WO2022019535A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2022019535A1
WO2022019535A1 PCT/KR2021/008670 KR2021008670W WO2022019535A1 WO 2022019535 A1 WO2022019535 A1 WO 2022019535A1 KR 2021008670 W KR2021008670 W KR 2021008670W WO 2022019535 A1 WO2022019535 A1 WO 2022019535A1
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substituted
carbon atoms
unsubstituted
compound
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윤정민
허동욱
홍성길
한미연
윤희경
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주식회사 엘지화학
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Priority to CN202180032989.2A priority Critical patent/CN115515951A/en
Publication of WO2022019535A1 publication Critical patent/WO2022019535A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
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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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X1 is O or S
  • At least one of Y1 to Y5 is N, and the others are each independently CR3,
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, may be combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,
  • R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a heteroaryl group containing S, or may combine with an adjacent group to form a substituted or unsubstituted ring,
  • L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • l1 is an integer from 1 to 5
  • n 1 or 2
  • n is an integer from 1 to 4,
  • L1 When l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
  • n 2 or more, the 2 or more are the same as or different from each other,
  • an exemplary embodiment of the present specification 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.
  • the compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using it, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
  • 1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • Formula 1 is a structure in which a cyano group and an N-containing monocyclic heterocyclic group derivative substituent are bonded to the xanthene or thioxanthene core, respectively, and is included in the organic material layer of the organic light emitting device to improve efficiency, low driving voltage and It is possible to improve the life characteristics.
  • the N-containing heterocyclic group derivative and the cyano group of Formula 1 have an electron depletion structure, the dipole moment of a molecule can be increased. By smoothly controlling the electron mobility at the time, the efficiency and lifespan of the organic light emitting device including the compound represented by Formula 1 can be improved.
  • the steric hindrance due to the structure of xanthene and thioxanthene of the compound of Formula 1 prevents crystallization occurring during film formation, and maintains high thermal stability, so that it has a very stable effect even at a high deposition temperature. Accordingly, in the organic light emitting device including the compound according to the exemplary embodiment of the present specification, it is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent.
  • substituents when two substituents are connected, a phenyl group and a naphthyl group are connected. or It can be a substituent of
  • (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1) include
  • a phenyl group, a naphthyl group and an isopropyl group are connected , , or It can be a substituent of
  • the above definition applies equally to a case in which 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spir
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like.
  • Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group
  • the examples of the aryl group may be applied to the aryl group of the arylsilyl group
  • the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, and a diphenyl boron group.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like but is not limited thereto.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • adjacent groups combine with each other to form a ring means a substituted or unsubstituted hydrocarbon ring by combining adjacent groups with each other; Or it means to form a substituted or unsubstituted heterocyclic ring.
  • each R3 may be an "adjacent group”.
  • R3 and L1 may be "adjacent groups”.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group except for those not monovalent.
  • the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
  • the alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that each of these groups is a divalent group, the description of the above-described alkyl group may be applied.
  • the alkenylene group means that the alkenyl group has two bonding sites, that is, a divalent group.
  • the description of the alkenyl group described above may be applied, except that each of these groups is a divalent group.
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
  • X1 is O.
  • X1 is S.
  • Formula 1 is represented by Formula 2 or 3 below.
  • R1, R2, Y1 to Y5, L1, 11, m, and n are the same as defined in Formula 1 above.
  • m is 1.
  • m is 2.
  • n 1
  • n is 2.
  • n 3.
  • n 4.
  • Chemical Formula 1 is represented by Chemical Formula 4 or 5 below.
  • X1, R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 6 to 9 below.
  • R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
  • l1 is 1.
  • l1 is 2.
  • l1 is 3.
  • each L1 means that they are connected in series.
  • L1 is 3 and L1 is a phenylene group, a naphthylene group, and a phenylene group, respectively, they may be connected as follows, but are not limited thereto, and the order or connection position of each L1 may be different.
  • At least one of Y1 to Y5 is N, and the rest are each independently CR3.
  • At least two of Y1 to Y5 are N, and the rest are each independently CR3.
  • At least three of Y1 to Y5 are N, and the rest are each independently CR3.
  • any one of Y1 to Y5 is N, and the others are each independently CR3.
  • any two of Y1 to Y5 are N, and the rest are each independently CR3.
  • any three of Y1 to Y5 are N, and the rest are each independently CR3.
  • Y1 is N
  • Y2 to Y5 are the same as or different from each other, and are each independently CR3.
  • Y2 is N
  • Y1 and Y3 to Y5 are the same as or different from each other, and are each independently CR3.
  • Y3 is N
  • Y1, Y2, Y4 and Y5 are the same as or different from each other, and each independently represents CR3.
  • Y1 and Y5 are N, Y2 to Y4 are the same as or different from each other, and each independently represents CR3.
  • Y1 and Y3 are N, Y2, Y4 and Y5 are the same as or different from each other, and are each independently CR3.
  • Y2 and Y4 are N
  • Y1, Y3 and Y5 are the same as or different from each other, and are each independently CR3.
  • Y3 and Y5 are N, Y1, Y2 and Y4 are the same as or different from each other, and are each independently CR3.
  • Y1 and Y2 are N, Y3 to Y5 are the same as or different from each other, and each independently represents CR3.
  • Y4 and Y5 are N, Y1 to Y3 are the same as or different from each other, and are each independently CR3.
  • Y2 and Y3 are N, Y1, Y4 and Y5 are the same as or different from each other, and are each independently CR3.
  • Y3 and Y4 are N, Y1, Y2 and Y5 are the same as or different from each other, and are each independently CR3.
  • Y1, Y3 and Y5 are N
  • Y2 and Y4 are the same as or different from each other, and are each independently CR3.
  • the is any one selected from the following structures.
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring may be formed by bonding with an adjacent group.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 20 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 10 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
  • R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other. rings can be formed.
  • R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 20 carbon atoms in combination with each other. rings can be formed.
  • R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 10 carbon atoms in combination with each other. rings can be formed.
  • R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; Or an isopropyl group, or cyclohexane bonded to each other; or cyclopentane.
  • R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; or an isopropyl group.
  • R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
  • R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
  • R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.
  • R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
  • R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
  • R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.
  • R1 and R2 are combined with each other to form cyclohexane; or cyclopentane.
  • R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.
  • R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.
  • R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms;
  • R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that
  • R3 is hydrogen; heavy hydrogen; methyl group; A cyano group, a pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group substituted or unsubstituted with a cyano group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group , a dibenzothiophene group substituted or unsubstituted with a phenothiazine group, a cyano group, a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a phenyl group unsub
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a mono
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or poly
  • R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; A pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group, a phenothiazine group, a dibenzothiophene group, a phenyl group unsubstituted or substituted with a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a naphthyl group substituted or unsubstituted
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; phenylene group; biphenylrylene group; terphenyl rylene group; naphthylene group; a divalent pyridine group; a divalent furan group; or a divalent thiophene group.
  • L1 is combined with R3 to form a substituted or unsubstituted ring.
  • L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • L1 is combined with R3 to form a ring.
  • L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • L1 is combined with R3 to form benzene.
  • R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other.
  • R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstit
  • the is any one selected from the following structures.
  • the is any one selected from the following structures.
  • L1 is the same as defined in Formula 1 above,
  • 11 is an integer of 1 to 4, and when 11 is 2 or more, L1 of 2 or more are the same as or different from each other,
  • R31 to R34 are the same as described above.
  • Formula 1 is any one selected from the following compounds.
  • the present specification provides an organic light emitting device including the compound represented by Formula 1 above.
  • the 'layer' means compatible with a 'film' mainly used in the present technical field, and refers to a coating covering a desired area.
  • the size of the 'layers' is not limited, and each of the 'layers' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
  • the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.
  • the present specification 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 represented by Formula 1 above. do.
  • 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.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
  • the organic material layer includes a light emitting layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
  • the organic material layer includes an electron blocking layer.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device includes a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. It further includes one or more floors selected from.
  • the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.
  • the two or more organic material layers include a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. Two or more may be selected from the group.
  • two or more hole transport layers are included between the light emitting layer and the first electrode.
  • the two or more hole transport layers may include the same or different materials.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate the structure of an organic light emitting device according to an exemplary embodiment of the present specification.
  • 1 and 2 illustrate an organic light emitting device, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102 , an organic material layer 111 , and a second electrode 110 are sequentially stacked on a substrate 101 .
  • the compound represented by Formula 1 is included in the organic layer.
  • the first electrode 102, the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron injection and transport layer 106, and the second electrode 110 on the substrate 101 are sequentially
  • the structure of the organic light-emitting device stacked with The compound represented by Formula 1 is included in the electron injection and transport layer.
  • the organic light emitting device of the present specification includes an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, or a hole blocking layer containing the compound, that is, a compound represented by Formula 1 Except that, it may be prepared by materials and methods known in the art.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • 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); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; 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 material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO 2 /Al, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
  • the host includes a compound represented by the following Chemical Formula H-1, but is not limited thereto.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R201 is hydrogen; heavy hydrogen; halogen 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,
  • r201 is an integer of 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 monocyclic to 4 ring heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted or substituted
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R201 is hydrogen
  • Formula H-1 is represented by the following compound.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each an integer of 1 to 4,
  • t5 is 2 or more, the 2 or more T5 are the same as or different from each other,
  • t6 is 2 or more
  • the 2 or more T6 are the same as or different from each other.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; isopropyl group; a phenyl group substituted with a cyano group; or a phenyl group substituted with a methyl group.
  • Formula D-1 is represented by the following compound.
  • the hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes so as to have a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection material metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole injection layer includes a compound represented by the following Chemical Formula HI-1, but is not limited thereto.
  • R300 to R308 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r301 and r302 are each an integer of 1 to 4,
  • r303 and r304 are each an integer of 1 to 3,
  • R301 is 2 or more, R301 is the same as or different from each other,
  • R302 is 2 or more, R302 is the same as or different from each other,
  • R303 is 2 or more, R303 is the same as or different from each other,
  • R304 is the same as or different from each other.
  • R301 to R304 are hydrogen.
  • R300 is a substituted or unsubstituted aryl group.
  • R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R300 is a phenyl group.
  • R305 to R308 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R305 to R308 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R305 to R308 are the same as or different from each other, and each independently a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
  • Formula HI-1 is represented by the following compound.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is preferable, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the hole transport layer includes a compound represented by the following Chemical Formula HT-1, but is not limited thereto.
  • At least one of X'1 to X'6 is N, the rest are CH,
  • R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by bonding with an adjacent group.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • Formula HT-1 is represented by the following compound.
  • the hole transport layer includes a compound represented by the following Chemical Formula HT-2, but is not limited thereto.
  • R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of a combination thereof, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r315 is an integer of 1 to 5, and when r315 is 2 or more, R315 of 2 or more are the same as or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same as or different from each other.
  • R317 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.
  • R317 is a carbazole group; phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.
  • R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R315 and R316 are the same as or different from each other, and are each independently a phenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.
  • Chemical Formula HT-2 is represented by the following compound.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer As such, a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material, as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver.
  • a layer of aluminum or silver there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.
  • the electron injection layer is a layer that receives electrons from the electrode.
  • the organic light-emitting device includes an additional electron injection layer other than the electron injection layer comprising Formula 1
  • the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an electron receiving effect from, and an excellent electron injection effect to the light emitting layer or the light emitting material.
  • a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; 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, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer.
  • a known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer.
  • the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Formula 1, specifically, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, There is an aluminum complex (aluminum complex), but is not limited thereto.
  • the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the organic light emitting diode according to the present specification may be included in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • the compound 2-1 (15.0 g, 30 mmol) and the compound 23-2 (17.0 g, 33 mmol) were added to tetrahydrofuran (300 mL).
  • 2M K 2 CO 3 200 mL
  • potassium acetate (0.14 g)
  • the compound 15-1 (15.0 g, 30 mmol) and the compound 25-2 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL).
  • the compound 26-1 (15.0 g, 30 mmol) and the compound 26-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL).
  • 2M K 2 CO 3 200 mL
  • potassium acetate (0.14 g)
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • 50 ⁇ of hexanitrile hexaazatriphenylene (HAT) of the following formula and the following compound [HT-A] (600 ⁇ ) were sequentially vacuum-deposited to form a hole transport layer.
  • HAT hexanitrile hexaazatriphenylene
  • the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 ⁇ on the hole transport layer to form a light emitting layer.
  • the compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 350 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ /sec
  • the aluminum was maintained at a deposition rate of 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10 -
  • an organic light emitting device was manufactured.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound ET7 below was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • the organic light emitting device manufactured by using each compound as an electron injection and transport layer material was measured for driving voltage and luminous efficiency at a current density of 10 mA/cm 2 .
  • the time (LT98) to be 98% of the initial luminance was measured.
  • the N-containing heterocyclic group derivative of Formula 1 and the cyano group have an electron depletion structure, so that the dipole moment of the molecule can be increased.
  • the electron mobility of the light emitting device is smoothly controlled. Therefore, it was confirmed that the driving voltage, current efficiency, and lifespan of the organic light emitting diodes of Examples 1 to 29 exhibited superior characteristics than the compounds of Comparative Examples 1 to 7.
  • Example 21 of the present application in which R3 includes a compound containing a 6-membered ring including N, than Comparative Example 5, in which R3 includes a compound containing a benzimidazole (5-membered ring including N),
  • R3 includes a compound containing a benzimidazole (5-membered ring including N)
  • Formula 1 is a structure in which xanthene (or thioxanthene), a cyano group, and an N-containing monocyclic heterocyclic group are organically bonded, Comparative Examples 6 and 7 are spirobifluorene (fluorene) structures instead of xanthene (or thioxanthene) It is an organic light emitting device comprising a compound comprising could

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Abstract

The present specification relates to a compound of chemical formula 1, and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device comprising same
본 출원은 2020년 7월 24일에 한국특허청에 제출된 한국 특허 출원 제 10-2020-0092277호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0092277, filed with the Korean Intellectual Property Office on July 24, 2020, the entire contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for the organic light emitting device as described above is continuously required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a compound and an organic light emitting device including the same.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
Figure PCTKR2021008670-appb-img-000001
Figure PCTKR2021008670-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
X1은 O 또는 S이고,X1 is O or S;
Y1 내지 Y5 중 적어도 하나는 N이고, 나머지는 각각 독립적으로 CR3이며,At least one of Y1 to Y5 is N, and the others are each independently CR3,
R1 및 R2은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리를 형성할 수 있으며, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, may be combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,
R3는 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a heteroaryl group containing S, or may combine with an adjacent group to form a substituted or unsubstituted ring,
L1은 직접결합; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 알케닐렌기; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
l1은 1 내지 5의 정수이고,l1 is an integer from 1 to 5,
m은 1 또는 2이며,m is 1 or 2,
n은 1 내지 4의 정수이고,n is an integer from 1 to 4,
상기 l1이 2 이상인 경우, 상기 2 이상의 L1는 서로 같거나 상이하며,When l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
상기 n이 2 이상인 경우, 상기 2 이상의
Figure PCTKR2021008670-appb-img-000002
는 서로 같거나 상이하고,When n is 2 or more, the 2 or more
Figure PCTKR2021008670-appb-img-000002
are the same as or different from each other,
Figure PCTKR2021008670-appb-img-000003
는 상기 L1이 화학식 1에 결합되는 부위를 의미한다.
Figure PCTKR2021008670-appb-img-000003
denotes a site at which L1 is bonded to Formula 1.
또한, 본 명세서의 일 실시상태는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification 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.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다.The compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using it, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
도 1 및 2는 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Explanation of code]
101: 기판101: substrate
102: 제1 전극102: first electrode
111: 유기물층111: organic layer
110: 제2 전극110: second electrode
103: 정공주입층103: hole injection layer
104: 정공수송층104: hole transport layer
105: 발광층105: light emitting layer
106: 전자 주입 및 수송층106: electron injection and transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 화합물을 제공한다.The present specification provides a compound represented by Formula 1 above.
본 명세서의 일 실시상태에 따른 화학식 1은 잔텐 또는 티오잔텐 코어에 시아노기와 N함유 단환 헤테로고리기 유도체 치환기가 각각 결합되는 구조이며, 유기 발광 소자의 유기물층에 포함되어 효율의 향상, 낮은 구동전압 및 수명 특성의 향상이 가능하다.Formula 1 according to an exemplary embodiment of the present specification is a structure in which a cyano group and an N-containing monocyclic heterocyclic group derivative substituent are bonded to the xanthene or thioxanthene core, respectively, and is included in the organic material layer of the organic light emitting device to improve efficiency, low driving voltage and It is possible to improve the life characteristics.
구체적으로, 상기 화학식 1의 N함유 헤테로고리기 유도체 및 시아노기는 전자 공핍 구조를 가짐으로 분자의 극성(dipole moment)을 높일 수 있기 때문에 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자의 제작 시 전자이동도를 원활히 조절하여, 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자의 효율 및 수명을 향상 시킬 수 있다.Specifically, since the N-containing heterocyclic group derivative and the cyano group of Formula 1 have an electron depletion structure, the dipole moment of a molecule can be increased. By smoothly controlling the electron mobility at the time, the efficiency and lifespan of the organic light emitting device including the compound represented by Formula 1 can be improved.
또한, 상기 화학식 1의 화합물의 잔텐 및 티오잔텐의 구조로 인한 입체 장애는 필름 형성 시 발생하는 결정화를 방지하고, 높은 열 안정성을 유지하여 높은 증착 온도에도 매우 안정한 효과가 있다. 따라서, 본 명세서의 일 실시상태에 따른 화합물을 포함하는 유기 발광 소자는 효율의 향상, 낮은 구동전압 및 수명 특성의 향상 등이 가능하다.In addition, the steric hindrance due to the structure of xanthene and thioxanthene of the compound of Formula 1 prevents crystallization occurring during film formation, and maintains high thermal stability, so that it has a very stable effect even at a high deposition temperature. Accordingly, in the organic light emitting device including the compound according to the exemplary embodiment of the present specification, it is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents in the present specification are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2021008670-appb-img-000004
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2021008670-appb-img-000004
means the part to be connected.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 할로알킬기; 실릴기; 붕소기; 아민기; 아릴기; 및 헤테로아릴기로 이루어진 군으로부터 선택되는 1 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
본 명세서에 있어서, 2 이상의 치환기가 연결된다는 것은 어느 하나의 치환기의 수소가 다른 치환기와 연결된 것을 말한다. 예컨대, 2개의 치환기가 연결되는 것은 페닐기와 나프틸기가 연결되어
Figure PCTKR2021008670-appb-img-000005
또는
Figure PCTKR2021008670-appb-img-000006
의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어
Figure PCTKR2021008670-appb-img-000007
,
Figure PCTKR2021008670-appb-img-000008
, 또는
Figure PCTKR2021008670-appb-img-000009
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.
Figure PCTKR2021008670-appb-img-000005
or
Figure PCTKR2021008670-appb-img-000006
It can be a substituent of In addition, when three substituents are connected, (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1) include For example, a phenyl group, a naphthyl group and an isopropyl group are connected
Figure PCTKR2021008670-appb-img-000007
,
Figure PCTKR2021008670-appb-img-000008
, or
Figure PCTKR2021008670-appb-img-000009
It can be a substituent of The above definition applies equally to a case in which 4 or more substituents are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸, 아다만틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 할로알킬기는 상기 알킬기의 정의 중 알킬기의 수소 대신 적어도 하나의 할로겐기가 치환되는 것을 의미한다.In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라센기, 페난트렌기, 트리페닐렌기, 파이렌기, 페날렌기, 페릴렌기, 크라이센기, 플루오렌기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오렌기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오렌기가 치환되는 경우,
Figure PCTKR2021008670-appb-img-000010
등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,
Figure PCTKR2021008670-appb-img-000010
and the like, but is not limited thereto.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난트리딘기(phenanthridine), 페난쓰롤린기(phenanthroline), 이소옥사졸기, 티아디아졸기, 디벤조퓨란기, 디벤조실롤기, 페노크산틴기(phenoxathiine), 페녹사진기(phenoxazine), 페노티아진기(phenothiazine), 디하이드로인데노카바졸기, 스피로플루오렌잔텐기 및 스피로플루오렌티옥산텐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene There is a thioxanthene group, but is not limited thereto.
본 명세서 있어서, 상기 실릴기는 알킬실릴기, 아릴실릴기, 헤테로아릴실릴기 등일 수 있다. 상기 알킬실릴기 중 알킬기는 전술한 알킬기의 예시가 적용될 수 있고, 상기 아릴실릴기 중 아릴기는 전술한 아릴기의 예시가 적용될 수 있으며, 상기 헤테로아릴실릴기 중 헤테로아릴기는 상기 헤테로아릴기의 예시가 적용될 수 있다.In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, the examples of the aryl group may be applied to the aryl group of the arylsilyl group, and the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.
본 명세서에 있어서, 붕소기는 -BR100R101일 수 있으며, 상기 R100 및 R101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸메틸붕소기, 디페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, and a diphenyl boron group.
본 명세서에 있어서, 아민기는 -NH2, 알킬아민기, N-알킬아릴아민기, 아릴아민기, N-아릴헤테로아릴아민기, N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre There is a nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like, but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다. 상기 N-알킬아릴아민기 중의 알킬기와 아릴기는 전술한 알킬기 및 아릴기의 예시와 같다.In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-아릴헤테로아릴아민기 중의 아릴기와 헤테로아릴기는 전술한 아릴기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-알킬헤테로아릴아민기 중의 알킬기와 헤테로아릴기는 전술한 알킬기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 또는 치환 또는 비치환된 디아릴아민기가 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 또는 치환 또는 비치환된 디헤테로아릴아민기가 있다. 상기 헤테로아릴기가 2 이상을 포함하는 헤테로아릴아민기는 단환식 헤테로아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다. 예컨대, 상기 헤테로아릴아민기 중의 헤테로아릴기는 전술한 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
본 명세서에 있어서, 치환기 중 "인접한 기는 서로 결합하여 고리를 형성한다"는 의미는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성하는 것을 의미한다. 예컨대, 상기 화학식 1에 있어서, 상기 Y2 및 Y3가 각각 독립적으로 CR3인 경우, 각각의 R3가 "인접한 기"일 수 있다. 또한, Y1이 CR3인 경우, R3와 L1이 "인접한 기"일 수 있다.In the present specification, among the substituents, "adjacent groups combine with each other to form a ring" means a substituted or unsubstituted hydrocarbon ring by combining adjacent groups with each other; Or it means to form a substituted or unsubstituted heterocyclic ring. For example, in Formula 1, when Y2 and Y3 are each independently CR3, each R3 may be an "adjacent group". Further, when Y1 is CR3, R3 and L1 may be "adjacent groups".
본 명세서에 있어서, 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
본 명세서에 있어서, 탄화수소고리는 방향족 탄화수소 고리, 지방족 탄화수소고리, 또는 방향족 탄화수소와 지방족 탄화수소의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group except for those not monovalent.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
본 명세서에 있어서, 알킬렌기는 알킬기에 결합위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 알킬기의 설명이 적용될 수 있다.In the present specification, the alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that each of these groups is a divalent group, the description of the above-described alkyl group may be applied.
본 명세서에 있어서, 알케닐렌기는 알케닐기에 결합위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 알케닐기의 설명이 적용될 수 있다.In the present specification, the alkenylene group means that the alkenyl group has two bonding sites, that is, a divalent group. The description of the alkenyl group described above may be applied, except that each of these groups is a divalent group.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
이하, 상기 화학식 1로 표시되는 화합물에 관하여 상세히 설명한다.Hereinafter, the compound represented by Formula 1 will be described in detail.
본 명세서의 일 실시상태에 따르면, 상기 X1은 O이다.According to an exemplary embodiment of the present specification, X1 is O.
본 명세서의 일 실시상태에 따르면, 상기 X1은 S이다.According to an exemplary embodiment of the present specification, X1 is S.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2 또는 3으로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 2 or 3 below.
[화학식 2][Formula 2]
Figure PCTKR2021008670-appb-img-000011
Figure PCTKR2021008670-appb-img-000011
[화학식 3][Formula 3]
Figure PCTKR2021008670-appb-img-000012
Figure PCTKR2021008670-appb-img-000012
상기 화학식 2 및 3에 있어서,In Formulas 2 and 3,
R1, R2, Y1 내지 Y5, L1, l1, m 및 n은 상기 화학식 1에서 정의한 바와 동일하다.R1, R2, Y1 to Y5, L1, 11, m, and n are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 m은 1이다.According to an exemplary embodiment of the present specification, m is 1.
본 명세서의 일 실시상태에 따르면, 상기 m은 2이다.According to an exemplary embodiment of the present specification, m is 2.
본 명세서의 일 실시상태에 따르면, 상기 n은 1 이다.According to an exemplary embodiment of the present specification, n is 1.
본 명세서의 일 실시상태에 따르면, 상기 n은 2 이다.According to an exemplary embodiment of the present specification, n is 2.
본 명세서의 일 실시상태에 따르면, 상기 n은 3이다.According to an exemplary embodiment of the present specification, n is 3.
본 명세서의 일 실시상태에 따르면, 상기 n은 4이다.According to an exemplary embodiment of the present specification, n is 4.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 4 또는 5로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 4 or 5 below.
[화학식 4][Formula 4]
Figure PCTKR2021008670-appb-img-000013
Figure PCTKR2021008670-appb-img-000013
[화학식 5][Formula 5]
Figure PCTKR2021008670-appb-img-000014
Figure PCTKR2021008670-appb-img-000014
상기 화학식 4 및 5에 있어서,In Formulas 4 and 5,
X1, R1, R2, Y1 내지 Y5, L1 및 l1은 상기 화학식 1에서 정의한 바와 동일하다.X1, R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 6 내지 9 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 6 to 9 below.
[화학식 6][Formula 6]
Figure PCTKR2021008670-appb-img-000015
Figure PCTKR2021008670-appb-img-000015
[화학식 7][Formula 7]
Figure PCTKR2021008670-appb-img-000016
Figure PCTKR2021008670-appb-img-000016
[화학식 8][Formula 8]
Figure PCTKR2021008670-appb-img-000017
Figure PCTKR2021008670-appb-img-000017
[화학식 9][Formula 9]
Figure PCTKR2021008670-appb-img-000018
Figure PCTKR2021008670-appb-img-000018
상기 화학식 6 내지 9에 있어서,In Formulas 6 to 9,
R1, R2, Y1 내지 Y5, L1 및 l1은 상기 화학식 1에서 정의한 바와 동일하다.R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 l1은 1이다.According to an exemplary embodiment of the present specification, l1 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l1은 2이다.According to an exemplary embodiment of the present specification, l1 is 2.
본 명세서의 일 실시상태에 따르면, 상기 l1은 3이다.According to an exemplary embodiment of the present specification, l1 is 3.
본 명세서에서 상기 화학식 1에 있어서, l1이 2 이상인 경우, 2 이상의 L1는 서로 같거나 상이하며, 각각의 L1은 직렬로 연결되는 것을 의미한다. 예컨대, l1이 3이고, L1가 각각 페닐렌기, 나프틸렌기, 및 페닐렌기인 경우, 하기와 같이 연결될 수 있으나, 이에만 한정되는 것이 아니고, 각 L1의 순서 또는 연결위치가 상이할 수 있다.In the present specification, in Formula 1, when l1 is 2 or more, two or more L1s are the same as or different from each other, and each L1 means that they are connected in series. For example, when l1 is 3 and L1 is a phenylene group, a naphthylene group, and a phenylene group, respectively, they may be connected as follows, but are not limited thereto, and the order or connection position of each L1 may be different.
Figure PCTKR2021008670-appb-img-000019
Figure PCTKR2021008670-appb-img-000019
또한, 상기 화학식 1의
Figure PCTKR2021008670-appb-img-000020
은 예컨대, 상기 l1가 3인 경우, 상기 예시된 구조에서 세번째 위치한 말단의 치환기 즉, 페닐렌기에 결합되는 것을 의미한다.In addition, the formula (1)
Figure PCTKR2021008670-appb-img-000020
For example, when l1 is 3, it means that it is bonded to a substituent at the third position in the structure, that is, a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 적어도 1개는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, at least one of Y1 to Y5 is N, and the rest are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 적어도 2개는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, at least two of Y1 to Y5 are N, and the rest are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 적어도 3개는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, at least three of Y1 to Y5 are N, and the rest are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 어느 하나는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, any one of Y1 to Y5 is N, and the others are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 어느 2개는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, any two of Y1 to Y5 are N, and the rest are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y5 중 어느 3개는 N이고, 나머지는 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, any three of Y1 to Y5 are N, and the rest are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1는 N이고, Y2 내지 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y1 is N, Y2 to Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y2는 N이고, Y1 및 Y3 내지 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y2 is N, Y1 and Y3 to Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y3는 N이고, Y1, Y2, Y4 및 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y3 is N, Y1, Y2, Y4 and Y5 are the same as or different from each other, and each independently represents CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 및 Y5는 N이고, Y2 내지 Y4는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y1 and Y5 are N, Y2 to Y4 are the same as or different from each other, and each independently represents CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 및 Y3는 N이고, Y2, Y4 및 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y1 and Y3 are N, Y2, Y4 and Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y2 및 Y4는 N이고, Y1, Y3 및 Y5 는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y2 and Y4 are N, Y1, Y3 and Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y3 및 Y5는 N이고, Y1, Y2 및 Y4 는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y3 and Y5 are N, Y1, Y2 and Y4 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1 및 Y2는 N이고, Y3 내지 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y1 and Y2 are N, Y3 to Y5 are the same as or different from each other, and each independently represents CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y4 및 Y5는 N이고, Y1 내지 Y3는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y4 and Y5 are N, Y1 to Y3 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y2 및 Y3는 N이고, Y1, Y4 및 Y5는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y2 and Y3 are N, Y1, Y4 and Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y3 및 Y4는 N이고, Y1, Y2 및 Y5 는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y3 and Y4 are N, Y1, Y2 and Y5 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기 Y1, Y3 및 Y5는 N이고, Y2 및 Y4 는 서로 같거나 상이하며, 각각 독립적으로 CR3이다.According to an exemplary embodiment of the present specification, Y1, Y3 and Y5 are N, Y2 and Y4 are the same as or different from each other, and are each independently CR3.
본 명세서의 일 실시상태에 따르면, 상기
Figure PCTKR2021008670-appb-img-000021
는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the
Figure PCTKR2021008670-appb-img-000021
is any one selected from the following structures.
Figure PCTKR2021008670-appb-img-000022
Figure PCTKR2021008670-appb-img-000022
상기 구조에 있어서,In the structure,
R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring may be formed by bonding with an adjacent group.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 20의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 20 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 10의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 10 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other. rings can be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 탄소수 3 내지 20의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 20 carbon atoms in combination with each other. rings can be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 탄소수 3 내지 10의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 10 carbon atoms in combination with each other. rings can be formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 메틸기; 에틸기; 또는 이소프로필기이거나, 서로 결합하여 시클로헥산; 또는 시클로펜탄을 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; Or an isopropyl group, or cyclohexane bonded to each other; or cyclopentane.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 메틸기; 에틸기; 또는 이소프로필기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; or an isopropyl group.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 20의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 10의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 탄소수 3 내지 20의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 탄소수 3 내지 10의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 시클로헥산; 또는 시클로펜탄을 형성할 수 있다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form cyclohexane; or cyclopentane.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기; 또는 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 시아노기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기; 또는 시아노기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a 20 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 20 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 20 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; 중수소; 메틸기; 시아노기, 시아노기로 치환 또는 비치환된 피리딘기, 시아노기로 치환 또는 비치환된 디벤조퓨란기, 시아노기로 치환 또는 비치환된 터페닐기, 카바졸기, 페녹사진기, 퀴놀린기, 트리페닐렌기, 페노티아진기, 시아노기로 치환 또는 비치환된 디벤조티오펜기, 벤조카바졸기, 페닐기로 치환 또는 비치환된 페나진기, 플루오란텐기, 메틸기로 치환 또는 비치환된 디하이드로아크리딘기, 또는 시아노기로 치환 또는 비치환된 나프틸기로 치환 또는 비치환된 페닐기; 메틸기, 또는 시아노기로 치환 또는 비치환된 피리딘기; 페난트렌기; 시아노기, 또는 시아노기로 치환 또는 비치환된 페닐기로 치환 또는 비치환된 나프틸기; 터페닐기; 쿼터페닐기; 시아노기, 또는 카바졸기로 치환 또는 비치환된 바이페닐기; 시아노기로 치환 또는 비치환된 디벤조퓨란기; 시아노기로 치환 또는 비치환된 디벤조티오펜기; 페날렌기; 메틸기로 치환 또는 비치환된 플루오렌기; 트리페닐렌기; 또는 플루오란텐기이거나, 인접한 기와 서로 결합하여 벤젠; 또는 벤조퓨란을 형성할 수 있다.According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; methyl group; A cyano group, a pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group substituted or unsubstituted with a cyano group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group , a dibenzothiophene group substituted or unsubstituted with a phenothiazine group, a cyano group, a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a phenyl group unsubstituted or substituted with a naphthyl group unsubstituted or substituted with a cyano group; a pyridine group unsubstituted or substituted with a methyl group or a cyano group; phenanthrene group; a naphthyl group unsubstituted or substituted with a cyano group, or a phenyl group unsubstituted or substituted with a cyano group; terphenyl group; quarter phenyl group; a cyano group, or a biphenyl group unsubstituted or substituted with a carbazole group; a dibenzofuran group unsubstituted or substituted with a cyano group; a dibenzothiophene group unsubstituted or substituted with a cyano group; phenalene group; a fluorene group unsubstituted or substituted with a methyl group; triphenylene group; or a fluoranthene group, or benzene by bonding with adjacent groups; or benzofuran.
본 명세서의 일 실시상태에 따르면, 상기 R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.
본 명세서의 일 실시상태에 따르면, 상기 R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기; 또는 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 시아노기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기; 또는 시아노기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a 20 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 20 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 20 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R31 내지 R35는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 메틸기; 시아노기로 치환 또는 비치환된 피리딘기, 디벤조퓨란기, 시아노기로 치환 또는 비치환된 터페닐기, 카바졸기, 페녹사진기, 퀴놀린기, 트리페닐렌기, 페노티아진기, 디벤조티오펜기, 벤조카바졸기, 페닐기로 치환 또는 비치환된 페나진기, 플루오란텐기, 메틸기로 치환 또는 비치환된 디하이드로아크리딘기, 또는 시아노기로 치환 또는 비치환된 나프틸기로 치환 또는 비치환된 페닐기; 메틸기, 또는 시아노기로 치환 또는 비치환된 피리딘기; 페난트렌기; 페닐기로 치환 또는 비치환된 나프틸기; 터페닐기; 쿼터페닐기; 시아노기, 또는 카바졸기로 치환 또는 비치환된 바이페닐기; 디벤조퓨란기; 디벤조티오펜기; 페날렌기; 메틸기로 치환 또는 비치환된 플루오렌기; 트리페닐렌기; 또는 플루오란텐기이거나, 인접한 기와 서로 결합하여 벤젠; 벤조티오펜; 또는 벤조퓨란을 형성할 수 있다.According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; A pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group, a phenothiazine group, a dibenzothiophene group, a phenyl group unsubstituted or substituted with a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a naphthyl group substituted or unsubstituted with a cyano group; a pyridine group unsubstituted or substituted with a methyl group or a cyano group; phenanthrene group; a naphthyl group unsubstituted or substituted with a phenyl group; terphenyl group; quarter phenyl group; a cyano group, or a biphenyl group unsubstituted or substituted with a carbazole group; dibenzofuran group; dibenzothiophene group; phenalene group; a fluorene group unsubstituted or substituted with a methyl group; triphenylene group; or a fluoranthene group, or benzene by bonding with adjacent groups; benzothiophene; or benzofuran.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 페닐렌기; 바이페닐릴렌기; 터페닐릴렌기; 나프틸렌기; 2가의 피리딘기; 2가의 퓨란기; 또는 2가의 티오펜기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; phenylene group; biphenylrylene group; terphenyl rylene group; naphthylene group; a divalent pyridine group; a divalent furan group; or a divalent thiophene group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a ring.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 R3와 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, L1 is combined with R3 to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있고, 상기 R3는 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있으며, 상기 L1은 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other. may form a ring, wherein R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic group having 6 to 30 carbon atoms in combination with an adjacent group aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, wherein L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기
Figure PCTKR2021008670-appb-img-000023
는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the
Figure PCTKR2021008670-appb-img-000023
is any one selected from the following structures.
Figure PCTKR2021008670-appb-img-000024
Figure PCTKR2021008670-appb-img-000024
상기 구조에 있어서, R31 내지 R35의 정의는 전술한 바와 동일하다.In the above structure, definitions of R31 to R35 are the same as described above.
본 명세서의 일 실시상태에 따르면, 상기
Figure PCTKR2021008670-appb-img-000025
는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the
Figure PCTKR2021008670-appb-img-000025
is any one selected from the following structures.
Figure PCTKR2021008670-appb-img-000026
Figure PCTKR2021008670-appb-img-000026
상기 구조에 있어서, In the structure,
L1의 정의는 상기 화학식 1에서 정의한 바와 동일하고, The definition of L1 is the same as defined in Formula 1 above,
l11은 1 내지 4의 정수이며, 상기 l11이 2 이상인 경우, 2 이상의 L1은 서로 같거나 상이하며, 11 is an integer of 1 to 4, and when 11 is 2 or more, L1 of 2 or more are the same as or different from each other,
R31 내지 R34의 정의는 전술한 바와 동일하다.The definitions of R31 to R34 are the same as described above.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.
Figure PCTKR2021008670-appb-img-000027
Figure PCTKR2021008670-appb-img-000027
Figure PCTKR2021008670-appb-img-000028
Figure PCTKR2021008670-appb-img-000028
Figure PCTKR2021008670-appb-img-000029
Figure PCTKR2021008670-appb-img-000029
Figure PCTKR2021008670-appb-img-000030
Figure PCTKR2021008670-appb-img-000030
Figure PCTKR2021008670-appb-img-000031
Figure PCTKR2021008670-appb-img-000031
Figure PCTKR2021008670-appb-img-000032
Figure PCTKR2021008670-appb-img-000032
Figure PCTKR2021008670-appb-img-000033
Figure PCTKR2021008670-appb-img-000033
Figure PCTKR2021008670-appb-img-000034
Figure PCTKR2021008670-appb-img-000034
Figure PCTKR2021008670-appb-img-000035
Figure PCTKR2021008670-appb-img-000035
Figure PCTKR2021008670-appb-img-000036
Figure PCTKR2021008670-appb-img-000036
Figure PCTKR2021008670-appb-img-000037
Figure PCTKR2021008670-appb-img-000037
Figure PCTKR2021008670-appb-img-000038
Figure PCTKR2021008670-appb-img-000038
Figure PCTKR2021008670-appb-img-000039
Figure PCTKR2021008670-appb-img-000039
Figure PCTKR2021008670-appb-img-000040
Figure PCTKR2021008670-appb-img-000040
Figure PCTKR2021008670-appb-img-000041
Figure PCTKR2021008670-appb-img-000041
Figure PCTKR2021008670-appb-img-000042
Figure PCTKR2021008670-appb-img-000042
Figure PCTKR2021008670-appb-img-000043
Figure PCTKR2021008670-appb-img-000043
Figure PCTKR2021008670-appb-img-000044
Figure PCTKR2021008670-appb-img-000044
Figure PCTKR2021008670-appb-img-000045
Figure PCTKR2021008670-appb-img-000045
Figure PCTKR2021008670-appb-img-000046
Figure PCTKR2021008670-appb-img-000046
Figure PCTKR2021008670-appb-img-000047
Figure PCTKR2021008670-appb-img-000047
Figure PCTKR2021008670-appb-img-000048
Figure PCTKR2021008670-appb-img-000048
Figure PCTKR2021008670-appb-img-000049
Figure PCTKR2021008670-appb-img-000049
Figure PCTKR2021008670-appb-img-000050
Figure PCTKR2021008670-appb-img-000050
Figure PCTKR2021008670-appb-img-000051
Figure PCTKR2021008670-appb-img-000051
Figure PCTKR2021008670-appb-img-000052
Figure PCTKR2021008670-appb-img-000052
Figure PCTKR2021008670-appb-img-000053
Figure PCTKR2021008670-appb-img-000053
Figure PCTKR2021008670-appb-img-000054
Figure PCTKR2021008670-appb-img-000054
Figure PCTKR2021008670-appb-img-000055
Figure PCTKR2021008670-appb-img-000055
Figure PCTKR2021008670-appb-img-000056
Figure PCTKR2021008670-appb-img-000056
Figure PCTKR2021008670-appb-img-000057
Figure PCTKR2021008670-appb-img-000057
Figure PCTKR2021008670-appb-img-000058
Figure PCTKR2021008670-appb-img-000058
Figure PCTKR2021008670-appb-img-000059
Figure PCTKR2021008670-appb-img-000059
Figure PCTKR2021008670-appb-img-000060
Figure PCTKR2021008670-appb-img-000060
Figure PCTKR2021008670-appb-img-000061
Figure PCTKR2021008670-appb-img-000061
Figure PCTKR2021008670-appb-img-000062
Figure PCTKR2021008670-appb-img-000062
Figure PCTKR2021008670-appb-img-000063
Figure PCTKR2021008670-appb-img-000063
Figure PCTKR2021008670-appb-img-000064
Figure PCTKR2021008670-appb-img-000064
Figure PCTKR2021008670-appb-img-000065
Figure PCTKR2021008670-appb-img-000065
Figure PCTKR2021008670-appb-img-000066
Figure PCTKR2021008670-appb-img-000066
Figure PCTKR2021008670-appb-img-000067
Figure PCTKR2021008670-appb-img-000067
Figure PCTKR2021008670-appb-img-000068
Figure PCTKR2021008670-appb-img-000068
Figure PCTKR2021008670-appb-img-000069
Figure PCTKR2021008670-appb-img-000069
Figure PCTKR2021008670-appb-img-000070
Figure PCTKR2021008670-appb-img-000070
Figure PCTKR2021008670-appb-img-000071
Figure PCTKR2021008670-appb-img-000071
Figure PCTKR2021008670-appb-img-000072
Figure PCTKR2021008670-appb-img-000072
Figure PCTKR2021008670-appb-img-000073
Figure PCTKR2021008670-appb-img-000073
Figure PCTKR2021008670-appb-img-000074
Figure PCTKR2021008670-appb-img-000074
Figure PCTKR2021008670-appb-img-000075
Figure PCTKR2021008670-appb-img-000075
Figure PCTKR2021008670-appb-img-000076
Figure PCTKR2021008670-appb-img-000076
Figure PCTKR2021008670-appb-img-000077
Figure PCTKR2021008670-appb-img-000077
Figure PCTKR2021008670-appb-img-000078
Figure PCTKR2021008670-appb-img-000078
Figure PCTKR2021008670-appb-img-000079
Figure PCTKR2021008670-appb-img-000079
Figure PCTKR2021008670-appb-img-000080
Figure PCTKR2021008670-appb-img-000080
Figure PCTKR2021008670-appb-img-000081
Figure PCTKR2021008670-appb-img-000081
Figure PCTKR2021008670-appb-img-000082
Figure PCTKR2021008670-appb-img-000082
Figure PCTKR2021008670-appb-img-000083
Figure PCTKR2021008670-appb-img-000083
Figure PCTKR2021008670-appb-img-000084
Figure PCTKR2021008670-appb-img-000084
Figure PCTKR2021008670-appb-img-000085
Figure PCTKR2021008670-appb-img-000085
Figure PCTKR2021008670-appb-img-000086
Figure PCTKR2021008670-appb-img-000086
Figure PCTKR2021008670-appb-img-000087
Figure PCTKR2021008670-appb-img-000087
Figure PCTKR2021008670-appb-img-000088
Figure PCTKR2021008670-appb-img-000088
Figure PCTKR2021008670-appb-img-000089
Figure PCTKR2021008670-appb-img-000089
Figure PCTKR2021008670-appb-img-000090
Figure PCTKR2021008670-appb-img-000090
Figure PCTKR2021008670-appb-img-000091
Figure PCTKR2021008670-appb-img-000091
Figure PCTKR2021008670-appb-img-000092
Figure PCTKR2021008670-appb-img-000092
Figure PCTKR2021008670-appb-img-000093
Figure PCTKR2021008670-appb-img-000093
Figure PCTKR2021008670-appb-img-000094
Figure PCTKR2021008670-appb-img-000094
Figure PCTKR2021008670-appb-img-000095
Figure PCTKR2021008670-appb-img-000095
Figure PCTKR2021008670-appb-img-000096
Figure PCTKR2021008670-appb-img-000096
Figure PCTKR2021008670-appb-img-000097
Figure PCTKR2021008670-appb-img-000097
Figure PCTKR2021008670-appb-img-000098
Figure PCTKR2021008670-appb-img-000098
Figure PCTKR2021008670-appb-img-000099
Figure PCTKR2021008670-appb-img-000099
Figure PCTKR2021008670-appb-img-000100
Figure PCTKR2021008670-appb-img-000100
Figure PCTKR2021008670-appb-img-000101
Figure PCTKR2021008670-appb-img-000101
Figure PCTKR2021008670-appb-img-000102
Figure PCTKR2021008670-appb-img-000102
Figure PCTKR2021008670-appb-img-000103
Figure PCTKR2021008670-appb-img-000103
Figure PCTKR2021008670-appb-img-000104
Figure PCTKR2021008670-appb-img-000104
Figure PCTKR2021008670-appb-img-000105
Figure PCTKR2021008670-appb-img-000105
Figure PCTKR2021008670-appb-img-000106
Figure PCTKR2021008670-appb-img-000106
Figure PCTKR2021008670-appb-img-000107
Figure PCTKR2021008670-appb-img-000107
Figure PCTKR2021008670-appb-img-000108
Figure PCTKR2021008670-appb-img-000108
Figure PCTKR2021008670-appb-img-000109
Figure PCTKR2021008670-appb-img-000109
Figure PCTKR2021008670-appb-img-000110
Figure PCTKR2021008670-appb-img-000110
Figure PCTKR2021008670-appb-img-000111
Figure PCTKR2021008670-appb-img-000111
Figure PCTKR2021008670-appb-img-000112
Figure PCTKR2021008670-appb-img-000112
Figure PCTKR2021008670-appb-img-000113
Figure PCTKR2021008670-appb-img-000113
Figure PCTKR2021008670-appb-img-000114
Figure PCTKR2021008670-appb-img-000114
Figure PCTKR2021008670-appb-img-000115
Figure PCTKR2021008670-appb-img-000115
Figure PCTKR2021008670-appb-img-000116
Figure PCTKR2021008670-appb-img-000116
Figure PCTKR2021008670-appb-img-000117
Figure PCTKR2021008670-appb-img-000117
Figure PCTKR2021008670-appb-img-000118
Figure PCTKR2021008670-appb-img-000118
Figure PCTKR2021008670-appb-img-000119
Figure PCTKR2021008670-appb-img-000119
Figure PCTKR2021008670-appb-img-000120
Figure PCTKR2021008670-appb-img-000120
Figure PCTKR2021008670-appb-img-000121
Figure PCTKR2021008670-appb-img-000121
Figure PCTKR2021008670-appb-img-000122
Figure PCTKR2021008670-appb-img-000122
Figure PCTKR2021008670-appb-img-000123
Figure PCTKR2021008670-appb-img-000123
Figure PCTKR2021008670-appb-img-000124
Figure PCTKR2021008670-appb-img-000124
Figure PCTKR2021008670-appb-img-000125
Figure PCTKR2021008670-appb-img-000125
Figure PCTKR2021008670-appb-img-000126
Figure PCTKR2021008670-appb-img-000126
Figure PCTKR2021008670-appb-img-000127
Figure PCTKR2021008670-appb-img-000127
Figure PCTKR2021008670-appb-img-000128
Figure PCTKR2021008670-appb-img-000128
Figure PCTKR2021008670-appb-img-000129
Figure PCTKR2021008670-appb-img-000129
Figure PCTKR2021008670-appb-img-000130
Figure PCTKR2021008670-appb-img-000130
Figure PCTKR2021008670-appb-img-000131
Figure PCTKR2021008670-appb-img-000131
Figure PCTKR2021008670-appb-img-000132
Figure PCTKR2021008670-appb-img-000132
Figure PCTKR2021008670-appb-img-000133
Figure PCTKR2021008670-appb-img-000133
Figure PCTKR2021008670-appb-img-000134
Figure PCTKR2021008670-appb-img-000134
Figure PCTKR2021008670-appb-img-000135
Figure PCTKR2021008670-appb-img-000135
Figure PCTKR2021008670-appb-img-000136
Figure PCTKR2021008670-appb-img-000136
Figure PCTKR2021008670-appb-img-000137
Figure PCTKR2021008670-appb-img-000137
Figure PCTKR2021008670-appb-img-000138
Figure PCTKR2021008670-appb-img-000138
Figure PCTKR2021008670-appb-img-000139
Figure PCTKR2021008670-appb-img-000139
Figure PCTKR2021008670-appb-img-000140
Figure PCTKR2021008670-appb-img-000140
Figure PCTKR2021008670-appb-img-000141
Figure PCTKR2021008670-appb-img-000141
Figure PCTKR2021008670-appb-img-000142
Figure PCTKR2021008670-appb-img-000142
Figure PCTKR2021008670-appb-img-000143
Figure PCTKR2021008670-appb-img-000143
Figure PCTKR2021008670-appb-img-000144
Figure PCTKR2021008670-appb-img-000144
Figure PCTKR2021008670-appb-img-000145
Figure PCTKR2021008670-appb-img-000145
Figure PCTKR2021008670-appb-img-000146
Figure PCTKR2021008670-appb-img-000146
Figure PCTKR2021008670-appb-img-000147
Figure PCTKR2021008670-appb-img-000147
Figure PCTKR2021008670-appb-img-000148
Figure PCTKR2021008670-appb-img-000148
Figure PCTKR2021008670-appb-img-000149
Figure PCTKR2021008670-appb-img-000149
Figure PCTKR2021008670-appb-img-000150
Figure PCTKR2021008670-appb-img-000150
Figure PCTKR2021008670-appb-img-000151
Figure PCTKR2021008670-appb-img-000151
Figure PCTKR2021008670-appb-img-000152
Figure PCTKR2021008670-appb-img-000152
Figure PCTKR2021008670-appb-img-000153
Figure PCTKR2021008670-appb-img-000153
Figure PCTKR2021008670-appb-img-000154
Figure PCTKR2021008670-appb-img-000154
Figure PCTKR2021008670-appb-img-000155
Figure PCTKR2021008670-appb-img-000155
Figure PCTKR2021008670-appb-img-000156
Figure PCTKR2021008670-appb-img-000156
Figure PCTKR2021008670-appb-img-000157
Figure PCTKR2021008670-appb-img-000157
Figure PCTKR2021008670-appb-img-000158
Figure PCTKR2021008670-appb-img-000158
Figure PCTKR2021008670-appb-img-000159
Figure PCTKR2021008670-appb-img-000159
Figure PCTKR2021008670-appb-img-000160
Figure PCTKR2021008670-appb-img-000160
Figure PCTKR2021008670-appb-img-000161
Figure PCTKR2021008670-appb-img-000161
Figure PCTKR2021008670-appb-img-000162
Figure PCTKR2021008670-appb-img-000162
Figure PCTKR2021008670-appb-img-000163
Figure PCTKR2021008670-appb-img-000163
Figure PCTKR2021008670-appb-img-000164
Figure PCTKR2021008670-appb-img-000164
Figure PCTKR2021008670-appb-img-000165
Figure PCTKR2021008670-appb-img-000165
Figure PCTKR2021008670-appb-img-000166
Figure PCTKR2021008670-appb-img-000166
Figure PCTKR2021008670-appb-img-000167
Figure PCTKR2021008670-appb-img-000167
Figure PCTKR2021008670-appb-img-000168
Figure PCTKR2021008670-appb-img-000168
Figure PCTKR2021008670-appb-img-000169
Figure PCTKR2021008670-appb-img-000169
Figure PCTKR2021008670-appb-img-000170
Figure PCTKR2021008670-appb-img-000170
Figure PCTKR2021008670-appb-img-000171
Figure PCTKR2021008670-appb-img-000171
Figure PCTKR2021008670-appb-img-000172
Figure PCTKR2021008670-appb-img-000172
Figure PCTKR2021008670-appb-img-000173
Figure PCTKR2021008670-appb-img-000173
Figure PCTKR2021008670-appb-img-000174
Figure PCTKR2021008670-appb-img-000174
Figure PCTKR2021008670-appb-img-000175
Figure PCTKR2021008670-appb-img-000175
Figure PCTKR2021008670-appb-img-000176
Figure PCTKR2021008670-appb-img-000176
Figure PCTKR2021008670-appb-img-000177
Figure PCTKR2021008670-appb-img-000177
Figure PCTKR2021008670-appb-img-000178
Figure PCTKR2021008670-appb-img-000178
Figure PCTKR2021008670-appb-img-000179
Figure PCTKR2021008670-appb-img-000179
Figure PCTKR2021008670-appb-img-000180
Figure PCTKR2021008670-appb-img-000180
Figure PCTKR2021008670-appb-img-000181
Figure PCTKR2021008670-appb-img-000181
Figure PCTKR2021008670-appb-img-000182
Figure PCTKR2021008670-appb-img-000182
Figure PCTKR2021008670-appb-img-000183
Figure PCTKR2021008670-appb-img-000183
Figure PCTKR2021008670-appb-img-000184
Figure PCTKR2021008670-appb-img-000184
Figure PCTKR2021008670-appb-img-000185
Figure PCTKR2021008670-appb-img-000185
Figure PCTKR2021008670-appb-img-000186
Figure PCTKR2021008670-appb-img-000186
Figure PCTKR2021008670-appb-img-000187
Figure PCTKR2021008670-appb-img-000187
Figure PCTKR2021008670-appb-img-000188
Figure PCTKR2021008670-appb-img-000188
Figure PCTKR2021008670-appb-img-000189
Figure PCTKR2021008670-appb-img-000189
Figure PCTKR2021008670-appb-img-000190
Figure PCTKR2021008670-appb-img-000190
Figure PCTKR2021008670-appb-img-000191
Figure PCTKR2021008670-appb-img-000191
Figure PCTKR2021008670-appb-img-000192
Figure PCTKR2021008670-appb-img-000192
Figure PCTKR2021008670-appb-img-000193
Figure PCTKR2021008670-appb-img-000193
Figure PCTKR2021008670-appb-img-000194
Figure PCTKR2021008670-appb-img-000194
Figure PCTKR2021008670-appb-img-000195
Figure PCTKR2021008670-appb-img-000195
Figure PCTKR2021008670-appb-img-000196
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Figure PCTKR2021008670-appb-img-000207
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Figure PCTKR2021008670-appb-img-000208
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Figure PCTKR2021008670-appb-img-000210
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Figure PCTKR2021008670-appb-img-000211
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Figure PCTKR2021008670-appb-img-000212
Figure PCTKR2021008670-appb-img-000213
Figure PCTKR2021008670-appb-img-000213
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Figure PCTKR2021008670-appb-img-000215
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Figure PCTKR2021008670-appb-img-000216
Figure PCTKR2021008670-appb-img-000217
Figure PCTKR2021008670-appb-img-000217
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Figure PCTKR2021008670-appb-img-000219
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Figure PCTKR2021008670-appb-img-000220
Figure PCTKR2021008670-appb-img-000221
Figure PCTKR2021008670-appb-img-000221
Figure PCTKR2021008670-appb-img-000222
Figure PCTKR2021008670-appb-img-000222
Figure PCTKR2021008670-appb-img-000223
Figure PCTKR2021008670-appb-img-000223
Figure PCTKR2021008670-appb-img-000224
Figure PCTKR2021008670-appb-img-000224
Figure PCTKR2021008670-appb-img-000225
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Figure PCTKR2021008670-appb-img-000226
Figure PCTKR2021008670-appb-img-000226
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Figure PCTKR2021008670-appb-img-000227
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Figure PCTKR2021008670-appb-img-000228
Figure PCTKR2021008670-appb-img-000229
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Figure PCTKR2021008670-appb-img-000230
Figure PCTKR2021008670-appb-img-000230
Figure PCTKR2021008670-appb-img-000231
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Figure PCTKR2021008670-appb-img-000238
Figure PCTKR2021008670-appb-img-000239
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Figure PCTKR2021008670-appb-img-000247
Figure PCTKR2021008670-appb-img-000248
Figure PCTKR2021008670-appb-img-000248
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Figure PCTKR2021008670-appb-img-000249
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Figure PCTKR2021008670-appb-img-000251
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Figure PCTKR2021008670-appb-img-000255
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Figure PCTKR2021008670-appb-img-000256
Figure PCTKR2021008670-appb-img-000256
Figure PCTKR2021008670-appb-img-000257
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Figure PCTKR2021008670-appb-img-000260
Figure PCTKR2021008670-appb-img-000260
Figure PCTKR2021008670-appb-img-000261
Figure PCTKR2021008670-appb-img-000261
Figure PCTKR2021008670-appb-img-000262
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Figure PCTKR2021008670-appb-img-000263
Figure PCTKR2021008670-appb-img-000263
Figure PCTKR2021008670-appb-img-000264
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Figure PCTKR2021008670-appb-img-000265
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Figure PCTKR2021008670-appb-img-000267
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Figure PCTKR2021008670-appb-img-000268
Figure PCTKR2021008670-appb-img-000268
Figure PCTKR2021008670-appb-img-000269
Figure PCTKR2021008670-appb-img-000269
Figure PCTKR2021008670-appb-img-000270
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Figure PCTKR2021008670-appb-img-000271
Figure PCTKR2021008670-appb-img-000271
Figure PCTKR2021008670-appb-img-000272
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Figure PCTKR2021008670-appb-img-000273
Figure PCTKR2021008670-appb-img-000273
Figure PCTKR2021008670-appb-img-000274
Figure PCTKR2021008670-appb-img-000274
Figure PCTKR2021008670-appb-img-000275
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Figure PCTKR2021008670-appb-img-000276
Figure PCTKR2021008670-appb-img-000276
Figure PCTKR2021008670-appb-img-000277
Figure PCTKR2021008670-appb-img-000277
Figure PCTKR2021008670-appb-img-000278
Figure PCTKR2021008670-appb-img-000278
Figure PCTKR2021008670-appb-img-000279
Figure PCTKR2021008670-appb-img-000279
Figure PCTKR2021008670-appb-img-000280
Figure PCTKR2021008670-appb-img-000280
Figure PCTKR2021008670-appb-img-000281
Figure PCTKR2021008670-appb-img-000281
Figure PCTKR2021008670-appb-img-000282
Figure PCTKR2021008670-appb-img-000282
Figure PCTKR2021008670-appb-img-000283
Figure PCTKR2021008670-appb-img-000283
Figure PCTKR2021008670-appb-img-000284
Figure PCTKR2021008670-appb-img-000284
Figure PCTKR2021008670-appb-img-000285
Figure PCTKR2021008670-appb-img-000285
Figure PCTKR2021008670-appb-img-000286
Figure PCTKR2021008670-appb-img-000286
Figure PCTKR2021008670-appb-img-000287
Figure PCTKR2021008670-appb-img-000287
Figure PCTKR2021008670-appb-img-000288
.
Figure PCTKR2021008670-appb-img-000288
.
본 명세서는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.The present specification provides an organic light emitting device including the compound represented by Formula 1 above.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included, rather than excluding other components, unless otherwise stated.
본 명세서에 있어서, 상기 '층'은 본 기술분야에 주로 사용되는 '필름'과 호환되는 의미이며, 목적하는 영역을 덮는 코팅을 의미한다. 상기 '층'의 크기는 한정되지 않으며, 각각의 '층'은 그 크기가 같거나 상이할 수 있다. 일 실시상태에 따르면, '층'의 크기는 전체 소자와 같을 수 있고, 특정 기능성 영역의 크기에 해당할 수 있으며, 단일 서브픽셀(sub-pixel)만큼 작을 수도 있다. In the present specification, the 'layer' means compatible with a 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each of the 'layers' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
본 명세서에 있어서, 특정한 A 물질이 B층에 포함된다는 의미는 i) 1종 이상의 A 물질이 하나의 B층에 포함되는 것과 ii) B층이 1층 이상으로 구성되고, A 물질이 다층의 B층 중 1층 이상에 포함되는 것을 모두 포함한다.In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
본 명세서에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다.In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.
본 명세서는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.The present specification 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 represented by Formula 1 above. do.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 차단층, 정공 차단층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.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. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공주입층, 정공 수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층, 정공 수송층, 또는 정공주입 및 수송층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자 차단층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 차단층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. It further includes one or more floors selected from.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 및 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함한다. According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.
본 명세서의 일 실시상태에 따르면, 상기 2층 이상의 유기물층은 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.According to an exemplary embodiment of the present specification, the two or more organic material layers include a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. Two or more may be selected from the group.
본 명세서의 일 실시상태에 따르면, 상기 발광층과 상기 제1 전극 사이에 2층 이상의 정공수송층을 포함한다. 상기 2층 이상의 정공수송층은 서로 동일하거나 상이한 물질을 포함할 수 있다.According to an exemplary embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 애노드 또는 캐소드이다.According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 따르면, 상기 제2 전극은 캐소드 또는 애노드이다. According to an exemplary embodiment of the present specification, the second electrode is a cathode or an anode.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. According to an exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 및 2에 예시되어 있다. 상기 도 1 및 2는 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 . 1 and 2 illustrate an organic light emitting device, but is not limited thereto.
도 1에는 기판(101) 위에 제1 전극(102), 유기물층(111) 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 유기물층에 포함된다. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102 , an organic material layer 111 , and a second electrode 110 are sequentially stacked on a substrate 101 . The compound represented by Formula 1 is included in the organic layer.
도 2에는 기판(101) 위에 제1 전극(102), 정공주입층(103), 정공수송층(104), 발광층(105), 전자 주입 및 수송층(106), 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 전자 주입 및 수송층에 포함된다.2, the first electrode 102, the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron injection and transport layer 106, and the second electrode 110 on the substrate 101 are sequentially The structure of the organic light-emitting device stacked with The compound represented by Formula 1 is included in the electron injection and transport layer.
본 명세서의 유기 발광 소자는 전자주입층, 전자 수송층, 전자 주입 및 수송층, 정공주입층, 정공 수송층, 정공 주입 및 수송층, 또는 정공차단층이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification includes an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, or a hole blocking layer containing the compound, that is, a compound represented by Formula 1 Except that, it may be prepared by materials and methods known in the art.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질, 유기물층 및 애노드 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, 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.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다. In addition, the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 캐소드 물질로부터 유기물층, 애노드 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다. 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.
상기 애노드 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, 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); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 캐소드 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO 2 /Al, but is not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다. The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 호스트는 하기 화학식 H-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the host includes a compound represented by the following Chemical Formula H-1, but is not limited thereto.
[화학식 H-1][Formula H-1]
Figure PCTKR2021008670-appb-img-000289
Figure PCTKR2021008670-appb-img-000289
상기 화학식 H-1에 있어서,In Formula H-1,
L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R201은 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R201 is hydrogen; heavy hydrogen; halogen 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,
r201은 1 내지 8의 정수이며, 상기 r201이 2 이상인 경우, 2 이상의 R201은 서로 같거나 상이하다.r201 is an integer of 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 2가의 헤테로고리기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 나프틸렌기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 monocyclic to 4 ring heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 티오펜기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 바이페닐기; 터페닐기; 중수소로 치환 또는 비치환된 나프틸기; 페닐기로 치환 또는 비치환된 티오펜기; 페난트렌기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20은 치환 또는 비치환된 헤테로고리기이고, 상기 Ar21은 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R201은 수소이다.According to an exemplary embodiment of the present specification, R201 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 화학식 H-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula H-1 is represented by the following compound.
Figure PCTKR2021008670-appb-img-000290
Figure PCTKR2021008670-appb-img-000290
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다. Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 하기 화학식 D-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.
[화학식 D-1][Formula D-1]
Figure PCTKR2021008670-appb-img-000291
Figure PCTKR2021008670-appb-img-000291
상기 화학식 D-1에 있어서,In the formula D-1,
T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
t5 및 t6은 각각 1 내지 4의 정수이며,t5 and t6 are each an integer of 1 to 4,
상기 t5가 2 이상인 경우, 상기 2 이상의 T5는 서로 같거나 상이하고,When t5 is 2 or more, the 2 or more T5 are the same as or different from each other,
상기 t6가 2 이상인 경우, 상기 2 이상의 T6는 서로 같거나 상이하다.When t6 is 2 or more, the 2 or more T6 are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 이소프로필기; 시아노기로 치환된 페닐기; 또는 메틸기로 치환된 페닐기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; isopropyl group; a phenyl group substituted with a cyano group; or a phenyl group substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 D-1는 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.
Figure PCTKR2021008670-appb-img-000292
Figure PCTKR2021008670-appb-img-000292
상기 정공 주입층은 전극으로부터 정공을 수취하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 애노드로부터 정공 수취 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 애노드 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정 되는 것은 아니다. The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes so as to have a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by the following Chemical Formula HI-1, but is not limited thereto.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2021008670-appb-img-000293
Figure PCTKR2021008670-appb-img-000293
상기 화학식 HI-1에 있어서,In the formula HI-1,
R300 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R300 to R308 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by combining with an adjacent group,
r301 및 r302는 각각 1 내지 4의 정수이고,r301 and r302 are each an integer of 1 to 4,
r303 및 r304는 각각 1 내지 3의 정수이며,r303 and r304 are each an integer of 1 to 3,
상기 r301이 2 이상인 경우, 상기 R301은 서로 같거나 상이하고,When r301 is 2 or more, R301 is the same as or different from each other,
상기 r302가 2 이상인 경우, 상기 R302는 서로 같거나 상이하며,When r302 is 2 or more, R302 is the same as or different from each other,
상기 r303이 2 이상인 경우, 상기 R303은 서로 같거나 상이하고,When r303 is 2 or more, R303 is the same as or different from each other,
상기 r304가 2 이상인 경우, 상기 R304는 서로 같거나 상이하다.When r304 is 2 or more, R304 is the same as or different from each other.
본 명세서의 일시상태에 따르면, 상기 R301 내지 R304는 수소이다.According to the temporary state of the present specification, R301 to R304 are hydrogen.
본 명세서의 일시상태에 따르면, 상기 R300은 치환 또는 비치환된 아릴기이다.According to the temporary state of the present specification, R300 is a substituted or unsubstituted aryl group.
본 명세서의 일시상태에 따르면, 상기 R300은 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to the temporary state of the present specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일시상태에 따르면, 상기 R300은 페닐기이다.According to the temporary state of the present specification, R300 is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 페닐기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula HI-1 is represented by the following compound.
Figure PCTKR2021008670-appb-img-000294
Figure PCTKR2021008670-appb-img-000294
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 애노드나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is preferable, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-1, but is not limited thereto.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2021008670-appb-img-000295
Figure PCTKR2021008670-appb-img-000295
상기 화학식 HT-1에 있어서,In the formula HT-1,
X'1 내지 X'6 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of X'1 to X'6 is N, the rest are CH,
R309 내지 R314은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by bonding with an adjacent group.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'6는 N이다.According to an exemplary embodiment of the present specification, X'1 to X'6 are N.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 시아노기이다.According to an exemplary embodiment of the present specification, R309 to R314 are cyano groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula HT-1 is represented by the following compound.
Figure PCTKR2021008670-appb-img-000296
Figure PCTKR2021008670-appb-img-000296
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-2로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-2, but is not limited thereto.
[화학식 HT-2][Formula HT-2]
Figure PCTKR2021008670-appb-img-000297
Figure PCTKR2021008670-appb-img-000297
상기 화학식 HT-2에 있어서,In the formula HT-2,
R315 내지 R317는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of a combination thereof, or a substituted or unsubstituted ring by combining with an adjacent group,
r315은 1 내지 5의 정수이며, 상기 r315이 2 이상인 경우, 2 이상의 상기 R315은 서로 같거나 상이하며,r315 is an integer of 1 to 5, and when r315 is 2 or more, R315 of 2 or more are the same as or different from each other,
r316는 1 내지 5의 정수이고, 상기 r316가 2 이상인 경우, 2 이상의 상기 R316는 서로 같거나 상이하다.r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R317는 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R317는 카바졸기; 페닐기; 바이페닐기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R317 is a carbazole group; phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R315 및 R316는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 알킬기로 치환된 방향족탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R315 및 R316는 서로 같거나 상이하고, 각각 독립적으로 페닐기이거나, 인접한 기와 서로 결합하여 메틸기로 치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-2은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula HT-2 is represented by the following compound.
Figure PCTKR2021008670-appb-img-000298
Figure PCTKR2021008670-appb-img-000298
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자수송층 이외의 추가의 전자수송층을 포함하는 경우, 전자 수송 물질로는 캐소드로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron transport layer other than the electron transport layer comprising Formula 1, the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer As such, a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자주입층 이외의 추가의 전자주입층을 포함하는 경우, 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤이 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that receives electrons from the electrode. When the organic light-emitting device according to an exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer comprising Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an electron receiving effect from, and an excellent electron injection effect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로는 8-히드록시퀴놀리나토 리튬, 비스(8-히드록시퀴놀리나토)아연, 비스(8-히드록시퀴놀리나토)구리, 비스(8-히드록시퀴놀리나토)망간, 트리스(8-히드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-히드록시퀴놀리나토)알루미늄, 트리스(8-히드록시퀴놀리나토)갈륨, 비스(10-히드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-히드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.
상기 정공 차단층은 정공이 캐소드로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 정공차단층 이외의 추가의 정공차단층을 포함하는 경우, 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다. The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Formula 1, specifically, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, There is an aluminum complex (aluminum complex), but is not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.
본 명세서에 따른 유기 발광 소자는 다양한 전자 장치에 포함되어 사용될 수 있다. 예컨대, 상기 전자 장치는 디스플레이 패널, 터치 패널, 태양광 모듈, 조명 장치 등일 수 있고, 이에 한정되지 않는다.The organic light emitting diode according to the present specification may be included in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.
[일반식 1][General formula 1]
Figure PCTKR2021008670-appb-img-000299
Figure PCTKR2021008670-appb-img-000299
상기 일반식 1의 방법으로 하기 제조예 2와 같은 중간체를 합성할 수 있다.An intermediate such as in Preparation Example 2 below can be synthesized by the method of Formula 1 above.
제조예 1Preparation Example 1
Figure PCTKR2021008670-appb-img-000300
Figure PCTKR2021008670-appb-img-000300
상기 화합물 1-1a (95.8 g, 296.2 mmol) 및 dicyanozinc (16.1 g, 137.3 mmol)을 N,N-디메틸아세트아미드 (1000 mL)에 투입하였다. TTP(Tetrakis(triphenylphosphine)palladium, 9.3 g) 를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 물에 부어 얻은 고체를 여과하여 에틸아세테이트로 2회 재결정하여 상기 화합물 1-1b 를 제조하였다. (50.3 g, 수율 63 %, MS:[M+H]+= 270).The above compound 1-1a (95.8 g, 296.2 mmol) and dicyanozinc (16.1 g, 137.3 mmol) were added to N,N-dimethylacetamide (1000 mL). After TTP (Tetrakis(triphenylphosphine)palladium, 9.3 g) was added, the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid obtained by pouring in water was filtered and recrystallized twice with ethyl acetate to prepare the compound 1-1b. (50.3 g, yield 63%, MS:[M+H]+=270).
제조예 2Preparation 2
Figure PCTKR2021008670-appb-img-000301
Figure PCTKR2021008670-appb-img-000301
상기 화합물 1-1b (53.2 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (600 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) 를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 1-1 를 제조하였다. (59.9 g, 수율 84 %, MS:[M+H]+= 362).The compound 1-1b (53.2 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (600 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1-1. (59.9 g, yield 84%, MS:[M+H]+=362).
합성예 1Synthesis Example 1
Figure PCTKR2021008670-appb-img-000302
Figure PCTKR2021008670-appb-img-000302
상기 화합물 1-1 (10.8 g, 30 mmol) 및 상기 화합물 1-2 (16.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 1를 제조하였다. (13.3 g, 수율 82 %, MS:[M+H]+= 544).The compound 1-1 (10.8 g, 30 mmol) and the compound 1-2 (16.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1. (13.3 g, yield 82%, MS:[M+H]+= 544).
합성예 2Synthesis Example 2
Figure PCTKR2021008670-appb-img-000303
Figure PCTKR2021008670-appb-img-000303
상기 화합물 2-1 (15.0 g, 30 mmol) 및 상기 화합물 2-2 (17.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 2를 제조하였다. (11.6 g, 수율 65 %, MS:[M+H]+= 594).The compound 2-1 (15.0 g, 30 mmol) and the compound 2-2 (17.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 2. (11.6 g, yield 65%, MS:[M+H]+=594).
합성예 3Synthesis Example 3
Figure PCTKR2021008670-appb-img-000304
Figure PCTKR2021008670-appb-img-000304
상기 화합물 3-1 (15.0 g, 30 mmol) 및 상기 화합물 3-2 (17.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 3를 제조하였다. (13.7g, 수율 77 %, MS:[M+H]+= 593).The compound 3-1 (15.0 g, 30 mmol) and the compound 3-2 (17.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 3 above. (13.7 g, yield 77%, MS:[M+H]+=593).
합성예 4Synthesis Example 4
Figure PCTKR2021008670-appb-img-000305
Figure PCTKR2021008670-appb-img-000305
상기 화합물 4-1 (15.0 g, 30 mmol) 및 상기 화합물 4-2 (15.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 4를 제조하였다. (13.1g, 수율 85 %, MS:[M+H]+= 517).The compound 4-1 (15.0 g, 30 mmol) and the compound 4-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 4 above. (13.1 g, yield 85%, MS:[M+H]+=517).
합성예 5Synthesis Example 5
Figure PCTKR2021008670-appb-img-000306
Figure PCTKR2021008670-appb-img-000306
상기 화합물 5-1 (15.0 g, 30 mmol) 및 상기 화합물 5-2 (20.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 5를 제조하였다. (16.8g, 수율 84 %, MS:[M+H]+= 667).The compound 5-1 (15.0 g, 30 mmol) and the compound 5-2 (20.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 5. (16.8 g, yield 84%, MS:[M+H]+=667).
합성예 6Synthesis Example 6
Figure PCTKR2021008670-appb-img-000307
Figure PCTKR2021008670-appb-img-000307
상기 화합물 6-1 (15.0 g, 30 mmol) 및 상기 화합물 6-2 (14.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 6를 제조하였다. (11.9g, 수율 85 %, MS:[M+H]+= 467).The compound 6-1 (15.0 g, 30 mmol) and the compound 6-2 (14.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 6. (11.9 g, yield 85%, MS:[M+H]+=467).
합성예 7Synthesis Example 7
Figure PCTKR2021008670-appb-img-000308
Figure PCTKR2021008670-appb-img-000308
상기 화합물 3-1 (15.0 g, 30 mmol) 및 상기 화합물 7-2 (18.6 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 7를 제조하였다. (16.3g, 수율 88 %, MS:[M+H]+= 620).The compound 3-1 (15.0 g, 30 mmol) and the compound 7-2 (18.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 7. (16.3 g, yield 88%, MS:[M+H]+=620).
합성예 8Synthesis Example 8
Figure PCTKR2021008670-appb-img-000309
Figure PCTKR2021008670-appb-img-000309
상기 화합물 7-1 (15.0 g, 30 mmol) 및 상기 화합물 8-2 (19.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 8를 제조하였다. (16.7g, 수율 88 %, MS:[M+H]+= 634).The compound 7-1 (15.0 g, 30 mmol) and the compound 8-2 (19.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 8. (16.7 g, yield 88%, MS:[M+H]+=634).
합성예 9Synthesis Example 9
Figure PCTKR2021008670-appb-img-000310
Figure PCTKR2021008670-appb-img-000310
상기 화합물 7-1 (15.0 g, 30 mmol) 및 상기 화합물 9-2 (17.2 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 9를 제조하였다. (13.5g, 수율 79 %, MS:[M+H]+= 573).The compound 7-1 (15.0 g, 30 mmol) and the compound 9-2 (17.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 9. (13.5 g, yield 79%, MS:[M+H]+=573).
합성예 10Synthesis Example 10
Figure PCTKR2021008670-appb-img-000311
Figure PCTKR2021008670-appb-img-000311
상기 화합물 8-1 (15.0 g, 30 mmol) 및 상기 화합물 10-2 (17.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 10를 제조하였다. (12.7g, 수율 75 %, MS:[M+H]+= 567).The compound 8-1 (15.0 g, 30 mmol) and the compound 10-2 (17.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 10. (12.7 g, yield 75%, MS:[M+H]+=567).
합성예 11Synthesis Example 11
Figure PCTKR2021008670-appb-img-000312
Figure PCTKR2021008670-appb-img-000312
상기 화합물 1-1 (15.0 g, 30 mmol) 및 상기 화합물 11-2 (17.1 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 11를 제조하였다. (13.8g, 수율 81 %, MS:[M+H]+= 570).The compound 1-1 (15.0 g, 30 mmol) and the compound 11-2 (17.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 11. (13.8 g, yield 81%, MS:[M+H]+=570).
합성예 12Synthesis Example 12
Figure PCTKR2021008670-appb-img-000313
Figure PCTKR2021008670-appb-img-000313
상기 화합물 9-1 (15.0 g, 30 mmol) 및 상기 화합물 12-2 (18.4 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 12를 제조하였다. (13.2g, 수율 72 %, MS:[M+H]+= 613).The compound 9-1 (15.0 g, 30 mmol) and the compound 12-2 (18.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 12. (13.2 g, yield 72%, MS: [M+H] + = 613).
합성예 13Synthesis Example 13
Figure PCTKR2021008670-appb-img-000314
Figure PCTKR2021008670-appb-img-000314
상기 화합물 10-1 (15.0 g, 30 mmol) 및 상기 화합물 13-2 (16.7 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 13를 제조하였다. (13.5g, 수율 81 %, MS:[M+H]+= 558).The compound 10-1 (15.0 g, 30 mmol) and the compound 13-2 (16.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 13. (13.5 g, yield 81 %, MS: [M+H] + = 558).
합성예 14Synthesis Example 14
Figure PCTKR2021008670-appb-img-000315
Figure PCTKR2021008670-appb-img-000315
상기 화합물 11-1(15.0 g, 30 mmol) 및 상기 화합물 14-2 (19.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 14를 제조하였다. (15.8g, 수율 80 %, MS:[M+H]+= 660).The compound 11-1 (15.0 g, 30 mmol) and the compound 14-2 (19.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 14. (15.8 g, yield 80%, MS:[M+H]+=660).
합성예 15Synthesis Example 15
Figure PCTKR2021008670-appb-img-000316
Figure PCTKR2021008670-appb-img-000316
상기 화합물 5-1 (15.0 g, 30 mmol) 및 상기 화합물 15-2 (15.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 15를 제조하였다. (12.4g, 수율 80 %, MS:[M+H]+= 517).The compound 5-1 (15.0 g, 30 mmol) and the compound 15-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 15. (12.4 g, yield 80 %, MS: [M+H] + = 517).
합성예 16Synthesis Example 16
Figure PCTKR2021008670-appb-img-000317
Figure PCTKR2021008670-appb-img-000317
상기 화합물 5-1 (15.0 g, 30 mmol) 및 상기 화합물 16-2 (13.6 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 16를 제조하였다. (9.8 g, 수율 72 %, MS:[M+H]+= 456).The compound 5-1 (15.0 g, 30 mmol) and the compound 16-2 (13.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 16. (9.8 g, yield 72%, MS:[M+H]+=456).
합성예 17Synthesis Example 17
Figure PCTKR2021008670-appb-img-000318
Figure PCTKR2021008670-appb-img-000318
상기 화합물 3-1 (15.0 g, 30 mmol) 및 상기 화합물 17-2 (18.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 17를 제조하였다. (14.2g, 수율 75 %, MS:[M+H]+= 632).The compound 3-1 (15.0 g, 30 mmol) and the compound 17-2 (18.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 17. (14.2 g, yield 75%, MS:[M+H]+=632).
합성예 18Synthesis Example 18
Figure PCTKR2021008670-appb-img-000319
Figure PCTKR2021008670-appb-img-000319
상기 화합물 12-1 (15.0 g, 30 mmol) 및 상기 화합물 18-2 (19.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 18를 제조하였다. (15.2g, 수율 77 %, MS:[M+H]+= 660).The compound 12-1 (15.0 g, 30 mmol) and the compound 18-2 (19.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 18. (15.2 g, yield 77%, MS:[M+H]+=660).
합성예 19Synthesis Example 19
Figure PCTKR2021008670-appb-img-000320
Figure PCTKR2021008670-appb-img-000320
상기 화합물 13-1 (15.0 g, 30 mmol) 및 상기 화합물 19-2 (16.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 19를 제조하였다. (14.4g, 수율 90 %, MS:[M+H]+= 536).The compound 13-1 (15.0 g, 30 mmol) and the compound 19-2 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 19. (14.4 g, yield 90 %, MS: [M+H] + = 536).
합성예 20Synthesis Example 20
Figure PCTKR2021008670-appb-img-000321
Figure PCTKR2021008670-appb-img-000321
상기 화합물 11-1 (15.0 g, 30 mmol) 및 상기 화합물 20-2 (20.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 20를 제조하였다. (17.1g, 수율 82 %, MS:[M+H]+= 696).The compound 11-1 (15.0 g, 30 mmol) and the compound 20-2 (20.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 20. (17.1 g, yield 82 %, MS: [M+H] + = 696).
합성예 21Synthesis Example 21
Figure PCTKR2021008670-appb-img-000322
Figure PCTKR2021008670-appb-img-000322
상기 화합물 5-1 (15.0 g, 30 mmol) 및 상기 화합물 21-2 (15.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 21를 제조하였다. (13.2g, 수율 83 %, MS:[M+H]+= 532).The compound 5-1 (15.0 g, 30 mmol) and the compound 21-2 (15.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 21. (13.2 g, yield 83%, MS:[M+H]+=532).
합성예 22Synthesis Example 22
Figure PCTKR2021008670-appb-img-000323
Figure PCTKR2021008670-appb-img-000323
상기 화합물 3-1 (15.0 g, 30 mmol) 및 상기 화합물 22-2 (16.2 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 22를 제조하였다. (12.1g, 수율 75 %, MS:[M+H]+= 541).The compound 3-1 (15.0 g, 30 mmol) and the compound 22-2 (16.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 22. (12.1 g, yield 75%, MS:[M+H]+=541).
합성예 23Synthesis Example 23
Figure PCTKR2021008670-appb-img-000324
Figure PCTKR2021008670-appb-img-000324
상기 화합물 2-1 (15.0 g, 30 mmol) 및 상기 화합물 23-2 (17.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 23를 제조하였다. (10.4g, 수율 61 %, MS:[M+H]+= 569).The compound 2-1 (15.0 g, 30 mmol) and the compound 23-2 (17.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 23. (10.4 g, yield 61%, MS:[M+H]+=569).
합성예 24Synthesis Example 24
Figure PCTKR2021008670-appb-img-000325
Figure PCTKR2021008670-appb-img-000325
상기 화합물 14-1 (15.0 g, 30 mmol) 및 상기 화합물 24-2 (19.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 24를 제조하였다. (15.4g, 수율 81 %, MS:[M+H]+= 636).The compound 14-1 (15.0 g, 30 mmol) and the compound 24-2 (19.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 24. (15.4 g, yield 81 %, MS: [M+H] + = 636).
합성예 25Synthesis Example 25
Figure PCTKR2021008670-appb-img-000326
Figure PCTKR2021008670-appb-img-000326
상기 화합물 15-1 (15.0 g, 30 mmol) 및 상기 화합물 25-2 (16.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 25를 제조하였다. (12.6g, 수율 79 %, MS:[M+H]+= 533).The compound 15-1 (15.0 g, 30 mmol) and the compound 25-2 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 25. (12.6 g, yield 79%, MS:[M+H]+=533).
합성예 26Synthesis Example 26
Figure PCTKR2021008670-appb-img-000327
Figure PCTKR2021008670-appb-img-000327
상기 화합물 26-1 (15.0 g, 30 mmol) 및 상기 화합물 26-2 (8.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 26를 제조하였다. (9.8g, 수율 70 %, MS:[M+H]+= 467).The compound 26-1 (15.0 g, 30 mmol) and the compound 26-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 26. (9.8 g, yield 70%, MS:[M+H]+=467).
합성예 27Synthesis Example 27
Figure PCTKR2021008670-appb-img-000328
Figure PCTKR2021008670-appb-img-000328
상기 화합물 26-1 (15.0 g, 30 mmol) 및 상기 화합물 27-2 (12.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 27를 제조하였다. (13.0g, 수율 80 %, MS:[M+H]+= 543).The compound 26-1 (15.0 g, 30 mmol) and the compound 27-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 27. (13.0 g, yield 80%, MS:[M+H]+=543).
합성예 28Synthesis Example 28
Figure PCTKR2021008670-appb-img-000329
Figure PCTKR2021008670-appb-img-000329
상기 화합물 26-1 (15.0 g, 30 mmol) 및 상기 화합물 28-2 (15.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 28를 제조하였다. (14.3g, 수율 77 %, MS:[M+H]+= 619).The compound 26-1 (15.0 g, 30 mmol) and the compound 28-2 (15.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 28. (14.3 g, yield 77%, MS:[M+H]+=619).
합성예 29Synthesis Example 29
Figure PCTKR2021008670-appb-img-000330
Figure PCTKR2021008670-appb-img-000330
상기 화합물 26-1 (15.0 g, 30 mmol) 및 상기 화합물 29-2 (12.8g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Potassium acetate (0.14 g) 및 s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 29를 제조하였다. (12.9g, 수율 79 %, MS:[M+H]+= 543).The compound 26-1 (15.0 g, 30 mmol) and the compound 29-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 29. (12.9 g, yield 79 %, MS: [M+H] + = 543).
실시예 1Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 [HI-A]를 600Å의 두께로 열진공증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화학식의 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT)를 50Å및 하기 화합물 [HT-A] (600Å)를 순차적으로 진공증착하여 정공 수송층을 형성하였다.On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, 50 Å of hexanitrile hexaazatriphenylene (HAT) of the following formula and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited to form a hole transport layer.
이어서, 상기 정공 수송층 위에 막 두께 200Å으로 하기 화합물 [BH]와 [BD]를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 상기 화합물 1과 [LiQ](Lithiumquinolate)를 1:1 중량비로 진공증착하여 350Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 10Å두께로 리튬 플루라이드(LiF)와 1,000Å두께로 알루미늄을 증착하여 캐소드를 형성하였다.Then, the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer. On the light emitting layer, the compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 캐소드의 리튬플루오라이드는 0.3 Å/sec알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 내지 5 × 10-8torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å/sec and the aluminum was maintained at a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 1 × 10 - By maintaining 7 to 5 × 10 -8 torr, an organic light emitting device was manufactured.
Figure PCTKR2021008670-appb-img-000331
Figure PCTKR2021008670-appb-img-000331
실시예 2Example 2
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 3Example 3
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 4Example 4
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 4를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 5Example 5
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 5를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 6Example 6
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 6을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 7Example 7
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 7을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 8Example 8
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 8을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 9Example 9
상기 실시예 1에서 전자 주입 및 수송층으로 화합물 1 대신 화합물 9를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1.
실시예 10Example 10
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 10을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 11Example 11
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 11을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 12Example 12
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 12를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 13Example 13
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 13을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 14Example 14
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 14를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 15Example 15
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 15를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 16Example 16
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 16을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 17Example 17
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 17을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 18Example 18
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 18을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 19Example 19
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 19를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 20Example 20
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 20을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 21Example 21
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 21을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 22Example 22
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 22을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 23Example 23
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 23을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 24Example 24
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 24을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 25Example 25
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 25을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 26Example 26
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 26을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 27Example 27
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 27을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 28Example 28
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 28을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
실시예 29Example 29
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 29을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 of the electron injection and transport layer in Example 1.
비교예 1Comparative Example 1
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET1을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET1][ET1]
Figure PCTKR2021008670-appb-img-000332
Figure PCTKR2021008670-appb-img-000332
비교예 2Comparative Example 2
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET2][ET2]
Figure PCTKR2021008670-appb-img-000333
Figure PCTKR2021008670-appb-img-000333
비교예 3Comparative Example 3
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET3][ET3]
Figure PCTKR2021008670-appb-img-000334
Figure PCTKR2021008670-appb-img-000334
비교예 4Comparative Example 4
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET4을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET4][ET4]
Figure PCTKR2021008670-appb-img-000335
Figure PCTKR2021008670-appb-img-000335
비교예 5Comparative Example 5
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET5을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET5][ET5]
Figure PCTKR2021008670-appb-img-000336
Figure PCTKR2021008670-appb-img-000336
비교예 6Comparative Example 6
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET6을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET6][ET6]
Figure PCTKR2021008670-appb-img-000337
Figure PCTKR2021008670-appb-img-000337
비교예 7Comparative Example 7
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET7을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound ET7 below was used instead of Compound 1 in the electron injection and transport layer in Example 1.
[ET7][ET7]
Figure PCTKR2021008670-appb-img-000338
Figure PCTKR2021008670-appb-img-000338
상기 실시예 1 내지 29 및 비교예 1 내지 7과 같이 각각의 화합물을 전자 주입 및 수송층 물질로 사용하여 제조한 유기 발광 소자를 10 mA/cm2의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20mA/cm2의 전류밀도에서 초기 휘도 대비 98%가 되는 시간(LT98)을 측정하였다. As in Examples 1 to 29 and Comparative Examples 1 to 7, the organic light emitting device manufactured by using each compound as an electron injection and transport layer material was measured for driving voltage and luminous efficiency at a current density of 10 mA/cm 2 , At a current density of 20 mA/cm 2 , the time (LT98) to be 98% of the initial luminance was measured.
그 결과를 하기 표 1에 나타내었다.The results are shown in Table 1 below.
구분division 화합물compound 전압
(V)Voltage
(V) 		전류효율
(cd/A)current efficiency
(cd/A) 		Life Time 98 at 20mA/cm2 Life Time 98 at 20mA/cm 2
실시예 1Example 1 화합물 1compound 1 3.483.48 5.515.51 8080
실시예 2Example 2 화합물 2compound 2 3.623.62 5.505.50 9595
실시예 3Example 3 화합물 3compound 3 3.713.71 5.325.32 7070
실시예 4Example 4 화합물 4compound 4 3.753.75 5.225.22 7070
실시예 5Example 5 화합물 5compound 5 3.633.63 5.215.21 8080
실시예 6Example 6 화합물 6compound 6 3.833.83 5.505.50 9595
실시예 7Example 7 화합물 7compound 7 3.523.52 5.245.24 7575
실시예 8Example 8 화합물 8compound 8 3.753.75 5.155.15 7070
실시예 9Example 9 화합물 9compound 9 3.813.81 5.125.12 8080
실시예 10Example 10 화합물 10compound 10 3.833.83 5.155.15 8080
실시예 11Example 11 화합물 11compound 11 3.913.91 5.215.21 7070
실시예 12Example 12 화합물 12compound 12 4.014.01 5.225.22 6565
실시예 13Example 13 화합물 13compound 13 3.533.53 5.355.35 8080
실시예 14Example 14 화합물 14compound 14 3.783.78 5.205.20 7575
실시예 15Example 15 화합물 15compound 15 3.883.88 5.265.26 7070
실시예 16Example 16 화합물 16compound 16 3.693.69 5.405.40 7575
실시예 17Example 17 화합물 17compound 17 3.783.78 5.495.49 7575
실시예 18Example 18 화합물 18compound 18 3.773.77 5.505.50 7070
실시예 19Example 19 화합물 19compound 19 3.703.70 5.515.51 6565
실시예 20Example 20 화합물 20compound 20 3.813.81 5.205.20 9090
실시예 21Example 21 화합물 21compound 21 3.883.88 5.135.13 8080
실시예 22Example 22 화합물 22compound 22 3.783.78 5.155.15 7070
실시예 23Example 23 화합물 23compound 23 3.793.79 5.125.12 7070
실시예 24Example 24 화합물 24compound 24 3.883.88 5.305.30 8080
실시예 25Example 25 화합물 25compound 25 3.903.90 5.205.20 7070
실시예 26Example 26 화합물 26compound 26 3.833.83 5.125.12 9090
실시예 27Example 27 화합물 27compound 27 3.603.60 5.485.48 6060
실시예 28Example 28 화합물 28compound 28 3.673.67 5.155.15 8585
실시예 29Example 29 화합물 29compound 29 3.703.70 5.215.21 7070
비교예 1Comparative Example 1 ET1ET1 4.354.35 4.524.52 3535
비교예 2Comparative Example 2 ET2ET2 5.005.00 3.503.50 4545
비교예 3Comparative Example 3 ET3ET3 5.115.11 3.703.70 3030
비교예 4Comparative Example 4 ET4ET4 5.105.10 3.203.20 5050
비교예 5Comparative Example 5 ET5ET5 5.055.05 3.153.15 5050
비교예 6Comparative Example 6 ET6ET6 4.404.40 4.554.55 3030
비교예 7Comparative Example 7 ET7ET7 4.524.52 4.604.60 2020
상기 표 1의 결과와 같이 상기 화학식 1의 N함유 헤테로고리기 유도체 및 시아노기가 전자 공핍 구조를 가짐으로 분자의 극성(dipole moment)을 높일 수 있기 때문에 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자의 전자이동도를 원활히 조절한다. 따라서, 상기 실시예 1 내지 29의 유기 발광 소자의 구동전압, 전류효율, 및 수명이 비교예 1 내지 7의 화합물 보다 우수한 특성을 나타내는 것을 확인할 수 있었다. 또한, 상기 R3가 N 포함 6원환을 포함하는 화합물을 포함하는 본원 실시예 21이 R3가 벤즈이미다졸(N포함 5원환)을 포함하는 화합물을 포함하는 비교예 5 보다 분자의 극성이 더 높고, 공명구조에 의하여, 전자이동이 상대적으로 원활히 조절될 수 있으므로, 구동전압, 전류효율 및 수명이 우수함을 알 수 있었다.As the result of Table 1, the N-containing heterocyclic group derivative of Formula 1 and the cyano group have an electron depletion structure, so that the dipole moment of the molecule can be increased. The electron mobility of the light emitting device is smoothly controlled. Therefore, it was confirmed that the driving voltage, current efficiency, and lifespan of the organic light emitting diodes of Examples 1 to 29 exhibited superior characteristics than the compounds of Comparative Examples 1 to 7. In addition, the polarity of the molecule is higher in Example 21 of the present application, in which R3 includes a compound containing a 6-membered ring including N, than Comparative Example 5, in which R3 includes a compound containing a benzimidazole (5-membered ring including N), By the resonance structure, since electron movement can be controlled relatively smoothly, it was found that the driving voltage, current efficiency, and lifespan were excellent.
상기 화학식 1은 잔텐(또는 티오잔텐), 시아노기, 및 N함유 단환 헤테로고리기가 유기적으로 결합하는 구조이며, 비교예 6 및 7은 잔텐(또는 티오잔텐) 대신 스피로비플루오렌(플루오렌) 구조를 포함하는 화합물을 포함하는 유기 발광 소자이며, 상기 화학식 1의 유기적 결합으로 상기 화학식 1의 유기 발광 소자인 실시예 1 내지 29 가 비교예 6 및 7 보다 구동전압, 전류효율 및 수명이 우수함을 알 수 있었다.Formula 1 is a structure in which xanthene (or thioxanthene), a cyano group, and an N-containing monocyclic heterocyclic group are organically bonded, Comparative Examples 6 and 7 are spirobifluorene (fluorene) structures instead of xanthene (or thioxanthene) It is an organic light emitting device comprising a compound comprising could

Claims (10)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2021008670-appb-img-000339
    Figure PCTKR2021008670-appb-img-000339
    상기 화학식 1에 있어서,In Formula 1,
    X1은 O 또는 S이고,X1 is O or S;
    Y1 내지 Y5 중 적어도 하나는 N이고, 나머지는 각각 독립적으로 CR3이며,At least one of Y1 to Y5 is N, and the others are each independently CR3,
    R1 및 R2은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리를 형성할 수 있으며, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, may be combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,
    R3는 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 헤테로아릴기; 또는 치환 또는 비치환되고, O, 또는 S를 포함하는 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a heteroaryl group including S, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    L1은 직접결합; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 알케닐렌기; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    l1은 1 내지 5의 정수이고,l1 is an integer from 1 to 5,
    m은 1 또는 2이며,m is 1 or 2,
    n은 1 내지 4의 정수이고,n is an integer from 1 to 4,
    상기 l1이 2 이상인 경우, 상기 2 이상의 L1는 서로 같거나 상이하며,When l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
    상기 n이 2 이상인 경우, 상기 2 이상의
    Figure PCTKR2021008670-appb-img-000340
    는 서로 같거나 상이하고,    When n is 2 or more, the 2 or more
    Figure PCTKR2021008670-appb-img-000340
    are the same as or different from each other,
    Figure PCTKR2021008670-appb-img-000341
    는 상기 L1이 화학식 1에 결합되는 부위를 의미한다.
    Figure PCTKR2021008670-appb-img-000341
    denotes a site at which L1 is bonded to Formula 1.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 또는 3으로 표시되는 것인 화합물:The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 2 or 3:
    [화학식 2][Formula 2]
    Figure PCTKR2021008670-appb-img-000342
    Figure PCTKR2021008670-appb-img-000342
    [화학식 3][Formula 3]
    Figure PCTKR2021008670-appb-img-000343
    Figure PCTKR2021008670-appb-img-000343
    상기 화학식 2 및 3에 있어서,In Formulas 2 and 3,
    R1, R2, Y1 내지 Y5, L1, l1, m 및 n은 상기 화학식 1에서 정의한 바와 동일하다.R1, R2, Y1 to Y5, L1, 11, m and n are the same as defined in Formula 1 above.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 4 또는 5로 표시되는 것인 화합물:The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 4 or 5:
    [화학식 4][Formula 4]
    Figure PCTKR2021008670-appb-img-000344
    Figure PCTKR2021008670-appb-img-000344
    [화학식 5][Formula 5]
    Figure PCTKR2021008670-appb-img-000345
    Figure PCTKR2021008670-appb-img-000345
    상기 화학식 4 및 5에 있어서,In Formulas 4 and 5,
    X1, R1, R2, Y1 내지 Y5, L1 및 l1은 상기 화학식 1에서 정의한 바와 동일하다.X1, R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 6 내지 9 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 6 to 9:
    [화학식 6][Formula 6]
    Figure PCTKR2021008670-appb-img-000346
    Figure PCTKR2021008670-appb-img-000346
    [화학식 7][Formula 7]
    Figure PCTKR2021008670-appb-img-000347
    Figure PCTKR2021008670-appb-img-000347
    [화학식 8][Formula 8]
    Figure PCTKR2021008670-appb-img-000348
    Figure PCTKR2021008670-appb-img-000348
    [화학식 9][Formula 9]
    Figure PCTKR2021008670-appb-img-000349
    Figure PCTKR2021008670-appb-img-000349
    상기 화학식 6 내지 9에 있어서,In Formulas 6 to 9,
    R1, R2, Y1 내지 Y5, L1 및 l1은 상기 화학식 1에서 정의한 바와 동일하다.R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.
  5. 청구항 1에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 서로 결합하여 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리를 형성할 수 있고,The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. can,
    상기 R3는 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 시아노기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 시아노기로 치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, N을 포함하는 6원환을 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기; 또는 시아노기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환되고, O, 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성할 수 있으며,wherein R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms is substituted with a cyano group. A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms,
    상기 L1은 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기인 것인 화합물.L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a compound that is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  6. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:
    Figure PCTKR2021008670-appb-img-000350
    Figure PCTKR2021008670-appb-img-000350
    Figure PCTKR2021008670-appb-img-000351
    Figure PCTKR2021008670-appb-img-000351
    Figure PCTKR2021008670-appb-img-000352
    Figure PCTKR2021008670-appb-img-000352
    Figure PCTKR2021008670-appb-img-000353
    Figure PCTKR2021008670-appb-img-000353
    Figure PCTKR2021008670-appb-img-000354
    Figure PCTKR2021008670-appb-img-000354
    Figure PCTKR2021008670-appb-img-000355
    Figure PCTKR2021008670-appb-img-000355
    Figure PCTKR2021008670-appb-img-000356
    Figure PCTKR2021008670-appb-img-000356
    Figure PCTKR2021008670-appb-img-000357
    Figure PCTKR2021008670-appb-img-000357
    Figure PCTKR2021008670-appb-img-000358
    Figure PCTKR2021008670-appb-img-000358
    Figure PCTKR2021008670-appb-img-000359
    Figure PCTKR2021008670-appb-img-000359
    Figure PCTKR2021008670-appb-img-000360
    Figure PCTKR2021008670-appb-img-000360
    Figure PCTKR2021008670-appb-img-000361
    Figure PCTKR2021008670-appb-img-000361
    Figure PCTKR2021008670-appb-img-000362
    Figure PCTKR2021008670-appb-img-000362
    Figure PCTKR2021008670-appb-img-000363
    Figure PCTKR2021008670-appb-img-000363
    Figure PCTKR2021008670-appb-img-000364
    Figure PCTKR2021008670-appb-img-000364
    Figure PCTKR2021008670-appb-img-000365
    Figure PCTKR2021008670-appb-img-000365
    Figure PCTKR2021008670-appb-img-000366
    Figure PCTKR2021008670-appb-img-000366
    Figure PCTKR2021008670-appb-img-000367
    Figure PCTKR2021008670-appb-img-000367
    Figure PCTKR2021008670-appb-img-000368
    Figure PCTKR2021008670-appb-img-000368
    Figure PCTKR2021008670-appb-img-000369
    Figure PCTKR2021008670-appb-img-000369
    Figure PCTKR2021008670-appb-img-000370
    Figure PCTKR2021008670-appb-img-000370
    Figure PCTKR2021008670-appb-img-000371
    Figure PCTKR2021008670-appb-img-000371
    Figure PCTKR2021008670-appb-img-000372
    Figure PCTKR2021008670-appb-img-000372
    Figure PCTKR2021008670-appb-img-000373
    Figure PCTKR2021008670-appb-img-000373
    Figure PCTKR2021008670-appb-img-000374
    Figure PCTKR2021008670-appb-img-000374
    Figure PCTKR2021008670-appb-img-000375
    Figure PCTKR2021008670-appb-img-000375
    Figure PCTKR2021008670-appb-img-000376
    Figure PCTKR2021008670-appb-img-000376
    Figure PCTKR2021008670-appb-img-000377
    Figure PCTKR2021008670-appb-img-000377
    Figure PCTKR2021008670-appb-img-000378
    Figure PCTKR2021008670-appb-img-000378
    Figure PCTKR2021008670-appb-img-000379
    Figure PCTKR2021008670-appb-img-000379
    Figure PCTKR2021008670-appb-img-000380
    Figure PCTKR2021008670-appb-img-000380
    Figure PCTKR2021008670-appb-img-000381
    Figure PCTKR2021008670-appb-img-000381
    Figure PCTKR2021008670-appb-img-000382
    Figure PCTKR2021008670-appb-img-000382
    Figure PCTKR2021008670-appb-img-000383
    Figure PCTKR2021008670-appb-img-000383
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    Figure PCTKR2021008670-appb-img-000384
    Figure PCTKR2021008670-appb-img-000385
    Figure PCTKR2021008670-appb-img-000385
    Figure PCTKR2021008670-appb-img-000386
    Figure PCTKR2021008670-appb-img-000386
    Figure PCTKR2021008670-appb-img-000387
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    Figure PCTKR2021008670-appb-img-000388
    Figure PCTKR2021008670-appb-img-000389
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    Figure PCTKR2021008670-appb-img-000390
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    Figure PCTKR2021008670-appb-img-000397
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    Figure PCTKR2021008670-appb-img-000400
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    Figure PCTKR2021008670-appb-img-000424
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    Figure PCTKR2021008670-appb-img-000509
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    Figure PCTKR2021008670-appb-img-000571
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    Figure PCTKR2021008670-appb-img-000586
    Figure PCTKR2021008670-appb-img-000586
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    Figure PCTKR2021008670-appb-img-000589
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    Figure PCTKR2021008670-appb-img-000591
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    Figure PCTKR2021008670-appb-img-000592
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    Figure PCTKR2021008670-appb-img-000595
    Figure PCTKR2021008670-appb-img-000595
    Figure PCTKR2021008670-appb-img-000596
    Figure PCTKR2021008670-appb-img-000596
    Figure PCTKR2021008670-appb-img-000597
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    Figure PCTKR2021008670-appb-img-000598
    Figure PCTKR2021008670-appb-img-000598
    Figure PCTKR2021008670-appb-img-000599
    Figure PCTKR2021008670-appb-img-000599
    Figure PCTKR2021008670-appb-img-000600
    Figure PCTKR2021008670-appb-img-000600
    Figure PCTKR2021008670-appb-img-000601
    Figure PCTKR2021008670-appb-img-000601
    Figure PCTKR2021008670-appb-img-000602
    Figure PCTKR2021008670-appb-img-000602
    Figure PCTKR2021008670-appb-img-000603
    Figure PCTKR2021008670-appb-img-000603
    Figure PCTKR2021008670-appb-img-000604
    Figure PCTKR2021008670-appb-img-000604
    Figure PCTKR2021008670-appb-img-000605
    Figure PCTKR2021008670-appb-img-000605
    Figure PCTKR2021008670-appb-img-000606
    Figure PCTKR2021008670-appb-img-000606
    Figure PCTKR2021008670-appb-img-000607
    Figure PCTKR2021008670-appb-img-000607
    Figure PCTKR2021008670-appb-img-000608
    Figure PCTKR2021008670-appb-img-000608
    Figure PCTKR2021008670-appb-img-000609
    Figure PCTKR2021008670-appb-img-000609
    Figure PCTKR2021008670-appb-img-000610
    Figure PCTKR2021008670-appb-img-000610
    Figure PCTKR2021008670-appb-img-000611
    .
    Figure PCTKR2021008670-appb-img-000611
    .
  7. 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 6 중 어느 한 항의 화합물을 포함하는 것인 유기 발광 소자.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 comprises the compound of any one of claims 1 to 6.
  8. 청구항 7에 있어서, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 7 , wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
  9. 청구항 7에 있어서, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting diode of claim 7 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
  10. 청구항 7에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 7 , wherein the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
PCT/KR2021/008670 2020-07-24 2021-07-07 Compound and organic light-emitting device comprising same WO2022019535A1 (en)

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