WO2021241882A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2021241882A1
WO2021241882A1 PCT/KR2021/004754 KR2021004754W WO2021241882A1 WO 2021241882 A1 WO2021241882 A1 WO 2021241882A1 KR 2021004754 W KR2021004754 W KR 2021004754W WO 2021241882 A1 WO2021241882 A1 WO 2021241882A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
compound
formula
Prior art date
Application number
PCT/KR2021/004754
Other languages
English (en)
Korean (ko)
Inventor
최지영
홍완표
이우철
김훈준
하재승
김주호
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202180004857.9A priority Critical patent/CN114206875B/zh
Publication of WO2021241882A1 publication Critical patent/WO2021241882A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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]
    • H10K50/17—Carrier injection layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 KR 10-2016-0026661 A
  • Non-Patent Document 1 Org. Biomol Chem., 2018, 16, 6703-6707
  • Non-Patent Document 2 Organic Electronics 57 (2016) 359-366
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X1 and X2 are the same as or different from each other, and each independently O; S; or NRc,
  • Ar1 is a substituted or unsubstituted aryl group
  • L is a direct bond; Or a substituted or unsubstituted arylene group,
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or
  • n9 is an integer of 0 to 3, and when n9 is 2 or more, R9 of 2 or more are the same as or different from each other,
  • n10 is an integer of 0 to 4, and when n10 is 2 or more, R10 of 2 or more are the same as or different from each other.
  • one embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above.
  • the compound described herein may be used as a material for an organic layer of an organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 8 are sequentially stacked.
  • Figure 2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7) and cathode (8) are sequentially
  • the deuterium substitution rate of the compound is determined by using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), max.
  • TLC-MS Thin-Layer Chromatography/Mass Spectrometry
  • max max.
  • the dotted line refers to a site bonded to another substituent or bonding group.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group (-CN); nitro group; hydroxyl group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • substituted or unsubstituted refers to deuterium; And it means that it is substituted with one or more substituents selected from the group consisting of an aryl group, or is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • N% substitution with deuterium means that N% of hydrogen available in the structure is substituted with deuterium. For example, if 25% of dibenzofuran is substituted with deuterium, it means that 2 out of 8 hydrogens of dibenzofuran are substituted with deuterium.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are the same as or different from each other, and each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. does not
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include a methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .
  • the substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styrenyl group, and the like, but are not limited thereto.
  • the alkynyl group is a substituent including a triple bond between a carbon atom and a carbon atom, and may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
  • the amine group is -NH 2
  • the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10.
  • substituted amine group examples include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group.
  • phenylpyridylamine group phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group,
  • ditolylamine group a phenyltolylamine group, a diphenylamine group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • spirofluorenyl groups such as (9,9-dimethyl fluorenyl group), and a substituted fluorenyl group such as (9,9-diphenylfluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms.
  • heterocyclic group examples include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carba group
  • a sol group a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.
  • heterocyclic group In the present specification, the description of the above-described heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • ring in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.
  • the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of an aromatic and an aliphatic group, and may be selected from examples of the cycloalkyl group or the aryl group.
  • the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof.
  • the hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms.
  • the heterocycle means a ring including at least one selected from N, O, P, S, Si and Se.
  • the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring consisting only of carbon and hydrogen atoms.
  • Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc.
  • the present invention is not limited thereto.
  • the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms.
  • the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto.
  • the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.
  • the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
  • the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole.
  • the compound represented by Formula 1 of the present invention has a structure including a tetracyclic condensed ring including O, S or N in an anthracene structure, and the structure is formed by elevating the dipole moment of the molecule, thereby injecting electrons and holes and mobility can be improved. This can have the effect of lowering the driving voltage of the device and increasing the luminous efficiency.
  • the efficiency and lifespan of the device are improved.
  • the chemical properties of the compound hardly change, but the physical properties of the deuterated compound change and the vibrational energy level is lowered.
  • the compound substituted with deuterium can prevent a decrease in intermolecular van der Waals force or decrease in quantum efficiency due to collisions due to intermolecular vibration. C-D bonds may also improve the stability of the compound.
  • X1 and X2 are the same as or different from each other, and each independently O; S; or NRc,
  • Ar1 is a substituted or unsubstituted aryl group
  • L is a direct bond; Or a substituted or unsubstituted arylene group,
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or
  • n9 is an integer of 0 to 3, and when n9 is 2 or more, R9 of 2 or more are the same as or different from each other,
  • n10 is an integer of 0 to 4, and when n10 is 2 or more, R10 of 2 or more are the same as or different from each other.
  • X1 is O
  • X2 is O
  • S is O
  • NRc NR
  • X1 is S
  • X2 is O; S; or NRc.
  • X1 is NRc'
  • X2 is O; S; or NRc.
  • Rc' is the same as the definition of Rc described above.
  • X1 and X2 are O.
  • X1 is O
  • X2 is S
  • X1 is O
  • X2 is NRc
  • X1 and X2 are S.
  • X1 is S
  • X2 is O
  • X1 is S
  • X2 is NRc
  • X1 is NRc'
  • X2 is NRc.
  • Rc' is the same as the definition of Rc described above.
  • X1 is NRc
  • X2 is O
  • X1 is NRc
  • X2 is S.
  • Ar1 is a substituted or unsubstituted C6-C60 aryl group.
  • Ar1 is a substituted or unsubstituted C6-C30 aryl group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • Ar1 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.
  • Ar1 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms, or a group to which two or more groups selected from the group are connected. .
  • Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluoranthene group; Or a substituted or unsubstituted pyrene group.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium or an aryl group; a naphthyl group unsubstituted or substituted with deuterium or an aryl group; a biphenyl group unsubstituted or substituted with deuterium or an aryl group; a phenanthrenyl group unsubstituted or substituted with deuterium or an aryl group; a triphenylene group unsubstituted or substituted with deuterium or an aryl group; a fluoranthene group unsubstituted or substituted with deuterium or an aryl group; Or a pyrene group unsubstituted or substituted with deuterium or an aryl group.
  • Ar1 is a phenyl group; naphthyl group; biphenyl group; phenanthrenyl group; triphenylene group; fluoranthene group; Or a pyrene group, wherein the groups are unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and an aryl group or a group to which two or more groups selected from the group are connected.
  • Ar1 is a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a phenyl group, a naphthyl group and a phenanthrenyl group, or a group to which two or more groups selected from the group are connected; a naphthyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a phenyl group, a naphthyl group and a phenanthrenyl group, or a group to which two or more groups selected from the group are connected; a biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a phenyl group, a naphthyl group and a phenanthrenyl group, or a group to which two or more groups selected from the group are connected; a phenanthrenyl group unsubstit
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; a biphenyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; a phenanthrenyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; a triphenylene group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; a trip
  • Ar1 is a phenyl group unsubstituted or substituted with a naphthyl group or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; biphenyl group; phenanthrenyl group; triphenylene group; fluoranthene group; or pyrene.
  • Ar1 is a phenyl group unsubstituted or substituted with a naphthyl group or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; biphenyl group; phenanthrenyl group; triphenylene group; fluoranthene group; Or a pyrene group, the aforementioned groups are unsubstituted or substituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; Or a biphenyl group unsubstituted or substituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; or a biphenyl group.
  • Ar1 is represented by any one of the following structures.
  • the structure is unsubstituted or substituted with deuterium or an aryl group.
  • Ar1 is represented by any one of the following structures.
  • the structure is unsubstituted or substituted with deuterium or an aryl group.
  • Ar1 is represented by -L11-Ar11, L11 is a direct bond; or a substituted or unsubstituted arylene group, and Ar11 is a substituted or unsubstituted aryl group.
  • L11 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
  • L11 is a direct bond; or an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium;
  • L11 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • Ar11 is a substituted or unsubstituted C6-C30 aryl group.
  • Ar11 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • Ar11 is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; Or a phenanthrenyl group unsubstituted or substituted with deuterium.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a direct bond; or a substituted or unsubstituted C6-C20 arylene group.
  • L is a direct bond; or an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.
  • L is a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • L is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • L is a direct bond; a phenylene group unsubstituted or substituted with deuterium; or a naphthylene group.
  • L is a direct bond; phenylene group; or a naphthylene group.
  • L is a direct bond
  • L is a direct bond, or is represented by any one of the following structures.
  • the dotted line means the bonding position
  • the structure is unsubstituted or substituted with deuterium or an aryl group.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.
  • Rc and R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; or a naphthyl group.
  • Rc is a substituted or unsubstituted aryl group.
  • Rc is a substituted or unsubstituted C6-C30 aryl group.
  • Rc is a substituted or unsubstituted C6-C20 aryl group.
  • Rc is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • Rc is a substituted or unsubstituted phenyl group.
  • Rc is a phenyl group unsubstituted or substituted with deuterium.
  • Rc is a phenyl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C20 aryl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; or a naphthyl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R1 to R8 are hydrogen.
  • R1 to R8 are deuterium.
  • R1 to R5 and R8 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R6 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • R6 is hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C60 aryl group.
  • R6 is hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.
  • R6 is hydrogen; heavy hydrogen; or an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R6 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.
  • R7 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • R7 is hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C60 aryl group.
  • R7 is hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.
  • R7 is hydrogen; heavy hydrogen; or an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R7 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.
  • At least one of R2, R3, R6 and R7 is a substituted or unsubstituted aryl group, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R2, R3, R6 and R7 is an aryl group unsubstituted or substituted with deuterium, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R2, R3, R6 and R7 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R2, R3, R6 and R7 is a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium, the rest being the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R2, R3, R6 and R7 is a phenyl group; or a naphthyl group, the rest being the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of R2, R3, R6 and R7 is a phenyl group; or a naphthyl group, and the remainder is hydrogen.
  • At least one of R2, R3, R6 and R7 is a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium, and the remainder is deuterium.
  • R9 and R10 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R9 and R10 are hydrogen.
  • R9 and R10 are deuterium.
  • Chemical Formula 1 is represented by the following Chemical Formula 2-1 or 2-2.
  • the formula (1) is represented by any one of the following structural formulas. At this time, is a position coupled to L.
  • Rc is the same as the definition in Formula 1, and Rc' is the same as the definition of Rc.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 101 to 103, 201 to 203, and 301 to 303.
  • Ar1, L, Rc, R1 to R10, n9 and n10 have the same definitions as in Formula 1 above,
  • Rc' is hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsub
  • Rc' is a substituted or unsubstituted aryl group.
  • Rc' is a substituted or unsubstituted C6-C30 aryl group.
  • Rc' is a substituted or unsubstituted C6-C20 aryl group.
  • Rc' is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • Rc' is a substituted or unsubstituted phenyl group.
  • Rc' is a phenyl group unsubstituted or substituted with deuterium.
  • Rc' is a phenyl group.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-3.
  • G1 to G8 are the same as or different from each other, and each independently hydrogen; or deuterium,
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • G1 to G8 are hydrogen.
  • G1 to G8 are deuterium.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C60 aryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C30 aryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C20 aryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group; or a naphthyl group.
  • n9 is 0.
  • n9 is an integer of 1 to 3.
  • n9 is 1.
  • n9 is 3.
  • n10 is 0.
  • n10 is an integer of 1 to 4.
  • n10 is 1.
  • n10 is 4.
  • Ar1 is substituted with at least one deuterium. In another exemplary embodiment, Ar1 is substituted by 40% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 50% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 60% or more with deuterium. In another exemplary embodiment, Ar1 is substituted with deuterium by 70% or more. In another exemplary embodiment, Ar1 is substituted by 80% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 90% or more with deuterium. In another exemplary embodiment, Ar1 is 100% substituted with deuterium.
  • the substituent of Formula 1 is substituted with at least one deuterium.
  • the substituent is substituted with deuterium by 40% or more.
  • the substituent is 50% or more substituted with deuterium.
  • the substituent is substituted with deuterium by 60% or more.
  • the substituent is 70% or more substituted with deuterium.
  • the substituent is 80% or more substituted with deuterium.
  • the substituent is substituted with deuterium by 90% or more.
  • the substituent is 100% substituted with deuterium.
  • L is substituted with at least one deuterium. In another exemplary embodiment, L is substituted with deuterium by 40% or more. In another exemplary embodiment, L is substituted by 50% or more with deuterium. In another exemplary embodiment, L is substituted with deuterium by 60% or more. In another exemplary embodiment, L is substituted with deuterium by 70% or more. In another exemplary embodiment, L is 80% or more substituted with deuterium. In another exemplary embodiment, L is substituted with deuterium by 90% or more. In another exemplary embodiment, L is 100% substituted with deuterium.
  • Rc and R1 to R10 are each substituted with at least one deuterium.
  • each of Rc and R1 to R10 is substituted with deuterium by 40% or more.
  • each of Rc and R1 to R10 is substituted with deuterium by 50% or more.
  • each of Rc and R1 to R10 is substituted with deuterium by 60% or more.
  • each of Rc and R1 to R10 is substituted with deuterium by 70% or more.
  • each of Rc and R1 to R10 is substituted by 80% or more with deuterium.
  • each of Rc and R1 to R10 is substituted with deuterium by 90% or more.
  • each of Rc and R1 to R10 is 100% substituted with deuterium.
  • the compound represented by Formula 1 is substituted with at least one deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 20% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 30% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 40% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 50% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 60% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 70% or more.
  • the compound represented by Formula 1 is substituted with deuterium by 80% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 90% or more. In another exemplary embodiment, the compound represented by Formula 1 is 100% substituted with deuterium.
  • the compound represented by Formula 1 is substituted with deuterium by 40% to 60%. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 40% to 80%. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 60% to 80%. In another exemplary embodiment, the compound represented by Formula 1 is 80% to 100% substituted with deuterium.
  • R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, 5 or more of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, 6 or more of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, at least 7 of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, R1 to R8 are all deuterium. In this case, the remaining substituents (Rc, L, Ar1, R9 and R10) other than R1 to R8 are unsubstituted or substituted with deuterium.
  • Chemical Formula 1 is represented by any one of the following compounds.
  • the compound represented by Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above.
  • the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.
  • the present specification provides an organic light emitting device including the above-described compound.
  • the organic light emitting device includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1 described above.
  • the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the compound of Formula 1 above.
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention includes at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer.
  • the structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer
  • the hole injection layer, the hole transport layer, or the hole injection and transport layer is a compound represented by the above-mentioned Formula 1 may include
  • the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1 described above.
  • the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer or the hole blocking layer is the above-mentioned
  • the compound represented by Formula 1 may be included.
  • the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by the above formula (1) compounds may be included.
  • the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a dopant.
  • the organic light emitting device is a green organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.
  • the organic light emitting device is a red organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.
  • the organic light emitting device is a blue organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host, and may further include a dopant.
  • the content of the dopant may be included in an amount of 1 part by weight to 60 parts by weight based on 100 parts by weight of the host, preferably 1 part by weight to 10 parts by weight.
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, PPV-based polymer
  • a fluorescent material such as a polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.
  • the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 above.
  • the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
  • the dopant in the emission layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.
  • the maximum emission peak of the organic material layer is 400 nm to 500 nm.
  • the organic material layer may include an emission layer
  • the emission layer may include the compound represented by Formula 1 as a host, and may further include an additional host.
  • the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.
  • the fluorescent dopant may be selected from the following structures, but is not limited thereto.
  • an Ir complex may be used as the phosphorescent dopant, and for example, any one of the following structures may be used, but is not limited thereto.
  • the dopant may be a boron-based compound.
  • the boron-based compound refers to a compound containing a boron atom (B).
  • the boron-based compound is represented by the following Chemical Formula D-1.
  • A1 to A3 are the same as or different from each other, and are each independently a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle, or combine with an adjacent group to form a substituted or unsubstituted ring,
  • T1 and T2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring.
  • A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, Adjacent groups combine with each other to form a substituted or unsubstituted ring having 8 to 60 carbon atoms.
  • A1 to A3 are the same as or different from each other, and each independently one or more groups selected from the group consisting of an amine group, an alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to 30 carbon atoms, or the group It is a hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a group to which two or more groups selected from are connected.
  • A1 to A3 are the same as or different from each other, and each independently represents a benzene ring unsubstituted or substituted with a diphenylamine group, a methyl group, or a t-butyl group.
  • T1 and T2 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group or a substituted or unsubstituted C 2 to C 60 heterocyclic group .
  • T1 and T2 are the same as or different from each other, and each independently at least one group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms, or 2 selected from the group It is an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with a group to which the above groups are connected.
  • T1 and T2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a t-butyl group; or a biphenyl group unsubstituted or substituted with a t-butyl group.
  • the light emitting layer including the compound represented by Formula 1 has a blue color.
  • the content of the compound represented by Formula 1 may be 70 parts by weight to 99.99 parts by weight based on 100 parts by weight of the sum of the host and dopant of the emission layer; Preferably, 80 parts by weight to 99.9 parts by weight; More preferably, it is 90 parts by weight to 99.5 parts by weight.
  • the organic light emitting device of the present specification may further include an organic material layer of at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Formula 1 above.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and hole injection layer, and an electron blocking layer.
  • the two or more organic material layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • materials other than the compound represented by Formula 1 may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant those known in the art may be used, for example, a metal or a metal complex may be used.
  • the electron transport layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 may include
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic material layer may include an electron blocking layer, the electron blocking layer may be a material known in the art.
  • the organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.
  • the structure of the organic light emitting diode of the present specification may have a structure as shown in FIGS. 1 and 2 , but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 8 are sequentially stacked.
  • the compound may be included in the light emitting layer 6 .
  • Figure 2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7) and cathode (8) are sequentially
  • the structure of the organic light-emitting device stacked with the compound may be included in the hole injection layer 3 , the hole transport layer 4 , the light emitting layer 5 , the electron transport layer 6 , or the electron injection layer 7 .
  • the organic light emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto, and may have a single layer structure can
  • the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
  • the anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer.
  • the hole injection material holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material.
  • the hole injection layer may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.
  • the hole injection layer may include an N-containing polycyclic structure including a cyano group.
  • the N-containing polycyclic structure may be 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN).
  • the hole transport layer may serve to facilitate hole transport.
  • a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable, and a material having high hole mobility is suitable.
  • Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the hole transport layer may include at least one diamine compound including an aryl group or an amine compound including a carbazole group.
  • the above compounds may be included alone, or two or more types may be included.
  • the diamine compound may be deposited to be used as the first hole transport layer, and the amine compound including the carbazole group may be deposited thereon to be used as the second hole transport layer.
  • An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-described compound or a material known in the art may be used for the electron blocking layer.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include the aforementioned compound of Formula 1; 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
  • PSV Poly(p-phenylenevinylene)
  • Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the light-emitting dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • the present invention is not limited thereto.
  • the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • the light emitting layer may include the compound represented by Formula 1 of the present invention as a host.
  • the light emitting layer may include a condensed cyclic compound including boron as a dopant.
  • the host and the dopant may be included in an appropriate weight ratio, and according to an example, the host and the dopant may be included in a weight ratio of 99:1 to 90:10.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include the above-mentioned compound or Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being raised to improve the movement of electrons. There are advantages that can be
  • the electron transport layer may include a compound including benzimidazole.
  • the electron injection layer may serve to facilitate electron injection.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and also , a compound having excellent thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the organic light emitting diode according to the present specification may be included in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • Compound 7-a was obtained by the same synthesis as in Synthesis Example 4-1, except that benzo[b]thiophen-3-ylboronic acid was used instead of benzofuran-3-ylboronic acid.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer.
  • HTL1 was thermally vacuum deposited to a thickness of 100 nm
  • HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer.
  • compound 1 as a host and BD-A (weight ratio 95:5) as a dopant were simultaneously vacuum-deposited to form a light emitting layer with a thickness of 20 nm.
  • ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer.
  • LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer.
  • aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compound 1 as the host of the light emitting layer. At this time, among the following structures, the compound represented by Formula 1 of the present invention was prepared through the same process as in Synthesis Examples 1 to 11, respectively.
  • Comparative Example 1 using a host compound made of only aryl had a high driving voltage and was not advantageous in terms of efficiency and lifetime
  • Comparative Example 2 using a host compound including a dibenzofuran group had a higher driving voltage than Examples 1 to 11 It was confirmed that it is not advantageous in terms of efficiency and lifespan.
  • Comparative Example 3 had a low driving voltage, but showed a result that the efficiency was lowered due to current leakage and the lifespan was significantly reduced.
  • Comparative Example 4 using a compound in which X1 of Formula 1 of the present invention is carbon also showed a higher driving voltage than Examples 1 to 11 and not advantageous in terms of efficiency and lifespan.

Landscapes

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

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/004754 2020-05-29 2021-04-15 Composé et dispositif électroluminescent organique le comprenant WO2021241882A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202180004857.9A CN114206875B (zh) 2020-05-29 2021-04-15 化合物及包含其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20200065306 2020-05-29
KR10-2020-0065306 2020-05-29

Publications (1)

Publication Number Publication Date
WO2021241882A1 true WO2021241882A1 (fr) 2021-12-02

Family

ID=78744862

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/004754 WO2021241882A1 (fr) 2020-05-29 2021-04-15 Composé et dispositif électroluminescent organique le comprenant

Country Status (3)

Country Link
KR (1) KR102552978B1 (fr)
CN (1) CN114206875B (fr)
WO (1) WO2021241882A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115677709A (zh) * 2022-11-11 2023-02-03 深圳市华星光电半导体显示技术有限公司 有机化合物、混合物、组合物及有机电子器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130143579A (ko) * 2010-10-12 2013-12-31 신닛테츠 수미킨 가가쿠 가부시키가이샤 칼코겐 함유 방향족 화합물, 유기 반도체 재료 및 유기 전자 디바이스
KR20140093585A (ko) * 2013-01-18 2014-07-28 삼성전자주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20160113219A (ko) * 2014-03-07 2016-09-28 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자, 표시 장치, 조명 장치 및 발광성 조성물
KR20170078637A (ko) * 2014-10-31 2017-07-07 이 아이 듀폰 디 네모아 앤드 캄파니 전기활성 재료
KR20200018752A (ko) * 2018-08-10 2020-02-20 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 축합환 화합물

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130096666A (ko) * 2012-02-22 2013-08-30 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
WO2014038417A1 (fr) * 2012-09-07 2014-03-13 保土谷化学工業株式会社 Nouveaux dérivés de benzothiéno-indole et élément électroluminescent organique dans lequel le nouveau dérivé de benzothiéno-indole est utilisé
KR102394380B1 (ko) * 2013-12-03 2022-05-06 주식회사 동진쎄미켐 신규한 발광 화합물 및 이를 포함하는 유기발광소자
KR102402220B1 (ko) * 2013-12-03 2022-05-27 주식회사 동진쎄미켐 신규한 청색 형광 호스트 화합물 및 이를 포함하는 유기발광소자
KR102205400B1 (ko) * 2014-02-14 2021-01-21 삼성디스플레이 주식회사 인덴계 화합물 및 이를 포함한 유기 발광 소자
KR102413062B1 (ko) 2014-08-28 2022-06-24 에스에프씨주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130143579A (ko) * 2010-10-12 2013-12-31 신닛테츠 수미킨 가가쿠 가부시키가이샤 칼코겐 함유 방향족 화합물, 유기 반도체 재료 및 유기 전자 디바이스
KR20140093585A (ko) * 2013-01-18 2014-07-28 삼성전자주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20160113219A (ko) * 2014-03-07 2016-09-28 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자, 표시 장치, 조명 장치 및 발광성 조성물
KR20170078637A (ko) * 2014-10-31 2017-07-07 이 아이 듀폰 디 네모아 앤드 캄파니 전기활성 재료
KR20200018752A (ko) * 2018-08-10 2020-02-20 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 축합환 화합물

Also Published As

Publication number Publication date
CN114206875A (zh) 2022-03-18
CN114206875B (zh) 2024-06-18
KR102552978B1 (ko) 2023-07-07
KR20210147877A (ko) 2021-12-07

Similar Documents

Publication Publication Date Title
WO2019088799A1 (fr) Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2014208829A1 (fr) Composé hétérocyclique et diode électroluminescente organique le comprenant
WO2019225938A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2015046835A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2018182297A1 (fr) Composé à base de benzocarbazole et dispositif électroluminescent organique le comprenant
WO2020050619A1 (fr) Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2020159279A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2020085765A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2021172664A1 (fr) Dispositif électroluminescent organique
WO2021010656A1 (fr) Élément électroluminescent organique
WO2020122384A1 (fr) Composé cyclique condensé et dispositif électroluminescent organique le comprenant
WO2016137068A1 (fr) Composé hétérocyclique et élément luminescent organique comprenant celui-ci
WO2021172905A1 (fr) Dispositif électroluminescent organique
WO2021029709A1 (fr) Dispositif électroluminescent organique
WO2021020941A1 (fr) Dispositif électroluminescent organique
WO2021241882A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019132483A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2022239962A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2023282676A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2021020943A1 (fr) Dispositif électroluminescent organique
WO2021101112A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2020153652A1 (fr) Composé, et élément électroluminescent organique le comprenant
WO2020153654A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2017052212A1 (fr) Composé et dispositif optoélectronique organique le comprenant
WO2020153653A1 (fr) Composé et diode électroluminescente organique le comprenant

Legal Events

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

Ref document number: 21812019

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21812019

Country of ref document: EP

Kind code of ref document: A1