[go: up one dir, main page]

WO2021006532A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2021006532A1
WO2021006532A1 PCT/KR2020/008572 KR2020008572W WO2021006532A1 WO 2021006532 A1 WO2021006532 A1 WO 2021006532A1 KR 2020008572 W KR2020008572 W KR 2020008572W WO 2021006532 A1 WO2021006532 A1 WO 2021006532A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
compound
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2020/008572
Other languages
English (en)
Korean (ko)
Inventor
하재승
허정오
허동욱
김성소
천민승
조혜민
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN202080030276.8A priority Critical patent/CN113727980B/zh
Publication of WO2021006532A1 publication Critical patent/WO2021006532A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • An organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material.
  • the organic light emitting device can be divided into two types as follows according to the operating principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes, and used as a current source (voltage source). It is a type of light emitting device.
  • the second is a light emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made 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 control layer, a hole control layer, an electron transport layer, and an electron injection. It can be made of layers, etc.
  • organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as the organic material layer in the organic light-emitting device may be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, electron injection materials, and the like, according to their functions.
  • the light-emitting material includes blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.
  • a host/dopant system may be used as a light emitting material.
  • the principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
  • materials that form the organic material layer in the device such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc., are stable and efficient materials. As it is supported by, the development of new materials is continuously required.
  • 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 Formula 1 below.
  • X1 is O or S
  • L1 to L3 are each independently a direct bond; A substituted or unsubstituted divalent cycloalkyl group; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,
  • Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar3 is hydrogen; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted heteroaryl group including at least one of O and S as a hetero element,
  • a to c are each independently an integer of 1 to 4,
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.
  • the compound according to an exemplary embodiment of the present specification may improve electron transport ability by controlling electron affinity through structural bonding between oxadiazole or thiadiazole and pyrimidine. Accordingly, when used in an organic light-emitting device as an electron control layer, an electron transport layer, and/or a host, there is an effect of increasing the luminance of the device, lowering the driving voltage, improving luminous efficiency, and improving life characteristics.
  • FIG. 1 shows an example of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • X1 is O or S
  • L1 to L3 are each independently a direct bond; A substituted or unsubstituted divalent cycloalkyl group; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,
  • Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar3 is hydrogen; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted heteroaryl group including at least one of O and S as a hetero element,
  • a to c are each independently an integer of 1 to 4,
  • the compound represented by Formula 1 includes an oxadiazole or thiadiazole structure together with pyrimidine, it has an effect of improving electron transport ability by controlling electron affinity.
  • the oxadiazole or thiadiazole is substituted at the L3 position in Chemical Formula 1, which leads to the binding of the asymmetric structure of the subgens compared to the L2 position, thereby controlling the electron transport characteristics by improving the polarity in the molecule.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Silyl group; Amine group; Phosphine oxide group; Alkyl group; Cycloalkyl group; Alkenyl group; Alkoxy group; Alkylthio group; Aryl group; It means that it is substituted with one or two or more substituents selected from the group consisting of a sulfonyl group and a heterocyclic group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
  • a substituent to 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 to which two phenyl groups are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms.
  • the alkylthio group may be linear, branched or cyclic. Although the number of carbon atoms of the alkylthio group is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methylthio, ethylthio, n-propylthio, isopropylthio, i-propylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio , Isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio and p-methylbenzylthio, etc. , But is not limited thereto
  • the number of carbon atoms of the aryl group is not particularly limited, but may be 6 to 60 or 6 to 30, and the aryl group may be monocyclic or polycyclic.
  • aryl group when the aryl group is a monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group, it may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysene group, a fluorenyl group, and the like, but is not limited thereto.
  • the divalent aryl group may be selected from the examples of the aryl group described above except that it is a divalent group.
  • the heteroaryl group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms.
  • heteroaryl group examples include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, be
  • the divalent heteroaryl group may be selected from the examples of the aforementioned heteroaryl group except that it is a divalent group.
  • the divalent cycloalkyl group may be selected from the examples of the cycloalkyl group described above except that it is a divalent group.
  • the number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 30.
  • the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine Group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group And triphenylamine groups, but are not limited thereto.
  • the number of carbon atoms of the imide group, the carbonyl group and the ester group is not particularly limited, but it is preferably 1 to 50 carbon atoms.
  • the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group and a dinaphthylphosphine oxide, but is not limited thereto.
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40.
  • 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, and styrenyl group, but are not limited thereto.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR 104 R 105 R 106 , R 104 to R 106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group and phenylsilyl group. It is not limited.
  • the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent one.
  • the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • the heterocycle is an atom other than carbon and contains one or more heteroatoms, and specifically, the heterocycle may contain one or more atoms selected from the group consisting of O, N, Se, Si and S. have.
  • the heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.
  • X1 is S.
  • X1 is O.
  • Formula 1 may be represented by any one of Formulas 1-1 to 1-4 below.
  • L1 to L3, Ar1 to Ar3, and a to c are the same as defined in Formula 1.
  • L3 is a direct bond; A substituted or unsubstituted C 6 -C 30 divalent aryl group; Or a substituted or unsubstituted C 2 -C 15 heteroarylene group, wherein the substituents include deuterium, a C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, and at least one of N, O and S Of C 2 -C 30 made It is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a heteroaryl group and/or a substituent to which two or more substituents are connected among the aforementioned substituents.
  • L3 is a direct bond; A substituted or unsubstituted divalent phenyl group; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent naphthyl group; A substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent phenanthrenyl group; A substituted or unsubstituted divalent triphenylenyl group; A substituted or unsubstituted divalent cyclohexyl group; A substituted or unsubstituted divalent dibenzodioxin group; A substituted or unsubstituted divalent carbazolyl group; A substituted or unsubstituted divalent furanyl group; A substituted or unsubstituted divalent carbazoly
  • L3 is a direct bond; A substituted or unsubstituted divalent phenyl group; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent naphthyl group; A substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent phenanthrenyl group; A substituted or unsubstituted divalent triphenylenyl group; A substituted or unsubstituted divalent cyclohexyl group; A substituted or unsubstituted divalent dibenzodioxin group; A substituted or unsubstituted divalent carbazolyl group; A substituted or unsubstituted divalent furanyl group; A substituted or unsubstituted divalent carbazoly
  • L3 is a direct bond; A substituted or unsubstituted divalent phenyl group; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent naphthyl group; A substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent phenanthrenyl group; A substituted or unsubstituted divalent triphenylenyl group; A substituted or unsubstituted divalent cyclohexyl group; A substituted or unsubstituted divalent dibenzodioxin group; A substituted or unsubstituted divalent carbazolyl group; A substituted or unsubstituted divalent furanyl group; A substituted or unsubstituted divalent carbazoly
  • c is an integer of 1 to 4, and when c is 2 or more, 2 or more L3 are the same as or different from each other.
  • L3 may be represented by any one of the following structural formulas.
  • Q1 to Q3 are each independently NR, CR'R", O or S,
  • R1 to R5 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R, R'and R" are each independently hydrogen, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R'and R" may be bonded to each other to form a ring,
  • d2 is an integer from 0 to 2
  • d3 is an integer from 0 to 3
  • d4 is an integer from 0 to 4,
  • d5 is an integer from 0 to 5
  • d6 is an integer from 0 to 6
  • d7 is an integer from 0 to 7
  • d1 is an integer from 1 to 4,
  • d 1 or 2
  • Q1 and Q2 are each O.
  • Q3 is NR, CR'R", O or S.
  • R1 to R5 are each independently hydrogen; heavy hydrogen; A C 1 -C 10 alkyl group; C 6 -C 30 aryl group; Or a heteroaryl group including at least one of O and S.
  • R1 to R5 are each independently hydrogen, deuterium, methyl group, phenyl group, naphthyl group, benzoxazole group, benzothiazole group, benzothiophene group, or benzofuranyl group.
  • R, R'and R" are each independently hydrogen, a C 1 -C 10 alkyl group or a C 6 -C 30 aryl group, and R'and R" are bonded to each other It can form a cycloalkyl group or an aryl group.
  • R, R'and R" are each independently a hydrogen methyl group or a phenyl group, and R'and R" may be bonded to each other to form a fluorenyl group.
  • d1 is 1 to 3.
  • d1 is 1 or 2.
  • d1 is 1.
  • d is 1.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted C 6 -C 30 aryl group; Or a substituted or unsubstituted C 2 -C 30 heteroaryl group.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofuranyl group, and the substituents are deuterium, a nitrile group, a halogen group, a C 1 -C 10 alkyl group, a C 1 -C 10
  • Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofuranyl group, and the substituents are unsubstituted or substituted with one or more of deuterium, nitrile, methyl, trifluoromethoxy and phenyl.
  • Ar1 and Ar2 may each be represented by any one of the following structural formulas.
  • Each Q4 is independently NRa, CRbRc, O or S,
  • R6 and R7 are each independently hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ra, Rb and Rc are each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, and Rb and Rc may be bonded to each other to form a ring,
  • d4 is an integer from 0 to 4,
  • d5 is an integer from 0 to 5
  • d7 is an integer from 0 to 7
  • d8 is an integer from 0 to 8
  • d9 is an integer from 0 to 9
  • e is an integer from 1 to 3
  • R6 and R7 are each independently hydrogen; heavy hydrogen; A C 1 -C 10 alkyl group; C 6 -C 30 aryl group; Or a heteroaryl group including at least one of O and S.
  • R6 and R7 are each independently hydrogen, deuterium, methyl group, phenyl group, nitrile group, fluoromethoxy group, or naphthyl group.
  • Ra, Rb, and Rc are each independently hydrogen, a C 1 -C 10 alkyl group or a C 6 -C 30 aryl group, and Rb and Rc are bonded to each other to form a cycloalkyl group or aryl Can form groups.
  • Ra, Rb, and Rc are each independently a hydrogen methyl group or a phenyl group, and Rb and Rc may be bonded to each other to form a fluorenyl group.
  • e is 1 or 2.
  • e is 1.
  • Ar3 is hydrogen; Nitrile group; A substituted or unsubstituted C 3 -C 20 trialkylsilyl group; A substituted or unsubstituted C 18 -C 30 triarylsilyl group; A substituted or unsubstituted C 1 -C 20 alkyl group; A substituted or unsubstituted C 3 -C 20 cycloalkyl group; A substituted or unsubstituted C 6 -C 30 aryl group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted C 2 -C 30 heteroaryl group including at least one of O and S as a hetero element.
  • Ar3 is a monocyclic N-containing heteroaryl group such as pyridine or pyrimidine
  • the device balance is broken and the energy level with the adjacent layer is not harmonized, so that the efficiency and lifespan of the device are lowered.
  • Ar3 is hydrogen; Nitrile group; A linear or branched alkyl group; Monocyclic cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted benzofuranyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted
  • Ar3 is hydrogen; Nitrile group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted
  • the substituents are deuterium, nitrile group, C 1 -C 10 alkyl group, C 3 -C 20 trialkylsilyl group, C 18 -C 30 triarylsilyl group, C 6 -C 30 aryl group and C 2-
  • One or two or more substituents selected from the group consisting of C 30 heteroaryl groups and/or two or more substituents among the aforementioned substituents are substituted or unsubstituted with a connected substituent.
  • Ar3 is hydrogen; Nitrile group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted
  • the substituents include deuterium, nitrile group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, triphenylsilyl group, phenyl, naphthyl group, phenylnaphthyl group, phenanthrenyl group, carbazolyl group, dibenzofuranyl group, and It is unsubstituted or substituted with one or more substituents among the phenyldibenzofuranyl group.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted C 6 -C 30 divalent aryl group; Or a substituted or unsubstituted C 2 -C 30 divalent heteroaryl group.
  • the L1 and L2 are each independently a direct bond; A substituted or unsubstituted divalent phenyl group; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent anthracenyl group; Or a substituted or unsubstituted divalent dibenzofuranyl group.
  • a and b are 0 or 1, respectively.
  • the compound represented by Formula 1 may be any one selected from the following structural formulas.
  • the compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below.
  • the compound of Formula 1 may be prepared by the preparation examples described later, and the substituents may be bonded by methods known in the art, and the type, position, or number of the substituents is a technique known in the art. Subject to change.
  • energy level means the energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, a deep energy level means that the absolute value increases in the negative direction from the vacuum level.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • the HOMO energy level means the distance from the vacuum level to the HOMO.
  • the LUMO energy level means the distance from the vacuum level to the LUMO.
  • a bandgap means a difference in energy levels between HOMO and LUMO, that is, a HOMO-LUMO gap.
  • the present specification provides an organic light-emitting device including the above-described compound.
  • An exemplary embodiment of the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. have.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer includes an emission layer, and the emission layer includes the compound.
  • the light emitting layer includes a host and a dopant, and the compound is included as a host.
  • the emission layer is a red emission layer or a green emission layer.
  • the dopant material includes an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamine group, and the styrylamine compound is substituted or unsubstituted.
  • a compound in which at least one arylvinyl group is substituted on the cyclic arylamine, and one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group are substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the dopant when the compound is included in the host of the emission layer, is a metal complex, and preferably an iridium-based complex.
  • the dopant may be selected from the following structural formulas, but is not limited thereto.
  • the organic material layer includes one or more electron transport layers, and at least one of the electron transport layers includes the compound.
  • the electron transport layer including the compound further includes an organometallic complex.
  • the organic material layer includes an emission layer and an electron transport layer, and the emission layer and the electron transport layer include the compound.
  • the organic material layer includes one or more electron controlling layers, and at least one of the electron controlling layers includes the compound.
  • the organic material layer includes an electron controlling layer and an electron transport layer, and the electron controlling layer and the electron transport layer include the compound.
  • the organic material layer includes an emission layer
  • the emission layer may include 5 wt% to 99 wt% of the compound based on 100 wt% of the emission layer, and preferably 10 wt% to 30 wt% do.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound as a host of the emission layer, and may further include a dopant.
  • the content of the dopant may be 10 wt% to 99 wt%, and preferably 10 wt% to 50 wt% based on 100 wt% of the host.
  • the mass ratio of the two types of hosts is 1:9 to 9:1.
  • the organic material layer includes an electron transport layer
  • the electron transport layer may include 5wt% to 99wt% of the compound based on 100wt% of the electron transport layer, and preferably 10wt% to 30wt% Included in %.
  • the organic light emitting device may be an organic light emitting device having a structure (normal type) 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.
  • FIG. 1 the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIG. 1.
  • 1 is a first electrode (1), hole injection layer (2), hole transport layer (3), hole control layer (4), light emitting layer (5), electron control layer (6), electron transport layer (7), electron injection
  • the compound is the hole injection layer (2), the hole transport layer (3), the hole control layer (4), the light emitting layer (5), the electron control layer (6), the electron transport layer (7) and the electron injection It may be included in one or more of the layers 8, and specifically, may be included in the electron transport layer and/or the light emitting layer.
  • the organic light-emitting device of the present specification may have a structure in which a first electrode, a hole injection layer, a hole transport layer, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, a second electrode, and a capping layer are sequentially stacked.
  • a first electrode a hole injection layer, a hole transport layer, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, a second electrode, and a capping layer are sequentially stacked.
  • a capping layer may be sequentially stacked.
  • the organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers contains the compound of the present application, that is, the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form an anode.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • cathode material examples 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); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • 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)
  • ZnO Al or SnO 2: a combination of a metal and an oxide such as Sb
  • 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 multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 nm to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.
  • the hole transport layer may serve to facilitate transport of holes.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the hole control layer may be provided between the hole transport layer and the light emitting layer, and serves to effectively receive holes from the hole transport layer and control the amount of holes transferred to the light emitting layer by adjusting hole mobility.
  • the electrons supplied from the light emitting layer can simultaneously perform the role of an electron barrier to prevent passing to the hole transport layer. Through this, it is possible to maximize the balance of holes and electrons in the emission layer to increase luminous efficiency, and improve stability and lifespan. Materials known in the art may be used as the material for the hole control layer.
  • 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, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission 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 a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the emission dopants include 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), but is not limited thereto.
  • the emission dopant is a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium), or Alq3(tris(8-hydroxyquinolino)aluminum), anthracene compound, pyrene type A fluorescent material such as a compound or a boron-based compound may be used, but is not limited thereto.
  • the light emitting dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, a boron-based compound, or the like may be used, but is not limited thereto.
  • a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, a boron-based compound, or the like may be used, but is not limited thereto.
  • the electron control layer may be provided between the light emitting layer and the electron transport layer, and serves to control the amount of electrons transferred to the light emitting layer by effectively receiving electrons from the electron transport layer and controlling electron mobility. In addition, it can simultaneously serve as a hole barrier preventing holes supplied from the emission layer from passing over to the electron transport layer. Through this, it is possible to maximize the balance of holes and electrons in the emission layer to increase luminous efficiency, and improve stability and lifespan. Materials known in the art may be used as a material for the electron control layer in addition to the compound.
  • the electron transport layer may serve to facilitate transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable.
  • Specific examples other than the above compounds include Al complexes of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer may further include an organometallic complex, and the organometallic complex may be mixed with the compound to be included in one layer.
  • the compound and the organic metal complex may be mixed and then vacuum-deposited, or a mixed layer may be formed by depositing each.
  • the organometallic complex at least one selected from LiQ, NaQ, LiF, CsF, BaF, BaO, and Al 2 O 3 may be used, but is not limited thereto.
  • the thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for 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 , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • a capping layer may be provided on the cathode.
  • Materials known in the art such as a carbazole-based compound, may be used for the capping layer.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • intermediate S1-2 of Table 2 was prepared in the same manner as in the manufacturing process of S1-1, except that P6 prepared in Preparation Example 1 was used instead of S8.
  • SM1 (1eq) and SM2 (1.3eq) were added to 1,4-dioxane (12 times compared to SM1 by mass ratio), and potassium acetate (3eq) was added, followed by stirring and refluxing. Then, palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes and then added. After 2 hours, the reaction was confirmed and cooled to room temperature. After that, ethanol and water were added, filtered, and recrystallized with ethyl acetate to prepare D1 to D14 of Table 6 below.
  • a substrate on which ITO/Ag/ITO was deposited to a thickness of 70 ⁇ /1000 ⁇ /70 ⁇ as an anode was cut into a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, put in distilled water dissolved in a dispersant, and washed with ultrasonic waves.
  • the detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered twice with the product's filter was used. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
  • the following HI-1 was thermally vacuum deposited to a thickness of 50 ⁇ to form a hole injection layer, and the following HT1, a material for transporting holes, was vacuum-deposited to a thickness of 1,150 ⁇ to form a hole transport layer.
  • a hole control layer was formed using the following HT2 (150 ⁇ ), and the following BH1 as a host and the following BD1 (2% by weight) as a dopant were vacuum deposited to a thickness of 360 ⁇ to form a light emitting layer.
  • ETM1 was deposited to a thickness of 50 ⁇ to form an electron control layer
  • Compound 1 prepared in Preparation Example 9 and the following Liq were mixed at a mass ratio of 7:3 to form an electron transport layer having a thickness of 250 ⁇ .
  • magnesium and silver as the negative electrode were formed to be 200 ⁇ in a thickness ratio of 1:4, and then CP1 was used as the CPL (Capping layer) of the negative electrode.
  • the device was completed by depositing to a thickness of 600 ⁇ . In the above process, the deposition rate of the organic material was maintained at 1 ⁇ /sec.
  • Example 2 to Example 28 and Example 32 to Example 35
  • Example 2 The same as in Example 1, except that the electron control layer was not formed in Example 1, and the electron transport layer was formed to a thickness of 300 ⁇ using Compound 16 prepared in Preparation Example 9 instead of Compound 1.
  • An organic light emitting device was manufactured by the method.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of ETM1 when forming the electron control layer in Example 1, and Compound 14 was used instead of Compound 1 when forming the electron transport layer.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of ETM1 when forming the electron control layer in Example 1, and Compound 2 was used instead of Compound 1 when forming the electron transport layer.
  • Organic light emitting devices of Comparative Examples 1 and 2 were manufactured in the same manner as in Example 29, except that the following ET1 and ET2 were respectively used instead of Compound 16 when forming the electron transport layer in Example 29.
  • Organic light emitting devices of Comparative Examples 3 to 8 were manufactured in the same manner as in Example 1, except that the following ET1 to ET6 were used instead of Compound 1 when forming the electron transport layer in Example 1.
  • T95 is a measure of the time when the luminance becomes 95% of the initial luminance.
  • ET5 used in Comparative Example 7 has pyrimidine (electron attraction unit) introduced on both sides of the thiadiazole, but it is a factor that causes the overall device balance to be broken, and the energy level with the adjacent layer is not harmonized with low efficiency,
  • ET6 used in Comparative Example 8 exhibits low device performance because the chemical stability of the electron attracting unit is very low due to the fact that no substituent is introduced into the pyrimidine, and has a limitation in showing aromatic properties.
  • a substrate on which ITO/Ag/ITO was deposited to a thickness of 70 ⁇ /1000 ⁇ /70 ⁇ as an anode was cut into a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, put in distilled water dissolved in a dispersant, and washed with ultrasonic waves.
  • the detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered twice with the product's filter was used. After washing the anode for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
  • the HI-1 was thermally vacuum deposited to a thickness of 50 ⁇ to form a hole injection layer, and the HT1, a material for transporting holes, was vacuum deposited thereon to a thickness of 1150 ⁇ to form a hole transport layer.
  • a hole control layer was formed using the HT2 (150 ⁇ ), and the compound 25 synthesized in Preparation Example 9 and the following GH2 (wt%: 1:1) were used as a host, and the following GD1 (6wt. %) was vacuum deposited to a thickness of 400 ⁇ to form a light emitting layer.
  • ETM1 was deposited to form an electron control layer, and the following ET-A and Liq were mixed at a mass ratio of 7:3 to form an electron transport layer having a thickness of 250 ⁇ .
  • ET-A and Liq were mixed at a mass ratio of 7:3 to form an electron transport layer having a thickness of 250 ⁇ .
  • magnesium and silver as a negative electrode were formed to be 200 ⁇ in a thickness ratio of 1:4, and the CP1 was used as a capping layer (CPL) of the negative electrode.
  • the device was completed by depositing to a thickness of 600 ⁇ . In the above process, the deposition rate of the organic material was maintained at 1 ⁇ /sec.
  • An organic light-emitting device was manufactured in the same manner as in Example 36, except that Compound 26 was used instead of Compound 25 in Example 36.
  • An organic light-emitting device was manufactured in the same manner as in Example 36, except that the following GH1 was used instead of Compound 25 in Example 36.
  • T95 is a measure of the time when the luminance becomes 95% of the initial luminance.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Luminescent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1, et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/008572 2019-07-05 2020-07-01 Composé et dispositif électroluminescent organique le comprenant Ceased WO2021006532A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202080030276.8A CN113727980B (zh) 2019-07-05 2020-07-01 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
KR20190081380 2019-07-05
KR10-2019-0081380 2019-07-05

Publications (1)

Publication Number Publication Date
WO2021006532A1 true WO2021006532A1 (fr) 2021-01-14

Family

ID=74115130

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2020/008572 Ceased WO2021006532A1 (fr) 2019-07-05 2020-07-01 Composé et dispositif électroluminescent organique le comprenant

Country Status (3)

Country Link
KR (1) KR102445078B1 (fr)
CN (1) CN113727980B (fr)
WO (1) WO2021006532A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230114063A (ko) * 2022-01-24 2023-08-01 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자
CN116023374B (zh) * 2023-02-15 2025-04-01 北京八亿时空液晶科技股份有限公司 一种杂环化合物及其应用
CN117050103A (zh) * 2023-08-16 2023-11-14 长春海谱润斯科技股份有限公司 一种杂环化合物及其有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160082067A (ko) * 2014-12-30 2016-07-08 희성소재 (주) 화합물 및 이를 이용한 유기발광소자
KR20180003220A (ko) * 2016-06-30 2018-01-09 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광표시장치
CN109096279A (zh) * 2018-09-28 2018-12-28 武汉天马微电子有限公司 氮杂环化合物、显示面板以及显示装置
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用
CN111233840A (zh) * 2018-11-28 2020-06-05 北京鼎材科技有限公司 一类喹喔啉衍生物及其在有机发光器件中的应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160082067A (ko) * 2014-12-30 2016-07-08 희성소재 (주) 화합물 및 이를 이용한 유기발광소자
KR20180003220A (ko) * 2016-06-30 2018-01-09 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광표시장치
CN109096279A (zh) * 2018-09-28 2018-12-28 武汉天马微电子有限公司 氮杂环化合物、显示面板以及显示装置
CN111233840A (zh) * 2018-11-28 2020-06-05 北京鼎材科技有限公司 一类喹喔啉衍生物及其在有机发光器件中的应用
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用

Also Published As

Publication number Publication date
KR102445078B1 (ko) 2022-09-21
CN113727980A (zh) 2021-11-30
CN113727980B (zh) 2024-06-28
KR20210004860A (ko) 2021-01-13

Similar Documents

Publication Publication Date Title
WO2019168367A1 (fr) Diode électroluminescente organique
WO2019132506A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2014010823A1 (fr) Composé hétérocyclique et élément électronique organique comprenant ce composé
WO2017150859A1 (fr) Composé contenant de l'azote et dispositif électroluminescent organique contenant ce composé
WO2020076108A1 (fr) Dispositif électroluminescent organique
WO2019235902A1 (fr) Composé polycyclique et élément électronique organique le comprenant
WO2013191429A1 (fr) Composé hétérocyclique contenant de l'azote et élément électronique organique comprenant ce composé
WO2019147077A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019164301A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2019164218A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2019108033A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020256480A1 (fr) Dispositif électroluminescent organique
WO2020159279A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2017160068A1 (fr) Composé hétérocyclique et diode organique électroluminescente le comprenant
WO2020067823A9 (fr) Élément électroluminescent organique
WO2022108258A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2020009363A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2019143223A9 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2020262861A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020231242A1 (fr) Élément électroluminescent organique
WO2018074881A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2021006532A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2024091024A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019022562A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2019177393A1 (fr) Composé et dispositif électroluminescent organique le comprenant

Legal Events

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

Ref document number: 20836663

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 20836663

Country of ref document: EP

Kind code of ref document: A1