WO2020145693A1 - Composé et diode électroluminescente organique le comprenant - Google Patents

Composé et diode électroluminescente organique le comprenant Download PDF

Info

Publication number
WO2020145693A1
WO2020145693A1 PCT/KR2020/000405 KR2020000405W WO2020145693A1 WO 2020145693 A1 WO2020145693 A1 WO 2020145693A1 KR 2020000405 W KR2020000405 W KR 2020000405W WO 2020145693 A1 WO2020145693 A1 WO 2020145693A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
compound
light emitting
Prior art date
Application number
PCT/KR2020/000405
Other languages
English (en)
Korean (ko)
Inventor
윤홍식
김명곤
홍완표
김진주
서상덕
한시현
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202080006302.3A priority Critical patent/CN113056471B/zh
Publication of WO2020145693A1 publication Critical patent/WO2020145693A1/fr

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • 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
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present application relates to a compound and an organic light emitting device comprising the same.
  • the organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as a current source (voltage source). It is a light emitting device of the form.
  • the second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • 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, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. Can lose.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppressing materials, electron transport materials, and electron injection materials, depending on their function.
  • the light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.
  • a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and a higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, excitons generated from the host are transported as a dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.
  • materials constituting an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, an electron transport material, an electron injection material, are stable and efficient materials It is supported by, and the development of new materials continues to be required.
  • the present application provides a compound and an organic light emitting device including the same.
  • One embodiment of the present application provides a compound represented by Formula 1 below.
  • A is a substituted or unsubstituted triazine group; A substituted or unsubstituted quinazoline group; Or a substituted or unsubstituted quinoxaline group,
  • X is a cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted arylsilyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n, p and q are each independently an integer from 0 to 4,
  • n is an integer from 0 to 5.
  • the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer provides an organic light emitting device including the above-described compound.
  • the compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device.
  • an organic light emitting device When an organic light emitting device is manufactured using the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present application, an organic light emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.
  • benzene when benzene is introduced adjacent to carbazoles in a thermally activated delayed fluorescence (TADF) material containing carbazoles, benzene acts as a linker in the middle of the donor/acceptor.
  • TADF thermally activated delayed fluorescence
  • HOMO highest point molecular orbital
  • LUMO lowest molecular orbital
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection and transport layer ( 10) and an example of an organic light-emitting device comprising the cathode 4 is shown.
  • the present application relates to a novel organic compound that can be advantageously used in organic light emitting devices.
  • the present application relates to thermally active delayed fluorescence (TADF) materials and their use in organic light emitting devices.
  • TADF thermally active delayed fluorescence
  • Fluorescent light-emitting materials using thermally activated delayed fluorescence (TADF) and phenomena using reverse intersystem crossing (RISC) from triplet excitons to singlet excitons, and organic The possibility of use as a light emitting element has been reported.
  • TADF thermally activated delayed fluorescence
  • RISC reverse intersystem crossing
  • One embodiment of the present application provides a compound represented by Formula 1 below.
  • A is a substituted or unsubstituted triazine group; A substituted or unsubstituted quinazoline group; Or a substituted or unsubstituted quinoxaline group,
  • X is a cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted arylsilyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n, p and q are each independently an integer from 0 to 4,
  • n is an integer from 0 to 5.
  • benzene is introduced adjacent to carbazoles in a thermally activated delayed fluorescence (TADF) material containing carbazoles. Accordingly, since benzene acts as a linker in the middle of the donor/acceptor, some of the highest point molecular orbital (HOMO) and lowest molecular orbital (LUMO) in the molecule are mixed to increase stability, It shows the effect of increasing the quantum efficiency.
  • TADF thermally activated delayed fluorescence
  • 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 in this specification is deuterium (-D); Halogen group; Nitrile group; Nitro group; Hydroxy group; Silyl group; Boron group; Alkoxy groups; Alkyl groups; Cycloalkyl group; Aryl group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents of the above-exemplified substituents, or having no substituents.
  • a substituent having two or more substituents may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.
  • the alkylsilyl group is a silyl group substituted with an alkyl group, and may be selected from examples of the silyl group.
  • the arylsilyl group is a silyl group substituted with an aryl group, and may be selected from examples of the silyl group.
  • the boron group may be represented by the formula -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
  • 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 20 carbon atoms.
  • Substituents comprising alkyl, alkoxy, and other alkyl group moieties described in this application include both straight-chain or ground forms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 39. According to one embodiment, the carbon number of the aryl group is 6 to 30.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorene group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorene groups such as (9,9-dimethylfluorene group
  • It may be a substituted fluorene group such as (9,9-diphenylfluorene group).
  • substituted fluorene group such as (9,9-diphenylfluorene group
  • the heterocyclic group is a heteroatom as a ring group containing at least one of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 36 carbon atoms.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, Carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited thereto.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • the amine group is -NH 2 ; Monoalkylamine groups; Monoarylamine group; Diarylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of a monoheteroarylamine group and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine 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-biphenylfluorenylamine group, and the
  • the N-aryl heteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group of the N-aryl heteroarylamine group is the same as the exemplified aryl group described above.
  • the N-aryl heteroarylamine group In the present application, the N-aryl heteroarylamine group; The heteroaryl group of the monoheteroarylamine group and the diheteroarylamine group is the same as the above-described heteroaryl group.
  • the formula 1 may be represented by any one of the following formulas 2 to 9.
  • A, X, R1 to R4, m, n, p and q are as defined in Formula 1.
  • a in Formula 1 is a triazine group unsubstituted or substituted with an aryl group; A quinazoline group unsubstituted or substituted with an aryl group; Or a quinoxaline group unsubstituted or substituted with an aryl group, wherein the aryl group may be independently substituted or unsubstituted with a deuterium or alkyl group.
  • a in Formula 1 is a triazine group unsubstituted or substituted with a phenyl group; A quinazoline group unsubstituted or substituted with a phenyl group; Or it is a quinoxaline group unsubstituted or substituted with a phenyl group, wherein the phenyl group may be independently substituted or unsubstituted with deuterium or methyl groups.
  • X in Chemical Formula 1 is a cyano group; Alkyl groups; Aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group, wherein the aryl group may be independently substituted or unsubstituted with a deuterium or alkyl group.
  • X in Chemical Formula 1 is a cyano group; Methyl group; Phenyl group; Or a triazine group unsubstituted or substituted with a phenyl group, wherein the phenyl group may be independently substituted or unsubstituted with deuterium or methyl groups.
  • R1 to R4 in Chemical Formula 1 may each independently be hydrogen or deuterium.
  • the formula 1 may be represented by any one of the following compounds.
  • the triplet energy level of the compound represented by Formula 1 is 2.1eV or more, preferably 2.1eV or more and 3.0eV or less, 2.2eV or more, 3.0eV or less, 2.3eV or more It may be 2.9 eV or less.
  • the triplet energy level of the compound represented by Chemical Formula 1 satisfies the above range, electron injection is facilitated and the exciton formation rate is increased, so that the luminous efficiency is increased.
  • the difference between the singlet energy level and the triplet energy level of the compound represented by Formula 1 is 0 eV or more and 0.3 eV or less, and preferably 0 eV or more and 0.2 eV or less .
  • the exciton generated in the triplet is converted into a singlet by inverse transition (RISC).
  • RISC inverse transition
  • the triplet energy can be measured using a spectral instrument capable of measuring fluorescence and phosphorescence, and in the case of measurement conditions, a solution at a concentration of 10 -6 M using toluene or thiophene as a solvent in a cryogenic state using liquid nitrogen It is confirmed by analyzing the spectrum emitted from the triplet, except for singlet emission from the spectrum emitting light by irradiating the light source of the absorption wavelength band of the material to the solution. When the electron is reversed from the light source, the time for the electron to stay in the triplet is much longer than the time in the singlet, so it is possible to separate the two components in the cryogenic state.
  • the singlet energy is measured using a fluorescent device, and the light source is irradiated at room temperature, unlike the triplet energy measurement method described above.
  • compounds having various energy band gaps may be synthesized by introducing various substituents to the core structure of the compound represented by Chemical Formula 1.
  • the HOMO and LUMO energy levels of the compound may be adjusted by introducing various substituents to the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one layer of an organic material provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes a compound represented by Chemical Formula 1.
  • the organic light emitting device may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 described above. have.
  • an organic light emitting device having an organic material layer including the compound represented by Compound 1 it may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • the organic material layer of the organic light emitting device 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 according to an exemplary embodiment of the present application is a hole transport layer, a hole injection layer, an electron blocking layer, a layer simultaneously performing hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron as an organic material layer It may have a structure including at least one layer of the layer for simultaneous transport and electron injection.
  • the structure of the organic light emitting device according to the exemplary embodiment of the present application is not limited thereto, and may include a smaller number or a larger number of organic material layers.
  • the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by Formula 1 described above.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound in 10 parts by weight to 100 parts by weight in the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound as a host of the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound as a dopant in the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a dopant in the light emitting layer
  • the content of the dopant may be included in 10 parts by weight to 99 parts by weight based on 100 parts by weight of the host, preferably 30 parts by weight to 50 parts by weight.
  • the life and efficiency of the device are improved. More specifically, according to an exemplary embodiment of the present application, when benzene is introduced adjacent to carbazoles in a thermally activated delayed fluorescence (TADF) material containing carbazoles, benzene is a linker in the middle of the donor/acceptor. Since it acts as a molecule, the highest peak molecular orbit (HOMO) and the lowest molecular orbit (LUMO) in the molecule are partially mixed to increase stability and increase quantum efficiency. In addition, it is possible to control the triplet energy level by controlling the benzene ring, thereby preventing quantum efficiency reduction due to triplet quenching, and additionally adjusting the bonding force between carbazoles and benzene to increase the lifespan. have.
  • TADF thermally activated delayed fluorescence
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound as an auxiliary dopant or sensitizer of the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound
  • the compound acts as an auxiliary dopant or a sensitizer.
  • the compound receives holes and electrons from a host to form excitons. , It plays a role of delivering the generated exciton as a fluorescent dopant.
  • the number of excitons generated in singlet and triplet is generated at a ratio of 25:75 (single term: triplet), and fluorescent emission, phosphorescence emission, and thermal activation delayed fluorescence depending on the emission type according to exciton movement It can be divided into luminescence.
  • the phosphorescence emission it means that the exciton of the triplet excited state moves to the ground state and emits light
  • the exciton of the singlet excited state is the ground state ( It means that it moves to the ground state and emits light
  • the thermally activated delayed fluorescence emission reverses the transition from the triplet excited state to the singlet excited state, and the singlet excited state. It means that the exciton moves to the ground state and causes fluorescence emission.
  • excitons in a triplet excited state are generally reverse-transferred to a singlet excited state to transfer the energy as a dopant It is possible to implement an organic light emitting device having high efficiency.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • electroctron transport layer/electron injection layer may be replaced with “electron injection and transport layer”.
  • the structure of the organic light emitting device according to the exemplary embodiment of the present application may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer 3.
  • the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the hole blocking layer 9, the electron injection and transport layer ( 10) and the structure of the organic light emitting device in which the cathode 4 is sequentially stacked is illustrated.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and a metal oxide having a metal or conductivity on a substrate
  • PVD metal vapor deposition
  • an anode is formed by depositing these alloys, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode It can be prepared by depositing.
  • 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 organic material layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs electron injection and electron transport, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron injection and electron transport.
  • the present invention is not limited thereto, and may be a single layer structure.
  • the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than deposition using various polymer materials. Can be prepared in layers.
  • the positive electrode is an electrode for injecting holes
  • a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
  • Specific examples of the positive electrode material that can be used in the present application 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); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an 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;
  • There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer.
  • a hole injection material can be well injected from the anode at a low voltage, and HOMO (highest occupied) of the hole injection material It is preferable that the 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.
  • the hole injection material may be hexanitrile hexaazatriphenylene-based organic material. More specifically, the hole injection material may be hexanitrile hexaazatriphenylene-hexanitrile (HAT-CN), but is not limited thereto.
  • the hole injection layer may have a thickness of 1 nm to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated. If it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable for 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.
  • the hole transport material may be an arylamine-based organic material.
  • the hole transport material may be N4,N4'-di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (NPB) However, it is not limited thereto.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer may be a material known in the art, for example, a heteroarylamine compound, but is not limited thereto.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • 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 (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • Alq 3 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)-based polymers
  • Spiro compounds Polyfluorene, rubrene, and the like, but are not limited to these.
  • the host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. More specifically, a carbazole derivative may be used as a host material of the light emitting layer, but is not limited thereto.
  • PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium are used as the light emitting dopant.
  • phosphorescent materials such as octaethylporphyrin platinum (PtOEP), and fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited thereto.
  • a phosphorescent material such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) is used as a light emitting dopant, but Alq 3 (tris(8-hydroxyquinolino)aluminum), anthracene-based compound, pi Fluorescent materials such as ren-based compounds and boron-based compounds may be used, but are not limited thereto.
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic is used as a light emitting dopant, but spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are not limited thereto.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 nm to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There is an advantage.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, , A compound having excellent thin film formation ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene 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-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the electron injection and transport layer is a layer that performs electron injection and transport simultaneously.
  • the electron injection and transport layer material any material applicable to the electron injection layer and the electron transport layer can be used without limitation.
  • benzoimidazole derivatives and metal complex compounds may be used simultaneously, but are not limited thereto.
  • the hole blocking layer is a layer that prevents the cathode from reaching the hole, 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 compound represented by Chemical Formula 1 may be formed by introducing various types of nitrogen-containing hetero groups into a substituted fluorophenyl boronic acid as follows. After introducing the nitrogen-containing hetero group, finally, the expanded form of indolocarbazole was introduced to synthesize the compounds.
  • the triplet energy level (T1) was measured at a cryogenic condition using the characteristics of a triplet exciton with a long lifetime. Specifically, after dissolving the compound in a toluene solvent to prepare a sample having a concentration of 10 -5 M, the sample is put in a quartz kit, cooled to 77K, and irradiated with a 300 nm light source for a phosphorescence measurement sample to change the phosphorescence Spectra were measured. A spectrophotometer (FP-8600 spectrophotometer, JASCO) was used to measure the spectrum.
  • the vertical axis of the phosphorescence spectrum was the phosphorescence intensity, and the horizontal axis was the wavelength.
  • a tangent line was drawn with respect to the rise of the short wavelength side of the phosphorescence spectrum, and the wavelength value ( ⁇ edge1 (nm)) of the intersection of the tangent line and the horizontal axis was determined, and the wavelength value was substituted into the following conversion formula 1 to calculate the triplet energy. .
  • the tangent to the rise of the short wavelength side of the phosphorescence spectrum was drawn as follows. First, the maximum value of the shortest wavelength side among the maximum values of the spectrum was confirmed. At this time, the maximum point having a peak intensity of 15% or less of the maximum peak intensity in the spectrum was not included in the maximum value on the shortest wavelength side described above. The tangent at each point on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value was considered. The tangent with the largest inclination value (that is, the tangent at the inflection point) among these tangents was used as the tangent to the rise on the short wavelength side of the phosphorescence spectrum.
  • the singlet energy level (S1) was measured by the following method.
  • a 10 -5 M toluene solution of the compound to be measured was prepared, placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of the 300 nm light source of the sample at room temperature (300K) was measured.
  • a tangent line was drawn with respect to the rise of the short wavelength side of this emission spectrum, and the wavelength value ( ⁇ edge2 (nm)) at the intersection of the tangent line and the horizontal axis was substituted into Equation 2 below to calculate the singlet energy.
  • the emission spectrum was measured using a JASCO spectrophotometer (FP-8600 spectrophotometer).
  • the tangent to the rise of the short wavelength side of the emission spectrum was drawn as follows. First, the maximum value of the shortest wavelength side among the maximum values of the spectrum was confirmed. The tangent at each point on the spectrum curve from the short wavelength side of the emission spectrum to the maximum value was considered. The tangent with the largest inclination value (that is, the tangent at the inflection point) among these tangents was used as the tangent to the rise on the short wavelength side of the emission spectrum. The maximum point having the peak intensity of 15% or less of the maximum peak intensity of the spectrum was not included in the maximum value on the shortest wavelength side described above.
  • T1 The triplet energy level (T1), the singlet energy level (S1), and the difference between the singlet energy level and the triplet energy level ( ⁇ EST) measured by the above method are shown in Table 1 below.
  • the glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily by a filter of Millipore Co.
  • ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • HAT-CN hexaazatriphenylene-hexanitrile
  • the following compound NPB was vacuum deposited on the hole injection layer to form a hole transport layer (300 kPa).
  • An electron blocking layer was formed by vacuum-depositing the following compound EB1 with a thickness of 100 mm 2 on the hole transport layer.
  • the compound m-CBP and 4CzIPN having a thickness of 300 mm 3 were vacuum deposited on the electron blocking layer at a weight ratio of 70:30 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the following compound HB1 with a thickness of 100 mm 2 on the light emitting layer.
  • the following compound ET1 and the compound LiQ were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Pa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 2,000 ⁇ were sequentially deposited to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ /sec and aluminum at 2 ⁇ /sec
  • the vacuum degree during deposition was 2x10. - 7 torr to 5x10 - holding a 6 torr, was produced in the organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1-1 except for using the compound of Table 2 below instead of the compound 4CzIPN in Comparative Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1-1 except for using the compounds of Z1 to Z3 below instead of the compound 4CzIPN in Comparative Example 1-1.
  • the CIE color coordinate measured at the luminance of /m2 and the time (T95) until the brightness was reduced to 95% at 3000 cd/m 2 were measured and are shown in Table 2 below.
  • the compound according to the present invention has excellent luminescence ability and high color purity, and thus can be applied to a delayed fluorescent organic light emitting device.
  • the glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily by a filter of Millipore Co.
  • ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • HAT-CN hexaazatriphenylene-hexanitrile
  • the following compound NPB was vacuum deposited on the hole injection layer to form a hole transport layer (300 kPa).
  • An electron blocking layer was formed by vacuum-depositing the following compound EB1 with a thickness of 100 mm 2 on the hole transport layer.
  • the compound m-CBP, 4CzIPN, and GD1 having a thickness of 300 mm 3 were vacuum deposited on the electron blocking layer at a weight ratio of 68:30:2 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the following compound HB1 with a thickness of 100 mm 2 on the light emitting layer.
  • the following compound ET1 and the compound LiQ were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Pa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 2,000 ⁇ were sequentially deposited to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ /sec and aluminum at 2 ⁇ /sec
  • the vacuum degree during deposition was 2x10. - 7 torr to 5x10 - holding a 6 torr, was produced in the organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 2-1, except for using the compound of Table 3 instead of the compound 4CzIPN in Comparative Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 2-1, except for using the compound of Table 3 instead of the compound 4CzIPN in Comparative Example 2-1.
  • the compound according to the present invention has excellent luminescence ability and is capable of tuning the emission wavelength, thereby realizing an organic light emitting device having high color purity.

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2020/000405 2019-01-09 2020-01-09 Composé et diode électroluminescente organique le comprenant WO2020145693A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202080006302.3A CN113056471B (zh) 2019-01-09 2020-01-09 化合物及包含其的有机发光二极管

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20190002613 2019-01-09
KR10-2019-0002613 2019-01-09

Publications (1)

Publication Number Publication Date
WO2020145693A1 true WO2020145693A1 (fr) 2020-07-16

Family

ID=71521707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2020/000405 WO2020145693A1 (fr) 2019-01-09 2020-01-09 Composé et diode électroluminescente organique le comprenant

Country Status (3)

Country Link
KR (1) KR102301359B1 (fr)
CN (1) CN113056471B (fr)
WO (1) WO2020145693A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024062997A1 (fr) * 2022-09-22 2024-03-28 保土谷化学工業株式会社 Composé, film mince organique et élément de conversion photoélectrique

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2023166630A (ja) * 2020-07-29 2023-11-22 出光興産株式会社 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス発光装置、及び電子機器
WO2023140706A1 (fr) * 2022-01-21 2023-07-27 Samsung Display Co., Ltd. Molécules organiques pour dispositifs optoélectroniques

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140000611A (ko) * 2012-06-22 2014-01-03 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
US20140353640A1 (en) * 2013-05-29 2014-12-04 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
KR20150135220A (ko) * 2013-03-29 2015-12-02 이데미쓰 고산 가부시키가이샤 헤테로환 화합물, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
KR101793336B1 (ko) * 2014-09-30 2017-11-02 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180083152A (ko) * 2017-01-12 2018-07-20 덕산네오룩스 주식회사 지연형광 화합물 및 이를 이용한 유기전기소자 및 그 전자 장치
KR20200027447A (ko) * 2018-09-04 2020-03-12 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기발광소자

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101815909B1 (ko) 2009-07-27 2018-01-09 에스에프씨 주식회사 인돌로카바졸 유도체 및 이를 이용한 유기전계발광소자
KR101553737B1 (ko) * 2012-09-24 2015-09-16 주식회사 두산 카바졸계 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102167048B1 (ko) * 2013-12-03 2020-10-19 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR101907292B1 (ko) * 2016-01-22 2018-10-12 주식회사 엘지화학 아민계 화합물 및 이를 포함하는 유기 발광 소자
KR102107086B1 (ko) * 2017-06-05 2020-05-06 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140000611A (ko) * 2012-06-22 2014-01-03 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20150135220A (ko) * 2013-03-29 2015-12-02 이데미쓰 고산 가부시키가이샤 헤테로환 화합물, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
US20140353640A1 (en) * 2013-05-29 2014-12-04 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
KR101793336B1 (ko) * 2014-09-30 2017-11-02 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180083152A (ko) * 2017-01-12 2018-07-20 덕산네오룩스 주식회사 지연형광 화합물 및 이를 이용한 유기전기소자 및 그 전자 장치
KR20200027447A (ko) * 2018-09-04 2020-03-12 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기발광소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024062997A1 (fr) * 2022-09-22 2024-03-28 保土谷化学工業株式会社 Composé, film mince organique et élément de conversion photoélectrique

Also Published As

Publication number Publication date
CN113056471A (zh) 2021-06-29
CN113056471B (zh) 2023-09-15
KR102301359B1 (ko) 2021-09-13
KR20200086646A (ko) 2020-07-17

Similar Documents

Publication Publication Date Title
WO2019132506A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2017204594A1 (fr) Elément électroluminescent organique
WO2020085842A1 (fr) Composé contenant du deutérium, et dispositif électroluminescent organique le comprenant
WO2020145725A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020076108A1 (fr) Dispositif électroluminescent organique
WO2020138963A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2018182297A1 (fr) Composé à base de benzocarbazole et dispositif électroluminescent organique le comprenant
WO2019190223A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2020159279A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2020085765A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2020122451A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019164218A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2017146522A1 (fr) Composé hétérocyclique et diode électroluminescente organique contenant ce composé
WO2020145693A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2020145692A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019143223A9 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2021125648A1 (fr) Nouveau composé, et élément électroluminescent organique l'utilisant
WO2020262861A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020149610A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2022108258A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2022059923A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020153652A1 (fr) Composé, et élément électroluminescent organique le comprenant
WO2020153653A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2021006532A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2020149663A1 (fr) Dispositif électroluminescent organique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20738065

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20738065

Country of ref document: EP

Kind code of ref document: A1