[go: up one dir, main page]

WO2022080715A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2022080715A1
WO2022080715A1 PCT/KR2021/013360 KR2021013360W WO2022080715A1 WO 2022080715 A1 WO2022080715 A1 WO 2022080715A1 KR 2021013360 W KR2021013360 W KR 2021013360W WO 2022080715 A1 WO2022080715 A1 WO 2022080715A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
group
layer
mmol
substituted
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2021/013360
Other languages
English (en)
Korean (ko)
Inventor
이성재
차용범
홍성길
조우진
이용한
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
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 LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN202180061908.1A priority Critical patent/CN116057040A/zh
Publication of WO2022080715A1 publication Critical patent/WO2022080715A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, it may be made of an electron injection layer, etc.
  • a voltage when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1):
  • L 1 and L 2 are each independently a direct bond; substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • L 3 is a direct bond; Or a substituted or unsubstituted C 6-60 arylene,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
  • A is each independently substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 1 are each independently hydrogen; heavy hydrogen; halogen; nitrile; silyl; substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 2 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 6-60 aryl,
  • p is an integer from 1 to 4,
  • a is an integer of 0 to 3, provided that a+p is 1 to 4,
  • b is an integer from 0 to 4.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1 above. do.
  • the compound represented by Chemical Formula 1 described above may be used as a material for an organic layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.
  • the compound represented by the above formula (1) may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a hole transport layer 3 , a light emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 .
  • FIG. 2 is a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light emitting layer (4), a hole blocking layer (9), an electron injection and transport layer ( 5) and an example of an organic light-emitting device including a cathode 6 are shown.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocycl
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • 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 carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, etc. can be
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothioph
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group.
  • the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied.
  • the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group.
  • the description of the above-described aryl group may be applied, except that arylene is a divalent group.
  • the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents.
  • the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
  • the present invention provides a compound represented by Formula 1 above.
  • Formula 1 may be represented by any one selected from the group consisting of the following Formulas 1-1 to 1-3:
  • L 1 , L 2 , L 3 , Ar 1 , Ar 2 , A, R 1 , R 2 , p, a, and b are as defined in claim 1 .
  • L 1 and L 2 are each independently a direct bond, phenylene, or biphenylylene.
  • it is L 3 direct bond, or phenylene.
  • Ar 1 and Ar 2 are each independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with adamantyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenylcarbazolyl.
  • each A is independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with carbazol-9-yl, biphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.
  • R 1 is hydrogen or phenyl.
  • R 2 is hydrogen or phenyl.
  • p is 1 or 2.
  • a and b are each 0 or 1.
  • the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 1 below.
  • the reaction as an amine substitution reaction, is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • the present invention provides an organic light emitting device comprising the compound represented by Formula 1 above.
  • the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 It may include the indicated compound.
  • the organic material layer may include an electron blocking layer, and an electron blocking layer between the anode and the light emitting layer.
  • the electron blocking layer is included in contact with the anode side of the light emitting layer.
  • the electron suppression layer serves to improve the efficiency of the organic light emitting device by suppressing electrons injected from the cathode from being transferred to the anode without recombination in the light emitting layer.
  • the electron blocking layer may include a compound represented by Formula 1 above.
  • the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.
  • the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1 above.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention further comprises a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode in addition to the light emitting layer as an organic layer can have a structure that
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of the organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a hole transport layer 3 , a light emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 .
  • the compound represented by Formula 1 may be included in the hole transport layer.
  • the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.
  • the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
  • the organic light emitting diode according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode
  • it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • the anode material 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); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, 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 anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • a compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material.
  • organic substances anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer.
  • the electron suppression layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, adjusts hole mobility, prevents excessive movement of electrons, and increases the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device It means a layer that plays a role in improving
  • the electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible ray region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group.
  • styrylamine compound a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex include, but are not limited to, an iridium complex and a platinum complex.
  • the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes to increase the hole-electron coupling probability, thereby improving the efficiency of the organic light emitting device layer that plays a role.
  • the hole blocking layer includes a hole blocking material.
  • the hole blocking material include an electron withdrawing group such as an azine derivative including triazine, a triazole derivative, an oxadiazole derivative, a phenanthroline derivative, and a phosphine oxide derivative. compounds may be used, but the present invention is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer.
  • Do Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that injects electrons from the electrode, 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, and hole injection of excitons generated in the light emitting layer.
  • a compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the "electron injection and transport layer” is a layer that performs both the role of the electron injection layer and the electron transport layer, and the materials serving the respective layers may be used alone or in combination, but limited thereto. doesn't happen
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Tetrahydrofuran (THF) (240 ml) was added to Compound 1-A (50.00 g, 115.81 mmol) and phenylboronic acid (14.83 g, 121.60 mmol) obtained in Step 1 of Synthesis Example 1, followed by heating and stirring. .
  • potassium carbonate 48.02 g, 347.43 mmol
  • aqueous solution 120 ml
  • [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.68 g, 0.93 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After removal of the solvent, it was recrystallized from ethyl acetate to obtain compound 1-B (38.0 g, 76.49 % yield).
  • Example 1 using Compound 1-A (50.00 g, 115.81 mmol) and [1,1'-biphenyl]-4-ylboronic acid (24.08 g, 121.60 mmol) obtained in Step 1 of Example 1
  • Compound 8-A (45.0 g, 76.93 % yield) was obtained in the same manner as in step 2.
  • Example 1 using compound 14-A (50.00 g, 115.81 mmol) and [1,1'-biphenyl]-4-ylboronic acid (24.08 g, 121.60 mmol) obtained in step 1 of Example 14
  • Compound 21-A (46.0 g, 78.64 % yield) was obtained in the same manner as in step 2.
  • a glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermal vacuum deposition of a compound represented by the following formula HAT on the prepared ITO transparent electrode to a thickness of 100 ⁇ .
  • the compound 1 prepared in Example 1 was thermally vacuum deposited to a thickness of 150 ⁇ as an electron suppression layer.
  • the compound represented by the following formula BH and the compound represented by the following formula BD were vacuum-deposited to a thickness of 200 ⁇ in a weight ratio of 25:1.
  • a compound represented by the following Chemical Formula HB1 was vacuum-deposited to a thickness of 50 ⁇ .
  • a compound represented by the following formula ET1 and a compound represented by the following LiQ were thermally vacuum deposited to a thickness of 310 ⁇ in a weight ratio of 1:1.
  • An organic light-emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron transport and electron injection layers to form a cathode.
  • LiF lithium fluoride
  • T95 means the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the compound of the present invention has excellent electron suppression ability, and it was confirmed that the organic light emitting device using the same as the electron suppression layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.
  • T95 denotes a time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the compound of the present invention has excellent hole transport ability, and it was confirmed that the organic light emitting device using the compound as a hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.
  • Substrate 2 Anode
  • hole transport layer 4 light emitting layer
  • Electron injection and transport layer 6 Cathode

Landscapes

  • 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)
  • Optics & Photonics (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/013360 2020-10-12 2021-09-29 Nouveau composé et dispositif électroluminescent organique le comprenant Ceased WO2022080715A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202180061908.1A CN116057040A (zh) 2020-10-12 2021-09-29 新型化合物及包含其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020200131023A KR102688630B1 (ko) 2020-10-12 2020-10-12 신규한 화합물 및 이를 포함한 유기 발광 소자
KR10-2020-0131023 2020-10-12

Publications (1)

Publication Number Publication Date
WO2022080715A1 true WO2022080715A1 (fr) 2022-04-21

Family

ID=81209306

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/013360 Ceased WO2022080715A1 (fr) 2020-10-12 2021-09-29 Nouveau composé et dispositif électroluminescent organique le comprenant

Country Status (3)

Country Link
KR (1) KR102688630B1 (fr)
CN (1) CN116057040A (fr)
WO (1) WO2022080715A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115010609A (zh) * 2022-06-02 2022-09-06 南京高光半导体材料有限公司 一种含有二苯基芴结构的胺基化合物及有机电致发光器件
WO2023210698A1 (fr) * 2022-04-26 2023-11-02 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN119654313A (zh) * 2022-07-25 2025-03-18 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116730846B (zh) * 2023-06-27 2025-06-13 长春海谱润斯科技股份有限公司 一种含苯基芴的有机化合物及其有机发光器件
CN116874380A (zh) * 2023-06-27 2023-10-13 长春海谱润斯科技股份有限公司 一种芳胺化合物及其有机电致发光器件
CN117126190A (zh) * 2023-08-23 2023-11-28 长春海谱润斯科技股份有限公司 一种三芳胺衍生物及其有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150132837A (ko) * 2013-03-26 2015-11-26 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 화합물, 유기 화합물, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 조명 장치 및 전자 기기
KR20160074630A (ko) * 2013-10-23 2016-06-28 메르크 파텐트 게엠베하 전자 소자용 물질
KR20170075877A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자
KR20170076600A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자
CN111233674A (zh) * 2019-09-26 2020-06-05 吉林奥来德光电材料股份有限公司 芴类化合物及其制备方法和有机电致发光器件

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법
JP6576631B2 (ja) * 2014-12-15 2019-09-18 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． アミン化合物、および有機電界発光素子
CN107093675B (zh) * 2015-12-23 2022-05-03 三星显示有限公司 有机发光器件
KR102585186B1 (ko) * 2017-11-24 2023-10-06 삼성디스플레이 주식회사 아민 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101857632B1 (ko) * 2018-02-02 2018-05-14 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150132837A (ko) * 2013-03-26 2015-11-26 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 화합물, 유기 화합물, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 조명 장치 및 전자 기기
KR20160074630A (ko) * 2013-10-23 2016-06-28 메르크 파텐트 게엠베하 전자 소자용 물질
KR20170075877A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자
KR20170076600A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자
CN111233674A (zh) * 2019-09-26 2020-06-05 吉林奥来德光电材料股份有限公司 芴类化合物及其制备方法和有机电致发光器件

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023210698A1 (fr) * 2022-04-26 2023-11-02 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN115010609A (zh) * 2022-06-02 2022-09-06 南京高光半导体材料有限公司 一种含有二苯基芴结构的胺基化合物及有机电致发光器件
CN119654313A (zh) * 2022-07-25 2025-03-18 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置

Also Published As

Publication number Publication date
CN116057040A (zh) 2023-05-02
KR20220048180A (ko) 2022-04-19
KR102688630B1 (ko) 2024-07-24

Similar Documents

Publication Publication Date Title
WO2021182775A1 (fr) Dispositif électroluminescent organique
WO2020141949A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2019168367A1 (fr) Diode électroluminescente organique
WO2018151479A2 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2022080715A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020153713A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2021221475A1 (fr) Dispositif électroluminescent organique
WO2019135665A1 (fr) Dispositif électroluminescent organique
WO2019004790A1 (fr) Composé hétérocyclique et élément électroluminescent organique le contenant
WO2022231390A1 (fr) Dispositif électroluminescent organique
WO2023018267A1 (fr) Nouveau composé, et dispositif électroluminescent organique le comprenant
WO2022039520A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022086168A1 (fr) Dispositif électroluminescent organique
WO2020222569A1 (fr) Dispositif électroluminescent organique
WO2022045743A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021230681A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021251661A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021029634A1 (fr) Nouveau composé, et élément électroluminescent organique l'utilisant
WO2022102992A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022086171A1 (fr) Dispositif électroluminescent organique
WO2021125814A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2024167188A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2022250386A1 (fr) Dispositif électroluminescent organique
WO2022211500A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2022203246A1 (fr) Composé et dispositif électroluminescent organique le comprenant

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: 21880362

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: 21880362

Country of ref document: EP

Kind code of ref document: A1