WO2023085877A1 - Compound and organic light-emitting element comprising same - Google Patents

Compound and organic light-emitting element comprising same Download PDF

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WO2023085877A1
WO2023085877A1 PCT/KR2022/017844 KR2022017844W WO2023085877A1 WO 2023085877 A1 WO2023085877 A1 WO 2023085877A1 KR 2022017844 W KR2022017844 W KR 2022017844W WO 2023085877 A1 WO2023085877 A1 WO 2023085877A1
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group
compound
substituted
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unsubstituted
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French (fr)
Korean (ko)
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김민준
김주호
문현진
이성재
홍성길
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주식회사 엘지화학
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Priority to CN202280028003.9A priority Critical patent/CN117203210A/en
Publication of WO2023085877A1 publication Critical patent/WO2023085877A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

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 electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • X1 is N or CR1
  • X2 is N or CR2
  • X3 is N or CR3
  • X4 is N or CR4
  • X5 is N or CR5
  • X6 is N or CR6
  • X7 is N or CR7
  • X8 is N or CR8,
  • At least one of X1 to X8 is N, and any one of the other non-N of X1 to X8 is bonded to L1;
  • R1 to R8 and G1 to G4 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,
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • L3 is a direct bond; an arylene group unsubstituted or substituted with at least one of heavy hydrogen, an aryl group, and combinations thereof; Or a substituted or unsubstituted heteroarylene group,
  • l1 to l3 are each an integer of 1 to 3,
  • L1 When l1 is 2 or more, the two or more L1s are the same as or different from each other,
  • L2 When l2 is 2 or more, the two or more L2s are the same as or different from each other,
  • L3 When l3 is 2 or more, the two or more L3s are the same as or different from each other,
  • Ar1 is a substituted or unsubstituted monocyclic, bicyclic, tricyclic, or five- or more-cyclic aryl group; A substituted or unsubstituted Chrysen group; A substituted or unsubstituted benzophenanthrene group; Or a substituted or unsubstituted heteroaryl group,
  • A is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene.
  • an exemplary embodiment of the present specification includes a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes the aforementioned compound.
  • the compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device.
  • the compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, and light emitting materials.
  • 1 and 2 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • the compound of Formula 1 according to an exemplary embodiment of the present specification has a structure including an amine group including carbazole (or benzocarbazole) bonded to the benzofuropyrimidine core in the N direction as a substituent, and has an electron depletion structure Since the dipole moment of the molecule can be increased, the electron mobility is smoothly controlled when the organic light emitting device including the compound represented by Formula 1 is manufactured, and the organic light emitting device including the same has low voltage, high efficiency, and long lifespan. It works.
  • the term "combination thereof" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It means including one or more selected from the group consisting of.
  • 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 hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted means 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 heteroaryl groups, is substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or does not have any substituents.
  • two or more substituents are linked means that the hydrogen of any one substituent is linked to another substituent.
  • a phenyl group and a naphthyl group are connected. or can be a substituent of
  • the three substituents are connected not only by connecting (substituent 1)-(substituent 2)-(substituent 3) in succession, but also by connecting (substituent 2) and (substituent 3) to (substituent 1).
  • a phenyl group, a naphthyl group and an isopropyl group are linked , , or can be a substituent of
  • the above definition is equally applied to the case where 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 group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, 2-
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclo Pentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, A cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but are not limited thereto.
  • the alkoxy group may be straight chain, branched chain or cyclic chain.
  • the number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • 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 group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto .
  • haloalkyl group means that at least one halogen group is substituted for the hydrogen of 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 is 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 10-30 carbon atoms.
  • 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 bond to each other to form a ring.
  • adjacent refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted.
  • two substituents substituted at ortho positions 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 at least one atom or heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S.
  • 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.
  • heteroaryl 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, and 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 group), dihydroindenocarbazole group, s
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, and the like.
  • Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group
  • examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group
  • examples of the heteroaryl group of the heteroarylsilyl group may 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and 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 selected from the group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It 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.
  • Diphenylamine group ditolylamine group, N-phenyltolylamine 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-phenanthreate Nyl fluorenyl amine group, N-biphenyl fluorenyl amine group and the like, but are not limited thereto.
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl 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 N of the amine group is substituted with an aryl group and a heteroaryl group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.
  • the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-mentioned 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 examples of the above-described heteroaryl groups.
  • the arylene group means that the aryl group has two binding sites, that is, a divalent group.
  • the description of the aryl group described above can be applied except that each is a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group.
  • the above description of the heteroaryl group may be applied except that each is a divalent group.
  • a portion where a substituent is not indicated in Formula 1 may mean that hydrogen is substituted.
  • Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.
  • G5 to G12 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.
  • Formula 1 is any one of Formulas 1-5 to 1-12 below.
  • L1 to L3, l1 to l3, Ar1, G1 to G4 and A are the same as defined in Formula 1 above,
  • R101 and R102 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r101 is an integer from 1 to 3;
  • r'101 is 1 or 2;
  • r102 is an integer from 1 to 4.
  • r'102 is an integer from 1 to 3;
  • r101 is 2 or more, the two or more R101s are the same as or different from each other,
  • the two or more R102s are the same as or different from each other,
  • r′102 is 2 or more
  • the 2 or more R102s are the same as or different from each other.
  • l1 is 1.
  • l1 is 2.
  • l1 is 3.
  • l2 is 1.
  • l2 is 2.
  • l2 is 3.
  • l3 is 1.
  • l3 is 2.
  • l3 is 3.
  • each L3 means that they are connected in series.
  • L3 is 3 and L3 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 L3 may be different.
  • A is benzene; or naphthalene, wherein R1 to R8 and G1 to G4 are hydrogen; Or deuterium, wherein A is benzene unsubstituted or substituted with deuterium; or naphthalene unsubstituted or substituted with deuterium, wherein L1 and L2 are the same as or different from each other, and each independently a direct compound; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with at least one of deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof, and L3 is substituted or unsubstituted with deuterium is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, and Ar1 is a monocyclic
  • At least one of X1 to X8 is N.
  • any one of X1 to X8 is N.
  • any two of X1 to X8 are N.
  • X1 is N.
  • X2 is N.
  • X3 is N.
  • X4 is N.
  • X5 is N.
  • X6 is N.
  • X7 is N.
  • X8 is N.
  • A is benzene unsubstituted or substituted with deuterium; or naphthalene unsubstituted or substituted with deuterium.
  • A is benzene; or naphthalene.
  • G1 to G4 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • G5 to G12 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R101 and R102 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • G1 to G4 are hydrogen.
  • G5 to G12 are hydrogen.
  • R1 to R8 are hydrogen.
  • R101 and R102 are hydrogen.
  • G1 to G4 are deuterium.
  • G5 to G12 are deuterium.
  • R1 to R8 are deuterium.
  • R101 and R102 are deuterium.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group unsubstituted or substituted with at least one of deuterium, aryl, and combinations thereof.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.
  • the L1 and L2 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.
  • the L3 is a direct bond; or an arylene group unsubstituted or substituted with at least one of deuterium, aryl, and combinations thereof.
  • the L3 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.
  • the L3 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.
  • the L3 is a direct bond; A phenylene group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, a naphthyl group, and combinations thereof; a biphenylyl group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, a naphthyl group, and combinations thereof; Or a naphthylene group unsubstituted or substituted with deuterium.
  • Ar1 is a substituted or unsubstituted monocyclic, bicyclic, tricyclic, or five or more aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted Chrysen group; Or a substituted or unsubstituted benzophenanthrene group.
  • Ar1 is a monocyclic, bicyclic, tricyclic, or five- or more-cyclic aryl group unsubstituted or substituted with one or more of deuterium, an aryl group, and combinations thereof; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
  • Ar1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof. a ring or a 5 or more ring aryl group; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; a naphthyl group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; A terphenyl group unsubstituted or substituted with heavy hydrogen; A phenanthrene group unsubstituted or substituted with heavy hydrogen; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
  • Formula 1 is any one selected from the following compounds.
  • the present specification provides an organic light emitting device including the aforementioned compound.
  • the 'layer' means compatible with 'film' mainly used in the art, and means a coating covering a target area.
  • the size of the 'layer' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.
  • the meaning that a specific material A is included in the C layer or the D layer means that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.
  • the present specification is a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or 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 fewer organic layers.
  • 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 an electron blocking layer, and the electron blocking layer includes the compound.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  • the light emitting layer includes the compound as a host of the light emitting layer.
  • the light emitting layer includes the compound as a phosphorescent host of the light emitting layer.
  • the light emitting layer includes a dopant, and the dopant is a phosphorescent dopant.
  • the phosphorescent dopant those conventionally used may be used without limitation.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device is a group consisting of 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 layer or two or more layers selected from.
  • the organic light emitting device may include 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 consist of 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 organic light emitting device of an inverted type 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 the organic light emitting diode, but are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1.
  • the compound is included in the organic material layer.
  • FIG. 1 shows a substrate 1 on a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, electron injection and
  • the structure of the organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked is illustrated.
  • the compound is included in the hole injection layer 5, the hole transport layer 6, or the electron blocking layer 7.
  • the organic light emitting device of the present specification is a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, or a light emitting layer with materials known in the art, except that the compound, that is, the compound of Formula 1 is included. can be produced in this way.
  • 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. At this time, by using a physical vapor deposition (PVD) 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 an anode. After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, 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.
  • PVD physical vapor deposition
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the manufacturing method is not limited thereto.
  • anode material a material having a high 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 and an oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function so as to facilitate electron injection into the organic material layer.
  • metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a heterocyclic ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are not limited thereto.
  • the host includes a compound represented by Formula H-1 below, but is not limited thereto.
  • L20 and L21 are the same as or different from each other, and are 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 are 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, two or more R201s are the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and are 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 are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; Divalent dibenzofuran group; or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents 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 represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-cyclic heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and each independently deuterium or a phenyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with heavy hydrogen 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
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; terphenyl group; A naphthyl group unsubstituted or substituted with heavy hydrogen; 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; or a phenyl group.
  • Formula H-1 is represented by the following compound.
  • Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • aromatic amine derivatives include pyrene, anthracene, chrysene, and periplanthene having an arylamine group as condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group.
  • the substituent is substituted or unsubstituted.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the dopant includes a compound represented by Formula D-1 below, 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 alkylsilyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each an integer from 1 to 4,
  • T5 When t5 is 2 or more, the two or more T5s are the same as or different from each other,
  • t6 is 2 or more
  • the 2 or more T6s 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a heavy hydrogen, 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; trimethylsilyl group; A phenyl group substituted with heavy hydrogen; A phenyl group substituted with a cyano group; A phenyl group substituted with a methyl group; or a dibenzofuran group.
  • Formula D-1 is represented by the following compound.
  • the hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is desirable. Also, a material having excellent thin film forming ability is preferred. 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 layer.
  • HOMO highest occupied molecular orbital
  • the hole injection material examples include metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials;
  • Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole injection layer includes a compound represented by Chemical Formula HI-1, 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 combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,
  • r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 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 of 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; triphenylene 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 each independently is a substituted or unsubstituted aryl group, or combines 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 each independently is a phenyl group, or combines with an adjacent group to form an indene substituted with a methyl group.
  • Formula HI-1 is represented by any one of the following compounds.
  • the hole injection layer includes a compound represented by Formula HI-2, but is not limited thereto.
  • At least one of X'1 to X'6 is N and the others 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 bonded to adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • Formula HI-2 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 may receive holes from the anode or the hole injection layer and transfer them to the light emitting layer.
  • a material having high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
  • the hole transport layer includes a compound represented by Formula HT-1, but is not limited thereto.
  • L501 and L502 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R501 and Ar501 to Ar504 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.
  • L501 and L502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L501 and L502 are phenylene groups.
  • R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a phenyl group or a naphthyl group.
  • R501 and Ar501 to Ar504 are phenyl groups.
  • R501 and Ar501 to Ar504 are naphthyl groups.
  • R501 is a naphthyl group.
  • Ar501 to Ar504 are naphthyl groups.
  • Formula HT-1 is represented by the following compound.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • a suitable cathode material is a conventional material having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., followed by an aluminum layer or a silver layer in each case.
  • the electron injection layer is a layer that receives electrons from an electrode.
  • the organic light emitting device includes an additional electron injection layer other than the electron injection layer including Formula 1
  • the electron injection material has excellent ability to transport electrons, and the second electrode It is desirable to have an excellent electron injection effect with respect to the electron-accepting effect from 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 forming ability is desirable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, 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-cresolato)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 injection and transport layer is a layer that transports electrons to the light emitting layer.
  • the electron injection and transport layer may use the materials exemplified in the electron transport layer and the electron injection layer, but are not limited thereto.
  • the electron injection and transport layer includes a compound represented by Formula ET-1, but is not limited thereto.
  • At least one of Z11 to Z13 is N and the others are CH,
  • At least one of Z21 to Z23 is N and the others are CH,
  • L601 and L602 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar604 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.
  • L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are phenylene groups.
  • Ar601 to Ar604 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar601 to Ar604 are phenyl groups.
  • Formula ET-1 is represented by the following compound.
  • the electron injection and transport layer may further include a metal complex compound.
  • the metal complex compound is as described above.
  • the electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer including Formula 1, known materials may be used without limitation, and in the description of the hole injection layer Examples of materials may be used, but are not limited thereto.
  • the electron blocking layer may be formed between the light emitting layer and the hole transport layer, between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.
  • the hole blocking layer includes a compound represented by Chemical Formula HB-1, but is not limited thereto.
  • At least one of Z31 to Z33 is N, the others are CH,
  • L603 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar605 and Ar606 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a ring,
  • l603 is an integer from 1 to 3, and when l603 is 2 or more, the two or more L603s are the same as or different from each other.
  • Z31 to Z33 are N.
  • the L603 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • the L603 is a direct bond; phenylene group; naphthylene group; or a biphenylylene group.
  • Ar605 and Ar606 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar605 and Ar606 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar605 and Ar606 are biphenyl groups.
  • Ar605 and Ar606 are phenyl groups.
  • Formula HB-1 is represented by the following compound.
  • An organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type depending on materials used.
  • the organic light emitting device may be included in and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, but is not limited thereto.
  • a glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • the following compound HI-1 was formed to a thickness of 1150 ⁇ as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited to form a hole transport layer having a thickness of 800 ⁇ .
  • Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 ⁇ as an electron blocking layer.
  • a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD were vacuum deposited to a thickness of 200 ⁇ at a weight ratio of 25:1.
  • a compound represented by Chemical Formula HB-1 was vacuum deposited to a thickness of 50 ⁇ .
  • a compound represented by Formula ET-1 and a compound represented by LiQ were thermally vacuum deposited to a thickness of 310 ⁇ at a weight ratio of 1:1.
  • An organic light emitting diode was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ to form a cathode on the electron transport and electron injection layers.
  • LiF lithium fluoride
  • Lifetime T95 means the time required for the luminance to decrease from the initial luminance (1000 nit) to 95%.
  • the compound of the present invention was used as an electron blocking layer. It has been confirmed that the organic light-emitting device exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan by substantially serving to block the movement of injected electrons so that they do not pass to the hole transport layer.
  • the organic light emitting device using the compound of Formula 1 of the present specification is Comparative Experimental Example 1-1 using benzothienopyrimidine instead of benzofuropyrimidine of Formula 1 of the present specification, instead of Ar1 of Formula 1 of the present specification Comparative Experimental Example 1-2 using a pyrene group, Comparative Experimental Examples 1-3 and 1-4 using an arylene group substituted with an aryl group substituted with an alkyl group instead of L3 in Formula 1 of the present specification, and Chemical Formulas of the present specification It was confirmed that the driving voltage, efficiency and lifetime were remarkably superior to those of Comparative Experimental Examples 1-5 to 1-8 using dibenzocarbazole instead of carbazole or benzocarbazole of No. 1.

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Abstract

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

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device including the same
본 출원은 2021년 11월 15일에 한국특허청에 제출된 한국 특허 출원 제 10-2021-0156701호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0156701 filed with the Korean Intellectual Property Office on November 15, 2021, all of which are incorporated herein.
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 electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.Development of new materials for the organic light emitting device as described above has been continuously demanded.
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 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2022017844-appb-img-000001
Figure PCTKR2022017844-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
X1은 N 또는 CR1이고, X2는 N 또는 CR2이며, X3는 N 또는 CR3이고, X4는 N 또는 CR4이며, X5는 N 또는 CR5이고, X6은 N 또는 CR6이며, X7은 N 또는 CR7이고, X8은 N 또는 CR8이며, X1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5, X6 is N or CR6, X7 is N or CR7, X8 is N or CR8,
상기 X1 내지 X8 중 적어도 하나는 N이고, 상기 X1 내지 X8 중 N이 아닌 나머지 중 어느 하나는 L1에 결합되고, At least one of X1 to X8 is N, and any one of the other non-N of X1 to X8 is bonded to L1;
상기 R1 내지 R8 및 G1 내지 G4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R1 to R8 and G1 to G4 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,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
L3는 직접결합; 중수소, 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L3 is a direct bond; an arylene group unsubstituted or substituted with at least one of heavy hydrogen, an aryl group, and combinations thereof; Or a substituted or unsubstituted heteroarylene group,
l1 내지 l3는 각각 1 내지 3의 정수이며, l1 to l3 are each an integer of 1 to 3,
상기 l1이 2 이상인 경우, 상기 2 이상의 L1은 서로 같거나 상이하고,When l1 is 2 or more, the two or more L1s are the same as or different from each other,
상기 l2가 2 이상인 경우, 상기 2 이상의 L2은 서로 같거나 상이하며,When l2 is 2 or more, the two or more L2s are the same as or different from each other,
상기 l3이 2 이상인 경우, 상기 2 이상의 L3은 서로 같거나 상이하고,When l3 is 2 or more, the two or more L3s are the same as or different from each other,
Ar1은 치환 또는 비치환된 단환, 2환, 3환, 또는 5환 이상의 아릴기; 치환 또는 비치환된 크라이센기; 치환 또는 비치환된 벤조페난트렌기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar1 is a substituted or unsubstituted monocyclic, bicyclic, tricyclic, or five- or more-cyclic aryl group; A substituted or unsubstituted Chrysen group; A substituted or unsubstituted benzophenanthrene group; Or a substituted or unsubstituted heteroaryl group,
A는 치환 또는 비치환된 벤젠; 또는 치환 또는 비치환된 나프탈렌이다.A is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene.
또한, 본 명세서의 일 실시상태는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes the aforementioned compound.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 명세서의 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자차단, 발광 재료로 사용될 수 있다. 또한, 기존 유기 발광 소자에 비하여, 낮은 구동전압, 고효율 및/또는 장수명의 효과가 있다.The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, and light emitting materials. In addition, compared to conventional organic light emitting devices, there are effects of low driving voltage, high efficiency, and/or long lifespan.
도 1 및 2은 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Description of code]
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 제2 전극3: second electrode
4: 유기물층4: organic material layer
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 전자차단층7: electron blocking layer
8: 발광층8: light emitting layer
9: 정공차단층9: hole blocking layer
10: 전자주입 및 수송층10: electron injection and transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this 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 1의 화합물은 벤조퓨로피리미딘 코어에 치환기로 N방향으로 결합되는 카바졸(또는 벤조카바졸)을 포함하는 아민기를 포함하는 구조이며, 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, 이를 포함하는 유기 발광 소자는 저전압, 고효율 및 장수명의 효과가 있다.The compound of Formula 1 according to an exemplary embodiment of the present specification has a structure including an amine group including carbazole (or benzocarbazole) bonded to the benzofuropyrimidine core in the N direction as a substituent, and has an electron depletion structure Since the dipole moment of the molecule can be increased, the electron mobility is smoothly controlled when the organic light emitting device including the compound represented by Formula 1 is manufactured, and the organic light emitting device including the same has low voltage, high efficiency, and long lifespan. It works.
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 PCTKR2022017844-appb-img-000002
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2022017844-appb-img-000002
indicates the connecting part.
본원 명세서 전체에서, 마쿠시 형식의 표현에 포함된 "이들의 조합"의 용어는 마쿠시 형식의 표현에 기재된 구성 요소들로 이루어진 군에서 선택되는 하나 이상의 혼합 또는 조합을 의미하는 것으로서, 상기 구성 요소들로 이루어진 군에서 선택되는 하나 이상을 포함하는 것을 의미한다.Throughout the present specification, the term "combination thereof" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It means including one or more selected from the group consisting of.
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 hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are 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.In this specification, the term "substituted or unsubstituted" means 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 heteroaryl groups, is substituted with substituents in which two or more substituents among 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 PCTKR2022017844-appb-img-000003
또는
Figure PCTKR2022017844-appb-img-000004
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 PCTKR2022017844-appb-img-000005
,
Figure PCTKR2022017844-appb-img-000006
, 또는
Figure PCTKR2022017844-appb-img-000007
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, two or more substituents are linked means that the hydrogen of any one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.
Figure PCTKR2022017844-appb-img-000003
or
Figure PCTKR2022017844-appb-img-000004
can be a substituent of In addition, the three substituents are connected not only by connecting (substituent 1)-(substituent 2)-(substituent 3) in succession, but also by connecting (substituent 2) and (substituent 3) to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are linked
Figure PCTKR2022017844-appb-img-000005
,
Figure PCTKR2022017844-appb-img-000006
, or
Figure PCTKR2022017844-appb-img-000007
can be a substituent of The above definition is equally applied to the case where 4 or more substituents are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this 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 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥실메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 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 group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 3-메틸시클로펜틸기, 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기, 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, specifically cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclo Pentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, A cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but are 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, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, Isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p - It may be a methylbenzyloxy group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 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 group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are 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 the hydrogen of 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 is 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 10-30 carbon atoms. 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 bond to each other to form a ring.
상기 플루오렌기가 치환되는 경우,
Figure PCTKR2022017844-appb-img-000008
When the fluorene group is substituted,
Figure PCTKR2022017844-appb-img-000008
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" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. can For example, two substituents substituted at ortho positions 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. 헤테로아릴기의 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 at least one atom or heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S. 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 heteroaryl 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, and 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 group), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene Thioxanthene group and the like, 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, and the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and examples of the heteroaryl group of the heteroarylsilyl group may 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and 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, 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 selected from the group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It 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, 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-phenanthreate Nyl fluorenyl amine group, N-biphenyl fluorenyl amine group and the like, but are 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 means an amine group in which N of the amine group is substituted with an alkyl group and an aryl 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 N of the amine group is substituted with an aryl group and a heteroaryl group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.
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 means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-mentioned 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 examples of the above-described heteroaryl groups.
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 binding sites, that is, a divalent group. The description of the aryl group described above can be applied except that each is a divalent group.
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 a heteroaryl group having two bonding sites, that is, a divalent group. The above description of the heteroaryl group may be applied except that each is a divalent group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1 중 치환기가 표시되지 않은 부분은 수소가 치환된 것을 의미할 수 있다.In an exemplary embodiment of the present specification, a portion where a substituent is not indicated in Formula 1 may mean that hydrogen is substituted.
이하 본 발명의 바람직한 실시상태를 상세히 설명한다. 그러나 본 발명의 실시상태는 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 설명하는 실시상태들에 한정되지는 않는다.Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.
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 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나이다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2022017844-appb-img-000009
Figure PCTKR2022017844-appb-img-000009
[화학식 1-2][Formula 1-2]
Figure PCTKR2022017844-appb-img-000010
Figure PCTKR2022017844-appb-img-000010
[화학식 1-3][Formula 1-3]
Figure PCTKR2022017844-appb-img-000011
Figure PCTKR2022017844-appb-img-000011
[화학식 1-4][Formula 1-4]
Figure PCTKR2022017844-appb-img-000012
Figure PCTKR2022017844-appb-img-000012
상기 화학식 1-1 내지 1-4에 있어서,In Formulas 1-1 to 1-4,
X1 내지 X8, L1 내지 L3, l1 내지 l3, Ar1 및 G1 내지 G4의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1 to X8, L1 to L3, l1 to l3, Ar1 and G1 to G4 are the same as defined in Formula 1 above,
G5 내지 G12는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.G5 to G12 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-5 내지 1-12 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 1-5 to 1-12 below.
[화학식 1-5][Formula 1-5]
Figure PCTKR2022017844-appb-img-000013
Figure PCTKR2022017844-appb-img-000013
[화학식 1-6][Formula 1-6]
Figure PCTKR2022017844-appb-img-000014
Figure PCTKR2022017844-appb-img-000014
[화학식 1-7][Formula 1-7]
Figure PCTKR2022017844-appb-img-000015
Figure PCTKR2022017844-appb-img-000015
[화학식 1-8][Formula 1-8]
Figure PCTKR2022017844-appb-img-000016
Figure PCTKR2022017844-appb-img-000016
[화학식 1-9][Formula 1-9]
Figure PCTKR2022017844-appb-img-000017
Figure PCTKR2022017844-appb-img-000017
[화학식 1-10][Formula 1-10]
Figure PCTKR2022017844-appb-img-000018
Figure PCTKR2022017844-appb-img-000018
[화학식 1-11][Formula 1-11]
Figure PCTKR2022017844-appb-img-000019
Figure PCTKR2022017844-appb-img-000019
[화학식 1-12][Formula 1-12]
Figure PCTKR2022017844-appb-img-000020
Figure PCTKR2022017844-appb-img-000020
상기 화학식 1-5 내지 1-12에 있어서,In Formulas 1-5 to 1-12,
L1 내지 L3, l1 내지 l3, Ar1, G1 내지 G4 및 A의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of L1 to L3, l1 to l3, Ar1, G1 to G4 and A are the same as defined in Formula 1 above,
R101 및 R102는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R101 and R102 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r101은 1 내지 3의 정수이고,r101 is an integer from 1 to 3;
r'101은 1 또는 2 이며,r'101 is 1 or 2;
r102는 1 내지 4의 정수이고,r102 is an integer from 1 to 4;
r'102는 1 내지 3의 정수이며,r'102 is an integer from 1 to 3;
상기 r101이 2 이상인 경우, 상기 2 이상의 R101은 서로 같거나 상이하고,When r101 is 2 or more, the two or more R101s are the same as or different from each other,
상기 r'101이 2 인 경우, 2개의 R101은 서로 같거나 상이하며,When r'101 is 2, two R101's are the same as or different from each other,
상기 r102가 2 이상인 경우, 상기 2 이상의 R102는 서로 같거나 상이하고,When the r102 is 2 or more, the two or more R102s are the same as or different from each other,
상기 r'102가 2 이상인 경우, 상기 2 이상의 R102는 서로 같거나 상이하다.When r′102 is 2 or more, the 2 or more R102s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 l1은 1 이다.According to an exemplary embodiment of the present specification, l1 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l1은 2 이다.According to an exemplary embodiment of the present specification, l1 is 2.
본 명세서의 일 실시상태에 따르면, 상기 l1은 3 이다.According to one embodiment of the present specification, l1 is 3.
본 명세서의 일 실시상태에 따르면, 상기 l2은 1 이다.According to an exemplary embodiment of the present specification, l2 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l2은 2 이다.According to an exemplary embodiment of the present specification, l2 is 2.
본 명세서의 일 실시상태에 따르면, 상기 l2은 3 이다.According to an exemplary embodiment of the present specification, l2 is 3.
본 명세서의 일 실시상태에 따르면, 상기 l3은 1 이다.According to an exemplary embodiment of the present specification, l3 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l3은 2 이다.According to an exemplary embodiment of the present specification, l3 is 2.
본 명세서의 일 실시상태에 따르면, 상기 l3은 3 이다.According to an exemplary embodiment of the present specification, l3 is 3.
본 명세서에서 상기 화학식 1에 있어서, l3이 2 이상인 경우, 2 이상의 L3는 서로 같거나 상이하며, 각각의 L3은 직렬로 연결되는 것을 의미한다. 예컨대, l3이 3이고, L3가 각각 페닐렌기, 나프틸렌기, 및 페닐렌기인 경우, 하기와 같이 연결될 수 있으나, 이에만 한정되는 것이 아니고, 각 L3의 순서 또는 연결위치가 상이할 수 있다.In the present specification, in Formula 1, when l3 is 2 or more, two or more L3s are the same as or different from each other, and each L3 means that they are connected in series. For example, when l3 is 3 and L3 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 L3 may be different.
Figure PCTKR2022017844-appb-img-000021
Figure PCTKR2022017844-appb-img-000021
또한, 상기
Figure PCTKR2022017844-appb-img-000022
은 예컨대, 상기 l3가 3인 경우, 상기 예시된 구조에서 세번째 위치한 말단의 치환기 즉, 페닐렌기에 결합되는 것을 의미하고, *는 상기 화학식 1의 N에 결합되는 부위를 의미하고,
Figure PCTKR2022017844-appb-img-000023
는 상기 L3의 말단에 결합되는 부위를 의미한다.Also, the above
Figure PCTKR2022017844-appb-img-000022
For example, when l3 is 3, it means that it is bonded to the third terminal substituent, that is, a phenylene group in the structure exemplified above, * means a site bonded to N in Formula 1,
Figure PCTKR2022017844-appb-img-000023
Means a site coupled to the end of the L3.
상기 l3에 대한 설명은 l1 및 l2에도 동일하게 적용된다.The description of l3 is equally applicable to l1 and l2.
본 명세서의 일 실시상태에 따르면, 상기 A는 벤젠; 또는 나프탈렌이고, 상기 R1 내지 R8 및 G1 내지 G4는 수소; 또는 중수소이며, 상기 A는 중수소로 치환 또는 비치환된 벤젠; 또는 중수소로 치환 또는 비치환된 나프탈렌이고, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접겹합; 또는 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이고, 상기 L3는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이며, 상기 Ar1은 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환, 2환, 3환, 또는 5환 이상의 아릴기; 중수소로 치환 또는 비치환된 크라이센기; 또는 중수소로 치환 또는 비치환된 벤조페난트렌기이다.According to an exemplary embodiment of the present specification, A is benzene; or naphthalene, wherein R1 to R8 and G1 to G4 are hydrogen; Or deuterium, wherein A is benzene unsubstituted or substituted with deuterium; or naphthalene unsubstituted or substituted with deuterium, wherein L1 and L2 are the same as or different from each other, and each independently a direct compound; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with at least one of deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof, and L3 is substituted or unsubstituted with deuterium is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, and Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a monocyclic ring having 6 to 20 carbon atoms unsubstituted or substituted with at least one of these groups. , 2-ring, 3-ring, or 5-ring or more aryl group; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X8 중 적어도 하나는 N이다.According to an exemplary embodiment of the present specification, at least one of X1 to X8 is N.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X8 중 어느 하나는 N이다.According to an exemplary embodiment of the present specification, any one of X1 to X8 is N.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X8 중 어느 두 개는 N이다.According to an exemplary embodiment of the present specification, any two of X1 to X8 are N.
본 명세서의 일 실시상태에 따르면, 상기 X1은 N이다.According to an exemplary embodiment of the present specification, X1 is N.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N이다.According to one embodiment of the present specification, X2 is N.
본 명세서의 일 실시상태에 따르면, 상기 X3는 N이다.According to an exemplary embodiment of the present specification, X3 is N.
본 명세서의 일 실시상태에 따르면, 상기 X4는 N이다.According to an exemplary embodiment of the present specification, X4 is N.
본 명세서의 일 실시상태에 따르면, 상기 X5는 N이다.According to an exemplary embodiment of the present specification, X5 is N.
본 명세서의 일 실시상태에 따르면, 상기 X6은 N이다.According to an exemplary embodiment of the present specification, X6 is N.
본 명세서의 일 실시상태에 따르면, 상기 X7은 N이다.According to an exemplary embodiment of the present specification, X7 is N.
본 명세서의 일 실시상태에 따르면, 상기 X8은 N이다.According to an exemplary embodiment of the present specification, X8 is N.
본 명세서의 일 실시상태에 따르면, 상기 A는 중수소로 치환 또는 비치환된 벤젠; 또는 중수소로 치환 또는 비치환된 나프탈렌이다.According to an exemplary embodiment of the present specification, A is benzene unsubstituted or substituted with deuterium; or naphthalene unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 A는 벤젠; 또는 나프탈렌이다.According to an exemplary embodiment of the present specification, A is benzene; or naphthalene.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G4는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently hydrogen; or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G5 내지 G12는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, G5 to G12 are the same as or different from each other, and each independently hydrogen; or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R8는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R101 및 R102는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G4는 수소이다.According to an exemplary embodiment of the present specification, G1 to G4 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 G5 내지 G12는 수소이다.According to an exemplary embodiment of the present specification, G5 to G12 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R8는 수소이다.According to an exemplary embodiment of the present specification, R1 to R8 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R101 및 R102는 수소이다.According to an exemplary embodiment of the present specification, R101 and R102 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G4는 중수소이다.According to an exemplary embodiment of the present specification, G1 to G4 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G5 내지 G12는 중수소이다.According to an exemplary embodiment of the present specification, G5 to G12 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R8는 중수소이다.According to an exemplary embodiment of the present specification, R1 to R8 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R101 및 R102는 중수소이다.According to an exemplary embodiment of the present specification, R101 and R102 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group unsubstituted or substituted with at least one of deuterium, aryl, and combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소, 페닐기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 또는 중수소로 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L3는 직접결합; 또는 중수소, 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 아릴렌기이다.According to one embodiment of the present specification, the L3 is a direct bond; or an arylene group unsubstituted or substituted with at least one of deuterium, aryl, and combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 L3는 직접결합; 또는 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to one embodiment of the present specification, the L3 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.
본 명세서의 일 실시상태에 따르면, 상기 L3는 직접결합; 또는 중수소, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to one embodiment of the present specification, the L3 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.
본 명세서의 일 실시상태에 따르면, 상기 L3는 직접결합; 중수소, 페닐기, 나프틸기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 페닐렌기; 중수소, 페닐기, 나프틸기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 바이페닐릴렌기; 또는 중수소로 치환 또는 비치환된 나프틸렌기이다.According to one embodiment of the present specification, the L3 is a direct bond; A phenylene group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, a naphthyl group, and combinations thereof; a biphenylyl group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, a naphthyl group, and combinations thereof; Or a naphthylene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 치환 또는 비치환된 탄소수 6 내지 30의 단환, 2환, 3환, 또는 5환 이상의 아릴기; 치환 또는 비치환된 크라이센기; 또는 치환 또는 비치환된 벤조페난트렌기이다.According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic, bicyclic, tricyclic, or five or more aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted Chrysen group; Or a substituted or unsubstituted benzophenanthrene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 중수소, 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 단환, 2환, 3환, 또는 5환 이상의 아릴기; 중수소로 치환 또는 비치환된 크라이센기; 또는 중수소로 치환 또는 비치환된 벤조페난트렌기이다.According to an exemplary embodiment of the present specification, Ar1 is a monocyclic, bicyclic, tricyclic, or five- or more-cyclic aryl group unsubstituted or substituted with one or more of deuterium, an aryl group, and combinations thereof; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환, 2환, 3환, 또는 5환 이상의 아릴기; 중수소로 치환 또는 비치환된 크라이센기; 또는 중수소로 치환 또는 비치환된 벤조페난트렌기이다.According to an exemplary embodiment of the present specification, Ar1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof. a ring or a 5 or more ring aryl group; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 바이페닐기; 중수소, 페닐기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 나프틸기; 중수소로 치환 또는 비치환된 터페닐기; 중수소로 치환 또는 비치환된 페난트렌기; 중수소로 치환 또는 비치환된 크라이센기; 또는 중수소로 치환 또는 비치환된 벤조페난트렌기이다.According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; a naphthyl group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; A terphenyl group unsubstituted or substituted with heavy hydrogen; A phenanthrene group unsubstituted or substituted with heavy hydrogen; Chrysen group unsubstituted or substituted with deuterium; Or a benzophenanthrene group unsubstituted or substituted with deuterium.
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 PCTKR2022017844-appb-img-000024
Figure PCTKR2022017844-appb-img-000024
Figure PCTKR2022017844-appb-img-000025
Figure PCTKR2022017844-appb-img-000025
Figure PCTKR2022017844-appb-img-000026
Figure PCTKR2022017844-appb-img-000026
Figure PCTKR2022017844-appb-img-000027
Figure PCTKR2022017844-appb-img-000027
Figure PCTKR2022017844-appb-img-000028
Figure PCTKR2022017844-appb-img-000028
Figure PCTKR2022017844-appb-img-000029
Figure PCTKR2022017844-appb-img-000029
Figure PCTKR2022017844-appb-img-000030
Figure PCTKR2022017844-appb-img-000030
Figure PCTKR2022017844-appb-img-000031
Figure PCTKR2022017844-appb-img-000031
Figure PCTKR2022017844-appb-img-000032
Figure PCTKR2022017844-appb-img-000032
Figure PCTKR2022017844-appb-img-000033
Figure PCTKR2022017844-appb-img-000033
Figure PCTKR2022017844-appb-img-000034
Figure PCTKR2022017844-appb-img-000034
Figure PCTKR2022017844-appb-img-000035
Figure PCTKR2022017844-appb-img-000035
Figure PCTKR2022017844-appb-img-000036
Figure PCTKR2022017844-appb-img-000036
Figure PCTKR2022017844-appb-img-000037
Figure PCTKR2022017844-appb-img-000037
Figure PCTKR2022017844-appb-img-000038
Figure PCTKR2022017844-appb-img-000038
Figure PCTKR2022017844-appb-img-000039
Figure PCTKR2022017844-appb-img-000039
Figure PCTKR2022017844-appb-img-000040
Figure PCTKR2022017844-appb-img-000040
Figure PCTKR2022017844-appb-img-000041
Figure PCTKR2022017844-appb-img-000041
Figure PCTKR2022017844-appb-img-000042
Figure PCTKR2022017844-appb-img-000042
Figure PCTKR2022017844-appb-img-000043
Figure PCTKR2022017844-appb-img-000043
Figure PCTKR2022017844-appb-img-000044
Figure PCTKR2022017844-appb-img-000044
Figure PCTKR2022017844-appb-img-000045
Figure PCTKR2022017844-appb-img-000045
Figure PCTKR2022017844-appb-img-000046
Figure PCTKR2022017844-appb-img-000046
Figure PCTKR2022017844-appb-img-000047
Figure PCTKR2022017844-appb-img-000047
Figure PCTKR2022017844-appb-img-000048
Figure PCTKR2022017844-appb-img-000048
Figure PCTKR2022017844-appb-img-000049
Figure PCTKR2022017844-appb-img-000049
Figure PCTKR2022017844-appb-img-000050
Figure PCTKR2022017844-appb-img-000050
Figure PCTKR2022017844-appb-img-000051
Figure PCTKR2022017844-appb-img-000051
Figure PCTKR2022017844-appb-img-000052
Figure PCTKR2022017844-appb-img-000052
Figure PCTKR2022017844-appb-img-000053
.
Figure PCTKR2022017844-appb-img-000053
.
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present specification provides an organic light emitting device including the aforementioned compound.
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 this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists 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 this specification, when a part is said to "include" a certain component, it means that it may further include other components without 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 'film' mainly used in the art, and means a coating covering a target area. The size of the 'layer' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or 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 this specification, the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.
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 that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.
본 명세서는 제1 전극; 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 is a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. 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, or 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 fewer organic layers.
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 one 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 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화합물을 포함한다.According to one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함한다.According to one 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.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함한다.According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화합물을 발광층의 호스트로 포함한다.According to one embodiment of the present specification, the light emitting layer includes the compound as a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화합물을 발광층의 인광 호스트로 포함한다.According to one embodiment of the present specification, the light emitting layer includes the compound as a phosphorescent host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 도펀트를 포함하고, 상기 도펀트는 인광 도펀트이다. 상기 인광 도펀트는 종래에 사용하는 것을 제한없이 사용할 수 있다.According to one embodiment of the present specification, the light emitting layer includes a dopant, and the dopant is a phosphorescent dopant. As the phosphorescent dopant, those conventionally used may be used without limitation.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 차단층을 포함한다. According to one 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 is a group consisting of 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 layer or two or more layers 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 one embodiment of the present specification, the organic light emitting device may include 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 consist of 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 one 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 one 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 one 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 one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type 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 2은 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 the organic light emitting diode, but are not limited thereto.
도 1에는 기판(1) 위에 제1 전극(2), 유기물층(4) 및 제2 전극(3)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화합물은 유기물층에 포함된다.1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound is included in the organic material layer.
도 1에는 기판(1) 위에 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자차단층(7), 발광층(8), 정공차단층(9), 전자주입 및 수송층(10) 및 제2 전극(3)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화합물은 정공주입층(5), 정공 수송층(6), 또는 전자차단층(7)에 포함된다.1 shows a substrate 1 on a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, electron injection and The structure of the organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked is illustrated. The compound is included in the hole injection layer 5, the hole transport layer 6, or the electron blocking layer 7.
본 명세서의 유기 발광 소자는 정공주입층, 정공 수송층, 정공 주입 및 수송층, 전자차단층, 또는 발광층이 상기 화합물, 즉 상기 화학식 1의 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification is a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, or a light emitting layer with materials known in the art, except that the compound, that is, the compound of Formula 1 is included. can be produced in this way.
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 음극로 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 physical vapor deposition (PVD) 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 an anode. After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, 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 Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., 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 fabricated by sequentially depositing a cathode material, an organic material layer, and an anode 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 high 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 and an oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
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 so as to facilitate electron injection into the organic material layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 정공수송층 이외의 추가의 발광층 호스트를 포함하는 경우, 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 light emitting layer may include a host material and a dopant material. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional light emitting layer host other than the hole transport layer including Chemical Formula 1, the host material includes a condensed aromatic ring derivative or a compound containing a heterocyclic ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are 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 Formula H-1 below, but is not limited thereto.
[화학식 H-1][Formula H-1]
Figure PCTKR2022017844-appb-img-000054
Figure PCTKR2022017844-appb-img-000054
상기 화학식 H-1에 있어서,In the above 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 are 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 are 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, two or more R201s 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 one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are 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 one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; 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 one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents 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 one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-cyclic heterocyclic group having 6 to 20 carbon atoms.
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 one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently deuterium or a phenyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with heavy hydrogen 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 one 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; A biphenyl group unsubstituted or substituted with heavy hydrogen; terphenyl group; A naphthyl group unsubstituted or substituted with heavy hydrogen; 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 one 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 수소; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R201 is hydrogen; or a phenyl group.
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 PCTKR2022017844-appb-img-000055
Figure PCTKR2022017844-appb-img-000055
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, aromatic amine derivatives include pyrene, anthracene, chrysene, and periplanthene having an arylamine group as condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
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 Formula D-1 below, but is not limited thereto.
[화학식 D-1][Formula D-1]
Figure PCTKR2022017844-appb-img-000056
Figure PCTKR2022017844-appb-img-000056
상기 화학식 D-1에 있어서,In the above formula D-1,
T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알킬실릴기; 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 alkylsilyl 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 from 1 to 4,
상기 t5가 2 이상인 경우, 상기 2 이상의 T5는 서로 같거나 상이하고,When t5 is 2 or more, the two or more T5s 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 T6s 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 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; 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; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; 중수소, 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 straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a heavy hydrogen, 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; 트리메틸실릴기; 중수소로 치환된 페닐기; 시아노기로 치환된 페닐기; 메틸기로 치환된 페닐기; 또는 디벤조퓨란기이다.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; trimethylsilyl group; A phenyl group substituted with heavy hydrogen; A phenyl group substituted with a cyano group; A phenyl group substituted with a methyl group; or a dibenzofuran 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 PCTKR2022017844-appb-img-000057
Figure PCTKR2022017844-appb-img-000057
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 an electrode. It is preferable that the hole injection material has the ability to transport holes and has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is desirable. Also, a material having excellent thin film forming ability is preferred. 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 layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1로 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 Chemical Formula HI-1, but is not limited thereto.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2022017844-appb-img-000058
Figure PCTKR2022017844-appb-img-000058
상기 화학식 HI-1에 있어서,In the above formula HI-1,
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 combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,
r315은 1 내지 5의 정수이며, 상기 r315이 2 이상인 경우, 2 이상의 상기 R315은 서로 같거나 상이하며,r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 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 of 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; 트리페닐렌기; 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; triphenylene 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 방향족 탄화수소 고리를 형성한다.According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or combines 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 each independently is a phenyl group, or combines with an adjacent group to form an indene substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula HI-1 is represented by any one of the following compounds.
Figure PCTKR2022017844-appb-img-000059
Figure PCTKR2022017844-appb-img-000059
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-2로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by Formula HI-2, but is not limited thereto.
[화학식 HI-2][Formula HI-2]
Figure PCTKR2022017844-appb-img-000060
Figure PCTKR2022017844-appb-img-000060
상기 화학식 HI-2에 있어서,In the above formula HI-2,
X'1 내지 X'6 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of X'1 to X'6 is N and the others 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 bonded to adjacent groups to form a substituted or unsubstituted ring.
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 HI-2은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula HI-2 is represented by the following compound.
Figure PCTKR2022017844-appb-img-000061
Figure PCTKR2022017844-appb-img-000061
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 정공수송층 이외의 추가의 정공수송층을 포함하는 경우, 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. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole transport layer other than the hole transport layer including Chemical Formula 1, the hole transport material may receive holes from the anode or the hole injection layer and transfer them to the light emitting layer. A material having high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by Formula HT-1, but is not limited thereto.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2022017844-appb-img-000062
Figure PCTKR2022017844-appb-img-000062
상기 화학식 HT-1에 있어서,In the above formula HT-1,
L501 및 L502는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L501 and L502 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R501 및 Ar501 내지 Ar504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.R501 and Ar501 to Ar504 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 L501 및 L502는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L501 and L502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L501 및 L502는 페닐렌기이다.According to an exemplary embodiment of the present specification, L501 and L502 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 또는 나프틸기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a phenyl group or a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 페닐기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 나프틸기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are naphthyl groups.
본 명세서의 일 실시상태에 따르면, 상기 R501은 나프틸기이다.According to an exemplary embodiment of the present specification, R501 is a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar501 내지 Ar504는 나프틸기이다.According to an exemplary embodiment of the present specification, Ar501 to Ar504 are naphthyl 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 PCTKR2022017844-appb-img-000063
Figure PCTKR2022017844-appb-img-000063
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 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 the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, a suitable cathode material is a conventional material having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., followed by an aluminum layer or a silver layer in each case.
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 an 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 including Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is desirable to have an excellent electron injection effect with respect to the electron-accepting effect from 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 forming ability is desirable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 전자 주입 및 수송층은 전자를 발광층까지 수송하는 층이다. 상기 전자 주입 및 수송층은 상기 전자 수송층 및 전자주입층에서 예시한 물질을 사용할 수 있으나, 이에 한정되는 것은 아니다.According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light emitting layer. The electron injection and transport layer may use the materials exemplified in the electron transport layer and the electron injection layer, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 전자 주입 및 수송층은 하기 화학식 ET-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron injection and transport layer includes a compound represented by Formula ET-1, but is not limited thereto.
[화학식 ET-1][Formula ET-1]
Figure PCTKR2022017844-appb-img-000064
Figure PCTKR2022017844-appb-img-000064
상기 화학식 ET-1에 있어서,In the above formula ET-1,
Z11 내지 Z13 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z11 to Z13 is N and the others are CH,
Z21 내지 Z23 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of Z21 to Z23 is N and the others are CH,
L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L601 and L602 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar601 내지 Ar604는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar601 to Ar604 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 L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L601 및 L602는 페닐렌기이다.According to an exemplary embodiment of the present specification, L601 and L602 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar604는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar604는 페닐기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar604 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 ET-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula ET-1 is represented by the following compound.
Figure PCTKR2022017844-appb-img-000065
Figure PCTKR2022017844-appb-img-000065
본 명세서의 일 실시상태에 따르면, 상기 전자 주입 및 수송층은 금속 착체 화합물을 더 포함할 수 있다. 상기 금속 착체 화합물은 전술한 바와 같다.According to one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자 차단층 이외의 추가의 전자차단층을 포함하는 경우, 공지된 재료는 제한 없이 사용 가능하며, 상기 정공주입층의 설명에서 예시한 물질을 사용할 수 있으나, 이에만 한정되는 것은 아니다. 상기 전자차단층은 발광층과 정공수송층 사이에, 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 that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer including Formula 1, known materials may be used without limitation, and in the description of the hole injection layer Examples of materials may be used, but are not limited thereto. The electron blocking layer may be formed between the light emitting layer and the hole transport layer, between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.
상기 정공 차단층은 정공이 캐소드로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 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 holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공차단층은 하기 화학식 HB-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound represented by Chemical Formula HB-1, but is not limited thereto.
[화학식 HB-1][Formula HB-1]
Figure PCTKR2022017844-appb-img-000066
Figure PCTKR2022017844-appb-img-000066
상기 화학식 HB-1에 있어서,In the above formula HB-1,
Z31 내지 Z33 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of Z31 to Z33 is N, the others are CH,
L603는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L603 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 고리를 형성하고,Ar605 and Ar606 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a ring,
l603은 1 내지 3의 정수이며, 상기 l603이 2 이상인 경우, 상기 2 이상의 L603은 서로 같거나 상이하다.l603 is an integer from 1 to 3, and when l603 is 2 or more, the two or more L603s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 Z31 내지 Z33은 N이다.According to an exemplary embodiment of the present specification, Z31 to Z33 are N.
본 명세서의 일 실시상태에 따르면, 상기 L603는 직접결합; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, the L603 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L603는 직접결합; 페닐렌기; 나프틸렌기; 또는 바이페닐릴렌기이다.According to an exemplary embodiment of the present specification, the L603 is a direct bond; phenylene group; naphthylene group; or a biphenylylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 바이페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are biphenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HB-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula HB-1 is represented by the following compound.
Figure PCTKR2022017844-appb-img-000067
Figure PCTKR2022017844-appb-img-000067
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.An organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type depending on materials 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 device according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, 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, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in many different forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples detailed below. Examples and comparative examples in the present specification are provided to more completely explain the present specification to those skilled in the art.
합성예 1Synthesis Example 1
Figure PCTKR2022017844-appb-img-000068
Figure PCTKR2022017844-appb-img-000068
질소 분위기에서 sub1 (15 g, 42.4mmol), amine1 (19.6g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 1, 22.8g을 얻었다. (수율 69%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub1 (15 g, 42.4 mmol), amine1 (19.6 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.8 g of Compound 1. (Yield 69%, MS: [M+H]+= 780)
합성예 2Synthesis Example 2
Figure PCTKR2022017844-appb-img-000069
Figure PCTKR2022017844-appb-img-000069
질소 분위기에서 sub2 (15 g, 45.8mmol), amine2 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 2, 21g을 얻었다. (수율 73%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub2 (15 g, 45.8 mmol), amine2 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2 (21 g). (Yield 73%, MS: [M+H]+= 628)
합성예 3Synthesis Example 3
Figure PCTKR2022017844-appb-img-000070
Figure PCTKR2022017844-appb-img-000070
질소 분위기에서 sub3 (15 g, 54mmol), amine3 (22.3g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 3, 24g을 얻었다. (수율 68%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub3 (15 g, 54 mmol), amine3 (22.3 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3 (24 g). (Yield 68%, MS: [M+H]+= 654)
합성예 4Synthesis Example 4
Figure PCTKR2022017844-appb-img-000071
Figure PCTKR2022017844-appb-img-000071
질소 분위기에서 sub1 (15 g, 42.4mmol), amine4 (16.4g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 4, 21.5g을 얻었다. (수율 72%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub1 (15 g, 42.4 mmol), amine4 (16.4 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 4 (21.5 g). (Yield 72%, MS: [M+H]+= 704)
합성예 5Synthesis Example 5
Figure PCTKR2022017844-appb-img-000072
Figure PCTKR2022017844-appb-img-000072
질소 분위기에서 sub4 (15 g, 34.9mmol), amine5 (13.5g, 34.9 mmol), sodium tert-butoxide (5 g, 52.3 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 5, 18.8g을 얻었다. (수율 69%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub4 (15 g, 34.9 mmol), amine5 (13.5 g, 34.9 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.8 g of compound 5. (Yield 69%, MS: [M+H]+= 780)
합성예 6Synthesis Example 6
Figure PCTKR2022017844-appb-img-000073
Figure PCTKR2022017844-appb-img-000073
질소 분위기에서 sub5 (15 g, 42.4mmol), amine6 (14.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 6, 19.7g을 얻었다. (수율 71%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub5 (15 g, 42.4 mmol), amine6 (14.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.7 g of compound 6. (Yield 71%, MS: [M+H]+= 654)
합성예 7Synthesis Example 7
Figure PCTKR2022017844-appb-img-000074
Figure PCTKR2022017844-appb-img-000074
질소 분위기에서 sub6 (15 g, 45.8mmol), amine7 (17.7g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 7, 18.6g을 얻었다. (수율 60%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub6 (15 g, 45.8 mmol), amine7 (17.7 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7 (18.6 g). (Yield 60%, MS: [M+H]+= 678)
합성예 8Synthesis Example 8
Figure PCTKR2022017844-appb-img-000075
Figure PCTKR2022017844-appb-img-000075
질소 분위기에서 sub7 (15 g, 34.9mmol), amine6 (11.7g, 34.9 mmol), sodium tert-butoxide (5 g, 52.3 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 8, 18.8g을 얻었다. (수율 74%, MS: [M+H]+= 730)In a nitrogen atmosphere, sub7 (15 g, 34.9 mmol), amine6 (11.7 g, 34.9 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.8 g of compound 8. (Yield 74%, MS: [M+H]+= 730)
합성예 9Synthesis Example 9
Figure PCTKR2022017844-appb-img-000076
Figure PCTKR2022017844-appb-img-000076
질소 분위기에서 sub8 (15 g, 42.4mmol), amine8 (17.5g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 9, 21g을 얻었다. (수율 68%, MS: [M+H]+= 730)In a nitrogen atmosphere, sub8 (15 g, 42.4 mmol), amine8 (17.5 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9 (21 g). (Yield 68%, MS: [M+H]+= 730)
합성예 10Synthesis Example 10
Figure PCTKR2022017844-appb-img-000077
Figure PCTKR2022017844-appb-img-000077
질소 분위기에서 sub9 (15 g, 45.8mmol), amine9 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 10, 20.4g을 얻었다. (수율 71%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub9 (15 g, 45.8 mmol), amine9 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.4 g of Compound 10. (Yield 71%, MS: [M+H]+= 628)
합성예 11Synthesis Example 11
Figure PCTKR2022017844-appb-img-000078
Figure PCTKR2022017844-appb-img-000078
질소 분위기에서 sub10 (15 g, 33mmol), amine10 (10.3g, 33 mmol), sodium tert-butoxide (4.8 g, 49.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 11, 14.4g을 얻었다. (수율 60%, MS: [M+H]+= 728)In a nitrogen atmosphere, sub10 (15 g, 33 mmol), amine10 (10.3 g, 33 mmol), and sodium tert-butoxide (4.8 g, 49.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 11. (Yield 60%, MS: [M+H]+= 728)
합성예 12Synthesis Example 12
Figure PCTKR2022017844-appb-img-000079
Figure PCTKR2022017844-appb-img-000079
질소 분위기에서 sub11 (15 g, 31.2mmol), amine11 (8.1g, 31.2 mmol), sodium tert-butoxide (4.5 g, 46.9 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 12, 15.4g을 얻었다. (수율 70%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub11 (15 g, 31.2 mmol), amine11 (8.1 g, 31.2 mmol), and sodium tert-butoxide (4.5 g, 46.9 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12 (15.4 g). (Yield 70%, MS: [M+H]+= 704)
합성예 13Synthesis Example 13
Figure PCTKR2022017844-appb-img-000080
Figure PCTKR2022017844-appb-img-000080
질소 분위기에서 sub12 (15 g, 37.1mmol), amine12 (15.3g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 13, 17.4g을 얻었다. (수율 60%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub12 (15 g, 37.1 mmol), amine12 (15.3 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13 (17.4 g). (Yield 60%, MS: [M+H]+= 780)
합성예 14Synthesis Example 14
Figure PCTKR2022017844-appb-img-000081
Figure PCTKR2022017844-appb-img-000081
질소 분위기에서 sub13 (15 g, 34.9mmol), amine13 (13.5g, 34.9 mmol), sodium tert-butoxide (5 g, 52.3 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 14, 16.6g을 얻었다. (수율 61%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub13 (15 g, 34.9 mmol), amine13 (13.5 g, 34.9 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 14 (16.6 g). (Yield 61%, MS: [M+H]+= 780)
합성예 15Synthesis Example 15
Figure PCTKR2022017844-appb-img-000082
Figure PCTKR2022017844-appb-img-000082
질소 분위기에서 sub14 (15 g, 45.8mmol), amine14 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 15, 20.4g을 얻었다. (수율 71%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub14 (15 g, 45.8 mmol), amine14 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.4 g of compound 15. (Yield 71%, MS: [M+H]+= 628)
합성예 16Synthesis Example 16
Figure PCTKR2022017844-appb-img-000083
Figure PCTKR2022017844-appb-img-000083
질소 분위기에서 sub15 (15 g, 37.1mmol), amine15 (12.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 16, 16.7g을 얻었다. (수율 64%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub15 (15 g, 37.1 mmol), amine15 (12.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16 (16.7 g). (Yield 64%, MS: [M+H]+= 704)
합성예 17Synthesis Example 17
Figure PCTKR2022017844-appb-img-000084
Figure PCTKR2022017844-appb-img-000084
질소 분위기에서 sub16 (15 g, 37.1mmol), amine16 (12.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 17, 18g을 얻었다. (수율 69%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub16 (15 g, 37.1 mmol), amine16 (12.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compounds 17 and 18g. (Yield 69%, MS: [M+H]+= 704)
합성예 18Synthesis Example 18
Figure PCTKR2022017844-appb-img-000085
Figure PCTKR2022017844-appb-img-000085
질소 분위기에서 sub17 (13.1 g, 37.1mmol), amine17 (14.3g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 18, 16.7g을 얻었다. (수율 64%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub17 (13.1 g, 37.1 mmol), amine17 (14.3 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.7 g of compound 18. (Yield 64%, MS: [M+H]+= 704)
합성예 19Synthesis Example 19
Figure PCTKR2022017844-appb-img-000086
Figure PCTKR2022017844-appb-img-000086
질소 분위기에서 sub18 (15 g, 37.1mmol), amine18 (11.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 19, 16.3g을 얻었다. (수율 65%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub18 (15 g, 37.1 mmol), amine18 (11.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 19 (16.3 g). (Yield 65%, MS: [M+H]+= 678)
합성예 20Synthesis Example 20
Figure PCTKR2022017844-appb-img-000087
Figure PCTKR2022017844-appb-img-000087
질소 분위기에서 sub19 (15 g, 42.4mmol), amine19 (16.4g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 20, 20g을 얻었다. (수율 67%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub19 (15 g, 42.4 mmol), amine19 (16.4 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compounds 20 and 20 g. (Yield 67%, MS: [M+H]+= 704)
합성예 21Synthesis Example 21
Figure PCTKR2022017844-appb-img-000088
Figure PCTKR2022017844-appb-img-000088
질소 분위기에서 sub3 (15 g, 54mmol), amine20 (22.3g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 21, 25g을 얻었다. (수율 71%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub3 (15 g, 54 mmol), amine20 (22.3 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21 (25 g). (Yield 71%, MS: [M+H]+= 654)
합성예 22Synthesis Example 22
Figure PCTKR2022017844-appb-img-000089
Figure PCTKR2022017844-appb-img-000089
질소 분위기에서 sub20 (15 g, 37.1mmol), amine15 (12.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 22, 19.3g을 얻었다. (수율 74%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub20 (15 g, 37.1 mmol), amine15 (12.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.3 g of compound 22. (Yield 74%, MS: [M+H]+= 704)
합성예 23Synthesis Example 23
Figure PCTKR2022017844-appb-img-000090
Figure PCTKR2022017844-appb-img-000090
질소 분위기에서 sub21 (15 g, 45.8mmol), amine21 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 23, 21.2g을 얻었다. (수율 74%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub21 (15 g, 45.8 mmol), amine21 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 23 (21.2 g). (Yield 74%, MS: [M+H]+= 628)
합성예 24Synthesis Example 24
Figure PCTKR2022017844-appb-img-000091
Figure PCTKR2022017844-appb-img-000091
질소 분위기에서 sub3 (15 g, 54mmol), amine22 (25g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 24, 23.5g을 얻었다. (수율 62%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub3 (15 g, 54 mmol), amine22 (25 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 24 (23.5 g). (Yield 62%, MS: [M+H]+= 704)
합성예 25Synthesis Example 25
Figure PCTKR2022017844-appb-img-000092
Figure PCTKR2022017844-appb-img-000092
질소 분위기에서 sub22 (15 g, 37.1mmol), amine23 (15.3g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 25, 19.4g을 얻었다. (수율 67%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub22 (15 g, 37.1 mmol), amine23 (15.3 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.4 g of compound 25. (Yield 67%, MS: [M+H]+= 780)
합성예 26Synthesis Example 26
Figure PCTKR2022017844-appb-img-000093
Figure PCTKR2022017844-appb-img-000093
질소 분위기에서 sub1 (15 g, 42.4mmol), amine24 (18.5g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 26, 19.8g을 얻었다. (수율 62%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub1 (15 g, 42.4 mmol), amine24 (18.5 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.8 g of compound 26. (Yield 62%, MS: [M+H]+= 754)
합성예 27Synthesis Example 27
Figure PCTKR2022017844-appb-img-000094
Figure PCTKR2022017844-appb-img-000094
질소 분위기에서 sub23 (15 g, 34.9mmol), amine25 (11.7g, 34.9 mmol), sodium tert-butoxide (5 g, 52.3 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 27, 15.8g을 얻었다. (수율 62%, MS: [M+H]+= 730)In a nitrogen atmosphere, sub23 (15 g, 34.9 mmol), amine25 (11.7 g, 34.9 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.8 g of compound 27. (Yield 62%, MS: [M+H]+= 730)
합성예 28Synthesis Example 28
Figure PCTKR2022017844-appb-img-000095
Figure PCTKR2022017844-appb-img-000095
질소 분위기에서 sub24 (15 g, 45.8mmol), amine26 (17.7g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 28, 18g을 얻었다. (수율 61%, MS: [M+H]+= 645)In a nitrogen atmosphere, sub24 (15 g, 45.8 mmol), amine26 (17.7 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 28 (18 g). (Yield 61%, MS: [M+H]+= 645)
합성예 29Synthesis Example 29
Figure PCTKR2022017844-appb-img-000096
Figure PCTKR2022017844-appb-img-000096
질소 분위기에서 sub25 (15 g, 42.4mmol), amine27 (14.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 29, 19.9g을 얻었다. (수율 72%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub25 (15 g, 42.4 mmol), amine27 (14.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.9 g of compound 29. (Yield 72%, MS: [M+H]+= 654)
합성예 30Synthesis Example 30
Figure PCTKR2022017844-appb-img-000097
Figure PCTKR2022017844-appb-img-000097
질소 분위기에서 sub14 (15 g, 45.8mmol), amine28 (17.7g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 30, 19.2g을 얻었다. (수율 62%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub14 (15 g, 45.8 mmol), amine28 (17.7 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.2 g of compound 30. (Yield 62%, MS: [M+H]+= 678)
합성예 31Synthesis Example 31
Figure PCTKR2022017844-appb-img-000098
Figure PCTKR2022017844-appb-img-000098
질소 분위기에서 sub26 (15 g, 42.4mmol), amine29 (11g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 31, 15.2g을 얻었다. (수율 62%, MS: [M+H]+= 578)In a nitrogen atmosphere, sub26 (15 g, 42.4 mmol), amine29 (11 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of compound 31. (Yield 62%, MS: [M+H]+= 578)
합성예 32Synthesis Example 32
Figure PCTKR2022017844-appb-img-000099
Figure PCTKR2022017844-appb-img-000099
질소 분위기에서 sub20 (15 g, 37.1mmol), amine30 (12.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 32, 16.2g을 얻었다. (수율 62%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub20 (15 g, 37.1 mmol), amine30 (12.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.2 g of compound 32. (Yield 62%, MS: [M+H]+= 704)
합성예 33Synthesis Example 33
Figure PCTKR2022017844-appb-img-000100
Figure PCTKR2022017844-appb-img-000100
질소 분위기에서 sub27 (15 g, 54mmol), amine31 (23.6g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 33, 23.4g을 얻었다. (수율 64%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine31 (23.6 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.4 g of compound 33. (Yield 64%, MS: [M+H]+= 678)
합성예 34Synthesis Example 34
Figure PCTKR2022017844-appb-img-000101
Figure PCTKR2022017844-appb-img-000101
질소 분위기에서 sub28 (15 g, 33mmol), amine32 (11.9g, 33 mmol), sodium tert-butoxide (4.8 g, 49.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 34, 16.4g을 얻었다. (수율 64%, MS: [M+H]+= 778)In a nitrogen atmosphere, sub28 (15 g, 33 mmol), amine32 (11.9 g, 33 mmol), and sodium tert-butoxide (4.8 g, 49.6 mmol) were added to 300 ml of xylene and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.4 g of compound 34. (Yield 64%, MS: [M+H]+= 778)
합성예 35Synthesis Example 35
Figure PCTKR2022017844-appb-img-000102
Figure PCTKR2022017844-appb-img-000102
질소 분위기에서 sub29 (15 g, 42.4mmol), amine33 (17.5g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 35, 19.5g을 얻었다. (수율 63%, MS: [M+H]+= 730)In a nitrogen atmosphere, sub29 (15 g, 42.4 mmol), amine33 (17.5 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.5 g of compound 35. (Yield 63%, MS: [M+H]+= 730)
합성예 36Synthesis Example 36
Figure PCTKR2022017844-appb-img-000103
Figure PCTKR2022017844-appb-img-000103
질소 분위기에서 sub20 (15 g, 37.1mmol), amine34 (9.7g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 36, 16.8g을 얻었다. (수율 72%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub20 (15 g, 37.1 mmol), amine34 (9.7 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of compound 36. (Yield 72%, MS: [M+H]+= 628)
합성예 37Synthesis Example 37
Figure PCTKR2022017844-appb-img-000104
Figure PCTKR2022017844-appb-img-000104
질소 분위기에서 sub30 (15 g, 45.8mmol), amine35 (18.9g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 37, 19.3g을 얻었다. (수율 60%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub30 (15 g, 45.8 mmol), amine35 (18.9 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.3 g of compound 37. (Yield 60%, MS: [M+H]+= 704)
합성예 38Synthesis Example 38
Figure PCTKR2022017844-appb-img-000105
Figure PCTKR2022017844-appb-img-000105
질소 분위기에서 sub2 (15 g, 45.8mmol), amine36 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 38, 20.1g을 얻었다. (수율 70%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub2 (15 g, 45.8 mmol), amine36 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 38 (20.1 g). (Yield 70%, MS: [M+H]+= 628)
합성예 39Synthesis Example 39
Figure PCTKR2022017844-appb-img-000106
Figure PCTKR2022017844-appb-img-000106
질소 분위기에서 sub31 (15 g, 45.8mmol), amine37 (21.2g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 39, 22.7g을 얻었다. (수율 66%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub31 (15 g, 45.8 mmol), amine37 (21.2 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.7 g of compound 39. (Yield 66%, MS: [M+H]+= 754)
합성예 40Synthesis Example 40
Figure PCTKR2022017844-appb-img-000107
Figure PCTKR2022017844-appb-img-000107
질소 분위기에서 sub3 (15 g, 54mmol), amine38 (27.7g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 40, 29.7g을 얻었다. (수율 73%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub3 (15 g, 54 mmol), amine38 (27.7 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 29.7 g of Compound 40. (Yield 73%, MS: [M+H]+= 754)
합성예 41Synthesis Example 41
Figure PCTKR2022017844-appb-img-000108
Figure PCTKR2022017844-appb-img-000108
질소 분위기에서 sub32 (15 g, 33mmol), amine39 (13.6g, 33 mmol), sodium tert-butoxide (4.8 g, 49.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 41, 18.4g을 얻었다. (수율 67%, MS: [M+H]+= 830)In a nitrogen atmosphere, sub32 (15 g, 33 mmol), amine39 (13.6 g, 33 mmol), and sodium tert-butoxide (4.8 g, 49.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.4 g of compound 41. (Yield 67%, MS: [M+H]+= 830)
합성예 42Synthesis Example 42
Figure PCTKR2022017844-appb-img-000109
Figure PCTKR2022017844-appb-img-000109
질소 분위기에서 sub33 (15 g, 37.1mmol), amine40 (12.5g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 42, 15.7g을 얻었다. (수율 60%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub33 (15 g, 37.1 mmol), amine40 (12.5 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.7 g of compound 42. (Yield 60%, MS: [M+H]+= 704)
합성예 43Synthesis Example 43
Figure PCTKR2022017844-appb-img-000110
Figure PCTKR2022017844-appb-img-000110
질소 분위기에서 sub19 (15 g, 42.4mmol), amine40 (14.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 43, 19.1g을 얻었다. (수율 69%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub19 (15 g, 42.4 mmol), amine40 (14.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.1 g of compound 43. (Yield 69%, MS: [M+H]+= 654)
합성예 44Synthesis Example 44
Figure PCTKR2022017844-appb-img-000111
Figure PCTKR2022017844-appb-img-000111
질소 분위기에서 sub1 (15 g, 42.4mmol), amine41 (11g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 44, 17.1g을 얻었다. (수율 70%, MS: [M+H]+= 578)In a nitrogen atmosphere, sub1 (15 g, 42.4 mmol), amine41 (11 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of Compound 44. (Yield 70%, MS: [M+H]+= 578)
합성예 45Synthesis Example 45
Figure PCTKR2022017844-appb-img-000112
Figure PCTKR2022017844-appb-img-000112
질소 분위기에서 sub34 (15 g, 45.8mmol), amine41 (11.9g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 45, 18.9g을 얻었다. (수율 75%, MS: [M+H]+= 552)In a nitrogen atmosphere, sub34 (15 g, 45.8 mmol), amine41 (11.9 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.9 g of compound 45. (Yield 75%, MS: [M+H]+= 552)
합성예 46Synthesis Example 46
Figure PCTKR2022017844-appb-img-000113
Figure PCTKR2022017844-appb-img-000113
질소 분위기에서 sub35 (15 g, 37.1mmol), amine41 (9.7g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 46, 15.6g을 얻었다. (수율 67%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub35 (15 g, 37.1 mmol), amine41 (9.7 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound 46. (Yield 67%, MS: [M+H]+= 628)
합성예 47Synthesis Example 47
Figure PCTKR2022017844-appb-img-000114
Figure PCTKR2022017844-appb-img-000114
질소 분위기에서 sub25 (15 g, 42.4mmol), amine41 (11g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 47, 17.4g을 얻었다. (수율 71%, MS: [M+H]+= 578)In a nitrogen atmosphere, sub25 (15 g, 42.4 mmol), amine41 (11 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 47 (17.4 g). (Yield 71%, MS: [M+H]+= 578)
합성예 48Synthesis Example 48
Figure PCTKR2022017844-appb-img-000115
Figure PCTKR2022017844-appb-img-000115
질소 분위기에서 sub36 (15 g, 33mmol), amine42 (10.3g, 33 mmol), sodium tert-butoxide (4.8 g, 49.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 48, 17.3g을 얻었다. (수율 72%, MS: [M+H]+= 728)In a nitrogen atmosphere, sub36 (15 g, 33 mmol), amine42 (10.3 g, 33 mmol), and sodium tert-butoxide (4.8 g, 49.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of compound 48. (Yield 72%, MS: [M+H]+= 728)
합성예 49Synthesis Example 49
Figure PCTKR2022017844-appb-img-000116
Figure PCTKR2022017844-appb-img-000116
질소 분위기에서 sub37 (15 g, 45.8mmol), amine43 (18.9g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 49, 21.6g을 얻었다. (수율 67%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub37 (15 g, 45.8 mmol), amine43 (18.9 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 49 (21.6 g). (Yield 67%, MS: [M+H]+= 704)
합성예 50Synthesis Example 50
Figure PCTKR2022017844-appb-img-000117
Figure PCTKR2022017844-appb-img-000117
질소 분위기에서 sub27 (15 g, 54mmol), amine44 (20.9g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 50, 23.7g을 얻었다. (수율 70%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine44 (20.9 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.7 g of compound 50. (Yield 70%, MS: [M+H]+= 628)
합성예 51Synthesis Example 51
Figure PCTKR2022017844-appb-img-000118
Figure PCTKR2022017844-appb-img-000118
질소 분위기에서 sub38 (15 g, 31.2mmol), amine45 (10.5g, 31.2 mmol), sodium tert-butoxide (4.5 g, 46.9 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 51, 18g을 얻었다. (수율 74%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub38 (15 g, 31.2 mmol), amine45 (10.5 g, 31.2 mmol), and sodium tert-butoxide (4.5 g, 46.9 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 51 (18 g). (Yield 74%, MS: [M+H]+= 780)
합성예 52Synthesis Example 52
Figure PCTKR2022017844-appb-img-000119
Figure PCTKR2022017844-appb-img-000119
질소 분위기에서 sub34 (15 g, 45.8mmol), amine46 (11.9g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 52, 17.4g을 얻었다. (수율 69%, MS: [M+H]+= 552)In a nitrogen atmosphere, sub34 (15 g, 45.8 mmol), amine46 (11.9 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.4 g of compound 52. (Yield 69%, MS: [M+H]+= 552)
합성예 53Synthesis Example 53
Figure PCTKR2022017844-appb-img-000120
Figure PCTKR2022017844-appb-img-000120
질소 분위기에서 sub39 (15 g, 37.1mmol), amine47 (14.4g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 53, 17.6g을 얻었다. (수율 63%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub39 (15 g, 37.1 mmol), amine47 (14.4 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of compound 53. (Yield 63%, MS: [M+H]+= 754)
합성예 54Synthesis Example 54
Figure PCTKR2022017844-appb-img-000121
Figure PCTKR2022017844-appb-img-000121
질소 분위기에서 sub40 (15 g, 39.7mmol), amine46 (10.3g, 39.7 mmol), sodium tert-butoxide (5.7 g, 59.5 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 54, 15.8g을 얻었다. (수율 66%, MS: [M+H]+= 602)In a nitrogen atmosphere, sub40 (15 g, 39.7 mmol), amine46 (10.3 g, 39.7 mmol), and sodium tert-butoxide (5.7 g, 59.5 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.8 g of compound 54. (Yield 66%, MS: [M+H]+= 602)
합성예 55Synthesis Example 55
Figure PCTKR2022017844-appb-img-000122
Figure PCTKR2022017844-appb-img-000122
질소 분위기에서 sub27 (15 g, 54mmol), amine48 (22.3g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 55, 21.5g을 얻었다. (수율 61%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine48 (22.3 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.5 g of compound 55. (Yield 61%, MS: [M+H]+= 654)
합성예 56Synthesis Example 56
Figure PCTKR2022017844-appb-img-000123
Figure PCTKR2022017844-appb-img-000123
질소 분위기에서 sub6 (15 g, 45.8mmol), amine49 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 56, 20.7g을 얻었다. (수율 72%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub6 (15 g, 45.8 mmol), amine49 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.7 g of compound 56. (Yield 72%, MS: [M+H]+= 628)
합성예 57Synthesis Example 57
Figure PCTKR2022017844-appb-img-000124
Figure PCTKR2022017844-appb-img-000124
질소 분위기에서 sub6 (15 g, 54mmol), amine48 (22.3g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 57, 25g을 얻었다. (수율 71%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub6 (15 g, 54 mmol), amine48 (22.3 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 57 (25 g). (Yield 71%, MS: [M+H]+= 654)
합성예 58Synthesis Example 58
Figure PCTKR2022017844-appb-img-000125
Figure PCTKR2022017844-appb-img-000125
질소 분위기에서 sub41 (15 g, 45.8mmol), amine50 (22.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 58, 26.4g을 얻었다. (수율 74%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub41 (15 g, 45.8 mmol), amine50 (22.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.4 g of compound 58. (Yield 74%, MS: [M+H]+= 780)
합성예 59Synthesis Example 59
Figure PCTKR2022017844-appb-img-000126
Figure PCTKR2022017844-appb-img-000126
질소 분위기에서 sub27 (15 g, 54mmol), amine51 (20.9g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 59, 20g을 얻었다. (수율 64%, MS: [M+H]+= 578)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine51 (20.9 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 59 (20 g). (Yield 64%, MS: [M+H]+= 578)
합성예 60Synthesis Example 60
Figure PCTKR2022017844-appb-img-000127
Figure PCTKR2022017844-appb-img-000127
질소 분위기에서 sub27 (15 g, 54mmol), amine52 (20.9g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 60, 24.4g을 얻었다. (수율 72%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine52 (20.9 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.4 g of compound 60. (Yield 72%, MS: [M+H]+= 628)
합성예 61Synthesis Example 61
Figure PCTKR2022017844-appb-img-000128
Figure PCTKR2022017844-appb-img-000128
질소 분위기에서 sub25 (15 g, 42.4mmol), amine53 (14.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 61, 19.7g을 얻었다. (수율 71%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub25 (15 g, 42.4 mmol), amine53 (14.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.7 g of compound 61. (Yield 71%, MS: [M+H]+= 654)
합성예 62Synthesis Example 62
Figure PCTKR2022017844-appb-img-000129
Figure PCTKR2022017844-appb-img-000129
질소 분위기에서 sub23 (15 g, 34.9mmol), amine54 (10.8g, 34.9 mmol), sodium tert-butoxide (5 g, 52.3 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 62, 17.2g을 얻었다. (수율 70%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub23 (15 g, 34.9 mmol), amine54 (10.8 g, 34.9 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.2 g of compound 62. (Yield 70%, MS: [M+H]+= 704)
합성예 63Synthesis Example 63
Figure PCTKR2022017844-appb-img-000130
Figure PCTKR2022017844-appb-img-000130
질소 분위기에서 sub37 (15 g, 45.8mmol), amine55 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 63, 21g을 얻었다. (수율 73%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub37 (15 g, 45.8 mmol), amine55 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 63 (21 g). (Yield 73%, MS: [M+H]+= 628)
합성예 64Synthesis Example 64
Figure PCTKR2022017844-appb-img-000131
Figure PCTKR2022017844-appb-img-000131
질소 분위기에서 sub42 (15 g, 37.1mmol), amine56 (17.2g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 64, 20.6g을 얻었다. (수율 67%, MS: [M+H]+= 830)In a nitrogen atmosphere, sub42 (15 g, 37.1 mmol), amine56 (17.2 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.6 g of compound 64. (Yield 67%, MS: [M+H]+= 830)
합성예 65Synthesis Example 65
Figure PCTKR2022017844-appb-img-000132
Figure PCTKR2022017844-appb-img-000132
질소 분위기에서 sub25 (15 g, 42.4mmol), amine57 (15.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 65, 18.9g을 얻었다. (수율 66%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub25 (15 g, 42.4 mmol), amine57 (15.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.9 g of compound 65. (Yield 66%, MS: [M+H]+= 678)
합성예 66Synthesis Example 66
Figure PCTKR2022017844-appb-img-000133
Figure PCTKR2022017844-appb-img-000133
질소 분위기에서 sub43 (15 g, 39.7mmol), amine58 (13.4g, 39.7 mmol), sodium tert-butoxide (5.7 g, 59.5 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 66, 18g을 얻었다. (수율 67%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub43 (15 g, 39.7 mmol), amine58 (13.4 g, 39.7 mmol), and sodium tert-butoxide (5.7 g, 59.5 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18 g of compound 66. (Yield 67%, MS: [M+H]+= 678)
합성예 67Synthesis Example 67
Figure PCTKR2022017844-appb-img-000134
Figure PCTKR2022017844-appb-img-000134
질소 분위기에서 sub31 (15 g, 45.8mmol), amine58 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 67, 20.4g을 얻었다. (수율 71%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub31 (15 g, 45.8 mmol), amine58 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.4 g of compound 67. (Yield 71%, MS: [M+H]+= 628)
합성예 68Synthesis Example 68
Figure PCTKR2022017844-appb-img-000135
Figure PCTKR2022017844-appb-img-000135
질소 분위기에서 sub14 (15 g, 45.8mmol), amine58 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 68, 18.4g을 얻었다. (수율 64%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub14 (15 g, 45.8 mmol), amine58 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.4 g of compound 68. (Yield 64%, MS: [M+H]+= 628)
합성예 69Synthesis Example 69
Figure PCTKR2022017844-appb-img-000136
Figure PCTKR2022017844-appb-img-000136
질소 분위기에서 sub44 (15 g, 37.1mmol), amine59 (17.2g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 69, 18.5g을 얻었다. (수율 60%, MS: [M+H]+= 830)In a nitrogen atmosphere, sub44 (15 g, 37.1 mmol), amine59 (17.2 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.5 g of compound 69. (Yield 60%, MS: [M+H]+= 830)
합성예 70Synthesis Example 70
Figure PCTKR2022017844-appb-img-000137
Figure PCTKR2022017844-appb-img-000137
질소 분위기에서 sub45 (15 g, 37.1mmol), amine60 (9.7g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 70, 14.4g을 얻었다. (수율 62%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub45 (15 g, 37.1 mmol), amine60 (9.7 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 70. (Yield 62%, MS: [M+H]+= 628)
합성예 71Synthesis Example 71
Figure PCTKR2022017844-appb-img-000138
Figure PCTKR2022017844-appb-img-000138
질소 분위기에서 sub17 (15 g, 42.4mmol), amine61 (16.4g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 71, 22.1g을 얻었다. (수율 74%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub17 (15 g, 42.4 mmol), amine61 (16.4 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 71 (22.1 g). (Yield 74%, MS: [M+H]+= 704)
합성예 72Synthesis Example 72
Figure PCTKR2022017844-appb-img-000139
Figure PCTKR2022017844-appb-img-000139
질소 분위기에서 sub46 (15 g, 39.7mmol), amine62 (16.4g, 39.7 mmol), sodium tert-butoxide (5.7 g, 59.5 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 72, 21.5g을 얻었다. (수율 72%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub46 (15 g, 39.7 mmol), amine62 (16.4 g, 39.7 mmol), and sodium tert-butoxide (5.7 g, 59.5 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.5 g of compound 72. (Yield 72%, MS: [M+H]+= 754)
합성예 73Synthesis Example 73
Figure PCTKR2022017844-appb-img-000140
Figure PCTKR2022017844-appb-img-000140
질소 분위기에서 sub8 (15 g, 42.4mmol), amine63 (19.6g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 73, 22.8g을 얻었다. (수율 69%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub8 (15 g, 42.4 mmol), amine63 (19.6 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.8 g of compound 73. (Yield 69%, MS: [M+H]+= 780)
합성예 74Synthesis Example 74
Figure PCTKR2022017844-appb-img-000141
Figure PCTKR2022017844-appb-img-000141
질소 분위기에서 sub47 (15 g, 45.8mmol), amine64 (21.2g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 74, 25.9g을 얻었다. (수율 75%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub47 (15 g, 45.8 mmol), amine64 (21.2 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25.9 g of compound 74. (Yield 75%, MS: [M+H]+= 754)
합성예 75Synthesis Example 75
Figure PCTKR2022017844-appb-img-000142
Figure PCTKR2022017844-appb-img-000142
질소 분위기에서 sub48 (15 g, 37.1mmol), amine65 (14.4g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 75, 18.5g을 얻었다. (수율 66%, MS: [M+H]+= 754)In a nitrogen atmosphere, sub48 (15 g, 37.1 mmol), amine65 (14.4 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.5 g of compound 75. (Yield 66%, MS: [M+H]+= 754)
합성예 76Synthesis Example 76
Figure PCTKR2022017844-appb-img-000143
Figure PCTKR2022017844-appb-img-000143
질소 분위기에서 sub40 (15 g, 39.7mmol), amine66 (15.3g, 39.7 mmol), sodium tert-butoxide (5.7 g, 59.5 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 76, 20.2g을 얻었다. (수율 70%, MS: [M+H]+= 728)In a nitrogen atmosphere, sub40 (15 g, 39.7 mmol), amine66 (15.3 g, 39.7 mmol), and sodium tert-butoxide (5.7 g, 59.5 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.2 g of compound 76. (Yield 70%, MS: [M+H]+= 728)
합성예 77Synthesis Example 77
Figure PCTKR2022017844-appb-img-000144
Figure PCTKR2022017844-appb-img-000144
질소 분위기에서 sub27 (15 g, 54mmol), amine67 (22.3g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 5시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 77, 22.2g을 얻었다. (수율 63%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub27 (15 g, 54 mmol), amine67 (22.3 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 77 (22.2 g). (Yield 63%, MS: [M+H]+= 654)
합성예 78Synthesis Example 78
Figure PCTKR2022017844-appb-img-000145
Figure PCTKR2022017844-appb-img-000145
질소 분위기에서 sub22 (15 g, 37.1mmol), amine68 (15.3g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 78, 17.9g을 얻었다. (수율 62%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub22 (15 g, 37.1 mmol), amine68 (15.3 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.9 g of compound 78. (Yield 62%, MS: [M+H]+= 780)
합성예 79Synthesis Example 79
Figure PCTKR2022017844-appb-img-000146
Figure PCTKR2022017844-appb-img-000146
질소 분위기에서 sub3 (15 g, 54mmol), amine69 (20.9g, 54 mmol), sodium tert-butoxide (7.8 g, 81 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 79, 23.7g을 얻었다. (수율 70%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub3 (15 g, 54 mmol), amine69 (20.9 g, 54 mmol), and sodium tert-butoxide (7.8 g, 81 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 79 (23.7 g). (Yield 70%, MS: [M+H]+= 628)
합성예 80Synthesis Example 80
Figure PCTKR2022017844-appb-img-000147
Figure PCTKR2022017844-appb-img-000147
질소 분위기에서 sub26 (15 g, 42.4mmol), amine70 (15.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 80, 20.1g을 얻었다. (수율 70%, MS: [M+H]+= 678)In a nitrogen atmosphere, sub26 (15 g, 42.4 mmol), amine70 (15.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.1 g of Compound 80. (Yield 70%, MS: [M+H]+= 678)
합성예 81Synthesis Example 81
Figure PCTKR2022017844-appb-img-000148
Figure PCTKR2022017844-appb-img-000148
질소 분위기에서 sub37 (15 g, 45.8mmol), amine71 (15.4g, 45.8 mmol), sodium tert-butoxide (6.6 g, 68.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 81, 18.4g을 얻었다. (수율 64%, MS: [M+H]+= 628)In a nitrogen atmosphere, sub37 (15 g, 45.8 mmol), amine71 (15.4 g, 45.8 mmol), and sodium tert-butoxide (6.6 g, 68.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.4 g of compound 81. (Yield 64%, MS: [M+H]+= 628)
합성예 82Synthesis Example 82
Figure PCTKR2022017844-appb-img-000149
Figure PCTKR2022017844-appb-img-000149
질소 분위기에서 sub49 (15 g, 39.7mmol), amine72 (15.3g, 39.7 mmol), sodium tert-butoxide (5.7 g, 59.5 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 4시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 82, 19.3g을 얻었다. (수율 67%, MS: [M+H]+= 728)In a nitrogen atmosphere, sub49 (15 g, 39.7 mmol), amine72 (15.3 g, 39.7 mmol), and sodium tert-butoxide (5.7 g, 59.5 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.3 g of compound 82. (Yield 67%, MS: [M+H]+= 728)
합성예 83Synthesis Example 83
Figure PCTKR2022017844-appb-img-000150
Figure PCTKR2022017844-appb-img-000150
질소 분위기에서 sub49 (15 g, 42.4mmol), amine73 (19.6g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 83, 21.1g을 얻었다. (수율 64%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub49 (15 g, 42.4 mmol), amine73 (19.6 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.1 g of Compound 83. (Yield 64%, MS: [M+H]+= 780)
합성예 84Synthesis Example 84
Figure PCTKR2022017844-appb-img-000151
Figure PCTKR2022017844-appb-img-000151
질소 분위기에서 sub19 (15 g, 42.4mmol), amine74 (14.3g, 42.4 mmol), sodium tert-butoxide (6.1 g, 63.6 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 3시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 84, 19.1g을 얻었다. (수율 69%, MS: [M+H]+= 654)In a nitrogen atmosphere, sub19 (15 g, 42.4 mmol), amine74 (14.3 g, 42.4 mmol), and sodium tert-butoxide (6.1 g, 63.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.1 g of compound 84. (Yield 69%, MS: [M+H]+= 654)
합성예 85Synthesis Example 85
Figure PCTKR2022017844-appb-img-000152
Figure PCTKR2022017844-appb-img-000152
질소 분위기에서 sub50 (15 g, 37.1mmol), amine75 (15.3g, 37.1 mmol), sodium tert-butoxide (5.4 g, 55.7 mmol)을 Xylene 300ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol)을 투입했다. 2시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 85, 21.7g을 얻었다. (수율 75%, MS: [M+H]+= 780)In a nitrogen atmosphere, sub50 (15 g, 37.1 mmol), amine75 (15.3 g, 37.1 mmol), and sodium tert-butoxide (5.4 g, 55.7 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.7 g of compound 85. (Yield 75%, MS: [M+H]+= 780)
[실험예][Experimental example]
실험예 1-1Experimental Example 1-1
ITO(Indium Tin Oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 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 ITO (Indium Tin Oxide) to a thickness of 1,400 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 하기 HI-1 화합물을 1150Å의 두께로 형성하되 하기 A-1 화합물을 1.5% 농도로 p-doping 했다. 상기 정공주입층 위에 하기 HT-1 화합물을 진공 증착 하여 막 두께 800Å의 정공수송층을 형성했다. 이어서 전자차단층으로 상기 합성예 1에서 제조된 화합물 1을 150Å의 두께로 열 진공 증착 하였다. 이어서, 발광층으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 200Å의 두께로 진공 증착 하였다. 이어서, 정공차단층으로 하기 화학식 HB-1으로 표시되는 화합물을 50Å의 두께로 진공 증착 하였다. 이어서, 전자 주입 및 수송층으로 하기 화학식 ET-1로 표시되는 화합물과 하기 LiQ로 표시되는 화합물을 1:1의 중량비로 310Å의 두께로 열 진공 증착 하였다. 상기 전자 수송 및 전자 주입층 위에 순차적으로 12Å의 두께로 리튬플로라이드(LiF)와 1000Å 두께로 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum deposited to form a hole transport layer having a thickness of 800 Å. Subsequently, Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 Å as an electron blocking layer. Subsequently, as a light emitting layer, a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD were vacuum deposited to a thickness of 200 Å at a weight ratio of 25:1. Then, as a hole blocking layer, a compound represented by Chemical Formula HB-1 was vacuum deposited to a thickness of 50 Å. Subsequently, as an electron injection and transport layer, a compound represented by Formula ET-1 and a compound represented by LiQ were thermally vacuum deposited to a thickness of 310 Å at a weight ratio of 1:1. An organic light emitting diode was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å to form a cathode on the electron transport and electron injection layers.
Figure PCTKR2022017844-appb-img-000153
Figure PCTKR2022017844-appb-img-000153
실험예 1-2 내지 1-85Experimental Examples 1-2 to 1-85
상기 실험예 1-1의 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 실험예 1-2 내지 1-85의 유기 발광 소자를 제조하였다.Organic light emitting devices of Experimental Examples 1-2 to 1-85 were prepared in the same manner as in Experimental Example 1-1, except for using the compound shown in Table 1 instead of Compound 1 of Experimental Example 1-1. .
비교실험예 1-1 내지 1-8Comparative Experimental Examples 1-1 to 1-8
상기 실험예 1-1의 화합물 1 대신 하기 화합물 EB1 내지 EB8을 각각 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 비교실험예 1-1 내지 1-8의 유기 발광 소자를 제조하였다.Organic light-emitting devices of Comparative Experimental Examples 1-1 to 1-8 were prepared in the same manner as in Experimental Example 1-1, except that the following compounds EB1 to EB8 were used instead of Compound 1 of Experimental Example 1-1.
Figure PCTKR2022017844-appb-img-000154
Figure PCTKR2022017844-appb-img-000154
실험예 1-1 내지 1-85 및 비교실험예 1-1 내지 1-8에서 제조한 유기 발광 소자에 10 mA/cm2의 전류를 인가하였을 때, 전압, 효율을 측정하고 그 결과를 하기 표 1에 나타내었다. 수명T95는 휘도가 초기 휘도(1000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다When a current of 10 mA/cm 2 was applied to the organic light emitting devices prepared in Experimental Examples 1-1 to 1-85 and Comparative Experimental Examples 1-1 to 1-8, voltage and efficiency were measured, and the results are shown in the table below. 1. Lifetime T95 means the time required for the luminance to decrease from the initial luminance (1000 nit) to 95%.
화합물compound 전압(V)Voltage (V) 효율(cd/A)Efficiency (cd/A) 수명T95(hr)Life T95 (hr) 발광색luminescent color
실험예 1-1Experimental Example 1-1 화합물 1compound 1 3.32 3.32 5.145.14 195195 청색blue
실험예 1-2Experimental Example 1-2 화합물 2compound 2 3.34 3.34 5.115.11 207207 청색blue
실험예 1-3Experimental Example 1-3 화합물 3compound 3 3.40 3.40 5.145.14 207207 청색blue
실험예 1-4Experimental Example 1-4 화합물 4compound 4 3.40 3.40 5.115.11 194194 청색blue
실험예 1-5Experimental Example 1-5 화합물 5compound 5 3.39 3.39 5.125.12 201201 청색blue
실험예 1-6Experimental Example 1-6 화합물 6compound 6 3.35 3.35 5.195.19 203203 청색blue
실험예 1-7Experimental Example 1-7 화합물 7compound 7 3.37 3.37 5.155.15 194194 청색blue
실험예 1-8Experimental Example 1-8 화합물 8compound 8 3.39 3.39 5.185.18 195195 청색blue
실험예 1-9Experimental Example 1-9 화합물 9compound 9 3.40 3.40 5.185.18 198198 청색blue
실험예 1-10Experimental Example 1-10 화합물 10compound 10 3.41 3.41 5.095.09 202202 청색blue
실험예 1-11Experimental Example 1-11 화합물 11compound 11 3.37 3.37 5.135.13 211211 청색blue
실험예 1-12Experimental Example 1-12 화합물 12compound 12 3.32 3.32 5.185.18 198198 청색blue
실험예 1-13Experimental Example 1-13 화합물 13compound 13 3.24 3.24 5.525.52 230230 청색blue
실험예 1-14Experimental Example 1-14 화합물 14compound 14 3.36 3.36 5.075.07 207207 청색blue
실험예 1-15Experimental Example 1-15 화합물 15compound 15 3.27 3.27 5.215.21 237237 청색blue
실험예 1-16Experimental Example 1-16 화합물 16compound 16 3.27 3.27 5.165.16 226226 청색blue
실험예 1-17Experimental Example 1-17 화합물 17compound 17 3.22 3.22 5.155.15 232232 청색blue
실험예 1-18Experimental Example 1-18 화합물 18compound 18 3.25 3.25 5.125.12 232232 청색blue
실험예 1-19Experimental Example 1-19 화합물 19compound 19 3.21 3.21 5.085.08 229229 청색blue
실험예 1-20Experimental Example 1-20 화합물 20compound 20 3.25 3.25 5.085.08 228228 청색blue
실험예 1-21Experimental Example 1-21 화합물 21compound 21 3.24 3.24 5.145.14 230230 청색blue
실험예 1-22Experimental Example 1-22 화합물 22compound 22 3.23 3.23 5.075.07 233233 청색blue
실험예 1-23Experimental Example 1-23 화합물 23compound 23 3.27 3.27 5.475.47 233233 청색blue
실험예 1-24Experimental Example 1-24 화합물 24compound 24 3.28 3.28 5.485.48 235235 청색blue
실험예 1-25Experimental Example 1-25 화합물 25compound 25 3.22 3.22 5.325.32 227227 청색blue
실험예 1-26Experimental Example 1-26 화합물 26compound 26 3.22 3.22 5.345.34 228228 청색blue
실험예 1-27Experimental Example 1-27 화합물 27compound 27 3.27 3.27 5.375.37 223223 청색blue
실험예 1-28Experimental Example 1-28 화합물 28compound 28 3.28 3.28 5.355.35 211211 청색blue
실험예 1-29Experimental Example 1-29 화합물 29compound 29 3.32 3.32 5.295.29 225225 청색blue
실험예 1-30Experimental Example 1-30 화합물 30compound 30 3.26 3.26 5.295.29 220220 청색blue
실험예 1-31Experimental Example 1-31 화합물 31compound 31 3.32 3.32 5.215.21 211211 청색blue
실험예 1-32Experimental Example 1-32 화합물 32compound 32 3.31 3.31 5.245.24 207207 청색blue
실험예 1-33Experimental Example 1-33 화합물 33compound 33 3.32 3.32 5.345.34 223223 청색blue
실험예 1-34Experimental Example 1-34 화합물 34compound 34 3.28 3.28 5.255.25 211211 청색blue
실험예 1-35Experimental Example 1-35 화합물 35compound 35 3.26 3.26 5.235.23 216216 청색blue
실험예 1-36Experimental Example 1-36 화합물 36compound 36 3.22 3.22 5.075.07 224224 청색blue
실험예 1-37Experimental Example 1-37 화합물 37compound 37 3.20 3.20 5.185.18 225225 청색blue
실험예 1-38Experimental Example 1-38 화합물 38compound 38 3.24 3.24 5.075.07 227227 청색blue
실험예 1-39Experimental Example 1-39 화합물 39compound 39 3.39 3.39 5.105.10 193193 청색blue
실험예 1-40Experimental Example 1-40 화합물 40compound 40 3.36 3.36 5.115.11 210210 청색blue
실험예 1-41Experimental Example 1-41 화합물 41compound 41 3.32 3.32 5.105.10 212212 청색blue
실험예 1-42Experimental Example 1-42 화합물 42compound 42 3.38 3.38 5.175.17 196196 청색blue
실험예 1-43Experimental Example 1-43 화합물 43compound 43 3.36 3.36 5.075.07 208208 청색blue
실험예 1-44Experimental Example 1-44 화합물 44compound 44 3.37 3.37 5.185.18 206206 청색blue
실험예 1-45Experimental Example 1-45 화합물 45compound 45 3.32 3.32 5.165.16 193193 청색blue
실험예 1-46Experimental Example 1-46 화합물 46compound 46 3.31 3.31 5.155.15 215215 청색blue
실험예 1-47Experimental Example 1-47 화합물 47compound 47 3.34 3.34 5.215.21 207207 청색blue
실험예 1-48Experimental Example 1-48 화합물 48compound 48 3.33 3.33 5.245.24 212212 청색blue
실험예 1-49Experimental Example 1-49 화합물 49compound 49 3.31 3.31 5.175.17 214214 청색blue
실험예 1-50Experimental Example 1-50 화합물 50compound 50 3.44 3.44 4.964.96 195195 청색blue
실험예 1-51Experimental Example 1-51 화합물 51compound 51 3.47 3.47 5.015.01 187187 청색blue
실험예 1-52Experimental Example 1-52 화합물 52compound 52 3.40 3.40 5.065.06 185185 청색blue
실험예 1-53Experimental Example 1-53 화합물 53compound 53 3.44 3.44 5.045.04 192192 청색blue
실험예 1-54Experimental Example 1-54 화합물 54compound 54 3.48 3.48 4.964.96 191191 청색blue
실험예 1-55Experimental Example 1-55 화합물 55compound 55 3.44 3.44 5.015.01 190190 청색blue
실험예 1-56Experimental Example 1-56 화합물 56compound 56 3.39 3.39 4.984.98 189189 청색blue
실험예 1-57Experimental Example 1-57 화합물 57compound 57 3.43 3.43 5.035.03 188188 청색blue
실험예 1-58Experimental Example 1-58 화합물 58compound 58 3.39 3.39 4.924.92 183183 청색blue
실험예 1-59Experimental Example 1-59 화합물 59compound 59 3.37 3.37 5.165.16 196196 청색blue
실험예 1-60Experimental Example 1-60 화합물 60compound 60 3.40 3.40 5.215.21 200200 청색blue
실험예 1-61Experimental Example 1-61 화합물 61compound 61 3.35 3.35 5.165.16 202202 청색blue
실험예 1-62Experimental Example 1-62 화합물 62compound 62 3.34 3.34 5.175.17 199199 청색blue
실험예 1-63Experimental Example 1-63 화합물 63compound 63 3.38 3.38 5.075.07 200200 청색blue
실험예 1-64Experimental Example 1-64 화합물 64compound 64 3.39 3.39 5.175.17 199199 청색blue
실험예 1-65Experimental Example 1-65 화합물 65compound 65 3.36 3.36 5.195.19 195195 청색blue
실험예 1-66Experimental Example 1-66 화합물 66compound 66 3.40 3.40 5.175.17 202202 청색blue
실험예 1-67Experimental Example 1-67 화합물 67compound 67 3.34 3.34 5.185.18 205205 청색blue
실험예 1-68Experimental Example 1-68 화합물 68compound 68 3.34 3.34 5.085.08 202202 청색blue
실험예 1-69Experimental Example 1-69 화합물 69compound 69 3.38 3.38 5.175.17 189189 청색blue
실험예 1-70Experimental Example 1-70 화합물 70compound 70 3.32 3.32 5.075.07 182182 청색blue
실험예 1-71Experimental Example 1-71 화합물 71compound 71 3.33 3.33 5.105.10 189189 청색blue
실험예 1-72Experimental Example 1-72 화합물 72compound 72 3.37 3.37 5.165.16 195195 청색blue
실험예 1-73Experimental Example 1-73 화합물 73compound 73 3.36 3.36 5.215.21 184184 청색blue
실험예 1-74Experimental Example 1-74 화합물 74compound 74 3.37 3.37 5.135.13 184184 청색blue
실험예 1-75Experimental Example 1-75 화합물 75compound 75 3.41 3.41 5.215.21 190190 청색blue
실험예 1-76Experimental Example 1-76 화합물 76compound 76 3.36 3.36 5.155.15 193193 청색blue
실험예 1-77Experimental Example 1-77 화합물 77compound 77 3.39 3.39 4.964.96 187187 청색blue
실험예 1-78Experimental Example 1-78 화합물 78compound 78 3.42 3.42 4.924.92 194194 청색blue
실험예 1-79Experimental Example 1-79 화합물 79compound 79 3.41 3.41 4.924.92 190190 청색blue
실험예 1-80Experimental Example 1-80 화합물 80compound 80 3.42 3.42 4.974.97 193193 청색blue
실험예 1-81Experimental Example 1-81 화합물 81compound 81 3.39 3.39 5.025.02 193193 청색blue
실험예 1-82Experimental Example 1-82 화합물 82compound 82 3.40 3.40 5.085.08 183183 청색blue
실험예 1-83Experimental Example 1-83 화합물 83compound 83 3.32 3.32 5.175.17 188188 청색blue
실험예 1-84Experimental Example 1-84 화합물 84compound 84 3.38 3.38 5.185.18 190190 청색blue
실험예 1-85Experimental Example 1-85 화합물 85compound 85 3.41 3.41 5.215.21 189189 청색blue
비교실험예 1-1Comparative Experimental Example 1-1 EB1EB1 3.82 3.82 4.484.48 8484 청색blue
비교실험예 1-2Comparative Experimental Example 1-2 EB2EB2 3.593.59 4.654.65 113113 청색blue
비교실험예 1-3Comparative Experimental Example 1-3 EB3EB3 3.68 3.68 4.514.51 106106 청색blue
비교실험예 1-4Comparative Experimental Example 1-4 EB4EB4 3.74 3.74 4.534.53 8787 청색blue
비교실험예 1-5Comparative Experimental Example 1-5 EB5EB5 3.61 3.61 4.764.76 132132 청색blue
비교실험예 1-6Comparative Experimental Example 1-6 EB6EB6 3.68 3.68 4.804.80 145145 청색blue
비교실험예 1-7Comparative Experimental Example 1-7 EB7EB7 3.73 3.73 4.714.71 8484 청색blue
비교실험예 1-8Comparative Experimental Example 1-8 EB8EB8 3.57 3.57 4.764.76 156156 청색blue
상기 표 1에 나타난 바와 같이, 본 발명의 화합물은 전자차단층으로 사용하였다. 실질적으로는 주입된 전자가 정공 수송층으로 넘어가지 않도록 전자의 이동을 차단하는 역할을 함으로써 유기 발광 소자는 구동 전압, 효율 및 수명 면에서 현저한 효과를 나타내는 것으로 확인되었다.As shown in Table 1, the compound of the present invention was used as an electron blocking layer. It has been confirmed that the organic light-emitting device exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan by substantially serving to block the movement of injected electrons so that they do not pass to the hole transport layer.
구체적으로, 본 명세서의 화학식 1의 화합물을 사용한 유기 발광 소자는 본 명세서의 화학식 1의 벤조퓨로피리미딘 대신 벤조티에노피리미딘을 사용한 비교실험예 1-1, 본 명세서의 화학식 1의 Ar1 대신 피렌기(pyrene)를 사용한 비교실험예 1-2, 본 명세서의 화학식 1의 L3 대신 알킬기로 치환된 아릴기로 치환된 아릴렌기를 사용한 비교실험예 1-3 및 1-4, 및 본원 명세서의 화학식 1의 카바졸, 또는 벤조카바졸 대신 디벤조카바졸을 사용한 비교실험예 1-5 내지 1-8 보다 구동전압, 효율 및 수명이 현저하게 우수한 것을 확인할 수 있었다.Specifically, the organic light emitting device using the compound of Formula 1 of the present specification is Comparative Experimental Example 1-1 using benzothienopyrimidine instead of benzofuropyrimidine of Formula 1 of the present specification, instead of Ar1 of Formula 1 of the present specification Comparative Experimental Example 1-2 using a pyrene group, Comparative Experimental Examples 1-3 and 1-4 using an arylene group substituted with an aryl group substituted with an alkyl group instead of L3 in Formula 1 of the present specification, and Chemical Formulas of the present specification It was confirmed that the driving voltage, efficiency and lifetime were remarkably superior to those of Comparative Experimental Examples 1-5 to 1-8 using dibenzocarbazole instead of carbazole or benzocarbazole of No. 1.
본 발명은 전자차단층에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.The present invention is not limited to the electron blocking layer, and various modifications and implementations are possible within the scope of the claims and the detailed description of the invention, which also belong to the scope of the invention.

Claims (10)

  1. 하기 화학식 1의 화합물:A compound of Formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2022017844-appb-img-000155
    Figure PCTKR2022017844-appb-img-000155
    상기 화학식 1에 있어서,In Formula 1,
    X1은 N 또는 CR1이고, X2는 N 또는 CR2이며, X3는 N 또는 CR3이고, X4는 N 또는 CR4이며, X5는 N 또는 CR5이고, X6은 N 또는 CR6이며, X7은 N 또는 CR7이고, X8은 N 또는 CR8이며, X1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5, X6 is N or CR6, X7 is N or CR7, X8 is N or CR8,
    상기 X1 내지 X8 중 적어도 하나는 N이고, 상기 X1 내지 X8 중 N이 아닌 나머지 중 어느 하나는 L1에 결합되고, At least one of X1 to X8 is N, and any one of the other non-N of X1 to X8 is bonded to L1;
    상기 R1 내지 R8 및 G1 내지 G4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R1 to R8 and G1 to G4 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,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    L3는 직접결합; 중수소, 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L3 is a direct bond; an arylene group unsubstituted or substituted with at least one of heavy hydrogen, an aryl group, and combinations thereof; Or a substituted or unsubstituted heteroarylene group,
    l1 내지 l3는 각각 1 내지 3의 정수이며, l1 to l3 are each an integer of 1 to 3,
    상기 l1이 2 이상인 경우, 상기 2 이상의 L1은 서로 같거나 상이하고,When l1 is 2 or more, the two or more L1s are the same as or different from each other,
    상기 l2가 2 이상인 경우, 상기 2 이상의 L2은 서로 같거나 상이하며,When l2 is 2 or more, the two or more L2s are the same as or different from each other,
    상기 l3이 2 이상인 경우, 상기 2 이상의 L3은 서로 같거나 상이하고,When l3 is 2 or more, the two or more L3s are the same as or different from each other,
    Ar1은 치환 또는 비치환된 단환, 2환, 3환, 또는 5환 이상의 아릴기; 치환 또는 비치환된 크라이센기; 치환 또는 비치환된 벤조페난트렌기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar1 is a substituted or unsubstituted monocyclic, bicyclic, tricyclic, or five- or more-cyclic aryl group; A substituted or unsubstituted Chrysen group; A substituted or unsubstituted benzophenanthrene group; Or a substituted or unsubstituted heteroaryl group,
    A는 치환 또는 비치환된 벤젠; 또는 치환 또는 비치환된 나프탈렌이다.A is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2022017844-appb-img-000156
    Figure PCTKR2022017844-appb-img-000156
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2022017844-appb-img-000157
    Figure PCTKR2022017844-appb-img-000157
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2022017844-appb-img-000158
    Figure PCTKR2022017844-appb-img-000158
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2022017844-appb-img-000159
    Figure PCTKR2022017844-appb-img-000159
    상기 화학식 1-1 내지 1-4에 있어서,In Formulas 1-1 to 1-4,
    X1 내지 X8, L1 내지 L3, l1 내지 l3, Ar1 및 G1 내지 G4의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1 to X8, L1 to L3, l1 to l3, Ar1 and G1 to G4 are the same as defined in Formula 1 above,
    G5 내지 G12는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.G5 to G12 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.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-5 내지 1-12 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-5 to 1-12:
    [화학식 1-5][Formula 1-5]
    Figure PCTKR2022017844-appb-img-000160
    Figure PCTKR2022017844-appb-img-000160
    [화학식 1-6][Formula 1-6]
    Figure PCTKR2022017844-appb-img-000161
    Figure PCTKR2022017844-appb-img-000161
    [화학식 1-7][Formula 1-7]
    Figure PCTKR2022017844-appb-img-000162
    Figure PCTKR2022017844-appb-img-000162
    [화학식 1-8][Formula 1-8]
    Figure PCTKR2022017844-appb-img-000163
    Figure PCTKR2022017844-appb-img-000163
    [화학식 1-9][Formula 1-9]
    Figure PCTKR2022017844-appb-img-000164
    Figure PCTKR2022017844-appb-img-000164
    [화학식 1-10][Formula 1-10]
    Figure PCTKR2022017844-appb-img-000165
    Figure PCTKR2022017844-appb-img-000165
    [화학식 1-11][Formula 1-11]
    Figure PCTKR2022017844-appb-img-000166
    Figure PCTKR2022017844-appb-img-000166
    [화학식 1-12][Formula 1-12]
    Figure PCTKR2022017844-appb-img-000167
    Figure PCTKR2022017844-appb-img-000167
    상기 화학식 1-5 내지 1-12에 있어서,In Formulas 1-5 to 1-12,
    L1 내지 L3, l1 내지 l3, Ar1, G1 내지 G4 및 A의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of L1 to L3, l1 to l3, Ar1, G1 to G4 and A are the same as defined in Formula 1 above,
    R101 및 R102는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R101 and R102 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    r101은 1 내지 3의 정수이고,r101 is an integer from 1 to 3;
    r'101은 1 또는 2 이며,r'101 is 1 or 2;
    r102는 1 내지 4의 정수이고,r102 is an integer from 1 to 4;
    r'102는 1 내지 3의 정수이며,r'102 is an integer from 1 to 3;
    상기 r101이 2 이상인 경우, 상기 2 이상의 R101은 서로 같거나 상이하고,When r101 is 2 or more, the two or more R101s are the same as or different from each other,
    상기 r'101이 2 인 경우, 2개의 R101은 서로 같거나 상이하며,When r'101 is 2, two R101's are the same as or different from each other,
    상기 r102가 2 이상인 경우, 상기 2 이상의 R102는 서로 같거나 상이하고,When the r102 is 2 or more, the two or more R102s are the same as or different from each other,
    상기 r'102가 2 이상인 경우, 상기 2 이상의 R102는 서로 같거나 상이하다.When r′102 is 2 or more, the 2 or more R102s are the same as or different from each other.
  4. 청구항 1에 있어서, 상기 A는 벤젠; 또는 나프탈렌이고,The method according to claim 1, wherein A is benzene; or naphthalene;
    상기 R1 내지 R8 및 G1 내지 G4는 수소; 또는 중수소이며,R1 to R8 and G1 to G4 are hydrogen; or deuterium;
    상기 A는 중수소로 치환 또는 비치환된 벤젠; 또는 중수소로 치환 또는 비치환된 나프탈렌이고,A is benzene unsubstituted or substituted with deuterium; or naphthalene unsubstituted or substituted with deuterium;
    상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접겹합; 또는 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이고,Wherein L1 and L2 are the same as or different from each other, and are each independently combined directly; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with one or more of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof,
    상기 L3는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이며,L3 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium,
    상기 Ar1은 중수소, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환, 2환, 3환, 또는 5환 이상의 아릴기; 중수소로 치환 또는 비치환된 크라이센기; 또는 중수소로 치환 또는 비치환된 벤조페난트렌기인 것인 화합물.Ar1 is a monocyclic, bicyclic, tricyclic, or five or more aryl group having 6 to 20 carbon atoms unsubstituted or substituted with at least one of heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; Chrysen group unsubstituted or substituted with deuterium; Or a compound that is a benzophenanthrene group unsubstituted or substituted with deuterium.
  5. 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 PCTKR2022017844-appb-img-000168
    Figure PCTKR2022017844-appb-img-000168
    Figure PCTKR2022017844-appb-img-000169
    Figure PCTKR2022017844-appb-img-000169
    Figure PCTKR2022017844-appb-img-000170
    Figure PCTKR2022017844-appb-img-000170
    Figure PCTKR2022017844-appb-img-000171
    Figure PCTKR2022017844-appb-img-000171
    Figure PCTKR2022017844-appb-img-000172
    Figure PCTKR2022017844-appb-img-000172
    Figure PCTKR2022017844-appb-img-000173
    Figure PCTKR2022017844-appb-img-000173
    Figure PCTKR2022017844-appb-img-000174
    Figure PCTKR2022017844-appb-img-000174
    Figure PCTKR2022017844-appb-img-000175
    Figure PCTKR2022017844-appb-img-000175
    Figure PCTKR2022017844-appb-img-000176
    Figure PCTKR2022017844-appb-img-000176
    Figure PCTKR2022017844-appb-img-000177
    Figure PCTKR2022017844-appb-img-000177
    Figure PCTKR2022017844-appb-img-000178
    Figure PCTKR2022017844-appb-img-000178
    Figure PCTKR2022017844-appb-img-000179
    Figure PCTKR2022017844-appb-img-000179
    Figure PCTKR2022017844-appb-img-000180
    Figure PCTKR2022017844-appb-img-000180
    Figure PCTKR2022017844-appb-img-000181
    Figure PCTKR2022017844-appb-img-000181
    Figure PCTKR2022017844-appb-img-000182
    Figure PCTKR2022017844-appb-img-000182
    Figure PCTKR2022017844-appb-img-000183
    Figure PCTKR2022017844-appb-img-000183
    Figure PCTKR2022017844-appb-img-000184
    Figure PCTKR2022017844-appb-img-000184
    Figure PCTKR2022017844-appb-img-000185
    Figure PCTKR2022017844-appb-img-000185
    Figure PCTKR2022017844-appb-img-000186
    Figure PCTKR2022017844-appb-img-000186
    Figure PCTKR2022017844-appb-img-000187
    Figure PCTKR2022017844-appb-img-000187
    Figure PCTKR2022017844-appb-img-000188
    Figure PCTKR2022017844-appb-img-000188
    Figure PCTKR2022017844-appb-img-000189
    Figure PCTKR2022017844-appb-img-000189
    Figure PCTKR2022017844-appb-img-000190
    Figure PCTKR2022017844-appb-img-000190
    Figure PCTKR2022017844-appb-img-000191
    Figure PCTKR2022017844-appb-img-000191
    Figure PCTKR2022017844-appb-img-000192
    Figure PCTKR2022017844-appb-img-000192
    Figure PCTKR2022017844-appb-img-000193
    Figure PCTKR2022017844-appb-img-000193
    Figure PCTKR2022017844-appb-img-000194
    Figure PCTKR2022017844-appb-img-000194
    Figure PCTKR2022017844-appb-img-000195
    Figure PCTKR2022017844-appb-img-000195
    Figure PCTKR2022017844-appb-img-000196
    Figure PCTKR2022017844-appb-img-000196
    Figure PCTKR2022017844-appb-img-000197
    .
    Figure PCTKR2022017844-appb-img-000197
    .
  6. 제1 전극; 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 5 중 어느 한 항의 화합물을 포함하는 것인 유기 발광 소자.a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1 to 5.
  7. 청구항 6에 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 6, 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.
  8. 청구항 6에 있어서, 상기 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 6, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  9. 청구항 6에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 6, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  10. 청구항 9에 있어서, 상기 발광층은 상기 화합물을 발광층의 호스트로 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 9, wherein the light emitting layer includes the compound as a host of the light emitting layer.
PCT/KR2022/017844 2021-11-15 2022-11-14 Compound and organic light-emitting element comprising same WO2023085877A1 (en)

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