WO2024085607A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2024085607A1
WO2024085607A1 PCT/KR2023/016064 KR2023016064W WO2024085607A1 WO 2024085607 A1 WO2024085607 A1 WO 2024085607A1 KR 2023016064 W KR2023016064 W KR 2023016064W WO 2024085607 A1 WO2024085607 A1 WO 2024085607A1
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김민준
홍성길
이성재
전현수
김영석
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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

Definitions

  • the present invention relates to novel compounds and organic light-emitting devices containing them.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.
  • Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • a voltage is applied between the two electrodes
  • holes are injected from the anode and electrons from the cathode into the organic material layer.
  • an exciton is formed, and this exciton When it falls back to the ground state, it glows.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to novel compounds and organic light-emitting devices containing them.
  • the present invention provides a compound represented by the following formula (1):
  • R 1 , R 2 , R 4 to R 8 , and R 10 to R 14 is a bond with L 1 , and the others are each independently hydrogen or deuterium,
  • R 3 and R 9 are each independently hydrogen or deuterium
  • L 1 to L 3 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; or a C 2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • the present invention includes a first electrode; a second electrode provided opposite to the first electrode; And providing an organic light-emitting device comprising 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 a compound represented by Formula 1. do.
  • the compound represented by the above-mentioned formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device.
  • the compound represented by Formula 1 described above can be used as a hole transport auxiliary layer material.
  • Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a hole transport auxiliary layer (7), a light emitting layer (8), a hole blocking layer (9), and an electron transport layer (10). ), an electron injection layer 11, and a cathode 4.
  • FIG. 3 shows a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole transport auxiliary layer (7), light emitting layer (8), hole suppression layer (9), and electron injection and transport layer.
  • An example of an organic light emitting device consisting of (12) and a cathode (4) is shown.
  • the present invention provides a compound represented by Formula 1 above.
  • substituted or unsubstituted refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted with one or more substituents can be understood to mean “substituted with one to the maximum number of substitutable hydrogens.”
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a group with the following structure, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a group with the following structure, but is not limited thereto.
  • the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a group with the following structure, but is not limited thereto.
  • the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
  • the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.
  • halogen groups include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups 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, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, etc., but are not limited to these.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6.
  • Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.
  • 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
  • the fluorenyl group is substituted, It can be etc. However, it is not limited to this.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, and 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, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia
  • a zolyl group a phenothiazinyl group, and a dibenzofuranyl group.
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above.
  • the description regarding the heterocyclic group described above may be applied to heteroaryl among heteroarylamines.
  • the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above can be applied, except that arylene is a divalent group.
  • the description of the heterocyclic group described above can be applied, except that heteroarylene is a divalent group.
  • the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents.
  • the description of the heterocyclic group described above can be applied, except that the heterocycle is not a monovalent group and is formed by combining two substituents.
  • deuterated or substituted with deuterium means that at least one of the replaceable hydrogens in a compound, a divalent linking group, or a monovalent substituent is replaced with deuterium.
  • unsubstituted or substituted with deuterium or “substituted or unsubstituted with deuterium” means “one to the maximum number of unsubstituted or replaceable hydrogens is substituted with deuterium.”
  • the term “unsubstituted or deuterium-substituted phenanthryl” refers to “unsubstituted or deuterium-substituted phenanthryl", considering that the maximum number of hydrogens that can be substituted by deuterium in the phenanthryl structure is 9. It can be understood as “phenanthryl substituted with”.
  • deuterated structure refers to compounds of all structures in which at least one hydrogen is replaced with deuterium, a divalent linking group, or a monovalent substituent.
  • deuterated structure of phenyl can be understood to refer to monovalent substituents of all structures in which at least one replaceable hydrogen in the phenyl group is replaced with deuterium, as follows.
  • the “deuterium substitution rate” or “deuteration degree” of a compound is the number of substituted deuteriums relative to the total number of hydrogens that can be present in the compound (the total sum of the number of hydrogens that can be replaced by deuterium and the number of substituted deuteriums in the compound). It means calculating the ratio as a percentage. Therefore, when the “deuterium substitution rate” or “deuteration degree” of a compound is “K%”, it means that K% of the hydrogen replaceable by deuterium in the compound has been replaced with deuterium.
  • the “deuterium substitution rate” or “deuteration degree” is determined by MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1H NMR), TLC/MS (Thin -It can be measured according to commonly known methods using Layer Chromatography/Mass Spectrometry) or GC/MS (Gas Chromatography/Mass Spectrometry). More specifically, when using MALDI-TOF MS, the “deuterium substitution rate” or “deuteration degree” is calculated by calculating the number of deuterium substituted in the compound through MALDI-TOF MS analysis, and then comparing the total number of hydrogens that may exist in the compound. The ratio of the number of deuteriums formed can be calculated as a percentage.
  • the compound of Formula 1 satisfies the structure of an arylamine bonded to a specific position of the benzo[G]chrysene core, it is used in the organic material layer of an organic light-emitting device, especially the hole transport auxiliary layer. , may exhibit low voltage, high efficiency, and/or long life characteristics.
  • Formula 1 may be represented by any one of the following Formulas 1-1 to 1-12.
  • R 1 to R 14 , L 1 to L 3 , and Ar 1 to Ar 2 are as defined in Formula 1.
  • L 1 is a single bond; Phenylene substituted or unsubstituted with one or more deuterium; Or it is biphenyldiyl substituted or unsubstituted with one or more deuterium.
  • L 2 and L 3 are each independently a single bond; Phenylene substituted or unsubstituted with one or more deuterium; Or it is naphthalenediyl substituted or unsubstituted with one or more deuterium.
  • Ar 1 and Ar 2 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; (phenyl)naphthyl; phenanthrenyl; dibenzofuranyl; or dibenzothiophenyl, and Ar 1 and Ar 2 may each independently be substituted with one or more deuterium or unsubstituted.
  • the compound represented by Formula 1 may be one in which one or more hydrogens are replaced with deuterium. That is, in Formula 1, at least one of R 1 to R 14 that is not bonded to L 1 may be deuterium, and at least one substituent among L 1 to L 3 , Ar 1 , and Ar 2 in Formula 1 may be substituted with deuterium. It may have happened.
  • the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound is 4% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, or 40% or more, and is 100% or less, 97%. It may be 95% or less, 90% or less, or 89% or less.
  • the compound may not contain deuterium, or may contain 1 to 50 deuterium atoms. More specifically, the compound does not contain deuterium, or has 1 or more, 3 or more, 5 or more, 8 or more, or 10 or more and has 45 or less, 40 or less, 38 or less, 35. It may contain no more than 33 deuterium atoms.
  • Dn refers to the number of deuterium (D) substitutions in each compound listed in square brackets and is different for each compound, n is an integer greater than 0, and the maximum value of n is the total number of hydrogens contained in each compound in square brackets. It is a count.
  • n is an integer from 0 to 31, is not substituted with deuterium ; and It is used to encompass compounds in which 1 to 31 of the hydrogens are replaced with deuterium.
  • the substitution position of deuterium is not limited. for example silver This means that any 13 of the 31 hydrogens included in are replaced with deuterium.
  • the present invention provides a method for producing the compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be prepared by the method shown in Scheme 1 below.
  • Scheme 1 below illustrates a method for producing a compound of Formula 1 when R 10 and L 1 are combined.
  • Scheme 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed according to what is known in the art.
  • the manufacturing method may be further detailed in the manufacturing examples described later.
  • the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above.
  • the present invention includes a first electrode; a second electrode provided opposite to the first electrode; And providing an organic light-emitting device comprising 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 a compound represented by Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers.
  • the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a hole transport auxiliary layer, and the hole injection layer, the hole transport layer, or the hole transport auxiliary layer includes the compound represented by Formula 1 above.
  • 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 layers, and a cathode are sequentially stacked on a substrate. Additionally, 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 layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 to 3.
  • Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the organic layer.
  • the compound represented by Formula 1 may be included in the hole transport auxiliary layer, for example.
  • FIG. 3 shows a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole transport auxiliary layer (7), light emitting layer (8), hole suppression layer (9), and electron injection and transport layer.
  • An example of an organic light emitting device consisting of (12) and a cathode (4) is shown.
  • the compound represented by Formula 1 may be included in the hole transport auxiliary layer, for example.
  • the organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 above. Additionally, 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 device can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode.
  • PVD physical vapor deposition
  • It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can be made 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 as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited to this.
  • the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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 are included, but are not limited to these.
  • the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic 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;
  • multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
  • the hole injection layer is a layer that injects holes from an electrode.
  • the hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material.
  • a compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • organic materials anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • the hole transport auxiliary layer is a layer located between the hole transport layer and the light-emitting layer to control the transmission or injection rate of holes. It is not particularly limited as long as it is a material with a low hole injection barrier and high hole mobility, and is a material known in the art. can be used without restrictions.
  • the compound represented by Formula 1 can be used as a hole transport auxiliary layer material, and in this case, it is preferable because it can smoothly transfer holes to the light-emitting layer and increase the stability of excitons formed in the light-emitting layer.
  • An electron blocking layer may be interposed between the hole transport auxiliary layer and the light emitting layer.
  • the electron blocking layer serves to improve the efficiency of the organic light-emitting device by preventing electrons injected from the cathode from being transferred to the anode without recombining in the light-emitting layer.
  • a material with lower electron affinity than the electron transport layer is preferred for the electron blocking layer.
  • the light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with 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-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • the light emitting layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene
  • styrylamine compounds include substituted or unsubstituted arylamino groups.
  • substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer.
  • the electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. do. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed 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 excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • a compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. Complex compounds and nitrogen-containing five-membered ring derivatives are included, but are not limited thereto.
  • metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
  • the organic light emitting device may include an electron injection and transport layer that simultaneously performs these roles instead of the electron transport layer and the electron injection layer.
  • the electron injection and transport layer material one or more of the electron transport layer and electron injection layer materials described above may be used.
  • the organic light-emitting device according to the present invention may be a bottom-emitting device, a top-emitting device, or a double-sided light-emitting device. In particular, it may be a bottom-emitting device that requires relatively high luminous efficiency.
  • the compound represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.
  • amine16 (15 g, 57.8 mmol), sub15 (23.6 g, 60.7 mmol), and sodium tert-butoxide (8.3 g, 86.8 mmol) were added to 300 ml of Xylene, stirred, and refluxed. Afterwards, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • Compound 38_P1 (10 g, 16.7 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.4 g, 418.6 mmol) was added to Trifluoromethanesulfonic anhydride (23.6 g, 83.7 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 39_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.1 g, 402.4 mmol) was added to Trifluoromethanesulfonic anhydride (22.7 g, 80.5 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 4 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • amine16 (15 g, 57.8 mmol), sub5 (23.6 g, 60.7 mmol), and sodium tert-butoxide (8.3 g, 86.8 mmol) were added to 300 ml of Xylene, stirred, and refluxed. Afterwards, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • Compound 40_P1 (10 g, 16.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.2 g, 409 mmol) was added to Trifluoromethanesulfonic anhydride (23.1 g, 81.8 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 41_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.7 g, 386.2 mmol) was added to Trifluoromethanesulfonic anhydride (21.8 g, 77.2 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 4 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 42_P1 (10 g, 14.6 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.3 g, 363.8 mmol) was added to Trifluoromethanesulfonic anhydride (20.5 g, 72.8 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • amine32 (15 g, 37.7 mmol), sub8 (15.4 g, 39.6 mmol), and sodium tert-butoxide (5.4 g, 56.6 mmol) were added to 300 ml of Xylene, stirred, and refluxed. Afterwards, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours, the reaction was completed, the reaction was cooled to room temperature, and the solvent was removed under reduced pressure.
  • Compound 43_P1 (10 g, 13.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (6.7 g, 333.6 mmol) was added to Trifluoromethanesulfonic anhydride (18.8 g, 66.7 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 44_P1 (10 g, 16.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.2 g, 409 mmol) was added to Trifluoromethanesulfonic anhydride (23.1 g, 81.8 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 4 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 45_P1 (10 g, 14.9 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.4 g, 371.3 mmol) was added to Trifluoromethanesulfonic anhydride (21 g, 74.3 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 46_P1 (10 g, 14.9 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.4 g, 371.3 mmol) was added to Trifluoromethanesulfonic anhydride (21 g, 74.3 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 47_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.1 g, 402.4 mmol) was added to Trifluoromethanesulfonic anhydride (22.7 g, 80.5 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 48_P1 (10 g, 15.9 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8 g, 398.2 mmol) was added to Trifluoromethanesulfonic anhydride (22.5 g, 79.6 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 49_P1 (10 g, 14.9 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.4 g, 371.3 mmol) was added to Trifluoromethanesulfonic anhydride (21 g, 74.3 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 50_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.1 g, 402.4 mmol) was added to Trifluoromethanesulfonic anhydride (22.7 g, 80.5 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 51_P1 (10 g, 14.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.2 g, 358.5 mmol) was added to Trifluoromethanesulfonic anhydride (20.2 g, 71.7 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 52_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.7 g, 386.2 mmol) was added to Trifluoromethanesulfonic anhydride (21.8 g, 77.2 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 53_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (7.7 g, 386.2 mmol) was added to Trifluoromethanesulfonic anhydride (21.8 g, 77.2 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 54_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.1 g, 402.4 mmol) was added to Trifluoromethanesulfonic anhydride (22.7 g, 80.5 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 3 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 55_P1 (10 g, 16.7 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (8.4 g, 418.6 mmol) was added to Trifluoromethanesulfonic anhydride (23.6 g, 83.7 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 56_P1 (10 g, 17.5 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (12.6 g, 630.2 mmol) was added to Trifluoromethanesulfonic anhydride (44.5 g, 157.6 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 57_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.6 g, 579.5 mmol) was added to Trifluoromethanesulfonic anhydride (40.9 g, 144.9 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 58_P1 (10 g, 14.9 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.7 g, 534.7 mmol) was added to Trifluoromethanesulfonic anhydride (37.7 g, 133.7 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • amine45 15 g, 57.8 mmol
  • sub10 23.6 g, 60.7 mmol
  • sodium tert-butoxide 8.3 g, 86.8 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • Compound 59_P1 (10 g, 16.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.8 g, 589 mmol) was added to Trifluoromethanesulfonic anhydride (41.5 g, 147.2 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 10 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 60_P1 (10 g, 16 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.5 g, 575.8 mmol) was added to Trifluoromethanesulfonic anhydride (40.6 g, 144 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 10 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 61_P1 (10 g, 16.1 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.6 g, 579.5 mmol) was added to Trifluoromethanesulfonic anhydride (40.9 g, 144.9 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 62_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.1 g, 556.2 mmol) was added to Trifluoromethanesulfonic anhydride (39.2 g, 139 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 63_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.1 g, 556.2 mmol) was added to Trifluoromethanesulfonic anhydride (39.2 g, 139 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 64_P1 (10 g, 15.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.1 g, 556.2 mmol) was added to Trifluoromethanesulfonic anhydride (39.2 g, 139 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained.
  • Compound 65_P1 (10 g, 13.8 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10 g, 497.7 mmol) was added to Trifluoromethanesulfonic anhydride (35.1 g, 124.4 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 10 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • Compound 66_P1 (10 g, 16.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.8 g, 589 mmol) was added to Trifluoromethanesulfonic anhydride (41.5 g, 147.2 mmol) at 0°C, and stirred for 10 hours to prepare a solution.
  • the mixed solution of trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140 degrees and stirred while maintained. After reaction for 10 hours, it was cooled to room temperature and the organic layer and water layer were separated.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following HI-1 compound was formed as a hole injection layer to a thickness of 1100 ⁇ , and the following A-1 compound was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 ⁇ .
  • Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 100 ⁇ as a hole transport auxiliary layer.
  • compounds represented by the following chemical formulas BH-1 and BD-1 were vacuum deposited as a light emitting layer to a thickness of 250 ⁇ at a weight ratio of 25:1.
  • a compound represented by the following chemical formula HB-1 was vacuum deposited to a thickness of 50 ⁇ as a hole blocking layer.
  • a compound represented by the formula ET-1 and a compound represented by LiQ below were thermally vacuum deposited at a weight ratio of 1:1 to a thickness of 310 ⁇ .
  • lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ were sequentially deposited to form a cathode, thereby manufacturing an organic light-emitting device.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2x10 -7 ⁇
  • An organic light emitting device was manufactured by maintaining 5x10 -6 torr.
  • Organic light-emitting devices of Comparative Examples 1-1 to 1-11 were manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 were used instead of Compound 1.
  • Compounds C-1 to C-11 used in each comparative example are as follows.
  • the organic light-emitting devices of Examples 1-1 to 1-66 using the compound represented by Formula 1 as the hole transport auxiliary layer material of the blue light-emitting layer are compared with Comparative Examples 1-1 to 1-11.
  • the driving voltage is low and the efficiency and lifespan are significantly improved.
  • the lifespan characteristics of the organic light-emitting device were further improved when the compound represented by Formula 1 substituted with deuterium was used. It is believed that the reason that the device of the above example showed excellent characteristics in terms of driving voltage, efficiency, and lifespan is that the compound represented by Formula 1 contributed to the stability of the exciton formed in the light-emitting layer.
  • Substrate 2 Anode

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2023/016064 2022-10-17 2023-10-17 Nouveau composé et dispositif électroluminescent organique le comprenant WO2024085607A1 (fr)

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KR20160086482A (ko) * 2015-01-09 2016-07-20 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자
KR20160120386A (ko) * 2015-04-07 2016-10-18 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자
CN110526825A (zh) * 2018-05-25 2019-12-03 江苏三月光电科技有限公司 一种以异屈与三芳胺结构为核心的化合物及其应用
CN116239479A (zh) * 2023-03-17 2023-06-09 浙江八亿时空先进材料有限公司 一种氨基化合物及其应用

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