WO2020085765A1 - Composé polycyclique et élément électroluminescent organique le comprenant - Google Patents

Composé polycyclique et élément électroluminescent organique le comprenant Download PDF

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WO2020085765A1
WO2020085765A1 PCT/KR2019/013897 KR2019013897W WO2020085765A1 WO 2020085765 A1 WO2020085765 A1 WO 2020085765A1 KR 2019013897 W KR2019013897 W KR 2019013897W WO 2020085765 A1 WO2020085765 A1 WO 2020085765A1
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윤홍식
홍완표
김진주
이동훈
김명곤
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주식회사 엘지화학
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Priority to CN201980037279.1A priority Critical patent/CN112218861B/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present specification relates to a polycyclic compound and an organic light emitting device including the same.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in an organic thin film and then paired to disappear, thereby emitting light.
  • the organic thin film may be composed of a single layer or multiple layers if necessary.
  • the organic light emitting phenomenon refers to a phenomenon that converts 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 and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Korean Patent Publication No. 10-2012-032572
  • A1 and A2 are the same as or different from each other, and each independently a cyano group; Or a phenyl group substituted with a cyano group,
  • R1 to R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,
  • Y is an aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted heteroaryl group; Or a heteroaryl group containing O or S as a substituted or unsubstituted hetero element,
  • R not bonded to * is a substituted or unsubstituted aryl group
  • n1 to n6 are each an integer of 0 to 4, n1 + n2 + n3 + n4 + n5 + n6 is 1 or more,
  • n1 to n6 are each an integer of 2 or more, the substituents in 2 or more parentheses are the same or different from each other.
  • 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, and at least one layer of the organic material layer includes a compound represented by Chemical Formula 1 above.
  • the compounds described herein can be used as a material for an organic material layer of an organic light emitting device.
  • the organic light emitting device including the compound according to an exemplary embodiment of the present specification, it is possible to obtain an organic light emitting device having excellent light emission efficiency, low driving voltage, high efficiency and long life.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10.
  • FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and a cathode 10. It is done.
  • FIG. 3 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( 9) and an example of an organic light emitting device comprising a cathode 10 is shown.
  • A1 and A2 are the same as or different from each other, and each independently a cyano group; Or a phenyl group substituted with a cyano group,
  • R1 to R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,
  • Y is an aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted heteroaryl group; Or a heteroaryl group containing O or S as a substituted or unsubstituted hetero element,
  • R not bonded to * is a substituted or unsubstituted aryl group
  • n1 to n6 are each an integer of 0 to 4, n1 + n2 + n3 + n4 + n5 + n6 is 1 or more,
  • n1 to n6 are each an integer of 2 or more, the substituents in 2 or more parentheses are the same or different from each other.
  • the compound represented by Chemical Formula 1 is a delayed fluorescent material.
  • the delayed fluorescent substance is a substance that converts the singlet exciton into a singlet exciton and converts it into light
  • the delayed fluorescent substance is a substance that converts the triplet exciton into singlet excitons and converts it into light, and exhibits a delayed fluorescent characteristic due to this process.
  • the phenomenon of delayed fluorescence also referred to as thermally activated delayed fluorescence (hereinafter abbreviated as 'TADF') refers to 75% of triplet excitons generated by electric field excitation at room temperature or at the temperature of the light emitting layer in the light emitting device, which is singlet This is a phenomenon where reverse intersystem crossing (hereinafter abbreviated as 'RISC') occurs with excitons.
  • 'RISC' reverse intersystem crossing
  • the singlet exciton generated by the crossing between inverses is fluoresced like the 25% singlet exciton generated by direct excitation, thereby enabling 100% internal quantum efficiency.
  • the delayed fluorescent material can convert both singlet excitons and triplet excitons to light, so 100% internal quantum efficiency is possible, so it is possible to overcome the limitations of lifetime and efficiency of phosphorescent materials.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer of the organic light emitting device. Since the energy difference between the triplet and the singlet is small in the compound represented by Chemical Formula 1, the rate and speed at which the exciton generated in the triplet moves to the singlet by reverse inter system (RISC) crossing Thus, since the time for the exciton to stay in the triplet is reduced, it has a characteristic of thermally activated delayed fluorescence (TADF), thereby increasing efficiency and lifetime when applied to the light emitting layer of the organic light emitting device.
  • RISC reverse inter system
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted in this specification is deuterium (-D); Halogen group; Cyano group; Hydroxy group; Silyl group; Boron group; Alkoxy groups; Alkyl groups; Cycloalkyl group; Aryl group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-described substituents, or having no substituents.
  • a substituent having two or more substituents 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 (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group is specifically a trimethyl boron group, a triethyl boron group, a tert-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
  • the alkyl group may be a straight chain or a branched chain, and 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, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 40. According to one embodiment, the carbon number of the aryl group is 6 to 30.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorene group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorene groups such as, (9,9-dimethylfluorene group), and It may be a substituted fluorene group such as (9,9-diphenylfluorene group). However, it is not limited thereto.
  • the heterocyclic group is a hetero atom and is a ring group containing at least one of N, O, P, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 36.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, Carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited thereto.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • ring is a hydrocarbon ring; Or a heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group, except for the divalent group.
  • heterocyclic group can be applied to the heterocycle except that it is divalent.
  • A1 and A2 are the same as or different from each other, and each independently a cyano group; Or a phenyl group substituted with a cyano group.
  • A1 and A2 are respectively cyano groups.
  • A1 and A2 are each a phenyl group substituted with a cyano group.
  • one of A1 and A2 is a cyano group, and the other is a phenyl group substituted with a cyano group.
  • Y is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted heteroaryl group.
  • Y is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted heteroaryl group.
  • Y is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, and a substituted or unsubstituted 2 to 30 carbon atoms. It is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of heteroaryl groups.
  • Y is a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group with one or more substituents selected from the group consisting of a substituted or unsubstituted heteroaryl group, substituted with another substituent
  • Y is a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group with one or more substituents selected from the group consisting of a substituted or unsubstituted heteroaryl group, substituted with another substituent
  • Y is an aryl group substituted with a substituent containing a double bond
  • it forms radicals when exposed to electrons in the organic light emitting device, and thus has a lower luminescence lifetime than the compound of the present invention.
  • the compound of the present invention has a larger portion of overlap between the energy levels of HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) than the compound in which Y is a cyano group, resulting in a fluorescence quantum efficiency (PLQY). Yield) is high, so it has high efficiency when applied to organic light emitting devices.
  • Y is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group and an alkyl group having 1 to 20 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms containing O or S as a substituted or unsubstituted hetero element.
  • Y is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group and an alkyl group having 1 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group and an alkyl group having 1 to 20 carbon atoms; A fluorene group unsubstituted or substituted with a cyano group and an alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Y is 6 to 30 aryl groups unsubstituted or substituted with one or more substituents selected from the group consisting of cyano, methyl and butyl groups; Or a heteroaryl group having 2 to 30 carbon atoms containing O or S as a substituted or unsubstituted hetero element.
  • Y is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; A fluorene group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Y is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; A fluorene group substituted with a methyl group; Dibenzofuran group; Or dibenzothiophene group.
  • Y is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, a methyl group, and a butyl group; Naphthyl group; A fluorene group substituted with a methyl group; Dibenzofuran group; Or dibenzothiophene group.
  • Y is a phenyl group substituted with a cyano group
  • a phenyl group substituted with a methyl group a phenyl group substituted with tert-butyl group
  • Naphthyl group 9,9-dimethylfluorene group
  • Dibenzofuran group Or dibenzothiophene group.
  • the n1 to n6 are each an integer of 0 to 4, n1 + n2 + n3 + n4 + n5 + n6 is 1 or more, and 2 or more parentheses when n1 to n6 are each an integer of 2 or more Substituents in the same or different from each other.
  • At least one of the three types of carbazole bound to benzene has a substituent, or two or more substituents combine with each other to form a ring, so that the compound and ring having no substituent attached to the carbazole Compared to compounds that do not contain condensed carbazole, it has the advantage of having excellent luminous efficiency and long life characteristics when applied to an organic light emitting device.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 24.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 16.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 8.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 6.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 4.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 to 3.
  • n1 + n2 + n3 + n4 + n5 + n6 is 1 or 2.
  • n1 + n2 + n3 + n4 + n5 + n6 is two or more.
  • n1 + n2 + n3 + n4 + n5 + n6 is 3 or more.
  • n1 + n2 + n3 + n4 + n5 + n6 is 4 or more.
  • any one of R5 and R6 or R is combined with *.
  • R is not bonded to the * is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R which is not bonded to * is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R which is not bonded to the * is a substituted or unsubstituted phenyl group.
  • R which is not bonded to the * is a phenyl group.
  • the formula 1 is represented by the following formula 2 or 3.
  • R1 to R6, n1 to n6, Y, A1 and A2 are the same as defined in Formula 1,
  • R ' is a substituted or unsubstituted aryl group.
  • R ' is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R ' is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R ' is a substituted or unsubstituted phenyl group.
  • R ' is a phenyl group.
  • the R1 To R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted 6 to 30 carbon ring.
  • R1 to R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Cyano group; 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 combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • the R1 To R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted benzocarbazole group, or combines with adjacent groups to form a ring to form any one of the following structures.
  • R11 is a substituted or unsubstituted aryl group
  • R12 and R13 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group,
  • the structures are deuterium; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be substituted or unsubstituted with a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the R1 to R4; And R5 and R6 which do not bind to * are the same as or different from each other, and each independently deuterium; Cyano group; A methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; Phenyl group; Carbazole; Or a benzocarbazole group, or combines with adjacent groups to form a ring to form any one of the following structures.
  • R11 is a substituted or unsubstituted aryl group
  • R12 and R13 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group,
  • the structures are deuterium; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be substituted or unsubstituted with a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the structures are deuterium; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted carbazole group; Or it may be substituted or unsubstituted with a substituted or unsubstituted benzocarbazole group.
  • the structures are deuterium; Cyano group; A methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; Phenyl group; Carbazole; Or it may be substituted or unsubstituted with a benzocarbazole group.
  • the structures are deuterium; Cyano group; CH 3 ; CD 3 ; Isopropyl group; tert-butyl group; Phenyl group; Carbazole; Or it may be substituted or unsubstituted with a benzocarbazole group.
  • R11 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R11 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • R11 is a phenyl group; Or a biphenyl group.
  • R12 and R13 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R12 and R13 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group.
  • R12 and R13 are methyl groups.
  • the R1 To R4; And at least one of R5 and R6 which does not bind to * forms a ring by combining with an adjacent group to form a benzocarbazole ring.
  • the R1 To R4; And * and at least one of R5 and R6 which do not bind to form a ring by combining with an adjacent group to form a benzocarbazole ring one of the following structures.
  • the formula 1 is represented by any one of the following structures.
  • the triplet energy level of the compound represented by Chemical Formula 1 is 2.1 eV or more, preferably 2.1 eV or more and 3.0 eV or less, 2.2 eV or more, 3.0 eV or less, 2.4 eV or more 2.9 eV or less.
  • the triplet energy level of the compound represented by Chemical Formula 1 satisfies the above range, electron injection is facilitated and the exciton formation rate is increased, so that the luminous efficiency is increased.
  • the difference between the singlet energy level and the triplet energy level of the compound represented by Formula 1 is 0 eV or more and 0.3 eV or less, preferably 0 eV or more and 0.2 eV Is below.
  • the exciton generated in the triplet is converted into a singlet by inverse transition (RISC).
  • RISC inverse transition
  • the triplet energy can be measured using a spectral device such as JASCO FP-8600 capable of measuring fluorescence and phosphorescence, and in the case of measurement conditions, toluene or TIEF is used as a solvent in a cryogenic state using liquid nitrogen.
  • a spectral device such as JASCO FP-8600 capable of measuring fluorescence and phosphorescence
  • toluene or TIEF is used as a solvent in a cryogenic state using liquid nitrogen.
  • the electrons from the light source reverse, the time for the electrons to stay in the triplet is much longer than the time in the singlet, so it is possible to separate the two components in the cryogenic state.
  • the singlet energy is measured using a fluorescent device such as JASCO FP-8600, and the light source is irradiated at room temperature, unlike the triplet energy measurement method described above.
  • compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure of the compound represented by Chemical Formula 1.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.
  • 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, and at least one layer of the organic material layer comprises the above-described compound.
  • the organic light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming one or more organic material layers using the compound represented by Chemical Formula 1 above.
  • an organic light emitting device having an organic material layer including the compound represented by Compound 1 it may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention is a hole transport layer, a hole injection layer, an electron blocking layer, a layer simultaneously performing hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection as an organic material layer It may have a structure including one or more of the layers.
  • the structure of the organic light emitting device of the present specification is not limited thereto, and may include fewer or more organic material layers.
  • the organic material layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by Formula 1 described above.
  • 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 a compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include the compound as a host of the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound as a dopant in the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a dopant in the light emitting layer
  • the content of the dopant may be included in 1 part by weight to 60 parts by weight based on 100 parts by weight of the host, preferably 30 parts by weight to 50 parts by weight.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives , Dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission layer may include the compound as a dopant, and further include a compound represented by Formula F as a host, but is not limited thereto.
  • L13 is a substituted or unsubstituted (b + 1) valent aryl group; Or a substituted or unsubstituted (b + 1) valent heteroaryl group,
  • G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Or a heteroaryl group containing O or S,
  • b13 is an integer from 1 to 3, and when b13 is 2 or more, L13 is the same as or different from each other,
  • b is 1 or 2
  • if b is 2 Are the same or different from each other.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a dopant containing the above-described compound and a host represented by Formula F in a weight ratio of 1:99 to 50:50.
  • L13 is a substituted or unsubstituted (b + 1) valent aryl group having 6 to 16 carbon atoms; Or a substituted or unsubstituted (b + 1) valent heteroaryl group having 2 to 16 carbon atoms.
  • L13 is a substituted or unsubstituted (b + 1) valent aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted (b + 1) valent heteroaryl group having 2 to 12 carbon atoms.
  • L13 is a substituted or unsubstituted (b + 1) valent phenyl group; A substituted or unsubstituted (b + 1) valent biphenyl group; A substituted or unsubstituted (b + 1) valent dibenzofuranyl group; Or a substituted or unsubstituted (b + 1) valent pyridinyl group.
  • the substituent of the (b + 1) valent aryl group is an aryl group substituted with a heteroaryl group.
  • G11 and G12 are the same as or different from each other, and each independently hydrogen; Or cyano group.
  • b13 is 2.
  • the compound represented by Formula F is any one selected from the following compounds.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound
  • the content of the fluorescent light-emitting material may be included from 0 parts by weight to 10 parts by weight based on 100 parts by weight of the compound. Since the fluorescent light-emitting material receives excitons from the compound and finally emits light, it is possible to increase the color purity of the device using a fluorescent light-emitting material having a narrow half-width, and prevent exciton-polaron quenching of the compound Therefore, there is an advantage of increasing the life of the device.
  • the half width refers to the thickness of the peak at a height that is half (1/2) of the maximum emission peak height on the emission spectrum.
  • Examples of the fluorescent material may be represented by anthracene-based compounds, pyrene-based compounds, florantene-based compounds, perylene-based compounds, boron-based compounds, or the following structures, but are 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 organic light emitting device may have a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • an anode 2 a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and a cathode 10 are sequentially stacked on an organic light emitting device on a substrate 1
  • the structure is illustrated.
  • the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof
  • PVD metal vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer, and then depositing a material that can be used as a cathode thereon Can be.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may be a multi-layered structure including a hole injection layer, a hole transport layer, an electron injection and electron transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport layer, and the like. However, it is not limited thereto, and may be a single-layer structure.
  • the organic material layer may be made by using a variety of polymer materials, such as a solvent process (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer), not a deposition method. Can be prepared in layers.
  • the positive electrode is an electrode for injecting holes
  • a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and 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, but are not limited thereto.
  • the cathode is an electrode that injects electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an 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;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer.
  • a hole injection material can be well injected with holes from the anode, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • 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 characteristics from being deteriorated. If it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer may be a material known in the art.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Benzoxazole, benzthiazole and benzimidazole compounds
  • Poly (p-phenylenevinylene) (PPV) polymers Spiro compounds
  • Polyfluorene, rubrene, and the like but are not limited to these.
  • the host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • PIQIr (acac) bis (1-phenylisoquinoline) acetylacetonateiridium
  • PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium
  • PQIr (tris (1-phenylquinoline) iridium are used as emission dopants.
  • Phosphorescent materials such as octaethylporphyrin platinum (PtOEP), or fluorescent materials such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but is not limited thereto.
  • a phosphorescent material such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium), or Alq3 (tris (8-hydroxyquinolino) aluminum), anthracene-based compound, or pyrene-based light emitting dopant Fluorescent materials such as compounds and boron-based compounds may be used, but are not limited thereto.
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic is used as a light emitting dopant, but spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are not limited thereto.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
  • the thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There are advantages.
  • 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, has an excellent electron injection effect on the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that prevents the cathode from reaching 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 complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Chemical Formula 1 may be prepared from various types of isophthalonitrile substituted with halide as follows. Various compounds in the specific examples were synthesized through the following manufacturing method.
  • the glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • Fischer Fischer Co.
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice for 10 minutes with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • Each thin film was laminated on the prepared ITO transparent electrode with a vacuum degree of 5.0 ⁇ 10 -4 ⁇ by vacuum deposition.
  • a hole injection layer was formed by thermal vacuum deposition of hexaazatriphenylene-hexanitrile (HAT-CN) to a thickness of 500 Pa on ITO.
  • the following compound NPB was vacuum deposited on the hole injection layer to form a hole transport layer (300 kPa).
  • the following compound EB1 was vacuum deposited on the hole transport layer to a thickness of 100 mm 2 to form an electron blocking layer (100 mm 2).
  • the compound m-CBP and 4CzIPN having a thickness of 300 mm 3 were vacuum deposited on the electron blocking layer at a weight ratio of 70:30 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the following compound HB1 with a thickness of 100 mm 2 on the light emitting layer.
  • the following compound ET1 and the compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 300 Pa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 2,000 ⁇ were sequentially deposited to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ / sec to 0.7 ⁇ / sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ / sec
  • aluminum at 2 ⁇ / sec.
  • An organic light emitting device was manufactured by maintaining 10 ⁇ 7 torr to 5 ⁇ 10 ⁇ 6 torr.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1-1 except for using the compound of Table 1 below instead of the compound 4CzIPN in Comparative Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1-1 except for using the compounds of T1 to T3 below instead of the compound 4CzIPN in Comparative Example 1-1.
  • the device of Experimental Examples 1-1 to 1-12 using the compound of Formula 1 has a lower voltage and improved efficiency than the device of the compound 4CzIPN in Comparative Example 1-1. .
  • the compound according to the present invention has excellent luminescence ability and high color purity, and thus can be applied to a delayed fluorescent organic light emitting device.
  • the glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • Fischer Fischer Co.
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice for 10 minutes with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • Each thin film was laminated on the prepared ITO transparent electrode with a vacuum degree of 5.0 ⁇ 10 -4 ⁇ by vacuum deposition.
  • a hole injection layer was formed by thermal vacuum deposition of hexaazatriphenylene-hexanitrile (HAT-CN) to a thickness of 500 Pa on ITO.
  • the following compound NPB was vacuum deposited on the hole injection layer to form a hole transport layer (300 kPa).
  • the following compound EB1 was vacuum deposited on the hole transport layer to a thickness of 100 mm 2 to form an electron blocking layer (100 mm 2).
  • the following compound m-CBP 4CzIPN and GD1 were deposited on the electron blocking layer at a thickness of 300 mm 3 in a weight ratio of 68: 30: 2 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the following compound HB1 with a thickness of 100 mm 2 on the light emitting layer.
  • the following compound ET1 and the compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 300 Pa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 2,000 ⁇ were sequentially deposited to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ / sec to 0.7 ⁇ / sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ / sec
  • aluminum at 2 ⁇ / sec.
  • An organic light emitting device was manufactured by maintaining 10 ⁇ 7 torr to 5 ⁇ 10 ⁇ 6 torr.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 2-1 except for using the compound of Table 2 below instead of the compound 4CzIPN in Comparative Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 2-1 except for using the compound of Table 2 below instead of the compound 4CzIPN in Comparative Example 2-1.
  • the driving voltage (V) and the current efficiency (cd / A), 3000 cd, measured at a current density of 10 mA / cm 2 for the organic light emitting devices of Experimental Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-4 CIE color coordinates measured at a luminance of / m 2 were measured, and are shown in Table 2 below.
  • the compound according to the present invention has excellent luminescence ability and is capable of tuning the emission wavelength, thereby realizing an organic light emitting device having high color purity.

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Abstract

La présente invention concerne : un composé représenté par la formule chimique 1; et un élément électroluminescent organique le comprenant.
PCT/KR2019/013897 2018-10-22 2019-10-22 Composé polycyclique et élément électroluminescent organique le comprenant WO2020085765A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021066059A1 (fr) * 2019-10-01 2021-04-08 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2021235549A1 (fr) * 2020-05-22 2021-11-25 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
WO2022196634A1 (fr) * 2021-03-15 2022-09-22 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
US11482681B2 (en) 2018-07-27 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102306983B1 (ko) * 2019-06-24 2021-09-30 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN117343061A (zh) * 2022-06-24 2024-01-05 陕西莱特光电材料股份有限公司 含氮化合物及有机电致发光器件和电子装置

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011256143A (ja) * 2010-06-10 2011-12-22 Fujifilm Corp 特定構造のカルバゾール系化合物、並びにそれを用いた電荷輸送材料及び有機電界発光素子
KR20160000331A (ko) * 2014-06-24 2016-01-04 제일모직주식회사 화합물, 이를 포함하는 유기광전자소자 및 표시장치
JP2016036025A (ja) * 2014-07-31 2016-03-17 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子及びπ共役系化合物
US20170186973A1 (en) * 2015-12-25 2017-06-29 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent compound and organic photoelectric apparatus thereof
KR20170128517A (ko) * 2015-05-08 2017-11-22 코니카 미놀타 가부시키가이샤 π 공액계 화합물, 유기 일렉트로루미네센스 소자 재료, 발광 재료, 발광성 박막, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치
US20190173020A1 (en) * 2017-12-05 2019-06-06 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5457907B2 (ja) 2009-08-31 2014-04-02 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
JP2014135466A (ja) * 2012-04-09 2014-07-24 Kyushu Univ 有機発光素子ならびにそれに用いる発光材料および化合物
US9698358B2 (en) * 2014-11-18 2017-07-04 Lg Chem, Ltd. Nitrogen-containing polycyclic compound and organic electroluminescent device using the same
KR102493553B1 (ko) * 2014-12-12 2023-01-30 메르크 파텐트 게엠베하 가용성 기를 갖는 유기 화합물
KR101881212B1 (ko) * 2016-09-08 2018-07-23 성균관대학교산학협력단 유기발광소자
CN108264478B (zh) * 2016-12-30 2020-09-22 昆山国显光电有限公司 载流子传输材料及载流子传输层及有机发光器件
WO2018151479A2 (fr) * 2017-02-14 2018-08-23 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
KR102160860B1 (ko) * 2017-11-28 2020-10-06 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011256143A (ja) * 2010-06-10 2011-12-22 Fujifilm Corp 特定構造のカルバゾール系化合物、並びにそれを用いた電荷輸送材料及び有機電界発光素子
KR20160000331A (ko) * 2014-06-24 2016-01-04 제일모직주식회사 화합물, 이를 포함하는 유기광전자소자 및 표시장치
JP2016036025A (ja) * 2014-07-31 2016-03-17 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子及びπ共役系化合物
KR20170128517A (ko) * 2015-05-08 2017-11-22 코니카 미놀타 가부시키가이샤 π 공액계 화합물, 유기 일렉트로루미네센스 소자 재료, 발광 재료, 발광성 박막, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치
US20170186973A1 (en) * 2015-12-25 2017-06-29 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent compound and organic photoelectric apparatus thereof
US20190173020A1 (en) * 2017-12-05 2019-06-06 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11482681B2 (en) 2018-07-27 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
WO2021066059A1 (fr) * 2019-10-01 2021-04-08 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN114514234A (zh) * 2019-10-01 2022-05-17 出光兴产株式会社 化合物、用于有机电致发光元件的材料、有机电致发光元件以及电子设备
WO2021235549A1 (fr) * 2020-05-22 2021-11-25 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
JP7406260B2 (ja) 2020-05-22 2023-12-27 株式会社Kyulux 化合物、発光材料および発光素子
WO2022196634A1 (fr) * 2021-03-15 2022-09-22 出光興産株式会社 Élément électroluminescent organique et dispositif électronique

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