WO2024063592A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2024063592A1
WO2024063592A1 PCT/KR2023/014472 KR2023014472W WO2024063592A1 WO 2024063592 A1 WO2024063592 A1 WO 2024063592A1 KR 2023014472 W KR2023014472 W KR 2023014472W WO 2024063592 A1 WO2024063592 A1 WO 2024063592A1
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compound
deuterium
substituted
layer
mmol
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김영석
김민준
정민우
서상덕
김동희
오중석
김소연
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주식회사 엘지화학
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Publication of WO2024063592A1 publication Critical patent/WO2024063592A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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 is When it falls back to the ground state, it glows.
  • Patent Document 0001 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):
  • Y is each independently O or S
  • R 1 is each independently hydrogen or deuterium
  • L 1 , L 2 , and L 3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted O and S,
  • At least one of R 1 , L 1 to L 3 , Ar 1 , and Ar 2 is deuterium or substituted with deuterium.
  • the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and 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. to provide.
  • 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 the above-mentioned formula 1 can be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material.
  • Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • Figure 2 shows the substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), hole blocking layer (8), electron injection and transport layer ( 9), and a cathode (4).
  • 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.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound 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.
  • it may be a compound of the following structural formula, 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 compound 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 can 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.”
  • phenanthryl unsubstituted or substituted with deuterium means “unsubstituted or substituted with 1 to 9 deuteriums,” considering that the maximum number of hydrogens that can be substituted with deuterium in the phenanthryl structure is 9. It can be understood to mean “substituted phenanthryl.”
  • 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 present invention provides a compound represented by Formula 1 above.
  • the compound represented by Formula 1 is a specific position in the benzene ring at one end of the parent core structure of benzobisbenzofuran or benzobisbenzothiophene, that is, the oxygen in the terminal benzene ring condensed to benzothiophene or benzofuran.
  • it is a compound in which a tertiary amine group of a specific structure is bonded to the second carbon position from the sulfur atom, and at least one of the substituents of the compound is deuterium or is substituted with deuterium.
  • the compound has longer lifespan characteristics compared to compounds in which the substituent is light hydrogen, and therefore can be effectively applied to the light-emitting layer of an organic light-emitting device.
  • Y is each independently O or S
  • R 1 is each independently hydrogen or deuterium
  • L 1 , L 2 , and L 3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted O and S,
  • At least one of R 1 , L 1 to L 3 , Ar 1 , and Ar 2 is deuterium or substituted with deuterium.
  • all Y's are O, or all Y's are S, or one of the Y's is S and the others are O.
  • R 1 may be deuterium, and the remainder of R 1 may be hydrogen.
  • R 1 may be at least 3 or more or 3 to 9 deuteriums, or at least 4 or more or 4 to 9 deuteriums.
  • the remainder of R 1 may be hydrogen.
  • all of R 1 may be deuterium.
  • Y is each independently O or S
  • n is an integer from 1 to 9
  • L 1 , L 2 , and L 3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted O and S.
  • n is the number of deuterium substitutions in the parent nucleus structure of benzobisbenzofuran or benzobisbenzothiophene, and is indicated by b in relation to a representative example described later.
  • n 0, and n is at least 1 or 1 to 9.
  • L 1 , L 2 , and L 3 are each a single bond; Alternatively, it may be phenylene, phenylene substituted with at least one deuterium, naphthylene, or naphthylene substituted with at least one deuterium.
  • L 1 , L 2 , and L 3 are each a single bond; Alternatively, it may be phenylene, phenylene substituted with at least one or 1 to 4 deuteriums, naphthylene, or naphthylene substituted with at least 1 or 1 to 6 deuteriums.
  • L 1 , L 2 , and L 3 may each be a single bond or any one selected from the group consisting of the following.
  • L 1 and L 2 may each independently be a single bond or a hydrogen- or deuterium-substituted phenylene.
  • L 1 and L 2 may each independently be a single bond or phenylene, or phenylene with 4 deuterium substitutions, naphthylene, or naphthylene with 3 or more or 3 to 6 deuterium substitutions. there is.
  • L 1 and L 2 may each independently be a single bond, phenylene, or phenylene substituted with four deuteriums.
  • L 3 may be phenylene substituted with hydrogen or deuterium.
  • L 3 may be phenylene or phenylene substituted with four deuterium atoms.
  • At least one of L 1 , L 2 , and L 3 may be deuterium-substituted phenylene.
  • Ar 1 and Ar 2 are each independently C 6-19 aryl substituted with hydrogen or deuterium, C 6-14 aryl substituted with hydrogen or deuterium, or C 6-14 aryl substituted with hydrogen or deuterium. It may be C 2-19 heteroaryl substituted with or C 2-12 heteroaryl substituted with hydrogen or deuterium.
  • Ar 1 and Ar 2 is C 6-19 aryl substituted with deuterium, C 6-14 aryl substituted with hydrogen or deuterium, or C 2-19 heteroaryl substituted with deuterium or hydrogen or deuterium. It may be substituted C 2-12 heteroaryl.
  • Ar 1 and Ar 2 are each independently phenyl substituted with hydrogen or deuterium, biphenyl substituted with hydrogen or deuterium, naphthyl substituted with hydrogen or deuterium, phenanthryl substituted with hydrogen or deuterium, hydrogen or deuterium It may be dibenzofuranyl substituted with deuterium, dibenzothiophenyl substituted with hydrogen or deuterium, or carbazolyl substituted with hydrogen or deuterium.
  • Ar 1 and Ar 2 are each independently phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl, biphenyl substituted with 1 to 9 deuteriums, naphthyl, 1 to 7 deuteriums.
  • Ar 1 or Ar 2 may each be selected from the group consisting of:
  • Ar 1 and Ar 2 are each independently phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl, biphenyl substituted with 1 to 9 deuteriums, naphthyl, 1 to 7 deuteriums. Naphthyl substituted with deuterium, phenanthryl, phenanthryl substituted with 1 to 9 deuteriums, dibenzofuranyl, dibenzofuranyl substituted with 1 to 7 deuteriums, dibenzothiophenyl, or 1 to 9 deuteriums. It may be dibenzothiophenyl substituted with 7 deuteriums.
  • At least one of Ar 1 and Ar 2 may contain two or more benzene rings.
  • Ar 1 and Ar 2 is biphenyl substituted with hydrogen or deuterium, naphthyl substituted with hydrogen or deuterium, phenanthryl substituted with hydrogen or deuterium, and dibenzofuranyl substituted with hydrogen or deuterium. , or it may be dibenzothiophenyl substituted with hydrogen or deuterium.
  • Ar 1 and Ar 2 is biphenyl, biphenyl substituted with 1 to 9 deuteriums, naphthyl, naphthyl substituted with 1 to 7 deuteriums, phenanthryl, 1 to It may be phenanthryl, dibenzofuranyl substituted with 9 deuteriums, dibenzofuranyl substituted with 1 to 7 deuteriums, dibenzothiophenyl, or dibenzothiophenyl substituted with 1 to 7 deuteriums. .
  • Ar 1 and Ar 2 is biphenyl substituted with 5 or more or 5 to 9 deuteriums, naphthyl substituted with 4 or more or 4 to 7 deuteriums, or 4 or more or 4 deuteriums. It may be phenanthryl substituted with 2 to 9 deuteriums, dibenzofuranyl substituted with 2 or more or 2 to 7 deuteriums, and dibenzothiophenyl substituted with 2 or more or 2 to 7 deuteriums.
  • At least one of Ar 1 and Ar 2 may be C 6-19 aryl substituted with hydrogen or deuterium, or C 6-14 aryl substituted with hydrogen or deuterium.
  • Ar 1 and Ar 2 may be phenyl substituted with hydrogen or deuterium, biphenyl substituted with hydrogen or deuterium, naphthyl substituted with hydrogen or deuterium, or phenanthryl substituted with hydrogen or deuterium. there is.
  • Ar 1 and Ar 2 is phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl, biphenyl substituted with 1 to 9 deuteriums, naphthyl, 1 to 7 deuteriums. It may be naphthyl substituted with deuterium, phenanthryl, or phenanthryl substituted with 1 to 9 deuterium atoms.
  • Ar 1 and Ar 2 is phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl substituted with 5 or more or 5 to 9 deuteriums, 4 or more or 4 to 4 deuteriums. It may be naphthyl substituted with 7 deuteriums, or phenanthryl substituted with 4 or more or 4 to 9 deuteriums.
  • At least one of R 1 , L 1 to L 3 , Ar 1 , and Ar 2 may be deuterium or substituted with deuterium.
  • At least one of R 1 may be deuterium, or at least one of L 1 to L 3 may be phenylene substituted with deuterium, or at least one of Ar 1 and Ar 2 may be substituted with deuterium. .
  • At least one of R 1 is deuterium, and at least one of L 1 to L 3 is phenylene substituted with deuterium, or at least one of Ar 1 and Ar 2 is substituted with deuterium. You can.
  • Ar 1 when L 1 in Formula 1 and Formula 1-1 is a single bond, Ar 1 is C 6-19 aryl unsubstituted with deuterium, or C 2-19 heteroaryl substituted with hydrogen or deuterium. It may be, and when L 1 is substituted or unsubstituted C 6-60 arylene, Ar 1 is C 6-19 aryl substituted with hydrogen or deuterium, or C 2-19 heteroaryl substituted with hydrogen or deuterium. It can be.
  • Ar 2 when L 2 is a single bond, Ar 2 is deuterium-unsubstituted C 6-19 aryl, or hydrogen or deuterium-substituted C 2-19 heteroaryl, and L 2 is substituted or unsubstituted C 6- 60
  • Ar 2 may be C 6-19 aryl substituted with hydrogen or deuterium, or C 2-19 heteroaryl substituted with hydrogen or deuterium.
  • Ar 1 when L 1 is a single bond, Ar 1 is phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl substituted with hydrogen or deuterium, or hydrogen or deuterium. It may be substituted dibenzothiophenyl, and when L 1 is substituted or unsubstituted C 6-60 arylene, Ar 1 is phenyl substituted with hydrogen or deuterium, biphenyl substituted with hydrogen or deuterium, or hydrogen or deuterium.
  • Ar 2 may be naphthyl substituted with, phenanthryl substituted with hydrogen or deuterium, dibenzofuranyl substituted with hydrogen or deuterium, or dibenzothiophenyl substituted with hydrogen or deuterium.
  • Ar 2 may be phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl substituted with hydrogen or deuterium, or dibenzothiophenyl substituted with hydrogen or deuterium
  • L 2 is substituted or unsubstituted C 6-60 arylene
  • Ar 2 is phenyl substituted with hydrogen or deuterium, biphenyl substituted with hydrogen or deuterium, naphthyl substituted with hydrogen or deuterium, or hydrogen or deuterium. It may be substituted phenanthryl, dibenzofuranyl substituted with hydrogen or deuterium, or dibenzothiophenyl substituted with hydrogen or deuterium.
  • the compound contains at least one deuterium.
  • the total number of deuterium substitutions and the number of substitutions for each substituent of the compound are as described with a, b, c, d, e, f, and g in relation to the structural formula of a representative example described later, and detailed descriptions are omitted.
  • At least one of the substituents of the parent nucleus structure of benzobisbenzofuran or benzobisbenzothiophene in Formula 1 and Formula 1-1, that is, R 1 may be deuterium.
  • the deuterium substitution rate of the compound may be 1% to 100%.
  • the deuterium substitution rate of the compound is 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 28% or more, 30% or more, 32% or more, 35% or more, 38% or more, More than 40%, more than 42%, more than 45%, more than 48%, more than 50%, more than 52%, more than 55%, more than 58%, more than 60%, more than 62%, more than 65%, more than 68%, more than 70% It may be 72% or more, 75% or more, 78% or more, 80% or more, or 90% or more, and 100% or less.
  • the deuterium substitution rate of the compound is 20% or more, or 25% or more, 28% or more, 30% or more, 32% or more, 35% or more, 38% or more, 40% or more, 42% or more, 45% or more, 48% or more, 50% or more, but 100% or less, or 98% or less, 95% or less, 92% or less, 90% or less, 88% or less, 85% or less, 82% or less, 80% or less, 78% or less, It may be 75% or less, 72% or less, 70% or less, 68% or less, 65% or less, 62% or less, 60% or less, 58% or less, or 55% or less.
  • the compound may contain at least one deuterium or 1 to 50 deuteriums. More specifically, the compound contains at least 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 deuterium. , or 11 or more, but not more than 50, not more than 40, not more than 35, not more than 32, not more than 30, not more than 28, not more than 26, not more than 24, not more than 22, not more than 20, not more than 19. , may contain 18 or fewer, 17 or fewer, or 16 or fewer deuterium atoms.
  • the compounds represented by Formula 1 and Formula 1-1 may be those in which at least 3 or 3 to 35 deuteriums are substituted, and specifically, at least 4 or more or 4 to 30 deuteriums may be substituted. It may be substituted, or at least 6 or more or 6 to 25 deuteriums may be substituted, or at least 8 or more or 8 to 20 deuterium may be substituted. More specifically, at least 11 or 11 to 16 deuteriums may be substituted.
  • at least one of R 1 , L 1 to L 3 , and Ar 1 to Ar 2 may be at least 3 or 3 to 35 deuterium atoms or may be substituted with at least 3 or 3 to 35 deuterium atoms.
  • At least 4 or more or 4 to 30 deuteriums or at least 4 or more or 4 to 30 deuteriums, or at least 6 or more or 6 to 25 deuteriums, or at least 6 or more, or It may be substituted with 6 to 25 deuterium atoms, or may be substituted with at least 8 or 8 to 20 deuterium atoms, or may be substituted with at least 8 or 8 to 20 deuterium atoms. More specifically, at least one of R 1 , L 1 to L 3 , and Ar 1 to Ar 2 is at least 11 or 11 to 16 deuterium, or at least 11 or more or 11 to 16 deuterium. It may be substituted with deuterium
  • D is deuterium
  • a is the number of deuterium substitutions
  • a in the structural formula is the total number of deuterium substitutions in the compound, and a > 0, and is the total number of individual deuterium substitutions of each substituent.
  • a may be at least 1 or 1 to 50. More specifically, a in the structural formula is at least 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, or 11 or more, and is 50 or less, 40 or less. , 35 or less, 32 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 19 or less, 18 or less, 17 or less, or 16 or less.
  • a in the structural formula may be at least 3 or 3 to 35, or at least 4 or more or 4 to 30, or at least 6 or more, or 6 to 25, or at least 8 or more, or 8 to 20. More specifically, a in the structural formula may be at least 11 or more or 11 to 16.
  • the number of individual small and medium substitutions of each substituent constituting a in the structural formula can be expressed as b, c, d, e, f, and g, respectively, and can refer to the specific examples described below.
  • b is the number of deuterium substitutions in the parent nucleus structure of benzobisbenzofuran or benzobisbenzothiophene in Formula 1, and b > 0.
  • b may be at least 1 or 1 to 9.
  • c is the number of deuterium substituted in the L 1 substituent that is the linker in Formula 1
  • d is the number of deuterium substituted in the L 2 substituent that is the linker in Formula 1
  • e is the number of deuterium substituted in the L 2 substituent that is the linker in Formula 1.
  • f is the number of deuterium substituted in the Ar 1 substituent, which is the substituent of the tertiary amine group in Formula
  • g is the number of deuterium substituted by the Ar 2 substituent, which is the substituent of the tertiary amine group in Formula 1.
  • the total sum of c+d+e+f+g may be 0 to 49.
  • D is deuterium
  • a is the total number of deuterium substitutions
  • a > is the total number of individual deuterium substitutions of each substituent, and the specific range is as described above.
  • D is deuterium
  • a is the total number of deuterium substitutions in the compound
  • a may be at least 1 or 1 to 50, and the specific range is as described above.
  • b, c, d, e, f, g are the number of individual small and medium substitutions of each substituent in the structural formula
  • b may be at least 1 or 1 to 9
  • c+d+e+f+g The total may be 0 to 49, and the specific range is as described above.
  • the compound represented by Chemical Formula 1 can be prepared by the manufacturing method shown in Scheme 1 below.
  • the manufacturing method may be further detailed in the synthesis examples described later.
  • Q 1 is BO 2 C 2 (CH 3 ) 4 , or B(OH) 2 ,
  • p and q are each 0 or 1, provided that at least one of p and q is 0, and the remaining of p and q is 1.
  • Q 1 is B(OH) 2 .
  • Q 2 is Cl, Br, or I, preferably Cl, or Br, and more preferably Cl.
  • Scheme 1 is a specific position in the benzene ring at one end of the parent nucleus structure of benzobisbenzofuran or benzobisbenzothiophene, that is, an oxygen or sulfur atom in the terminal benzene ring condensed to benzothiophene or benzofuran.
  • This is a reaction to introduce a tertiary amine substituent of a specific structure at the second carbon position and replace it with deuterium.
  • the deuterium substitution reaction may be omitted, or the deuterium substitution reaction may be performed together to additionally substitute deuterium on the remaining substituents.
  • the base components include potassium carbonate (K 2 CO 3 ), sodium bicarbonate (NaHCO 3 ), cesium carbonate (Cs 2 CO 3 ), and sodium acetate (sodium).
  • acetate (NaOAc), potassium acetate (KOAc), sodium ethoxide (NaOEt), sodium tert-butoxide (NaOtBu), or triethylamine (Et 3 N), N,N-diisopropylethylamine (EtN(iPr) 2 ), etc. can be used.
  • the base component is potassium carbonate (K 2 CO 3 ), cesium carbonate (Cs 2 CO 3 ), potassium acetate (KOAc), and sodium tert-butoxide. butoxide, NaOtBu), or N,N-diisopropylethylamine (EtN(iPr) 2 ).
  • potassium carbonate (K 2 CO 3 ) can be used as a base component.
  • the palladium catalyst includes bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(t-Bu 3 P) 2 ), tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh 3 ) 4 ), tris(dibenzylideneacetone)dipalladium (0) (tris (dibenzylideneacetone)-dipalladium (0), bis(dibenzylideneacetone)palladium (0), Pd(dba) 2 ) or palladium(II) acetate (palladium(II) acetate, Pd (OAc) 2 ) can be used, etc.
  • the palladium catalyst is bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0 ), Pd(t-Bu 3 P) 2 ), tetrakis(triphenylphosphine)palladium (0), Pd(PPh 3 ) 4 ), or bis(dibenzylideneacetone ) It may be palladium (0) (bis(dibenzylideneacetone)palladium (0), Pd(dba) 2 ).
  • bis(tri-(tert-butyl)phosphine)palladium (0) bis (tri-(tert-butyl)phosphine)palladium(0), Pd(t-Bu 3 P) 2
  • bis(tri-(tert-butyl)phosphine)palladium(0), Pd(t-Bu 3 P) 2 can be used as a catalyst.
  • 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 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, an electron blocking layer, a light emitting layer, a hole blocking 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 to this and may include fewer organic layers.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 Contains the indicated compounds.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 Contains the indicated compounds.
  • the organic material layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.
  • the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.
  • the light emitting layer further includes a dopant compound.
  • the light-emitting layer includes the compound of Formula 1 and a dopant.
  • the light-emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in a weight ratio of 100:1 to 1:1.
  • the light-emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in an content ratio of 100:1 to 2:1.
  • the light-emitting layer includes the compound of Formula 1 and a dopant, and the compound of Formula 1 and the dopant are 100:1 to 5:1, or 100:1 to 10:1, or 100:1 to 20:1, or 100:1. It is included in a weight ratio of :1 to 30:1.
  • the dopant is a metal complex.
  • the dopant is an iridium-based metal complex.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes a dopant
  • the dopant material is selected from the structural formulas below.
  • the structure specified above is not limited to the dopant compound.
  • the organic material layer may include a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.
  • the organic material layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport, and the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron injection and transport is represented by Formula 1 Contains the indicated compounds.
  • the organic material layer includes a light-emitting layer and an electron-blocking layer
  • the light-emitting layer or the electron-blocking layer may include the compound represented by Formula 1.
  • 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. 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 and 2.
  • Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the light-emitting layer.
  • Figure 2 shows the substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), hole blocking layer (8), electron injection and transport layer ( 9) and a cathode 4.
  • An example of an organic light-emitting device is shown.
  • the compound represented by Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, and electron injection and transport layer.
  • the compound represented by Formula 1 may be included in the light-emitting layer, for example, as a host material of the light-emitting layer.
  • 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.
  • an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation.
  • a PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited on it. It can be manufactured.
  • 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 compound represented by Formula 1 has excellent solubility in the solvent used in the solution application method, making it easy to apply the solution application method.
  • 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.
  • the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.
  • the solvent is not particularly limited as long as it is capable of dissolving or dispersing the compound according to the present invention, and examples include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorine-based solvents such as dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such
  • Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol
  • Sulfoxide-based solvents such as dimethyl sulfoxide
  • amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide
  • Benzoate-based solvents such as butyl benzoate and methyl-2-methoxybenzoate
  • tetralin Solvents such as 3-phenoxy-toluene may be mentioned.
  • the above-mentioned solvents may be used individually or two or more types of solvents may be mixed.
  • the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within this range.
  • the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.
  • the present invention provides a method of forming a functional layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention described above by a solution process; and heat treating the coated coating composition.
  • the heat treatment temperature is preferably 150°C to 230°C. Additionally, the heat treatment time is 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. Additionally, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.
  • 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; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • 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.
  • 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 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
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • a compound according to the present invention is used as the host material.
  • 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.
  • arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group.
  • 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.
  • an iridium-based metal complex is used as the dopant material.
  • the light-emitting layer may be a red light-emitting layer, and when the compound according to the present invention is used as a host material, the stability of electrons and holes increases, energy is transferred from the host to the red dopant well, and the driving voltage of the organic light-emitting device, Luminous efficiency and lifespan characteristics can be improved.
  • 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 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 according to the present invention may be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.
  • compound sub 1 (15 g, 51.2 mmol) and amine compound amine 1 (15.6 g, 53.8 mmol) were added to 300 mL of tetrahydrofuran (THF), stirred and refluxed. Afterwards, potassium carbonate (K 2 CO 3 , 21.2 g, 153.7 mmol) was dissolved in 100 mL of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu 3 P) 2 , 0.3 g, 0.5 mmol) was added. After reaction for 5 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • K 2 CO 3 potassium carbonate
  • Pd(t-Bu 3 P) 2 bis(tri-tert-butylphosphine)palladium(0)
  • compound 1_P1 (10 g, 19.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene (TCB) and stirred at room temperature.
  • TB 1,2,4-trichlorobenzene
  • Deuterium oxide DO , 14.4 g, 717.7 mmol
  • Tf 2 O Trifluoromethanesulfonic anhydride
  • Tf 2 O Trifluoromethanesulfonic anhydride
  • 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 o C and stirred while maintained.
  • compound 2_P1 (10 g, 15.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.5 g, 573.5 mmol) was added to Trifluoromethanesulfonic anhydride (36 g, 127.4 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 3_P1 (10 g, 15.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide 11 g, 550.6 mmol was added to Trifluoromethanesulfonic anhydride (34.5 g, 122.4 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 4_P1 (10 g, 15.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.5 g, 573.5 mmol) was added to Trifluoromethanesulfonic anhydride (36 g, 127.4 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 5_P1 (10 g, 16.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (12.2 g, 608.4 mmol) was added to Trifluoromethanesulfonic anhydride (38.1 g, 135.2 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 6_P1 (10 g, 15 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.8 g, 539.1 mmol) was added to Trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 7_P1 (10 g, 15 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.8 g, 539.1 mmol) was added to Trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 8_P1 (10 g, 16.5 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (11.9 g, 592.4 mmol) was added to Trifluoromethanesulfonic anhydride (37.1 g, 131.6 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 9_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.5 g, 526.4 mmol) was added to Trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound sub 1 (15 g, 51.2 mmol) and amine compound amine 10 (29.5 g, 53.8 mmol) were added to 300 mL of THF, stirred, and refluxed. Afterwards, potassium carbonate (K 2 CO 3 , 21.2 g, 153.7 mmol) was dissolved in 100 mL of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu 3 P) 2 , 0.3 g, 0.5 mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • K 2 CO 3 potassium carbonate
  • Pd(t-Bu 3 P) 2 bis(tri-tert-butylphosphine)palladium(0)
  • the compound 10_P1 (10 g, 13.2 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (9.5 g, 473.7 mmol) was added to Trifluoromethanesulfonic anhydride (29.7 g, 105.3 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 11_P1 (10 g, 16.8 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (12.1 g, 606.3 mmol) was added to Trifluoromethanesulfonic anhydride (38 g, 134.7 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 12_P1 (10 g, 13.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10 g, 500.1 mmol) was added to Trifluoromethanesulfonic anhydride (31.4 g, 111.1 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 13_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10.5 g, 526.4 mmol) was added to Trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 14_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10.3 g, 514.4 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 15_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (9.3 g, 463.9 mmol) was added to Trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 16_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10.5 g, 526.4 mmol) was added to Trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 17_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10.5 g, 526.4 mmol) was added to Trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 18_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.3 g, 514.4 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 19_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene under a nitrogen atmosphere and stirred at room temperature.
  • Deuterium oxide (10.3 g, 514.4 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 20_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (9.3 g, 463.9 mmol) was added to Trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • compound 21_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.3 g, 514.4 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 22_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (9.3 g, 463.9 mmol) was added to Trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 23_P1 (10 g, 14 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.1 g, 502.8 mmol) was added to Trifluoromethanesulfonic anhydride (31.5 g, 111.7 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 24_P1 (10 g, 14 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (10.1 g, 502.8 mmol) was added to Trifluoromethanesulfonic anhydride (31.5 g, 111.7 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • the compound 25_P1 (10 g, 12.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature.
  • Deuterium oxide (9.1 g, 454.5 mmol) was added to Trifluoromethanesulfonic anhydride (28.5 g, 101 mmol) at 0 o C, and stirred for 5 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 o C and stirred while maintained.
  • 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 with ultrasonic waves.
  • 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 compound HI-1 was formed as a hole injection layer to a thickness of 1150 ⁇ , and the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following compound HT-1 was vacuum deposited to form a hole transport layer with a film thickness of 800 ⁇ .
  • the following compound EB-1 was vacuum deposited to form an electron blocking layer with a thickness of 150 ⁇ .
  • Compound 1 and Dp-7 were vacuum deposited at a weight ratio of 98:2 to form a red light-emitting layer with a thickness of 400 ⁇ .
  • the following compound HB-1 was vacuum deposited to form a hole blocking layer with a film thickness of 30 ⁇ .
  • the following ET-1 compound and the following LiQ compound were vacuum deposited at a weight ratio of 2:1 to form an electron injection and transport layer with a film thickness of 300 ⁇ .
  • lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ 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 ⁇ /sec to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • aluminum was maintained at 2 ⁇ /sec
  • Organic light-emitting devices were manufactured by maintaining 2*10 -7 torr to 5*10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds 2 to 25 listed in Table 1 below were used instead of compound 1 as a host when forming the light-emitting layer in the organic light-emitting device of Example 1.
  • An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 2 below were used instead of Compound 1 as a host when forming the light-emitting layer in the organic light-emitting device of Example 1.
  • Comparative compounds RH-1 to RH-6, comparative compound 1_P1, and compound 13_P1 used in Table 2 below are respectively as follows.
  • the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm 2 , and the lifespan T95 was 95% of the initial luminance at a current density of 50 mA/cm 2.
  • the time required to reduce to (T95, hr) was measured. The results are shown in Tables 1 and 2 below.
  • Example 1 Compound 1 4.03 24.01 170
  • Example 2 Compound 2 4.10 24.05 189
  • Example 3 Compound 3 4.15 24.12 184
  • Example 4 Compound 4 4.08 23.99 175
  • Example 5 Compound 5 4.11 24.09 182
  • Example 6 Compound 6 4.08 23.95
  • Example 7 Compound 7 4.07 24.11 191
  • Example 8 Compound 8 4.11 24.39 189
  • Example 9 Compound 9 4.10 24.38 187
  • Example 10 Compound 10 4.09 23.88 177
  • Example 11 Compound 11 4.12 24.05 181
  • Example 12 Compound 12 4.15 24.65 185
  • Example 13 Compound 13 4.09 24.15 180
  • Example 14 Compound 14 4.13 25.09 193
  • Example 15 Compound 15 4.02 25.69 192
  • Example 16 Compound 16 4.03 24.42 181
  • Example 17 Compound 17 4.12 23.95 185
  • Example 18 Compound 18 4.06 23.99
  • Example 19 Compound 19 4.08 24.
  • the red organic light emitting device of Example 1 used materials that were widely used in the past, and had a structure in which Compound 1 was used as the light emitting layer and Dp-7 was used as the dopant of the red light emitting layer.
  • organic light-emitting devices were manufactured using Compounds 2 to 25 instead of Compound 1, and in Comparative Examples 1 to 19, Comparative Compounds RH-1 to RH-6, Comparative Compound 1_P1, and Comparative Compound 13_P1 instead of Compound 1.
  • An organic light emitting device was manufactured using .
  • the compound represented by Formula 1 i.e., benzobisbenzofuran or benzobisbenzothiophene
  • the compound represented by Formula 1 is condensed at a specific position in the benzene ring at one end of the parent nucleus structure, i.e., benzothiophene or benzofuran.
  • the organic light emitting devices of Examples 1 to 25 could significantly improve lifespan characteristics while maintaining high efficiency. This can ultimately be judged to be because the compounds of the examples according to the present invention have higher stability to electrons and holes than the compounds of the comparative examples. In conclusion, it can be confirmed that the driving voltage, luminous efficiency, and lifespan characteristics of organic light-emitting devices can be improved when the compound of the present invention is used as a light-emitting layer or hole transport layer.
  • the organic light-emitting device manufactured using the compound according to the present invention as the host of the light-emitting layer exhibits superior performance in terms of efficiency and lifespan compared to the organic light-emitting device of the comparative example.
  • the compounds of the present invention exhibited superior properties in terms of efficiency and lifespan depending on the position and type of the substituent compared to the comparative compounds.
  • Substrate 2 Anode

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

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2023/014472 2022-09-23 2023-09-22 Nouveau composé et dispositif électroluminescent organique le comprenant WO2024063592A1 (fr)

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KR20220121090 2022-09-23
KR10-2022-0121090 2022-09-23
KR10-2023-0126570 2023-09-21
KR1020230126570A KR20240041838A (ko) 2022-09-23 2023-09-21 신규한 화합물 및 이를 이용한 유기 발광 소자

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190012468A (ko) * 2017-07-27 2019-02-11 에스에프씨 주식회사 저전압 구동이 가능하며, 고효율 및 장수명 특성을 가지는 유기 발광 소자
US20190152985A1 (en) * 2016-12-14 2019-05-23 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
KR20200000518A (ko) * 2018-06-22 2020-01-03 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20210067976A (ko) * 2019-11-29 2021-06-08 주식회사 엘지화학 유기 발광 소자
CN113563204A (zh) * 2021-08-30 2021-10-29 上海钥熠电子科技有限公司 三芳胺化合物及其在有机电致发光显示器件中的应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190152985A1 (en) * 2016-12-14 2019-05-23 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
KR20190012468A (ko) * 2017-07-27 2019-02-11 에스에프씨 주식회사 저전압 구동이 가능하며, 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20200000518A (ko) * 2018-06-22 2020-01-03 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20210067976A (ko) * 2019-11-29 2021-06-08 주식회사 엘지화학 유기 발광 소자
CN113563204A (zh) * 2021-08-30 2021-10-29 上海钥熠电子科技有限公司 三芳胺化合物及其在有机电致发光显示器件中的应用

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