WO2019172647A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019172647A1
WO2019172647A1 PCT/KR2019/002600 KR2019002600W WO2019172647A1 WO 2019172647 A1 WO2019172647 A1 WO 2019172647A1 KR 2019002600 W KR2019002600 W KR 2019002600W WO 2019172647 A1 WO2019172647 A1 WO 2019172647A1
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unsubstituted
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금수정
김명곤
구기동
이기곤
윤정민
김경희
김공겸
김동헌
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주식회사 엘지화학
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Priority to CN201980004940.9A priority Critical patent/CN111201233B/zh
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    • 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
    • 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
    • C07D491/22—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 four or more hetero rings
    • 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
    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
    • H—ELECTRICITY
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    • 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

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 an exchange of holes and / or electrons between an electrode and the organic semiconductor material.
  • the organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form.
  • the second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually 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 to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • organic light emitting devices are known to have characteristics such as self-luminous, 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 transport materials, electron injection materials and the like depending on their functions.
  • the luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light.
  • the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • the present specification describes a polycyclic 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).
  • A is a substituted or unsubstituted benzene ring
  • X 1 and X 2 are the same as or different from each other, and are each independently O, S, or N (Ra),
  • Ra, R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • B 1 to B 8 are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
  • Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Rb ' is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
  • At least one of B 1 to B 4 is C (Rb '), at least one of B 5 to B 8 is C (Rb'),
  • n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
  • n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • an organic light emitting device including the compound according to at least one embodiment it is possible to obtain an organic light emitting device having a high efficiency and a long life, when the compound of the present invention is included in the light emitting layer of the organic light emitting device, high color reproducibility It is possible to manufacture an organic light emitting device having a.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • FIG. 3 is a diagram showing an MS graph of Compound BD-A.
  • FIG. 5 is a diagram showing an MS graph of Compound BD-C.
  • FIG. 6 is a diagram showing an MS graph of Compound BD-D.
  • FIG. 7 is a diagram showing an MS graph of Compound BD-E.
  • the present specification provides a compound represented by the following Formula 1.
  • the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, the efficiency, color reproducibility and lifespan characteristics of the organic light emitting device are always.
  • A is a substituted or unsubstituted benzene ring
  • X 1 and X 2 are the same as or different from each other, and are each independently O, S, or N (Ra),
  • Ra, R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • B 1 to B 8 are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
  • Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Rb ' is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
  • At least one of B 1 to B 4 is C (Rb '), at least one of B 5 to B 8 is C (Rb'),
  • n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
  • n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium (-D); Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more substituents in the substituents exemplified above are substituted, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked 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 linked.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the silyl group may be represented by a chemical formula of -SiY 1 Y 2 Y 3 , wherein Y 1 , Y 2 and Y 3 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.
  • the boron group may be represented by a chemical formula of -BY 4 Y 5 , wherein Y 4 and Y 5 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. 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 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 and n-hexyl group , Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group and the like, but are not limited thereto.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl (ethenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, and the like. It is not limited to these.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; Arylalkylamine group; Arylamine group; Aryl heteroaryl amine group; Alkylheteroarylamine group It can be selected from the group consisting of a cycloalkylarylamine group and a heteroarylamine group, and carbon number is not particularly limited, but is preferably 1 to 60.
  • the alkylamine group is not particularly limited, but may be 1 to 40, according to one embodiment may be 1 to 20.
  • Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, and the like, but are not limited thereto.
  • a cycloalkylarylamine group means an amine group substituted with a cycloalkyl group and an aryl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, diphenylamine group, phenylnaphthylamine group, biphenylphenylamine group, dibiphenylamine group, and fluorine. And a phenylphenyl group, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group, may be a polycyclic heteroaryl group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.
  • arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.
  • an alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group.
  • 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 aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group include, for example, pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group , Indolocarbazole groups, naphthobenzofuran groups and the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the description of the heterocyclic group may be applied except that the heterocycle is divalent. have.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.
  • A is a substituted or unsubstituted benzene ring.
  • A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group and substituted or unsubstituted heteroaryl Or a benzene ring unsubstituted or substituted with one or more selected from the group consisting of groups.
  • A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C2-20 It is a benzene ring unsubstituted or substituted with one or more selected from the group consisting of an alkenyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, Or a substituted or unsubstituted benzene ring selected from the group consisting of a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted pyrimidine group.
  • A is hydrogen, deuterium, halogen, cyano (-CN), trimethylsilyl, methyl, ethyl, propyl, butyl, methylethenyl, trifluorophenyl, butyl It is a benzene ring unsubstituted or substituted with one or more selected from the group consisting of a phenyl group substituted or unsubstituted with a group and a pyrimidine group substituted with a phenyl group.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.
  • X 1 and X 2 are the same as or different from each other, and each independently O, S Or N (Ra),
  • Z 1 to Z 6 , Ra, R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • B 1 to B 8 are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
  • Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Rb ' is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
  • At least one of B 1 to B 4 is C (Rb '), at least one of B 5 to B 8 is C (Rb'),
  • n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
  • n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.
  • Z 1 to Z 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted alkyl group, substituted or Unsubstituted alkenyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.
  • Z 1 to Z 6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted carbon number 1 to 20 An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z 1 to Z 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted A substituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyrimidine group.
  • Z 1 to Z 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group , A methylethenyl group, a trifluorophenyl group, a phenyl group unsubstituted or substituted with a butyl group, or a pyrimidine group substituted with a phenyl group.
  • -CN cyano group
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-6.
  • X 1 and X 2 are the same as or different from each other, and each independently O, S Or N (Ra),
  • Z 21 to Z 32 , Ra, R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • B 1 to B 8 are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
  • Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Rb ' is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
  • At least one of B 1 to B 4 is C (Rb '), at least one of B 5 to B 8 is C (Rb'),
  • n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
  • n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.
  • Z 21 to Z 32 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, a substituted or Unsubstituted alkenyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.
  • Z 21 to Z 32 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted carbon number 1 to 20 An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Z 21 to Z 32 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted A substituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyrimidine group.
  • Z 21 to Z 32 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), trimethylsilyl group, a methyl group, an ethyl group, a propyl group, a butyl group , A methylethenyl group, a trifluorophenyl group, a phenyl group unsubstituted or substituted with a butyl group, or a pyrimidine group substituted with a phenyl group.
  • a cyano group cyano group
  • X 1 and X 2 are O.
  • X 1 and X 2 are S.
  • X 1 and X 2 are N (Ra).
  • one of X 1 and X 2 is O and the other is S.
  • one of X 1 and X 2 is O and the other is N (Ra).
  • one of X 1 and X 2 is S and the other is N (Ra).
  • Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ra is hydrogen; heavy hydrogen; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a halogen group or an alkyl group having 1 to 20 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a halogen group or an alkyl group having 1 to 20 carbon atoms.
  • Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • Ra is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a halogen group or a butyl group; Naphthyl group; Or a dibenzofuran group.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.
  • n1 is an integer of 0 to 2
  • the substituents in parentheses are the same as or different from each other.
  • n1 is an integer of 0 to 2
  • R1 is the same as or different from each other.
  • n1 is 0 or 1.
  • n2 is an integer of 0 to 2
  • R2 is the same as or different from each other.
  • n2 is 0 or 1.
  • B 1 to B 8 are the same as or different from each other, and each independently N, C (Rb) or C (Rb ').
  • At least one of B 1 to B 4 is C (Rb ' ), and at least one of the B 5 to B 8 is C (Rb').
  • one of B 1 to B 4 is C (Rb '), and the other three are C (Rb).
  • one of the B 1 to B 4 is N, one is C (Rb '), the other two are C (Rb).
  • two of the B 1 to B 4 is N, one is C (Rb '), the other is C (Rb).
  • one of B 5 to B 8 is C (Rb '), and the other three are C (Rb).
  • one of the B 5 to B 8 is N, one is C (Rb '), the other two are C (Rb).
  • two of the B 5 to B 8 is N, one is C (Rb '), the other is C (Rb).
  • the Rb ' is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N.
  • Rb ' is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N.
  • the aryl group may have 6 to 60 carbon atoms
  • the heteroaryl group and heterocyclic group may have 2 to 60 carbon atoms
  • the cycloalkyl group may have 3 to 60 carbon atoms.
  • Rb ' is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted carbazole group.
  • the aryl group may have 6 to 60 carbon atoms
  • the heteroaryl group and heterocyclic group may have 2 to 60 carbon atoms
  • the cycloalkyl group may have 3 to 60 carbon atoms.
  • Rb ' is 1 selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Substituted or unsubstituted arylamine group A heteroarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A cycloalkylarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; An arylheteroarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl
  • At least one of B 1 to B 4 is C (Rb ′), Rb 'is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group including one or more substituted or unsubstituted N, at least one of B 5 to B 8 is C (Rb '), and Rb' is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N
  • the Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • At least one of B 1 to B 4 is C (Rb '), Rb' is represented by the following Formula A, and at least one of B 5 to B 8 is C (Rb ').
  • Rb ' may be represented by the formula (A).
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted hetero ring,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted hetero ring having 2 to 60 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hetero ring having 2 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted pyridine group, or combine with each other to form a substituted or unsub
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-20 alkyl group, and a substituted or unsubstituted carbon number
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-20 alkyl group and a substituted or unsubstituted carbon number
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium, fluorine (-F), trimethylsilyl group, deuterium or fluorine (-F)
  • Chemical Formula 1 may be represented by any one of the following compounds.
  • -Ph means a phenyl group.
  • Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.
  • the compound of Formula 1 may be prepared in the core structure as shown in the following scheme.
  • 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.
  • X 1 and X 2 may be O or S, respectively, and when X 1 and X 2 are S ( ⁇ O) or SO 2 , respectively, they may be obtained by further oxidation.
  • Intermediate 3 (IM-3) is synthesized by a general Suzuki coupling reaction. Following ring closure reaction of intermediate 3, the hydroxyl group (hydroxyl group) can be made into a sulfone group (sulfone group) to make intermediate 4 (IM-4). It is possible to synthesize ⁇ Formula 1> by the Buckwaldamination between the intermediate 4 and various amine groups.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention 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 of the present invention includes a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes as an organic material layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electrons, etc. It may have a structure.
  • the structure of the organic light emitting device is not limited thereto and may include fewer organic layers or more organic layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the above-described compound.
  • the organic material layer may include a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer may include the above-described compound.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above as a dopant of the light emitting layer and further include a host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the above-described compound as a dopant of the light emitting layer, and may further include the following Chemical Formula 1-A as a host.
  • Ar 1 Ar 3 is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • q1 is an integer of 0-7, and when q1 is two or more, two or more R ⁇ 11> is same or different from each other.
  • the Ar 1 Ar 3 is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar 1 Ar 3 is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar 1 Ar 3 is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar 3 is hydrogen
  • Ar 1 is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.
  • Ar 1 is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms;
  • Ar 1 is hydrogen; A phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.
  • Ar 2 is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 2 is hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar 2 is hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cyclo
  • Ar 2 is hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • the L 1 to L 3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • the L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • the L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R 11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R 11 is hydrogen
  • q1 is an integer of 0 to 2.
  • q1 is 0 or 1.
  • Chemical Formula 1-A may be represented by any one of the following compounds.
  • the content of the dopant may be 1 part by weight to 10 parts by weight based on 100 parts by weight of the host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and includes at least two of the compounds represented by the following Chemical Formulas 1-B and 1-C as hosts. It may further include.
  • Ar 4 to Ar 8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,
  • Ar 9 is a substituted or unsubstituted heterocyclic group
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R 12 and R 13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in parentheses are the same or different from each other.
  • Ar 4 to Ar 8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • Ar 4 to Ar 8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 6 and Ar 8 are hydrogen.
  • Ar 5 and Ar 7 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar 5 and Ar 7 are the same as or different from each other, and each independently hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl
  • Ar 5 and Ar 7 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.
  • Ar 4 is hydrogen; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar 4 is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • Ar 4 is hydrogen; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with a methyl group.
  • Ar 9 is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar 9 is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar 9 is a substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.
  • Ar 9 is a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or an indolocarbazole group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • Ar 9 is a dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L 4 to L 9 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • R 12 and R 13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the R 12 and R 13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R 11 and R 12 are hydrogen.
  • q2 is an integer of 0 to 7, and when q2 is 2 or more, two or more R 12 are the same as or different from each other.
  • q2 is an integer of 0 to 2.
  • q2 is 0 or 1.
  • q3 is an integer of 0 to 7, and when q3 is 2 or more, two or more R 13 are the same as or different from each other.
  • q3 is an integer of 0 to 2.
  • q3 is 0 or 1.
  • Chemical Formula 1-B may be represented by any one of the following compounds.
  • Chemical Formula 1-C may be represented by any one of the following compounds.
  • the compound of the present invention is included as a dopant of the light emitting layer, and includes two or more of the compounds represented by Formulas 1-B and 1-C as a host, the content of the dopant is 1 part by weight based on 100 parts by weight of the host. It may be 10 parts by weight.
  • the compound may be included as a dopant of the emission layer, and the compound represented by Formula 1-B and the compound represented by Formula 1-C may be included as a host of the emission layer.
  • the mixed weight ratio of (1: B: 1-C) may be 95: 5 to 5:95.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound as a dopant of the light emitting layer, includes a fluorescent host or a phosphorescent host, and includes another organic compound, a metal, or a metal compound as a dopant. It may include.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer.
  • the organic material layer may include a light emitting layer, the light emitting layer may be included as a host of the light emitting layer described above, and further include a dopant.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the structure of the organic light emitting device of the present invention 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 an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7 or the electron transport layer (8).
  • the hole transport layer may be two or more layers.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate.
  • PVD metal vapor deposition
  • 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 be a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting holes and transporting holes, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and transporting electrons, and the like. It may be a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable as an anode material so that hole injection can be smoothly performed into an organic material layer.
  • the positive electrode material that can be used in the present invention 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); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, 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.
  • 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, the highest occupied hole injection material
  • the molecular orbital is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • 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 of preventing the hole injection characteristic from being lowered.
  • the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a hole transporting material a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including 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. If the thickness of the electron transporting layer is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. If the thickness of the electron transporting layer is 50 nm or less, the thickness of the electron transporting layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage to this.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • As the electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and The compound which is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that blocks the reaching of the cathode of the hole, 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 complexes, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • Synthesis Example 3 1.7 g of Compound BD-G was obtained by the same method as the method for synthesizing Compound BD-A, except that G-2 instead of A-2 and T-11 instead of T-3 were used.
  • Synthesis Example 3 1.9 g of Compound BD-I was obtained by the same method as the method of synthesizing Compound BD-A, except that G-2 instead of A-2 and T-13 instead of T-3 were used.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • the compound HAT was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound HT-A 1000 Pa was vacuum-deposited on the hole transport layer, and the compound HT-B 100 Pa was subsequently deposited.
  • the light emitting layer was vacuum deposited to a thickness of 200 ⁇ with BD-A at 2% by weight with BH-1 and dopant as a host.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • LiF was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-C instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-D instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-F instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-I instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using BH-2 instead of compound BH-1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-J instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-K instead of the compound BD-A.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-L instead of the compound BD-A.
  • the organic light emitting diodes of Examples 1 to 6 and Comparative Examples 1 to 3 measured driving voltage, luminous efficiency and color coordinate at a current density of 10 mA / cm 2 , and 95% of the initial luminance at a current density of 20 mA / cm 2 .
  • the time to become (LT95) was measured. The results are shown in Table 1 below.

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Abstract

La présente invention concerne un composé de formule 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/002600 2018-03-06 2019-03-06 Composé hétérocyclique et dispositif électroluminescent organique le comprenant WO2019172647A1 (fr)

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JP7456672B2 (ja) 2020-08-25 2024-03-27 エルジー・ケム・リミテッド 新規な化合物およびこれを含む有機発光素子

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