件

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EP3696167A4 (fr) 2018-07-27 2021-03-24 Idemitsu Kosan Co.,Ltd. Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique, et dispositif électronique
KR102645609B1 (ko) 2018-12-14 2024-03-07 엘지디스플레이 주식회사 내열 특성 및 발광 특성이 우수한 유기 화합물, 이를 포함하는 발광다이오드 및 유기발광장치
KR20220077298A (ko) * 2020-12-01 2022-06-09 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법

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CN112409241A (zh) * 2020-11-27 2021-02-26 清华大学 一种有机化合物及其应用及采用该化合物的有机电致发光器

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