WO2023172111A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2023172111A1
WO2023172111A1 PCT/KR2023/003330 KR2023003330W WO2023172111A1 WO 2023172111 A1 WO2023172111 A1 WO 2023172111A1 KR 2023003330 W KR2023003330 W KR 2023003330W WO 2023172111 A1 WO2023172111 A1 WO 2023172111A1
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substituted
group
unsubstituted
carbon atoms
same
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French (fr)
Korean (ko)
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김경희
김명곤
이다정
이우철
황성현
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주식회사 엘지화학
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Priority to CN202380012144.6A priority Critical patent/CN117425662A/en
Publication of WO2023172111A1 publication Critical patent/WO2023172111A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes

Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • 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 be composed of, 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 into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • This specification provides a compound and an organic light-emitting device containing the same.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • X1 and X2 are the same or different from each other and are each independently -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-
  • A1 is a substituted or unsubstituted hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle, or combines with R3 to form a substituted or unsubstituted ring,
  • n 0 or 1
  • n 0 or 1
  • At least one of n and m is 1,
  • R1 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R)(R'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R2 to R10 combine with each other to form a substituted or unsubstituted ring,
  • R and R' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r1 is an integer from 1 to 5, and when r1 is 2 or more, the 2 or more R1 are the same or different from each other,
  • r2 is an integer of 1 to 4, and when r2 is 2 or more, the 2 or more R2s are the same or different from each other,
  • r3 is 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
  • r4 is an integer from 0 to 2, and when r4 is 2, the two R4 are the same or different from each other,
  • r5 is an integer from 1 to 4, and when r5 is 2 or more, the 2 or more R5 are the same or different from each other,
  • r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other,
  • r4 is 1 or 2.
  • the present specification includes a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the one or more organic material layers contain the compound.
  • the compound according to an exemplary embodiment of the present specification can be used as a material for the organic layer of an organic light-emitting device, and by using it, high color purity, high efficiency, and/or improved lifespan characteristics can be achieved in the organic light-emitting device.
  • FIG. 1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
  • An exemplary embodiment of the present specification relates to the compound of Formula 1 above.
  • Organic light-emitting devices using conventional boron-based compounds have better efficiency than organic light-emitting devices using pyrene-based compounds, but have the disadvantage of having a shorter lifespan.
  • the compound of Formula 1 has a narrow half width, and organic light emitting devices containing it have the advantage of increased efficiency and lifespan. It maintains a narrow half width due to the hexagonal ring of boron and amine, but fills the missing electrons of boron through direct bonding between boron and amine on the other side, thereby increasing the stability of the core in the unstable polaron state. The lifespan increases, and the polaron transitions to the exciton state easily, thereby increasing the efficiency of the organic light-emitting device containing it.
  • the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, 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 changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; alkenyl group; Haloalkyl group; Haloalkoxy group; Arylalkyl group; silyl group; boron group; Amine group; Aryl group; A condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or is substituted with a substituent in which two or more of the substituents exemplified above are linked, or does not have any substituents.
  • linking two or more substituents means that the hydrogen of one substituent is linked to another substituent.
  • a phenyl group and a naphthyl group are connected. or It can be a substituent of .
  • connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group, and an isopropyl group are connected, , or It can be a substituent of .
  • the above definition equally applies to those in which 4 or more substituents are connected.
  • halogen groups include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, bicyclo [2.2.1]heptyl group, bicyclo[2.2.1]octyl group, norbornyl group, etc., but are not limited thereto.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the haloalkoxy group means that in the definition of the alkoxy group, at least one halogen group is substituted for hydrogen in the alkoxy 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, or a terphenyl group, 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 to have 10 to 30 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • fluorene group examples include
  • an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • an arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and alkyl group described above may be applied.
  • an aryloxy group refers to an aryl group being substituted for the alkyl group of the alkoxy group in the above definition of alkoxy group, and the aryloxy group includes phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenene Triloxy group, 9-phenanthryloxy group, etc. are included, but are not limited thereto.
  • alkyl group of the alkylthioxy group is the same as the example of the alkyl group described above.
  • alkylthioxy groups include methylthioxy group, ethylthioxy group, tert-butylthioxy group, hexylthioxy group, octylthioxy group, etc., but are not limited thereto.
  • the aryl group in the arylthioxy group is the same as the example of the aryl group described above.
  • the arylthioxy group includes phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenylthioxy group, but is not limited thereto.
  • the heterocyclic group includes one or more non-carbon atoms and heteroatoms.
  • the heterocyclic group may include one or more atoms selected from the group consisting of O, N, Se, and S, etc., Includes an aromatic heterocyclic group or an aliphatic heterocyclic group.
  • the aromatic heterocyclic group may be represented by a heteroaryl group.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and 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, benzyl group.
  • the silyl group is an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; It may be a heteroarylsilyl group, etc.
  • the alkyl group described above may be applied to the alkyl group among the alkylsilyl groups
  • examples of the aryl group described above may be applied to the aryl group among the arylsilyl group
  • examples of the alkyl group and aryl group in the alkylarylsilyl group include the alkyl group and the aryl group.
  • Examples of may be applied, and examples of the heterocyclic group may be applied to the heteroaryl group among the heteroarylsilyl groups.
  • the boron group may be -BR 100 R 101 , where R 100 and R 101 are the same or different, and are 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 alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • the alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.
  • N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as examples of the aryl group and heterocyclic group described above.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heterocyclic group described above.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a straight-chain or branched alkyl group.
  • the alkylamine group containing two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group.
  • the alkyl group in the alkylamine group may be selected from the examples of alkyl groups described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group containing 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 simultaneously.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of heterocyclic groups described above.
  • the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, an aryl group, and combinations thereof.
  • the hydrocarbon ring group includes phenyl group, cyclohexyl group, adamantyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.1]octyl group, tetrahydronaphthalene group, tetrahydroanthracene group, 1,2, Examples include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene group and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group.
  • the meaning of “adjacent” in “joining with adjacent groups to form a ring” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for the non-monovalent ones, the cycloalkyl group, the aryl group, and combinations thereof.
  • hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, These include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.
  • the aliphatic hydrocarbon ring includes a single bond hydrocarbon ring, a hydrocarbon ring containing a non-aromatic multiple bond, or a ring in the form of a condensation of a ring containing a single bond and a multiple bond.
  • the ring consisting of a single bond among the aliphatic hydrocarbon rings may be selected from the examples of cycloalkyl groups above, except that it is not a monovalent group, and includes cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, Hydrocarbon rings that contain single and double bonds but are not aromatic rings, such as cyclononene, cyclodecene, and cyclonorbornene, also belong to aliphatic hydrocarbon rings.
  • a heterocycle includes one or more non-carbon atoms and heteroatoms.
  • the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be an aromatic heterocycle; Aliphatic heterocycle; A condensed ring of an aromatic heterocycle and an aliphatic heterocycle; It may be a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic group, or a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocyclic group, except that the aromatic heterocycle is not monovalent. It may be selected from examples of heteroaryl groups.
  • an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms.
  • the aliphatic heterocycle includes a single bond aliphatic ring, an aliphatic ring containing multiple bonds, or an aliphatic ring in the form of a condensed ring containing a single bond and a multiple bond.
  • Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine.
  • thiocane tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.
  • the portion in Formula 1 where a substituent is not indicated may mean that hydrogen has been substituted.
  • Formula 1 is any one of Formulas 2 to 4 below.
  • A1, X1, X2, R1 to R6, and r1 to r6 are the same as those defined in Formula 1 above.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring;
  • it is a heterocycle that is substituted or unsubstituted and contains one or more of O, N, S, and Si.
  • the formula 1 is the formula 5 or 6 below.
  • X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
  • R11 to R16 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R11 to R16 are combined with each other to form a substituted or unsubstituted ring,
  • R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r11 is an integer from 1 to 4, and when r11 is 2 or more, the 2 or more R11 are the same or different from each other,
  • r12 is an integer of 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other.
  • Formula 1 is any one of Formulas 7 to 16 below.
  • X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
  • X4 and X5 are the same or different from each other and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
  • X6 and X7 are the same or different from each other and are each independently -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; or -S-,
  • Y1 to Y4 are the same or different from each other and are each independently -C(R28)- or N,
  • R'2, R"2, R'11, R"11 and R12 to R28 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R'2, R"2, R'11, R"11 and R12 to R28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.
  • R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r'11 is an integer of 1 to 4, and when r'11 is 2 or more, 2 or more R'11 are the same or different from each other,
  • r"11 is 1 or 2, and when r"11 is 2, the two R"11 are the same or different from each other,
  • r'2 is an integer of 1 to 4, and when r'2 is 2 or more, R'2 of 2 or more is the same or different,
  • r"2 is 1 or 2, and when r"2 is 2, the two R"2 are the same or different from each other,
  • r12 is an integer from 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other,
  • r17 is an integer of 1 to 4, and when r17 is 2 or more, the 2 or more R17 are the same or different from each other,
  • r18 is an integer of 1 to 4, and when r18 is 2 or more, the 2 or more R18s are the same or different from each other.
  • Formula 1 is the following Formula 1-1.
  • A1, R2 to R6, r2 to r6, n, m, X1 and X2 are the same as those defined in Formula 1.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"');
  • a heterocycle having 2 to 30 carbon atoms is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S Forming a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms,
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms;
  • R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms,
  • R5 and R6 are hydrogen
  • R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R, R', R", and R"' are the same or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
  • m is 1 and n is 0.
  • m is 0 and n is 1.
  • n 1
  • X1 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
  • X1 is -C(R7)(R8)-.
  • X1 is -Si(R9)(R10)-.
  • X1 is -O-.
  • X1 is -S-.
  • X2 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
  • X2 is -C(R7)(R8)-.
  • X2 is -Si(R9)(R10)-.
  • X2 is -O-.
  • X2 is -S-.
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms;
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms;
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic group having 6 to 30 carbon atoms substituted or unsubstituted with -N(R")(R"') Ring aromatic hydrocarbon ring;
  • ⁇ is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms.
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic group having 6 to 20 carbon atoms substituted or unsubstituted with -N(R")(R"').
  • Ring aromatic hydrocarbon ring A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or substituted or unsubstituted with one or more selected from a straight or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and combinations thereof, and includes one or more of O, N, and S.
  • ⁇ is a heterocycle having 2 to 20 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 20 carbon atoms.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocycl
  • A1 is a tert-butyl group, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzothiophene substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzoxazole substituted or unsubstituted with a phenyl group; Benzothiazole substituted or unsubstituted with a phenyl group; Benzimidazole substituted or unsubstituted with one or more selected from methyl group, phenyl
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; It is substituted or unsubstit
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 30 carbon atoms and 3 to 30 carbon atoms.
  • Aliphatic hydrocarbon ring A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ;
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 20 carbon atoms.
  • Aliphatic hydrocarbon ring A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof ;
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substitute
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substitute
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, or -N(R)(R') methyl group;
  • R1 is hydrogen; or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R1 is hydrogen; methyl group; tert-butyl group; Or it is a phenyl group.
  • R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms including N, O or S.
  • R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms;
  • it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 20 carbon atoms including N, O or S.
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydron
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted cyclohexene with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or any pair of adjacent R2s are bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, -N(R")(R"'), and combinations thereof; Benzofuran substituted or unsubstituted with a tert-
  • R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R3s are combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Alternatively, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a methyl group.
  • R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 20 carbon atoms.
  • R4 is hydrogen; Or it is a methyl group.
  • R5 and R6 are hydrogen.
  • R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R7 to R10 are the same as or different from each other, and are each independently a straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R7 to R10 are methyl groups; Or it is a phenyl group.
  • R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R, R', R", and R"' are the same or different from each other, and are each independently substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms and 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 30 to 30 members.
  • R, R', R", and R"' are the same or different from each other, and each independently is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted with 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 20 to 20 members.
  • R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
  • R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. .
  • R, R', R", and R"' are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a tert-butyl group.
  • R3 is hydrogen
  • R4 is hydrogen
  • Formula 1 includes at least one tert-butyl group.
  • Formula 1 is any one of the following compounds.
  • tBu refers to a tert-butyl group.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area.
  • the size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
  • a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
  • deuterated As used herein, “deuterated,” “substituted with deuterium,” or “deuterated” means that hydrogen at a replaceable position in a compound is replaced with deuterium.
  • X% substitution with deuterium means that It means that it has been dented.
  • the dibenzofuran is “25% substituted with deuterium,” the dibenzofuran is “25% deuterated,” the dibenzofuran is “deuterated by 25%,” or
  • the “deuterium substitution rate of 25%” of the dibenzofuran means that two of the eight hydrogens at the replaceable positions of the dibenzofuran are replaced with deuterium.
  • the degree of deuteration is determined by nuclear magnetic resonance spectroscopy ( 1H NMR), Thin-Layer Chromatography/Mass Spectrometry (TLC/MS), or Matrix assisted laser desorption/ionization Time-of-Flight Mass Spectrometry (MALDI-TOF MS). ) can be confirmed by known methods such as.
  • This specification includes: a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.
  • 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, etc.
  • the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes the compound of Formula 1 as a dopant of the light-emitting layer.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes the compound of Formula 1 as a blue fluorescent dopant of the light-emitting layer.
  • the organic light emitting device is a hole injection layer or a hole transport layer. It further includes one or two layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the light emitting layer further includes a host compound.
  • the light-emitting layer further includes a host compound, and the host compound is one in which at least one hydrogen at a replaceable position is replaced with deuterium.
  • the host compound when the host compound is substituted with deuterium, more than 30% of the host compound is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by more than 40% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 60% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 80% with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
  • the light-emitting layer further includes a compound of the following formula (H).
  • L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R200 and R201 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer from 1 to 7, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted
  • Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R200 is hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; heavy hydrogen; fluorine; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • R200 is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran
  • R200 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A naphthyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon
  • R200 is hydrogen; heavy hydrogen; Phenyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Biphenyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • R201 is hydrogen
  • R201 is deuterium
  • the compound of formula H when the compound of formula H is substituted with deuterium, more than 30% of the hydrogen at the replaceable position is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 40% of hydrogen at replaceable positions is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 60% of hydrogen at replaceable positions is replaced with deuterium.
  • the compound of formula H is any one selected from the following compounds.
  • the compound of formula H may be prepared by the following general formula 1, but is not limited thereto.
  • Ar 1 is the same as defined for -L20-Ar20 in Formula H above,
  • Ar 2 is the same as the definition of -L21-Ar21 in Formula H, and R200 and R201 may be additionally substituted in the anthracene core of Formula 1.
  • the compound of Formula 1 is used as a dopant and the compound of Formula H is used as a host in the light emitting layer.
  • the content of the dopant may be selected in the range of 0.01 to 10 parts by weight based on 100 parts by weight of the light-emitting layer, but is not limited thereto.
  • the light-emitting layer includes a host and a dopant, and the host and the dopant have a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30, and even more preferably 99:99. It is contained in a weight ratio of :1 to 90:10.
  • the light-emitting layer may further include a host material, and the host may be a condensed aromatic ring derivative or a heterocycle-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds.
  • furan compounds, pyrimidine derivatives, triazine derivatives, etc. and may be a mixture of two or more types thereof, but are not limited thereto.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of dopants and a host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed dopants and a host.
  • At least one of the two or more mixed dopants includes the formula (1), and the host includes a compound of the formula (H).
  • At least one of the two or more types of mixed dopants may include Formula 1, and the remaining dopant materials known in the art may be used, but are not limited thereto.
  • At least one of the two or more mixed dopants includes Formula 1, and the remainder includes at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1.
  • the remainder includes at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1.
  • it is not limited to this.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of hosts.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes two or more types of mixed hosts.
  • At least one of the two or more mixed hosts is a compound of formula H.
  • the two or more mixed hosts are different from each other and are each independently a compound of the formula H.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes two types of mixed hosts
  • the two types of mixed hosts are different from each other
  • the two types of hosts include the compound of Formula H am.
  • the organic material layer includes a light-emitting layer, and includes a first host of the formula H; and a second host of formula H, wherein the first host and the second host are different from each other.
  • the first host and the second host are included at a weight ratio of 95:5 to 5:95, and preferably at a weight ratio of 70:30 to 30:70.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes one or more types of hosts and a dopant.
  • the organic layer includes a light-emitting layer, the light-emitting layer includes one or more hosts, and a dopant, the host includes a compound of formula H, and the dopant includes a compound of formula (1) Contains compounds.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed hosts and a dopant.
  • At least one of the two or more types of mixed hosts includes a compound of Formula H, and the dopant includes a compound of Formula 1.
  • the two or more mixed hosts are different from each other.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts and a dopant.
  • the two types of mixed hosts are different from each other and each independently includes a compound of Formula H, and the dopant includes a compound of Formula 1.
  • a first host of Formula H a second host of formula H; and a dopant of Formula 1, wherein the first host and the second host are different from each other.
  • the organic material layer uses one or more types of hosts and one or more dopants
  • the one or more hosts include a compound of the formula H
  • the one or more dopants have the formula (1) Contains compounds of
  • the organic material layer uses two or more types of mixed hosts and two or more types of mixed dopants, the two or more types of mixed hosts may use the same materials as described above, and the two or more types of mixed hosts may be used.
  • the dopant may be the same material as described above.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes a dopant material
  • the dopant material includes the compound of Formula 1.
  • the light emitting layer further includes one or more types of dopants and a host.
  • the one or more types of dopants may be conventionally known dopant materials, but are not limited thereto.
  • the light emitting layer further includes one or more types of hosts.
  • the one or more hosts include compounds of formula H above.
  • the light emitting layer further includes two or more types of mixed hosts. At least one of the two or more mixed hosts includes a compound of formula H above.
  • the light emitting layer further includes two or more types of mixed hosts.
  • the two types of mixed hosts are different from each other, and each independently includes a compound of formula H.
  • the organic light emitting device includes a first electrode; second 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, and at least one of the two or more organic material layers includes the compound of Formula 1.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer that simultaneously performs hole transport and hole injection, and an electron blocking layer.
  • the organic light emitting device may include two or more electron transport layers, but is not limited thereto.
  • the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound of Formula 1.
  • the compound of Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the materials of each of the two or more electron transport layers may be the same or different from each other.
  • the organic light emitting device may include two or more hole injection layers, but is not limited thereto.
  • the materials of each of the two or more hole injection layers may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant may be one known in the art, for example, a metal or a metal complex.
  • the electron transport layer containing the compound of Formula 1 may further include lithium quinolate (LiQ).
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound of Formula 1.
  • the compound of Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • the organic material layer may further include a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound of Formula 1. You can.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, a first electrode 2, a light-emitting layer 3, and a second electrode 4 are sequentially stacked.
  • the compound may be included in the light-emitting layer 3.
  • FIG. 2 shows a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, and a light emitting layer 3.
  • the structure of an organic light-emitting device in which the first electron transport layer 9, the second electron transport layer 10, the electron injection layer 11, and the second electrode 4 are sequentially stacked is illustrated.
  • the compound may be included in the light-emitting layer 3.
  • the organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound of Formula 1 above.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or conductive metal oxide or alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode.
  • PVD physical vapor deposition
  • It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited to this.
  • the first electrode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
  • the second electrode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • metals or alloys thereof for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the light-emitting material of the light-emitting layer transmits holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines them to emit visible light.
  • a material capable of emitting light in a range a material with good quantum efficiency for fluorescence or phosphorescence is desirable.
  • 8-hydroxy-quinoline aluminum complex Alq 3
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Spiro compounds polyfluorene
  • rubrene but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
  • the dopant material includes additional compounds in addition to the compound of Formula 1, it includes aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group.
  • a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the hole injection layer is a layer that injects holes from an electrode.
  • the hole injection material preferably has the ability to transport holes and has an excellent hole injection effect in the first electrode and an excellent hole injection effect in the light-emitting layer or light-emitting material. Additionally, a material having an excellent ability to prevent movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Carbazole-based organic substances; Nitrile-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, or mixtures of two or more of the above examples, but are not limited thereto.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • R301 to R306 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • L301 and L302 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.
  • R301 and R302 are the same or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R301 and R302 are methyl groups.
  • R301 and R302 are combined with each other to form a substituted or unsubstituted heterocycle.
  • R301 and R302 are combined with each other to form a substituted or unsubstituted dihydroacridine ring; Or, it forms a substituted or unsubstituted indoloacridine ring.
  • R301 and R302 are combined with each other to form a dihydroacridine ring substituted or unsubstituted with a phenyl group; Or, it forms an indoloacridine ring.
  • L301 and L302 are a direct bond.
  • R303 to R306 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • R303 to R306 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R303 to R306 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
  • the formula HI-1 is represented by the following compound, but is not limited thereto.
  • the hole injection layer includes a compound represented by the following formula HI-2.
  • At least one of X'1 to X'6 is N, and the remainder is CH,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • the 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 is preferably a material that can transport holes from the first electrode or the hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
  • the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
  • R'314, R315 and R316 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with 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 or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same or different from each other.
  • R'314 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R'314 is a carbazole group; phenyl group; Biphenyl group; It is any one selected from the group consisting of naphthyl groups and combinations thereof.
  • R315 and R316 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an alkyl group, or an aromatic hydrocarbon substituted or unsubstituted with an aryl group. forms a ring
  • R315 and R316 are the same or different from each other, and are each independently a phenyl group, or are combined with adjacent groups to form benzene; Or, it forms indene substituted or unsubstituted with a phenyl group or a methyl group.
  • the 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 that can easily receive electrons from the second electrode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complex; triazine derivatives; LiQ, etc., but is not limited thereto.
  • the electron transport layer can be used with any desired first electrode material, as used according to the prior art.
  • suitable first electrode materials are conventional materials with a low work function, followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron transport layer includes a compound represented by the following formula ET-1.
  • At least one of X'7 to X'8 is N, and the rest are CH,
  • R317 to R322 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • L'1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • r322 is an integer from 1 to 7, and when r322 is 2 or more, R322 is the same as or different from each other,
  • l'1 is an integer from 1 to 5, and when l'1 is 2 or more, L'1 is the same or different from each other.
  • R317 to R322 are the same or different from each other, and are each independently hydrogen; Or it is a substituted or unsubstituted aryl group, and adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R317 to R322 are the same or different from each other, and are each independently hydrogen; phenyl group; Or it is a naphthyl group, or adjacent groups combine with each other to form benzene.
  • L'1 is a substituted or unsubstituted arylene group.
  • L'1 is a phenylene group.
  • the ET-1 is selected from the following compounds.
  • the electron transport layer includes a compound represented by the following formula ET-2.
  • T1 to T3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of substituted or unsubstituted heteroaryl groups, and combinations thereof, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • t1 is an integer from 1 to 4, and when t1 is 2 or more, 2 or more T1 are the same or different from each other,
  • t2 is an integer from 1 to 4, and when t2 is 2 or more, 2 or more T2 are the same or different from each other,
  • t3 is an integer from 1 to 10, and when t3 is 2 or more, 2 or more T3 are the same or different from each other.
  • T1 to T3 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl groups, and combinations thereof.
  • T1 to T3 are the same or different from each other, and are each independently hydrogen; carbazole group; phenyl group; Biphenyl group; triazine group; and any one selected from the group consisting of combinations thereof.
  • the ET-2 is selected from the following compounds.
  • the electron transport layer may further include a metal complex.
  • the metal may be a metal used in the industry.
  • the electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has an excellent ability to transport electrons and has an excellent electron injection effect from the second electrode and an excellent electron injection effect to the light-emitting layer or 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.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • the metal complex compounds 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) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
  • 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 passing through the light-emitting layer and entering the hole injection layer.
  • Known materials can be used without limitation, and can be formed between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
  • the electron blocking layer is represented by the formula HT-1.
  • the hole blocking layer is a layer that prevents holes from passing through the light emitting layer and reaching the cathode, and can generally be formed under the same conditions as the electron injection layer.
  • oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, etc. are included, but are not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.
  • the compounds according to the present specification may function in organic light-emitting devices, including organic phosphorescent devices, organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.
  • the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.
  • the organic light emitting device can be included and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • the organic light emitting device of the present specification can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

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Abstract

The present specification provides a compound of formula 1 and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compounds and organic light-emitting devices containing them
본 출원은 2022년 3월 11일에 한국특허청에 제출된 한국 특허 출원 제 10-2022-0030812호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0030812 filed with the Korea Intellectual Property Office on March 11, 2022, the entire contents of which are incorporated into this specification.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.This specification relates to compounds and organic light-emitting devices containing 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 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 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, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. 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 be composed of, 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 into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다. 그 중 청색 유기 발광 소자의 경우, 높은 색순도와 장수명 특성이 필수적이나 청색 물질의 높은 에너지로 인한 불안정성 때문에 이를 동시에 구현하는 기술이 부족하다. 최근, 보론을 포함한 코어구조를 가진 열활성지연형광물질이 새롭게 개발되어 높은 효율과 색순도로 주목 받았으나, 삼중항 에너지가 높고 역계간전이 속도가 느려 수명이 짧다는 단점이 있다. 따라서, 높은 색순도와 장수명 특성을 동시에 구현하는 청색 유기발광체의 개발이 요구되고 있다.The development of new materials for organic light-emitting devices as described above continues to be required. Among them, in the case of blue organic light-emitting devices, high color purity and long lifespan characteristics are essential, but due to instability due to the high energy of blue materials, there is a lack of technology to realize these simultaneously. Recently, thermally activated delayed fluorescent materials with a core structure containing boron have been newly developed and have attracted attention for their high efficiency and color purity, but they have the disadvantage of having a high triplet energy and a slow reverse intersystem transition speed, and a short lifespan. Therefore, there is a need for the development of a blue organic light emitting substance that simultaneously realizes high color purity and long lifespan characteristics.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.This specification provides a compound and an organic light-emitting device containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2023003330-appb-img-000001
Figure PCTKR2023003330-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 -C(R7)(R8)-, -Si(R9)(R10)-, -O-, 또는 -S-이고,X1 and X2 are the same or different from each other and are each independently -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-
A1은 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이거나, R3와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,A1 is a substituted or unsubstituted hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle, or combines with R3 to form a substituted or unsubstituted ring,
n은 0 또는 1이고,n is 0 or 1,
m은 0 또는 1이며,m is 0 or 1,
상기 n 및 m 중 적어도 하나는 1이고,At least one of n and m is 1,
R1 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R)(R'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R2 내지 R10 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R)(R'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R2 to R10 combine with each other to form a substituted or unsubstituted ring,
R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R and R' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
r1은 1 내지 5의 정수이며, 상기 r1이 2 이상인 경우, 상기 2 이상의 R1은 서로 같거나 상이하며,r1 is an integer from 1 to 5, and when r1 is 2 or more, the 2 or more R1 are the same or different from each other,
r2는 1 내지 4의 정수이고, 상기 r2가 2 이상인 경우, 상기 2 이상의 R2는 서로 같거나 상이하고,r2 is an integer of 1 to 4, and when r2 is 2 or more, the 2 or more R2s are the same or different from each other,
r3는 1 내지 4이고, 상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하며,r3 is 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
r4는 0 내지 2의 정수이며, 상기 r4가 2인 경우, 상기 2개의 R4는 서로 같거나 상이하고, r4 is an integer from 0 to 2, and when r4 is 2, the two R4 are the same or different from each other,
r5는 1 내지 4의 정수이며, 상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하며,r5 is an integer from 1 to 4, and when r5 is 2 or more, the 2 or more R5 are the same or different from each other,
r6는 1 내지 4의 정수이며, 상기 r6가 2 이상인 경우, 상기 2 이상의 R6는 서로 같거나 상이하며,r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other,
상기 n이 1 인 경우, 상기 r3는 1 또는 2이고,When n is 1, r3 is 1 or 2,
상기 n이 0 인 경우, 상기 r3는 1 내지 4이며,When n is 0, r3 is 1 to 4,
상기 m이 1 인 경우, 상기 r4는 0이며, When m is 1, r4 is 0,
상기 m이 0 인 경우, 상기 r4는 1 또는 2이다.When m is 0, r4 is 1 or 2.
또한, 본 명세서는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.Additionally, the present specification includes a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the one or more organic material layers contain the compound.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 높은 색 순도 고효율 및/또는 수명 특성의 향상이 가능하다.The compound according to an exemplary embodiment of the present specification can be used as a material for the organic layer of an organic light-emitting device, and by using it, high color purity, high efficiency, and/or improved lifespan characteristics can be achieved in the organic light-emitting device.
도 1 및 2는 본 명세서의 일 실시상태에 따른 유기 발광 소자를 도시한 것이다.1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Explanation of symbols]
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 발광층3: Light-emitting layer
4: 제2 전극4: second electrode
5: 제1 정공주입층5: First hole injection layer
6: 제2 정공주입층6: Second hole injection layer
7: 정공수송층7: Hole transport layer
8: 전자차단층8: Electronic blocking layer
9: 제1 전자수송층9: first electron transport layer
10: 제2 전자수송층10: Second electron transport layer
11: 전자주입층11: Electron injection layer
이하, 본 명세서에 대하여 더욱 상세히 설명한다.Hereinafter, this specification will be described in more detail.
본 명세서의 일 실시상태는 상기 화학식 1의 화합물에 관한 것이다.An exemplary embodiment of the present specification relates to the compound of Formula 1 above.
종래의 보론계 화합물을 적용한 유기 발광 소자는 파이렌계 화합물을 적용한 유기 발광 소자 보다 효율은 좋으나, 수명이 짧은 단점이 있다. 그러나, 상기 화학식 1의 화합물은 좁은 반치폭을 가지며, 이를 포함하는 유기 발광 소자는 효율 및 수명이 증가하는 장점이 있다. 보론과 아민의 6각 고리로 인해 좁은 반치폭을 유지하되 반대편의 보론과 아민의 직접결합을 통하여 보론의 부족한 전자를 채워줌으로서, 폴라론(polaron)상태의 불안정한 상태에서의 코어의 안정성을 증가 시켜 수명이 증가하고, 폴라론(polaron)이 여기자(exciton) 상태로의 전이가 잘 되어 이를 포함하는 유기 발광 소자의 효율이 증가하는 모습을 보인다.Organic light-emitting devices using conventional boron-based compounds have better efficiency than organic light-emitting devices using pyrene-based compounds, but have the disadvantage of having a shorter lifespan. However, the compound of Formula 1 has a narrow half width, and organic light emitting devices containing it have the advantage of increased efficiency and lifespan. It maintains a narrow half width due to the hexagonal ring of boron and amine, but fills the missing electrons of boron through direct bonding between boron and amine on the other side, thereby increasing the stability of the core in the unstable polaron state. The lifespan increases, and the polaron transitions to the exciton state easily, thereby increasing the efficiency of the organic light-emitting device containing it.
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 this specification, the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, It means including one or more selected from the group consisting of.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents in this specification are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2023003330-appb-img-000002
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2023003330-appb-img-000002
means the connected part.
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 changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알케닐기; 할로알킬기; 할로알콕시기; 아릴알킬기; 실릴기; 붕소기; 아민기; 아릴기; 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 및 헤테로고리기로 이루어진 군으로부터 선택되는 1 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; alkenyl group; Haloalkyl group; Haloalkoxy group; Arylalkyl group; silyl group; boron group; Amine group; Aryl group; A condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or is substituted with a substituent in which two or more of the substituents exemplified above are linked, 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 PCTKR2023003330-appb-img-000003
또는
Figure PCTKR2023003330-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 PCTKR2023003330-appb-img-000005
,
Figure PCTKR2023003330-appb-img-000006
, 또는
Figure PCTKR2023003330-appb-img-000007
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In this specification, linking two or more substituents means that the hydrogen of one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.
Figure PCTKR2023003330-appb-img-000003
or
Figure PCTKR2023003330-appb-img-000004
It can be a substituent of . In addition, connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1). Includes. For example, a phenyl group, a naphthyl group, and an isopropyl group are connected,
Figure PCTKR2023003330-appb-img-000005
,
Figure PCTKR2023003330-appb-img-000006
, or
Figure PCTKR2023003330-appb-img-000007
It can be a substituent of . The above definition equally applies to those in which 4 or more substituents are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸, 아다만틸기, 바이시클로[2.2.1]헵틸기, 바이시클로[2.2.1]옥틸기, 노보닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, bicyclo [2.2.1]heptyl group, bicyclo[2.2.1]octyl group, norbornyl group, etc., 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, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n. -It can be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, 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 hydrogen in the alkyl group in the definition of the alkyl group.
본 명세서에 있어서, 상기 할로알콕시기는 상기 알콕시기의 정의 중 알콕시기의 수소 대신 적어도 하나의 할로겐기가 치환되는 것을 의미한다.In the present specification, the haloalkoxy group means that in the definition of the alkoxy group, at least one halogen group is substituted for hydrogen in the alkoxy 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, or a terphenyl group, 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. If the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 플루오렌기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오렌기의 예시로는
Figure PCTKR2023003330-appb-img-000008
Examples of the fluorene group include
Figure PCTKR2023003330-appb-img-000008
등이 있으나, 이에 한정되지 않는다.etc., but is not limited to this.
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, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
본 명세서에 있어서, 아릴알킬기는 상기 알킬기가 아릴기로 치환된 것을 의미하며, 상기 아릴알킬기의 아릴기 및 알킬기는 전술한 아릴기 및 알킬기의 예시가 적용될 수 있다.In the present specification, an arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and alkyl group described above may be applied.
본 명세서에 있어서, 아릴옥시기는 상기 알콕시기의 정의 중 알콕시기의 알킬기 대신 아릴기로 치환되는 것을 의미하며, 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, p-tert-부틸페녹시기, 3-바이페닐옥시기, 4-바이페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, an aryloxy group refers to an aryl group being substituted for the alkyl group of the alkoxy group in the above definition of alkoxy group, and the aryloxy group includes phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenene Triloxy group, 9-phenanthryloxy group, etc. are included, but are not limited thereto.
본 명세서에 있어서, 알킬티옥시기의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the alkyl group of the alkylthioxy group is the same as the example of the alkyl group described above. Specifically, alkylthioxy groups include methylthioxy group, ethylthioxy group, tert-butylthioxy group, hexylthioxy group, octylthioxy group, etc., but are not limited thereto.
본 명세서에 있어서, 아릴티옥시기 중의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴티옥시기로는 페닐티옥시기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the aryl group in the arylthioxy group is the same as the example of the aryl group described above. Specifically, the arylthioxy group includes phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenylthioxy group, but is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 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 있으며, 방향족 헤테로고리기, 또는 지방족 헤테로고리기를 포함한다. 상기 방향족 헤테로고리기는 헤테로아릴기로 표시될 수 있다. 상기 헤테로고리기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로고리기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난트리딘기(phenanthridine), 페난쓰롤린기(phenanthroline), 이소옥사졸기, 티아디아졸기, 디벤조퓨란기, 디벤조실롤기, 페노크산틴기(phenoxathiine), 페녹사진기(phenoxazine), 페노티아진기(phenothiazine), 데카하이드로벤조카바졸기, 헥사하이드로카바졸기, 디하이드로벤조아자실린기, 디하이드로인데노카바졸기, 스피로플루오렌잔텐기, 스피로플루오렌티옥산텐기, 테트라하이드로나프토티오펜기, 테트라하이드로나프토퓨란기, 테트라하이드로벤조티오펜기, 및 테트라하이드로벤조퓨란기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heterocyclic group includes one or more non-carbon atoms and heteroatoms. Specifically, the heterocyclic group may include one or more atoms selected from the group consisting of O, N, Se, and S, etc., Includes an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and 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, benzyl group. 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, phenoxazine group, phenothiazine group, decahydrobenzocarbazole group, hexahydrocarbazole group, dihydrobenzoazacillin group, dihydroindenocarbazole group, spirofluorenexanthene group, spirofluorenethioxanthene group, tetrahydronaphthothiophene group, tetrahydronaphthofuran group, tetrahydrobenzothiophene group, and tetrahydrobenzofuran group, etc. However, it is not limited to this.
본 명세서 있어서, 상기 실릴기는 알킬실릴기, 아릴실릴기, 알킬아릴실릴기; 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 알킬아릴실릴기 중의 알킬기 및 아릴기는 상기 알킬기 및 아릴기의 예시가 적용될 수 있고, 상기 헤테로아릴실릴기 중 헤테로아릴기는 상기 헤테로고리기의 예시가 적용될 수 있다.In the present specification, the silyl group is an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; It may be a heteroarylsilyl group, etc. Examples of the alkyl group described above may be applied to the alkyl group among the alkylsilyl groups, examples of the aryl group described above may be applied to the aryl group among the arylsilyl group, and examples of the alkyl group and aryl group in the alkylarylsilyl group include the alkyl group and the aryl group. Examples of may be applied, and examples of the heterocyclic group may be applied to the heteroaryl group among the heteroarylsilyl groups.
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 헤테로고리기로 이루어진 군으로부터 선택될 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be -BR 100 R 101 , where R 100 and R 101 are the same or different, and are 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 alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
본 명세서에 있어서, 아민기는 -NH2, 알킬아민기, N-알킬아릴아민기, 아릴아민기, N-아릴헤테로아릴아민기, N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
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, N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and 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 헤테로고리기의 예시와 같다.In the present specification, N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as examples of the aryl group and heterocyclic 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 헤테로고리기의 예시와 같다.In the present specification, N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heterocyclic group described above.
본 명세서에 있어서, 알킬아민기의 예로는 치환 또는 비치환된 모노알킬아민기, 또는 치환 또는 비치환된 디알킬아민기가 있다. 상기 알킬아민기 중의 알킬기는 직쇄 또는 분지쇄의 알킬기일 수 있다. 상기 알킬기를 2 이상 포함하는 알킬아민기는 직쇄의 알킬기, 분지쇄의 알킬기, 또는 직쇄의 알킬기와 분지쇄의 알킬기를 동시에 포함할 수 있다. 예컨대, 상기 알킬아민기 중의 알킬기는 전술한 알킬기의 예시 중에서 선택될 수 있다.In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group containing two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group. For example, the alkyl group in the alkylamine group may be selected from the examples of alkyl groups 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 헤테로고리기의 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 containing 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 simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of heterocyclic groups described above.
본 명세서에 있어서, 탄화수소고리기는 방향족 탄화수소고리기, 지방족 탄화수소고리기, 또는 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기일 수 있으며, 상기 시클로알킬기, 아릴기, 및 이들의 조합의 예시 중에서 선택될 수 있으며, 상기 탄화수소고리기는 페닐기, 시클로헥실기, 아다만틸기, 바이시클로[2.2.1]헵틸기, 바이시클로[2.2.1]옥틸기, 테트라하이드로나프탈렌기, 테트라하이드로안트라센기, 1,2,3,4-테트라하이드로-1,4-메타노나프탈렌기, 및 1,2,3,4-테트라하이드로-1,4-에타노나프탈렌기 등이 있으나, 이에만 한정되는 것은 아니다.In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, an aryl group, and combinations thereof. The hydrocarbon ring group includes phenyl group, cyclohexyl group, adamantyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.1]octyl group, tetrahydronaphthalene group, tetrahydroanthracene group, 1,2, Examples include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene group and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group.
본 명세서에 있어서, "인접한 기와 서로 결합하여 고리를 형성"에서 "인접한"의 의미는 전술한 바와 동일하며, 상기 "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, the meaning of “adjacent” in “joining with adjacent groups to form a ring” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
본 명세서에 있어서, 탄화수소고리는 방향족 탄화수소고리, 지방족 탄화수소고리, 또는 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기, 아릴기, 및 이들의 조합의 예시 중에서 선택될 수 있으며, 상기 탄화수소고리는 벤젠, 시클로헥산, 아다만탄, 바이시클로[2.2.1]헵탄, 바이시클로[2.2.1]옥탄, 테트라하이드로나프탈렌, 테트라하이드로안트라센, 1,2,3,4-테트라하이드로-1,4-메타노나프탈렌, 및 1,2,3,4-테트라하이드로-1,4-에타노나프탈렌 등이 있으나, 이에만 한정되는 것은 아니다.In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for the non-monovalent ones, the cycloalkyl group, the aryl group, and combinations thereof. It can be selected from examples, and the hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, These include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.
또한, 상기 지방족 탄화수소고리는 단결합의 탄화수소고리, 방향족이 아닌 다중결합을 포함하는 탄화수소고리, 또는 단결합과 다중결합을 포함하는 고리가 축합된 형태의 고리를 모두 포함한다. 따라서, 지방족 탄화수소고리 중 단일결합으로 이루어진 고리는 1가기가 아닌 것을 제외하고는 상기 시클로알킬기의 예시 중에 선택될 수 있고, 시클로프로펜, 시클로부텐, 시클로펜텐, 시클로헥센, 시클로헵텐, 시클로옥텐, 시클로노넨, 시클로데켄, 시클로노보넨 등 단일결합과 이중결합을 포함하나 방향족 고리가 아닌 탄화수소고리도 지방족 탄화수소고리에 속한다.In addition, the aliphatic hydrocarbon ring includes a single bond hydrocarbon ring, a hydrocarbon ring containing a non-aromatic multiple bond, or a ring in the form of a condensation of a ring containing a single bond and a multiple bond. Therefore, the ring consisting of a single bond among the aliphatic hydrocarbon rings may be selected from the examples of cycloalkyl groups above, except that it is not a monovalent group, and includes cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, Hydrocarbon rings that contain single and double bonds but are not aromatic rings, such as cyclononene, cyclodecene, and cyclonorbornene, also belong to aliphatic hydrocarbon rings.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족 헤테로고리; 지방족 헤테로고리; 방향족 헤테로고리와 지방족 헤테로고리의 축합고리; 지방족 탄화수소고리, 방향족 탄화수소고리 및 방향족 헤테로고리기의 축합고리, 또는 지방족 탄화수소고리, 방향족 탄화수소고리 및 지방족 헤테로고리기의 축합고리일 수 있으며, 상기 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로고리기 중 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, a heterocycle includes one or more non-carbon atoms and heteroatoms. Specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic heterocycle; Aliphatic heterocycle; A condensed ring of an aromatic heterocycle and an aliphatic heterocycle; It may be a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic group, or a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocyclic group, except that the aromatic heterocycle is not monovalent. It may be selected from examples of heteroaryl groups.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리는 단결합의 지방족고리, 다중결합을 포함하는 지방족고리, 또는 단결합과 다중결합을 포함하는 고리가 축합된 형태의 지방족고리를 모두 포함한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인, 테트라하이드로나프토티오펜, 테트라하이드로나프토퓨란, 테트라하이드로벤조티오펜, 및 테트라하이드로벤조퓨란 등이 있으나, 이에 한정되지 않는다.As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. The aliphatic heterocycle includes a single bond aliphatic ring, an aliphatic ring containing multiple bonds, or an aliphatic ring in the form of a condensed ring containing a single bond and a multiple bond. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.
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, the portion in Formula 1 where a substituent is not indicated may mean that hydrogen has been substituted.
본 명세서에서 달리 정의되지 않는 한, 본 명세서에서 사용되는 모든 기술적 및 과학적 용어는 본 발명이 속하는 기술 분야의 당업자에 의해 통상적으로 이해되는 바와 동일한 의미를 갖는다. 본 명세서에서 설명되는 것과 유사하거나 등가인 방법 및 재료가 본 발명의 실시 형태의 실시 또는 시험에서 사용될 수 있지만, 적합한 방법 및 재료가 후술된다. 본 명세서에서 언급되는 모든 간행물, 특허 출원, 특허 및 다른 참고 문헌은 전체적으로 본 명세서에 참고로 포함되며, 상충되는 경우 특정 어구(passage)가 언급되지 않으면, 정의를 비롯한 본 명세서가 우선할 것이다. 게다가, 재료, 방법, 및 실시예는 단지 예시적인 것이며 제한하고자 하는 것은 아니다.Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is mentioned. Moreover, the materials, methods, and examples are illustrative only and are not intended to be limiting.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2 내지 4 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 2 to 4 below.
[화학식 2][Formula 2]
Figure PCTKR2023003330-appb-img-000009
Figure PCTKR2023003330-appb-img-000009
[화학식 3][Formula 3]
Figure PCTKR2023003330-appb-img-000010
Figure PCTKR2023003330-appb-img-000010
[화학식 4][Formula 4]
Figure PCTKR2023003330-appb-img-000011
Figure PCTKR2023003330-appb-img-000011
상기 화학식 2 내지 4에 있어서,In Formulas 2 to 4,
A1, X1, X2, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하다.The definitions of A1, X1, X2, R1 to R6, and r1 to r6 are the same as those defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 A1은 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, O, N, S, 및 Si 중 1 이상을 포함하는 헤테로고리이다.According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted aromatic hydrocarbon ring; A condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a heterocycle that is substituted or unsubstituted and contains one or more of O, N, S, and Si.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 5 또는 6이다.According to an exemplary embodiment of the present specification, the formula 1 is the formula 5 or 6 below.
[화학식 5][Formula 5]
Figure PCTKR2023003330-appb-img-000012
Figure PCTKR2023003330-appb-img-000012
[화학식 6][Formula 6]
Figure PCTKR2023003330-appb-img-000013
Figure PCTKR2023003330-appb-img-000013
상기 화학식 5 및 6에 있어서,In Formulas 5 and 6,
X1, X2, m, n, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1, X2, m, n, R1 to R6 and r1 to r6 are the same as those defined in Formula 1 above,
X3는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
R11 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R")(R"'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R11 내지 R16 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R11 to R16 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R11 to R16 are combined with each other to form a substituted or unsubstituted ring,
R" 및 R"'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
r11은 1 내지 4의 정수이고, 상기 r11이 2 이상인 경우, 상기 2 이상의 R11은 서로 같거나 상이하며,r11 is an integer from 1 to 4, and when r11 is 2 or more, the 2 or more R11 are the same or different from each other,
r12는 1 내지 4의 정수이며, 상기 r12가 2 이상인 경우, 상기 2 이상의 R12는 서로 같거나 상이하다.r12 is an integer of 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 7 내지 16 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 7 to 16 below.
[화학식 7][Formula 7]
Figure PCTKR2023003330-appb-img-000014
Figure PCTKR2023003330-appb-img-000014
[화학식 8][Formula 8]
Figure PCTKR2023003330-appb-img-000015
Figure PCTKR2023003330-appb-img-000015
[화학식 9][Formula 9]
Figure PCTKR2023003330-appb-img-000016
Figure PCTKR2023003330-appb-img-000016
[화학식 10][Formula 10]
Figure PCTKR2023003330-appb-img-000017
Figure PCTKR2023003330-appb-img-000017
[화학식 11][Formula 11]
Figure PCTKR2023003330-appb-img-000018
Figure PCTKR2023003330-appb-img-000018
[화학식 12][Formula 12]
Figure PCTKR2023003330-appb-img-000019
Figure PCTKR2023003330-appb-img-000019
[화학식 13][Formula 13]
Figure PCTKR2023003330-appb-img-000020
Figure PCTKR2023003330-appb-img-000020
[화학식 14][Formula 14]
Figure PCTKR2023003330-appb-img-000021
Figure PCTKR2023003330-appb-img-000021
[화학식 15][Formula 15]
Figure PCTKR2023003330-appb-img-000022
Figure PCTKR2023003330-appb-img-000022
[화학식 16][Formula 16]
Figure PCTKR2023003330-appb-img-000023
Figure PCTKR2023003330-appb-img-000023
상기 화학식 7 내지 16에 있어서,In Formulas 7 to 16,
X1, X2, m, n, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1, X2, m, n, R1 to R6 and r1 to r6 are the same as those defined in Formula 1 above,
X3는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
X4 및 X5는 서로 같거나 상이하고, 각각 독립적으로 -C(R19)(R20)-; -Si(R21)(R22)-; -O-; 또는 -S-이며,X4 and X5 are the same or different from each other and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
X6 및 X7은 서로 같거나 상이하고, 각각 독립적으로 -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; 또는 -S-이며,X6 and X7 are the same or different from each other and are each independently -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; or -S-,
Y1 내지 Y4는 서로 같거나 상이하고, 각각 독립적으로 -C(R28)- 또는 N이고,Y1 to Y4 are the same or different from each other and are each independently -C(R28)- or N,
R'2, R"2, R'11, R"11 및 R12 내지 R28은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R")(R"'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R'2, R"2, R'11, R"11 및 R12 내지 R28 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리를 형성하며,R'2, R"2, R'11, R"11 and R12 to R28 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R'2, R"2, R'11, R"11 and R12 to R28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring. forming,
R" 및 R"'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
r'11은 1 내지 4의 정수이고, 상기 r'11이 2 이상인 경우, 상기 2 이상의 R'11은 서로 같거나 상이하며,r'11 is an integer of 1 to 4, and when r'11 is 2 or more, 2 or more R'11 are the same or different from each other,
r"11은 1 또는 2이고, 상기 r"11이 2인 경우, 상기 2개의 R"11은 서로 같거나 상이하고,r"11 is 1 or 2, and when r"11 is 2, the two R"11 are the same or different from each other,
r'2은 1 내지 4의 정수이고, 상기 r'2이 2 이상인 경우, 상기 2 이상의 R'2은 서로 같거나 상이하며,r'2 is an integer of 1 to 4, and when r'2 is 2 or more, R'2 of 2 or more is the same or different,
r"2은 1 또는 2이고, 상기 r"2이 2인 경우, 상기 2개의 R"2은 서로 같거나 상이하고,r"2 is 1 or 2, and when r"2 is 2, the two R"2 are the same or different from each other,
r12는 1 내지 4의 정수이며, 상기 r12가 2 이상인 경우, 상기 2 이상의 R12는 서로 같거나 상이하며,r12 is an integer from 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other,
r17는 1 내지 4의 정수이며, 상기 r17가 2 이상인 경우, 상기 2 이상의 R17는 서로 같거나 상이하고,r17 is an integer of 1 to 4, and when r17 is 2 or more, the 2 or more R17 are the same or different from each other,
r18는 1 내지 4의 정수이며, 상기 r18가 2 이상인 경우, 상기 2 이상의 R18는 서로 같거나 상이하다.r18 is an integer of 1 to 4, and when r18 is 2 or more, the 2 or more R18s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1이다.According to an exemplary embodiment of the present specification, Formula 1 is the following Formula 1-1.
[화학식 1-1][Formula 1-1]
Figure PCTKR2023003330-appb-img-000024
Figure PCTKR2023003330-appb-img-000024
상기 화학식 1-1에 있어서,In Formula 1-1,
A1, R2 내지 R6, r2 내지 r6, n, m, X1 및 X2의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of A1, R2 to R6, r2 to r6, n, m, X1 and X2 are the same as those defined in Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 -N(R")(R"')로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 30의 헤테로고리이거나, R3와 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 30의 단환 또는 다환의 헤테로고리를 형성하고,According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"'); A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or is substituted or unsubstituted with one or more selected from a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof, and includes one or more of O, N and S. is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S Forming a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms,
상기 R1은 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이며,R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
상기 R2는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하고,R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic hetero alkyl group having 2 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"'), and containing N, O or S. forming a ring,
상기 R3는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리를 형성하며,R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. forming,
상기 R4는 수소; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이고,R4 is hydrogen; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms,
상기 R5 및 R6은 수소이고,R5 and R6 are hydrogen,
상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이고,R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.R, R', R", and R"' are the same or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 m은 1이고, n은 0이다.According to an exemplary embodiment of the present specification, m is 1 and n is 0.
본 명세서의 일 실시상태에 따르면, 상기 m은 0이고, n은 1이다.According to an exemplary embodiment of the present specification, m is 0 and n is 1.
본 명세서의 일 실시상태에 따르면, 상기 m은 1이고, n은 1이다.According to an exemplary embodiment of the present specification, m is 1 and n is 1.
본 명세서의 일 실시상태에 따르면, 상기 X1은 -C(R7)(R8)-, -Si(R9)(R10)-, -O-, 또는 -S-이다.According to an exemplary embodiment of the present specification, X1 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
본 명세서의 일 실시상태에 따르면, 상기 X1은 -C(R7)(R8)-이다.According to an exemplary embodiment of the present specification, X1 is -C(R7)(R8)-.
본 명세서의 일 실시상태에 따르면, 상기 X1은 -Si(R9)(R10)-이다.According to an exemplary embodiment of the present specification, X1 is -Si(R9)(R10)-.
본 명세서의 일 실시상태에 따르면, 상기 X1은 -O-이다.According to an exemplary embodiment of the present specification, X1 is -O-.
본 명세서의 일 실시상태에 따르면, 상기 X1은 -S-이다.According to an exemplary embodiment of the present specification, X1 is -S-.
본 명세서의 일 실시상태에 따르면, 상기 X2은 -C(R7)(R8)-, -Si(R9)(R10)-, -O-, 또는 -S-이다.According to an exemplary embodiment of the present specification, X2 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
본 명세서의 일 실시상태에 따르면, 상기 X2은 -C(R7)(R8)-이다.According to an exemplary embodiment of the present specification, X2 is -C(R7)(R8)-.
본 명세서의 일 실시상태에 따르면, 상기 X2은 -Si(R9)(R10)-이다.According to an exemplary embodiment of the present specification, X2 is -Si(R9)(R10)-.
본 명세서의 일 실시상태에 따르면, 상기 X2은 -O-이다.According to an exemplary embodiment of the present specification, X2 is -O-.
본 명세서의 일 실시상태에 따르면, 상기 X2은 -S-이다.According to an exemplary embodiment of the present specification, X2 is -S-.
본 명세서의 일 실시상태에 따르면, 상기 A1은 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 30의 헤테로고리이거나, R3와 서로 결합하여 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a heterocycle that is substituted or unsubstituted and has 2 to 30 carbon atoms and contains one or more of O, N and S, or is substituted or unsubstituted by bonding with R3 and contains 6 to 30 carbon atoms and contains N, O or S. It forms a monocyclic or polycyclic heterocycle.
본 명세서의 일 실시상태에 따르면, 상기 A1은 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 20의 헤테로고리이거나, R3와 서로 결합하여 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or a heterocycle that is substituted or unsubstituted and has 2 to 20 carbon atoms and contains one or more of O, N and S, or is substituted or unsubstituted by bonding with R3 and has 6 to 20 carbon atoms and contains N, O or S. It forms a monocyclic or polycyclic heterocycle.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 30의 헤테로고리이거나, R3와 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic group having 6 to 30 carbon atoms substituted or unsubstituted with -N(R")(R"') Ring aromatic hydrocarbon ring; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or substituted or unsubstituted with one or more selected from a straight or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof, and includes one or more of O, N, and S. is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 20의 헤테로고리이거나, R3와 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic group having 6 to 20 carbon atoms substituted or unsubstituted with -N(R")(R"'). Ring aromatic hydrocarbon ring; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or substituted or unsubstituted with one or more selected from a straight or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and combinations thereof, and includes one or more of O, N, and S. is a heterocycle having 2 to 20 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤젠; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 디벤조퓨란; 디벤조티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조티오펜; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤즈옥사졸; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조티아졸; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤즈이미다졸; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜이거나, R3와 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인돌; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디하이드로퀴놀린을 형성한다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzoxazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Benzothiazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzimidazole substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or indole substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms in combination with R3; Alternatively, it forms a substituted or unsubstituted dihydroquinoline with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤젠; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 디벤조퓨란; 디벤조티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조티오펜; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤즈옥사졸; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조티아졸; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤즈이미다졸; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜이거나, R3와 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인돌; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디하이드로퀴놀린을 형성한다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzoxazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Benzothiazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzimidazole substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or indole substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms when combined with R3; Alternatively, it forms a substituted or unsubstituted dihydroquinoline with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1은 tert-부틸기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤젠; 메틸기로 치환 또는 비치환된 플루오렌; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 디벤조퓨란; 디벤조티오펜; tert-부틸기, 또는 페닐기로 치환 또는 비치환된 벤조퓨란; tert-부틸기, 또는 페닐기로 치환 또는 비치환된 벤조티오펜; 페닐기로 치환 또는 비치환된 벤즈옥사졸; 페닐기로 치환 또는 비치환된 벤조티아졸; 메틸기, 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤즈이미다졸; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 또는 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜이거나, R3와 서로 결합하여 tert-부틸기로 치환 또는 비치환된 인돌; 또는 tert-부틸기, 또는 페닐기로 치환 또는 비치환된 디하이드로퀴놀린을 형성한다.According to an exemplary embodiment of the present specification, A1 is a tert-butyl group, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzothiophene substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzoxazole substituted or unsubstituted with a phenyl group; Benzothiazole substituted or unsubstituted with a phenyl group; Benzimidazole substituted or unsubstituted with one or more selected from methyl group, phenyl group, and combinations thereof; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; or tetrahydronaphthothiophene substituted or unsubstituted with a methyl group, or indole substituted or unsubstituted with a tert-butyl group when combined with R3; Or, it forms a substituted or unsubstituted dihydroquinoline with a tert-butyl group, or a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms including N, O or S.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기 이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; It is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 20 carbon atoms including N, O or S.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"'), 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 30 carbon atoms and 3 to 30 carbon atoms. Aliphatic hydrocarbon ring; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or -N(R")(R"'), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted, and N, O or S It forms a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"'), 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 20 carbon atoms. Aliphatic hydrocarbon ring; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or -N(R")(R"'), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and N, O or S It forms a monocyclic or polycyclic heterocycle containing 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 메틸기; tert-부틸기; 또는 페닐기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"') 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 인덴; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디하이드로피리미딘을 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; benzodioxin; indene substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof; benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or -N(R")(R"'); benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or -N(R")(R"'); Alternatively, it forms a dihydropyrimidine substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 메틸기; tert-부틸기; 또는 페닐기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"') 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 인덴; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디하이드로피리미딘을 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; benzodioxin; indene substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof; benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or -N(R")(R"'); benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or -N(R")(R"'); Alternatively, it forms a dihydropyrimidine substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R3는 서로 같거나 상이하고, 각각 독립적으로 수소; -N(R)(R'); 메틸기; tert-부틸기; 또는 페닐기이거나, 상기 R2 및 R3 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 메틸기로 치환 또는 비치환된 시클로헥센; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 메틸기, tert-부틸기, 또는 -N(R")(R"') 중에서 선택된 1 이상으로 치환 또는 비치환된 인덴; tert-부틸기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; tert-부틸기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜; 또는 메틸기, 또는 페닐기로 치환 또는 비치환된 디하이드로피리미딘을 형성한다.According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, or -N(R")(R"'); Benzofuran substituted or unsubstituted with a tert-butyl group or -N(R")(R"'); benzothiophene substituted or unsubstituted with a tert-butyl group or -N(R")(R"'); Or, it forms a dihydropyrimidine substituted or unsubstituted with a methyl group, or a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R1 is hydrogen; or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R1 is hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 메틸기; tert-부틸기; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R1 is hydrogen; methyl group; tert-butyl group; Or it is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms including N, O or S.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; Or, it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 20 carbon atoms including N, O or S.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic hetero alkyl group having 2 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"'), and containing N, O or S. forms a ring
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic hetero alkyl group having 2 to 20 carbon atoms, substituted or unsubstituted with -N(R")(R"'), and containing N, O or S. forms a ring
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 인덴; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; benzodioxin; indene substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof; benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or -N(R")(R"'); Alternatively, it forms a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or benzothiophene substituted or unsubstituted with -N(R")(R"').
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 인덴; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted cyclohexene with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; benzodioxin; indene substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof; benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or -N(R")(R"'); Alternatively, it forms a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or benzothiophene substituted or unsubstituted with -N(R")(R"').
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 메틸기로 치환 또는 비치환된 시클로헥센; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 벤조다이옥신; 메틸기, tert-부틸기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1이상으로 치환 또는 비치환된 인덴; tert-부틸기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조퓨란; 또는 tert-부틸기, 또는 -N(R")(R"')로 치환 또는 비치환된 벤조티오펜을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or any pair of adjacent R2s are bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, -N(R")(R"'), and combinations thereof; Benzofuran substituted or unsubstituted with a tert-butyl group or -N(R")(R"'); or tert-butyl group, or -N(R")(R"') to form a substituted or unsubstituted benzothiophene.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R3s are combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. form
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. form
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센을 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센을 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Alternatively, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소; -N(R)(R'); 또는 tert-부틸기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 메틸기로 치환 또는 비치환된 시클로헥센을 형성한다.According to an exemplary embodiment of the present specification, R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소; 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소; 또는 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소; 또는 메틸기이다.According to an exemplary embodiment of the present specification, R4 is hydrogen; Or it is a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 수소이다.According to an exemplary embodiment of the present specification, R5 and R6 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R7 to R10 are the same as or different from each other, and are each independently a straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R7 내지 R10은 메틸기; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R7 to R10 are methyl groups; Or it is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 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, R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and are each independently substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms and 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 30 to 30 members.
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and each independently is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted with 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 20 to 20 members.
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 tert-부틸기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R, R', R", and R"' are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a tert-butyl group.
본 명세서의 일 실시상태에 따르면, 상기 m이 1 인 경우, 상기 R3는 수소이다.According to an exemplary embodiment of the present specification, when m is 1, R3 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 n이 0인 경우, 상기 R4는 수소이다.According to an exemplary embodiment of the present specification, when n is 0, R4 is hydrogen.
본 명세서의 일 실상태에 따르면, 상기 화학식 1은 적어도 하나의 tert-부틸기를 포함한다.According to an actual state of the present specification, Formula 1 includes at least one tert-butyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of the following compounds.
Figure PCTKR2023003330-appb-img-000025
Figure PCTKR2023003330-appb-img-000025
Figure PCTKR2023003330-appb-img-000026
Figure PCTKR2023003330-appb-img-000026
Figure PCTKR2023003330-appb-img-000027
Figure PCTKR2023003330-appb-img-000027
Figure PCTKR2023003330-appb-img-000028
Figure PCTKR2023003330-appb-img-000028
Figure PCTKR2023003330-appb-img-000029
Figure PCTKR2023003330-appb-img-000029
Figure PCTKR2023003330-appb-img-000030
Figure PCTKR2023003330-appb-img-000030
Figure PCTKR2023003330-appb-img-000031
Figure PCTKR2023003330-appb-img-000031
Figure PCTKR2023003330-appb-img-000032
Figure PCTKR2023003330-appb-img-000032
Figure PCTKR2023003330-appb-img-000033
Figure PCTKR2023003330-appb-img-000033
Figure PCTKR2023003330-appb-img-000034
Figure PCTKR2023003330-appb-img-000034
Figure PCTKR2023003330-appb-img-000035
Figure PCTKR2023003330-appb-img-000035
Figure PCTKR2023003330-appb-img-000036
Figure PCTKR2023003330-appb-img-000036
Figure PCTKR2023003330-appb-img-000037
Figure PCTKR2023003330-appb-img-000037
Figure PCTKR2023003330-appb-img-000038
Figure PCTKR2023003330-appb-img-000038
Figure PCTKR2023003330-appb-img-000039
Figure PCTKR2023003330-appb-img-000039
Figure PCTKR2023003330-appb-img-000040
Figure PCTKR2023003330-appb-img-000040
Figure PCTKR2023003330-appb-img-000041
Figure PCTKR2023003330-appb-img-000041
Figure PCTKR2023003330-appb-img-000042
Figure PCTKR2023003330-appb-img-000042
Figure PCTKR2023003330-appb-img-000043
Figure PCTKR2023003330-appb-img-000043
Figure PCTKR2023003330-appb-img-000044
Figure PCTKR2023003330-appb-img-000044
Figure PCTKR2023003330-appb-img-000045
Figure PCTKR2023003330-appb-img-000045
Figure PCTKR2023003330-appb-img-000046
Figure PCTKR2023003330-appb-img-000046
Figure PCTKR2023003330-appb-img-000047
Figure PCTKR2023003330-appb-img-000047
Figure PCTKR2023003330-appb-img-000048
Figure PCTKR2023003330-appb-img-000048
Figure PCTKR2023003330-appb-img-000049
Figure PCTKR2023003330-appb-img-000049
Figure PCTKR2023003330-appb-img-000050
Figure PCTKR2023003330-appb-img-000050
Figure PCTKR2023003330-appb-img-000051
Figure PCTKR2023003330-appb-img-000051
Figure PCTKR2023003330-appb-img-000052
Figure PCTKR2023003330-appb-img-000052
Figure PCTKR2023003330-appb-img-000053
Figure PCTKR2023003330-appb-img-000053
Figure PCTKR2023003330-appb-img-000054
Figure PCTKR2023003330-appb-img-000054
Figure PCTKR2023003330-appb-img-000055
Figure PCTKR2023003330-appb-img-000055
Figure PCTKR2023003330-appb-img-000056
Figure PCTKR2023003330-appb-img-000056
Figure PCTKR2023003330-appb-img-000057
Figure PCTKR2023003330-appb-img-000057
Figure PCTKR2023003330-appb-img-000058
Figure PCTKR2023003330-appb-img-000058
Figure PCTKR2023003330-appb-img-000059
Figure PCTKR2023003330-appb-img-000059
Figure PCTKR2023003330-appb-img-000060
Figure PCTKR2023003330-appb-img-000060
Figure PCTKR2023003330-appb-img-000061
Figure PCTKR2023003330-appb-img-000061
Figure PCTKR2023003330-appb-img-000062
Figure PCTKR2023003330-appb-img-000062
Figure PCTKR2023003330-appb-img-000063
Figure PCTKR2023003330-appb-img-000063
Figure PCTKR2023003330-appb-img-000064
Figure PCTKR2023003330-appb-img-000064
Figure PCTKR2023003330-appb-img-000065
Figure PCTKR2023003330-appb-img-000065
Figure PCTKR2023003330-appb-img-000066
Figure PCTKR2023003330-appb-img-000066
Figure PCTKR2023003330-appb-img-000067
Figure PCTKR2023003330-appb-img-000067
Figure PCTKR2023003330-appb-img-000068
Figure PCTKR2023003330-appb-img-000068
Figure PCTKR2023003330-appb-img-000069
Figure PCTKR2023003330-appb-img-000069
Figure PCTKR2023003330-appb-img-000070
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Figure PCTKR2023003330-appb-img-000071
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Figure PCTKR2023003330-appb-img-000139
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Figure PCTKR2023003330-appb-img-000148
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Figure PCTKR2023003330-appb-img-000161
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Figure PCTKR2023003330-appb-img-000163
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Figure PCTKR2023003330-appb-img-000164
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Figure PCTKR2023003330-appb-img-000167
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Figure PCTKR2023003330-appb-img-000168
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Figure PCTKR2023003330-appb-img-000200
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Figure PCTKR2023003330-appb-img-000226
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Figure PCTKR2023003330-appb-img-000231
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Figure PCTKR2023003330-appb-img-000234
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Figure PCTKR2023003330-appb-img-000236
Figure PCTKR2023003330-appb-img-000237
Figure PCTKR2023003330-appb-img-000237
Figure PCTKR2023003330-appb-img-000238
Figure PCTKR2023003330-appb-img-000238
Figure PCTKR2023003330-appb-img-000239
Figure PCTKR2023003330-appb-img-000239
Figure PCTKR2023003330-appb-img-000240
Figure PCTKR2023003330-appb-img-000240
Figure PCTKR2023003330-appb-img-000241
Figure PCTKR2023003330-appb-img-000241
Figure PCTKR2023003330-appb-img-000242
Figure PCTKR2023003330-appb-img-000242
Figure PCTKR2023003330-appb-img-000243
Figure PCTKR2023003330-appb-img-000243
Figure PCTKR2023003330-appb-img-000244
Figure PCTKR2023003330-appb-img-000244
Figure PCTKR2023003330-appb-img-000245
Figure PCTKR2023003330-appb-img-000245
Figure PCTKR2023003330-appb-img-000246
Figure PCTKR2023003330-appb-img-000246
Figure PCTKR2023003330-appb-img-000247
Figure PCTKR2023003330-appb-img-000247
Figure PCTKR2023003330-appb-img-000248
Figure PCTKR2023003330-appb-img-000248
Figure PCTKR2023003330-appb-img-000249
Figure PCTKR2023003330-appb-img-000249
Figure PCTKR2023003330-appb-img-000250
Figure PCTKR2023003330-appb-img-000250
Figure PCTKR2023003330-appb-img-000251
Figure PCTKR2023003330-appb-img-000251
Figure PCTKR2023003330-appb-img-000252
Figure PCTKR2023003330-appb-img-000252
Figure PCTKR2023003330-appb-img-000253
Figure PCTKR2023003330-appb-img-000253
Figure PCTKR2023003330-appb-img-000254
Figure PCTKR2023003330-appb-img-000254
Figure PCTKR2023003330-appb-img-000255
Figure PCTKR2023003330-appb-img-000255
Figure PCTKR2023003330-appb-img-000256
Figure PCTKR2023003330-appb-img-000256
Figure PCTKR2023003330-appb-img-000257
Figure PCTKR2023003330-appb-img-000257
Figure PCTKR2023003330-appb-img-000258
Figure PCTKR2023003330-appb-img-000258
Figure PCTKR2023003330-appb-img-000259
Figure PCTKR2023003330-appb-img-000259
Figure PCTKR2023003330-appb-img-000260
Figure PCTKR2023003330-appb-img-000260
Figure PCTKR2023003330-appb-img-000261
Figure PCTKR2023003330-appb-img-000261
Figure PCTKR2023003330-appb-img-000262
Figure PCTKR2023003330-appb-img-000262
Figure PCTKR2023003330-appb-img-000263
Figure PCTKR2023003330-appb-img-000263
Figure PCTKR2023003330-appb-img-000264
Figure PCTKR2023003330-appb-img-000264
Figure PCTKR2023003330-appb-img-000265
Figure PCTKR2023003330-appb-img-000265
Figure PCTKR2023003330-appb-img-000266
Figure PCTKR2023003330-appb-img-000266
Figure PCTKR2023003330-appb-img-000267
Figure PCTKR2023003330-appb-img-000267
Figure PCTKR2023003330-appb-img-000268
Figure PCTKR2023003330-appb-img-000268
Figure PCTKR2023003330-appb-img-000269
Figure PCTKR2023003330-appb-img-000269
Figure PCTKR2023003330-appb-img-000270
Figure PCTKR2023003330-appb-img-000270
Figure PCTKR2023003330-appb-img-000271
Figure PCTKR2023003330-appb-img-000271
Figure PCTKR2023003330-appb-img-000272
Figure PCTKR2023003330-appb-img-000272
Figure PCTKR2023003330-appb-img-000273
Figure PCTKR2023003330-appb-img-000273
Figure PCTKR2023003330-appb-img-000274
Figure PCTKR2023003330-appb-img-000274
Figure PCTKR2023003330-appb-img-000275
Figure PCTKR2023003330-appb-img-000275
Figure PCTKR2023003330-appb-img-000276
Figure PCTKR2023003330-appb-img-000276
Figure PCTKR2023003330-appb-img-000277
Figure PCTKR2023003330-appb-img-000277
Figure PCTKR2023003330-appb-img-000278
Figure PCTKR2023003330-appb-img-000278
Figure PCTKR2023003330-appb-img-000279
Figure PCTKR2023003330-appb-img-000279
Figure PCTKR2023003330-appb-img-000280
Figure PCTKR2023003330-appb-img-000280
Figure PCTKR2023003330-appb-img-000281
Figure PCTKR2023003330-appb-img-000281
Figure PCTKR2023003330-appb-img-000282
Figure PCTKR2023003330-appb-img-000282
Figure PCTKR2023003330-appb-img-000283
Figure PCTKR2023003330-appb-img-000283
Figure PCTKR2023003330-appb-img-000284
Figure PCTKR2023003330-appb-img-000284
Figure PCTKR2023003330-appb-img-000285
Figure PCTKR2023003330-appb-img-000285
Figure PCTKR2023003330-appb-img-000286
Figure PCTKR2023003330-appb-img-000286
Figure PCTKR2023003330-appb-img-000287
Figure PCTKR2023003330-appb-img-000287
Figure PCTKR2023003330-appb-img-000288
Figure PCTKR2023003330-appb-img-000288
Figure PCTKR2023003330-appb-img-000289
Figure PCTKR2023003330-appb-img-000289
Figure PCTKR2023003330-appb-img-000290
Figure PCTKR2023003330-appb-img-000290
Figure PCTKR2023003330-appb-img-000291
Figure PCTKR2023003330-appb-img-000291
Figure PCTKR2023003330-appb-img-000292
Figure PCTKR2023003330-appb-img-000292
Figure PCTKR2023003330-appb-img-000293
Figure PCTKR2023003330-appb-img-000293
Figure PCTKR2023003330-appb-img-000294
Figure PCTKR2023003330-appb-img-000294
Figure PCTKR2023003330-appb-img-000295
Figure PCTKR2023003330-appb-img-000295
Figure PCTKR2023003330-appb-img-000296
Figure PCTKR2023003330-appb-img-000296
Figure PCTKR2023003330-appb-img-000297
Figure PCTKR2023003330-appb-img-000297
Figure PCTKR2023003330-appb-img-000298
Figure PCTKR2023003330-appb-img-000298
Figure PCTKR2023003330-appb-img-000299
Figure PCTKR2023003330-appb-img-000299
Figure PCTKR2023003330-appb-img-000300
Figure PCTKR2023003330-appb-img-000300
Figure PCTKR2023003330-appb-img-000301
Figure PCTKR2023003330-appb-img-000301
Figure PCTKR2023003330-appb-img-000302
Figure PCTKR2023003330-appb-img-000302
Figure PCTKR2023003330-appb-img-000303
Figure PCTKR2023003330-appb-img-000303
Figure PCTKR2023003330-appb-img-000304
Figure PCTKR2023003330-appb-img-000304
Figure PCTKR2023003330-appb-img-000305
Figure PCTKR2023003330-appb-img-000305
Figure PCTKR2023003330-appb-img-000306
Figure PCTKR2023003330-appb-img-000306
Figure PCTKR2023003330-appb-img-000307
Figure PCTKR2023003330-appb-img-000307
Figure PCTKR2023003330-appb-img-000308
Figure PCTKR2023003330-appb-img-000308
Figure PCTKR2023003330-appb-img-000309
Figure PCTKR2023003330-appb-img-000309
Figure PCTKR2023003330-appb-img-000310
Figure PCTKR2023003330-appb-img-000310
Figure PCTKR2023003330-appb-img-000311
Figure PCTKR2023003330-appb-img-000311
Figure PCTKR2023003330-appb-img-000312
Figure PCTKR2023003330-appb-img-000312
Figure PCTKR2023003330-appb-img-000313
Figure PCTKR2023003330-appb-img-000313
Figure PCTKR2023003330-appb-img-000314
Figure PCTKR2023003330-appb-img-000314
Figure PCTKR2023003330-appb-img-000315
Figure PCTKR2023003330-appb-img-000315
Figure PCTKR2023003330-appb-img-000316
Figure PCTKR2023003330-appb-img-000316
Figure PCTKR2023003330-appb-img-000317
Figure PCTKR2023003330-appb-img-000317
Figure PCTKR2023003330-appb-img-000318
Figure PCTKR2023003330-appb-img-000318
Figure PCTKR2023003330-appb-img-000319
Figure PCTKR2023003330-appb-img-000319
Figure PCTKR2023003330-appb-img-000320
Figure PCTKR2023003330-appb-img-000320
Figure PCTKR2023003330-appb-img-000321
Figure PCTKR2023003330-appb-img-000321
Figure PCTKR2023003330-appb-img-000322
Figure PCTKR2023003330-appb-img-000322
Figure PCTKR2023003330-appb-img-000323
Figure PCTKR2023003330-appb-img-000323
Figure PCTKR2023003330-appb-img-000324
Figure PCTKR2023003330-appb-img-000324
Figure PCTKR2023003330-appb-img-000325
Figure PCTKR2023003330-appb-img-000325
Figure PCTKR2023003330-appb-img-000326
Figure PCTKR2023003330-appb-img-000326
Figure PCTKR2023003330-appb-img-000327
Figure PCTKR2023003330-appb-img-000327
Figure PCTKR2023003330-appb-img-000328
Figure PCTKR2023003330-appb-img-000328
Figure PCTKR2023003330-appb-img-000329
Figure PCTKR2023003330-appb-img-000329
Figure PCTKR2023003330-appb-img-000330
Figure PCTKR2023003330-appb-img-000330
Figure PCTKR2023003330-appb-img-000331
Figure PCTKR2023003330-appb-img-000331
Figure PCTKR2023003330-appb-img-000332
Figure PCTKR2023003330-appb-img-000332
Figure PCTKR2023003330-appb-img-000333
Figure PCTKR2023003330-appb-img-000333
Figure PCTKR2023003330-appb-img-000334
Figure PCTKR2023003330-appb-img-000334
Figure PCTKR2023003330-appb-img-000335
Figure PCTKR2023003330-appb-img-000335
Figure PCTKR2023003330-appb-img-000336
Figure PCTKR2023003330-appb-img-000336
Figure PCTKR2023003330-appb-img-000337
Figure PCTKR2023003330-appb-img-000337
Figure PCTKR2023003330-appb-img-000338
Figure PCTKR2023003330-appb-img-000338
Figure PCTKR2023003330-appb-img-000339
Figure PCTKR2023003330-appb-img-000339
Figure PCTKR2023003330-appb-img-000340
Figure PCTKR2023003330-appb-img-000340
Figure PCTKR2023003330-appb-img-000341
Figure PCTKR2023003330-appb-img-000341
Figure PCTKR2023003330-appb-img-000342
Figure PCTKR2023003330-appb-img-000342
Figure PCTKR2023003330-appb-img-000343
Figure PCTKR2023003330-appb-img-000343
Figure PCTKR2023003330-appb-img-000344
Figure PCTKR2023003330-appb-img-000344
Figure PCTKR2023003330-appb-img-000345
Figure PCTKR2023003330-appb-img-000345
Figure PCTKR2023003330-appb-img-000346
Figure PCTKR2023003330-appb-img-000346
Figure PCTKR2023003330-appb-img-000347
Figure PCTKR2023003330-appb-img-000347
Figure PCTKR2023003330-appb-img-000348
Figure PCTKR2023003330-appb-img-000348
Figure PCTKR2023003330-appb-img-000349
Figure PCTKR2023003330-appb-img-000349
Figure PCTKR2023003330-appb-img-000350
Figure PCTKR2023003330-appb-img-000350
Figure PCTKR2023003330-appb-img-000351
Figure PCTKR2023003330-appb-img-000351
Figure PCTKR2023003330-appb-img-000352
Figure PCTKR2023003330-appb-img-000352
상기 화합물에 있어서, tBu는 tert-부틸기를 의미한다.In the above compounds, tBu refers to a tert-butyl group.
본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.The present specification provides an organic light-emitting device containing the above-mentioned 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 “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
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 this specification, the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area. The size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, 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 inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
본 명세서에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다.In this specification, the meaning that a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
본 명세서에 있어서, "중수소화", "중수소로 치환된" 또는 "중수소화된"은 화합물의 치환 가능한 위치의 수소가 중수소로 치환되는 것을 의미한다.As used herein, “deuterated,” “substituted with deuterium,” or “deuterated” means that hydrogen at a replaceable position in a compound is replaced with deuterium.
본 명세서에 있어서, "중수소로 X% 치환", "X% 중수소화된", "중수소화도 X%", 또는 "중수소 치환율 X%"는 해당 구조에서 치환 가능한 위치의 수소 중 X%가 중수소로 치횐된 것을 의미한다. 예컨대, 해당 구조가 디벤조퓨란인 경우, 상기 디벤조퓨란이 "중수소로 25% 치환", 상기 디벤조퓨란이 "25% 중수소화된", 상기 디벤조퓨란의 "중수소화도 25%", 또는 상기 디벤조퓨간의 "중수소 치환율 25%"는 상기 디벤조퓨란의 치환 가능한 위치의 8개의 수소 중 2개가 중수소로 치환된 것을 의미한다.In this specification, “X% substitution with deuterium,” “X% deuteration,” “X% deuteration degree,” or “X% deuterium substitution rate” means that It means that it has been dented. For example, when the structure in question is dibenzofuran, the dibenzofuran is “25% substituted with deuterium,” the dibenzofuran is “25% deuterated,” the dibenzofuran is “deuterated by 25%,” or The “deuterium substitution rate of 25%” of the dibenzofuran means that two of the eight hydrogens at the replaceable positions of the dibenzofuran are replaced with deuterium.
본 명세서에 있어서, 중수소화도는 핵자기 공명 분광법(1H NMR), TLC/MS(Thin-Layer Chromatography/Mass Spectrometry), 또는 MALDI-TOF MS(Matrix assisted laser desorption/ionization Time-of-Flight Mass Spectrometry)등의 공지의 방법으로 확인할 수 있다.In the present specification, the degree of deuteration is determined by nuclear magnetic resonance spectroscopy ( 1H NMR), Thin-Layer Chromatography/Mass Spectrometry (TLC/MS), or Matrix assisted laser desorption/ionization Time-of-Flight Mass Spectrometry (MALDI-TOF MS). ) can be confirmed by known methods such as.
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 1의 화합물을 포함하는 것인 유기 발광 소자를 제공한다.This specification includes: a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.
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, etc. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 화합물을 발광층의 도펀트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1 as a dopant of the light-emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 화합물을 발광층의 청색 형광 도펀트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1 as a blue fluorescent dopant of the light-emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공 주입층, 정공 수송층. 발광층, 전자 수송층, 전자 주입층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.In one embodiment of the present specification, the organic light emitting device is a hole injection layer or a hole transport layer. It further includes one or two layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 호스트 화합물을 더 포함한다.In one embodiment of the present specification, the light emitting layer further includes a host compound.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 호스트 화합물을 더 포함하고, 상기 호스트 화합물은 치환 가능한 위치의 적어도 하나의 수소가 중수소로 치환된 것이다.In one embodiment of the present specification, the light-emitting layer further includes a host compound, and the host compound is one in which at least one hydrogen at a replaceable position is replaced with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 호스트 화합물이 중수소로 치환된 경우, 중수소로 30% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 40% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 60% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 80% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 100% 치환된다.In an exemplary embodiment of the present specification, when the host compound is substituted with deuterium, more than 30% of the host compound is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by more than 40% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 60% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 80% with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 하기 화학식 H의 화합물을 더 포함한다.In an exemplary embodiment of the present specification, the light-emitting layer further includes a compound of the following formula (H).
[화학식 H][Formula H]
Figure PCTKR2023003330-appb-img-000353
Figure PCTKR2023003330-appb-img-000353
상기 화학식 H에 있어서,In the formula H,
L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R200 및 R201은 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R200 and R201 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r201은 1 내지 7의 정수이며, 상기 r201이 2 이상인 경우, 2 이상의 R201은 서로 같거나 상이하다.r201 is an integer from 1 to 7, and when r201 is 2 or more, 2 or more R201 are the same 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 헤테로아릴렌기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 나프틸렌기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is 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 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 페날렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a naphthobenzothiophene group substituted or unsubstituted 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; 페난트렌기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is 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 있어서, 상기 R200은 수소; 중수소; 할로겐기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 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, R200 is hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 중수소; 불소; 치환 또는 비치환된 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 3 내지 10의 단환 또는 다환의 시클로알킬기; 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, R200 is hydrogen; heavy hydrogen; fluorine; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 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, R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기다.In one embodiment of the present specification, R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 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, R200 is hydrogen; A substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 페날렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다.In one embodiment of the present specification, R200 is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 중수소; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프틸기; 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, R200 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A naphthyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R200은 수소; 중수소; 중수소, 페닐기, 또는 나프틸기로 치환 또는 비치환된 페닐기; 바이페닐기; 중수소, 페닐기, 또는 나프틸기로 치환 또는 비치환된 나프틸기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In one embodiment of the present specification, R200 is hydrogen; heavy hydrogen; Phenyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Biphenyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 R201은 수소이다.According to an exemplary embodiment of the present specification, R201 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R201은 중수소이다.According to an exemplary embodiment of the present specification, R201 is deuterium.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H의 화합물이 중수소로 치환된 경우, 치환 가능한 위치의 수소가 중수소로 30% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 치환 가능한 위치의 수소가 중수소로 40% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 치환 가능한 위치의 수소가 중수소로 60% 이상 치환된다. In an exemplary embodiment of the present specification, when the compound of formula H is substituted with deuterium, more than 30% of the hydrogen at the replaceable position is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 40% of hydrogen at replaceable positions is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 60% of hydrogen at replaceable positions is replaced with deuterium.
또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 치환 가능한 위치의 수소가 중수소로 80% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 치환 가능한 위치의 수소가 중수소로 100% 치환된다.In another exemplary embodiment, in the structure of Formula H, more than 80% of hydrogen at replaceable positions is replaced with deuterium. In another exemplary embodiment, in the structure of Chemical Formula H, hydrogen at a replaceable position is 100% replaced with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H의 화합물은 하기 화합물 중에서 선택되는 어느 하나이다.In an exemplary embodiment of the present specification, the compound of formula H is any one selected from the following compounds.
Figure PCTKR2023003330-appb-img-000354
Figure PCTKR2023003330-appb-img-000354
Figure PCTKR2023003330-appb-img-000355
Figure PCTKR2023003330-appb-img-000355
Figure PCTKR2023003330-appb-img-000356
Figure PCTKR2023003330-appb-img-000356
Figure PCTKR2023003330-appb-img-000357
Figure PCTKR2023003330-appb-img-000357
Figure PCTKR2023003330-appb-img-000358
Figure PCTKR2023003330-appb-img-000358
Figure PCTKR2023003330-appb-img-000359
Figure PCTKR2023003330-appb-img-000359
Figure PCTKR2023003330-appb-img-000360
Figure PCTKR2023003330-appb-img-000360
Figure PCTKR2023003330-appb-img-000361
Figure PCTKR2023003330-appb-img-000361
Figure PCTKR2023003330-appb-img-000362
Figure PCTKR2023003330-appb-img-000362
Figure PCTKR2023003330-appb-img-000363
Figure PCTKR2023003330-appb-img-000363
Figure PCTKR2023003330-appb-img-000364
Figure PCTKR2023003330-appb-img-000364
Figure PCTKR2023003330-appb-img-000365
Figure PCTKR2023003330-appb-img-000365
Figure PCTKR2023003330-appb-img-000366
Figure PCTKR2023003330-appb-img-000366
Figure PCTKR2023003330-appb-img-000367
Figure PCTKR2023003330-appb-img-000367
Figure PCTKR2023003330-appb-img-000368
Figure PCTKR2023003330-appb-img-000368
Figure PCTKR2023003330-appb-img-000369
Figure PCTKR2023003330-appb-img-000369
Figure PCTKR2023003330-appb-img-000370
Figure PCTKR2023003330-appb-img-000370
Figure PCTKR2023003330-appb-img-000371
Figure PCTKR2023003330-appb-img-000371
Figure PCTKR2023003330-appb-img-000372
Figure PCTKR2023003330-appb-img-000372
Figure PCTKR2023003330-appb-img-000373
Figure PCTKR2023003330-appb-img-000373
Figure PCTKR2023003330-appb-img-000374
Figure PCTKR2023003330-appb-img-000374
Figure PCTKR2023003330-appb-img-000375
Figure PCTKR2023003330-appb-img-000375
Figure PCTKR2023003330-appb-img-000376
Figure PCTKR2023003330-appb-img-000376
Figure PCTKR2023003330-appb-img-000377
Figure PCTKR2023003330-appb-img-000377
본 명세서의 일 실시상태에 따르면, 상기 화학식 H의 화합물은 하기 일반식 1로 제조될 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the compound of formula H may be prepared by the following general formula 1, but is not limited thereto.
[일반식 1][General Formula 1]
Figure PCTKR2023003330-appb-img-000378
Figure PCTKR2023003330-appb-img-000378
상기 일반식 1에 있어서,In General Formula 1,
Ar1은 상기 화학식 H의 -L20-Ar20을 정의와 동일하고,Ar 1 is the same as defined for -L20-Ar20 in Formula H above,
Ar2는 상기 화학식 H의 -L21-Ar21의 정의와 동일하며, 상기 일반식 1의 안트라센 코어에 R200 및 R201이 추가로 치환될 수 있다.Ar 2 is the same as the definition of -L21-Ar21 in Formula H, and R200 and R201 may be additionally substituted in the anthracene core of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 발광층에서 화학식 1의 화합물은 도펀트로, 상기 화학식 H의 화합물은 호스트로 사용된다. In one embodiment of the present specification, the compound of Formula 1 is used as a dopant and the compound of Formula H is used as a host in the light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층이 호스트 및 도펀트를 포함할 경우, 도펀트의 함량은 발광층의 100 중량부를 기준으로 0.01 내지 10 중량부의 범위에서 선택될 수 있으며, 이에 한정되지 않는다.In one embodiment of the present specification, when the light-emitting layer includes a host and a dopant, the content of the dopant may be selected in the range of 0.01 to 10 parts by weight based on 100 parts by weight of the light-emitting layer, but is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 발광층이 호스트 및 도펀트를 포함하고, 상기 호스트 및 도펀트는 99: 1 내지 1:99 중량비, 바람직하게는 99: 1 내지 70: 30 중량비, 더욱더 바람직하게는 99:1 내지 90: 10의 중량비로 포함한다.In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host and the dopant have a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30, and even more preferably 99:99. It is contained in a weight ratio of :1 to 90:10.
상기 발광층은 호스트 재료를 더 포함할 수 있고, 상기 호스트는 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 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 또는 트리아진 유도체 등이 있으며, 이들의 2 종 이상의 혼합물일 수 있으나, 이에 한정되지 않는다. The light-emitting layer may further include a host material, and the host may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. There are furan compounds, pyrimidine derivatives, triazine derivatives, etc., and may be a mixture of two or more types thereof, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 1 종 이상의 도펀트, 및 호스트를 더 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of dopants and a host.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 2종 이상의 혼합 도펀트 및 호스트를 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed dopants and a host.
본 명세서의 일 실시상태에 따르면, 상기 2종 이상의 혼합 도펀트 중 1 이상은 상기 화학식 1을 포함하고, 상기 호스트는 상기 화학식 H의 화합물을 포함한다. 상기 2종 이상의 혼합 도펀트 중 1 이상은 상기 화학식 1을 포함하고, 나머지는 종래에 알려진 도펀트 물질을 사용할 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes the formula (1), and the host includes a compound of the formula (H). At least one of the two or more types of mixed dopants may include Formula 1, and the remaining dopant materials known in the art may be used, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 2종 이상의 혼합 도펀트 중 1 이상은 상기 화학식 1을 포함하고, 나머지는 상기 화학식 1과 상이한 보론계 화합물, 파이렌계 화합물 및 지연형광계 화합물 중 1 이상을 사용할 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes Formula 1, and the remainder includes at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1. However, it is not limited to this.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 1 종 이상의 호스트를 더 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of hosts.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 2종 이상의 혼합 호스트를 더 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer further includes two or more types of mixed hosts.
본 명세서의 일 실시상태에 따르면, 상기 2 종 이상의 혼합 호스트 중 1 이상은 상기 화학식 H의 화합물이다.According to an exemplary embodiment of the present specification, at least one of the two or more mixed hosts is a compound of formula H.
본 명세서의 일 실시상태에 따르면, 상기 2 종 이상의 혼합 호스트는 서로 상이하고, 각각 독립적으로 상기 화학식 H의 화합물이다.According to an exemplary embodiment of the present specification, the two or more mixed hosts are different from each other and are each independently a compound of the formula H.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 2종의 혼합 호스트를 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층 2 종의 혼합 호스트를 포함하고, 상기 2 종의 혼합 호스트는 서로 상이하며, 상기 2 종의 호스트는 상기 화학식 H의 화합물이다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer includes two types of mixed hosts, the two types of mixed hosts are different from each other, and the two types of hosts include the compound of Formula H am.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 화학식 H의 제1 호스트; 및 상기 화학식 H의 제2 호스트를 포함하고, 상기 제1 호스트 및 제2 호스트는 서로 상이하다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and includes a first host of the formula H; and a second host of formula H, wherein the first host and the second host are different from each other.
본 명세서의 일 실시상태에 따르면, 상기 제1 호스트: 제2 호스트는 95:5 내지 5:95의 중량비로 포함되고, 바람직하게는 70: 30 내지 30: 70의 중량비로 포합된다.According to an exemplary embodiment of the present specification, the first host and the second host are included at a weight ratio of 95:5 to 5:95, and preferably at a weight ratio of 70:30 to 30:70.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 1 종 이상의 호스트, 및 도펀트를 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes one or more types of hosts and a dopant.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 1 종 이상의 호스트, 및 도펀트를 포함하고, 상기 호스트는 상기 화학식 H의 화합물을 포함하고, 상기 도펀트는 상기 화학식 1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes one or more hosts, and a dopant, the host includes a compound of formula H, and the dopant includes a compound of formula (1) Contains compounds.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 2 종 이상의 혼합 호스트, 및 도펀트를 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed hosts and a dopant.
본 명세서의 일 실시상태에 따르면, 상기 2종 이상의 혼합 호스트 중 1 이상은 상기 화학식 H의 화합물을 포함하고, 도펀트는 상기 화학식 1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, at least one of the two or more types of mixed hosts includes a compound of Formula H, and the dopant includes a compound of Formula 1.
본 명세서에서 상기 2종 이상의 혼합 호스트는 서로 상이하다.In the present specification, the two or more mixed hosts are different from each other.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 2 종의 혼합 호스트, 및 도펀트를 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts and a dopant.
본 명세서의 일 실시상태에 따르면, 상기 2 종의 혼합 호스트는 서로 상이하고, 각각 독립적으로 상기 화학식 H의 화합물을 포함하고, 상기 도펀트는 상기 화학식 1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the two types of mixed hosts are different from each other and each independently includes a compound of Formula H, and the dopant includes a compound of Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 화학식 H의 제1 호스트; 상기 화학식 H의 제2 호스트; 및 상기 화학식 1의 도펀트를 포함하고, 상기 제1 호스트 및 제2 호스트는 서로 상이하다.According to an exemplary embodiment of the present specification, a first host of Formula H; a second host of formula H; and a dopant of Formula 1, wherein the first host and the second host are different from each other.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 1 종 이상의 호스트, 및 1 종 이상의 도펀트를 사용하고, 상기 1 종 이상의 호스트는 상기 화학식 H의 화합물을 포함하고, 상기 1 종 이상의 도펀트는 상기 화학식 1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer uses one or more types of hosts and one or more dopants, the one or more hosts include a compound of the formula H, and the one or more dopants have the formula (1) Contains compounds of
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 2 종 이상의 혼합 호스트, 및 2 종 이상의 혼합 도펀트를 사용하고, 상기 2 종 이상의 혼합 호스트는 전술한 바와 동일한 재료를 사용할 수 있으며, 상기 2 종 이상의 혼합 도펀트는 전술한 바와 동일한 재료를 사용할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer uses two or more types of mixed hosts and two or more types of mixed dopants, the two or more types of mixed hosts may use the same materials as described above, and the two or more types of mixed hosts may be used. The dopant may be the same material as described above.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 도펀트 물질을 포함하며, 상기 도펀트 물질은 상기 화학식 1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer includes a dopant material, and the dopant material includes the compound of Formula 1.
본 명세의 일 실시상태에 따르면, 상기 발광층은 1 종 이상의 도펀트 및 호스트를 더 포함한다. 상기 1 종 이상의 도펀트는 종래에 알려진 도펀트 물질을 사용할 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the light emitting layer further includes one or more types of dopants and a host. The one or more types of dopants may be conventionally known dopant materials, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 1 종 이상의 호스트를 더 포함한다. 상기 1종 이상의 호스트는 상기 화학식 H의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer further includes one or more types of hosts. The one or more hosts include compounds of formula H above.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2종 이상의 혼합 호스트를 더 포함한다. 상기 2 종 이상의 혼합 호스트 중 1 종 이상은 상기 화학식 H의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer further includes two or more types of mixed hosts. At least one of the two or more mixed hosts includes a compound of formula H above.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2종 이상의 혼합 호스트를 더 포함한다. 상기 2 종의 혼합 호스트는 서로 상이하고, 각각 독립적으로 상기 화학식 H의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer further includes two or more types of mixed hosts. The two types of mixed hosts are different from each other, and each independently includes a compound of formula H.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 제1 전극; 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 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화학식 1의 화합물을 포함한다. In one embodiment of the present specification, the organic light emitting device includes a first electrode; second 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, and at least one of the two or more organic material layers includes the compound of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 발광층, 정공 수송층, 정공 주입층, 정공 수송과 정공 주입을 동시에 하는 층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer that simultaneously performs hole transport and hole injection, and an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 2층 이상의 전자 수송층을 포함할 수 있으나, 이에만 한정되는 것은 아니다.In one embodiment of the present specification, the organic light emitting device may include two or more electron transport layers, but is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자 수송층을 포함하고, 상기 2층 이상의 전자 수송층 중 적어도 하나는 상기 화학식 1의 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 상기 2층 이상의 전자 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자 수송층에 포함될 수 있다. In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound of Formula 1. Specifically, in one embodiment of the present specification, the compound of Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 명세서의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자 수송층에 포함되는 경우, 상기 화학식 1의 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.Additionally, in an exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except the compound of Formula 1 may be the same or different from each other.
또한, 본 명세서의 일 실시상태에 있어서, 상기 각각의 2층 이상의 전자 수송층의 재료들은 서로 동일하거나 상이할 수 있다.Additionally, in one embodiment of the present specification, the materials of each of the two or more electron transport layers may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 2층 이상의 정공주입층을 포함할 수 있으나, 이에만 한정되는 것은 아니다.In one embodiment of the present specification, the organic light emitting device may include two or more hole injection layers, but is not limited thereto.
또한, 본 명세서의 일 실시상태에 있어서, 상기 각각의 2층 이상의 정공주입층의 재료들은 서로 동일하거나 상이할 수 있다.Additionally, in one embodiment of the present specification, the materials of each of the two or more hole injection layers may be the same or different from each other.
상기 화학식 1의 화합물을 포함하는 유기물층이 전자 수송층인 경우, 상기 전자 수송층은 n형 도펀트를 더 포함할 수 있다. 상기 n형 도펀트는 당 기술분야에 알려져 있는 것들을 사용할 수 있으며, 예컨대 금속 또는 금속착체를 사용할 수 있다. 예를 들어, 상기 화학식 1의 화합물을 포함하는 전자 수송층은 LiQ(Lithium Quinolate)를 더 포함할 수 있다.When the organic layer containing the compound of Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may be one known in the art, for example, a metal or a metal complex. For example, the electron transport layer containing the compound of Formula 1 may further include lithium quinolate (LiQ).
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 정공수송층을 포함하고, 상기 2층 이상의 정공 수송층 중 적어도 하나는 상기 화학식 1의 화합물을 포함한다. 구체적으로, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 상기 2층 이상의 정공 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 정공 수송층에 포함될 수 있다.In one embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound of Formula 1. Specifically, in one embodiment of the present specification, the compound of Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
또한, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물이 상기 각각의 2층 이상의 정공 수송층에 포함되는 경우, 상기 화학식 1의 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.Additionally, in an exemplary embodiment of the present specification, when the compound of Formula 1 is included in each of the two or more hole transport layers, other materials except the compound of Formula 1 may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 상기 화학식 1의 화합물을 포함하는 유기물층 이외에 아릴아민기, 카바졸릴기 또는 벤조카바졸릴기를 포함하는 화합물을 포함하는 정공 주입층 또는 정공 수송층을 더 포함할 수 있다.In one embodiment of the present specification, the organic material layer may further include a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound of Formula 1. You can.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 애노드 또는 캐소드이다.In one embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 있어서, 상기 제2 전극은 캐소드 또는 애노드이다. In one embodiment of the present specification, the second electrode is a cathode or anode.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드가 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In 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 있어서, 상기 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 및 2에 예시되어 있다. 상기 도 1 및 2는 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
도 1은 기판(1), 제1 전극(2), 발광층(3) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다. Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, a first electrode 2, a light-emitting layer 3, and a second electrode 4 are sequentially stacked. In this structure, the compound may be included in the light-emitting layer 3.
도 2는 기판(1), 제1 전극(2), 제1 정공주입층(5), 제2 정공주입층(6), 정공수송층(7), 전자차단층(8), 발광층(3), 제1 전자수송층(9), 제2 전자수송층(10), 전자주입층(11), 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다.2 shows a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, and a light emitting layer 3. , the structure of an organic light-emitting device in which the first electron transport layer 9, the second electron transport layer 10, the electron injection layer 11, and the second electrode 4 are sequentially stacked is illustrated. In this structure, the compound may be included in the light-emitting layer 3.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 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 can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound of Formula 1 above.
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 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질, 유기물층 및 애노드 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or conductive metal oxide or alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1의 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. Additionally, the compound of Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method refers to 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 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited to this.
상기 제1 전극 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. The first electrode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
상기 제2 전극 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 second electrode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. metals or alloys thereof, for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
본 명세서에서, 상기 화학식 1의 화합물이 발광층 이외의 유기물층에 포함되거나, 추가의 발광층이 구비되는 경우, 상기 발광층의 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 예를 들어, 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 및 루브렌 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, when the compound of Formula 1 is included in an organic material layer other than the light-emitting layer, or an additional light-emitting layer is provided, the light-emitting material of the light-emitting layer transmits holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines them to emit visible light. As a material capable of emitting light in a range, a material with good quantum efficiency for fluorescence or phosphorescence is desirable. For example, 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; polyfluorene; and rubrene, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료로는 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. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
상기 도펀트 재료로는 상기 화학식 1의 화합물 이외에 추가의 화합물을 포함하는 경우, 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. When the dopant material includes additional compounds in addition to the compound of Formula 1, it includes aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group. In addition, a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
상기 정공 주입층은 전극으로부터 정공을 주입하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 제1 전극에서의 정공 주입 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 여기자의 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 제1 전극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 카르바졸 계열의 유기물; 니트릴 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등 또는 상기 예 중 2 이상을 혼합물 등이 있으나, 이에 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from an electrode. The hole injection material preferably has the ability to transport holes and has an excellent hole injection effect in the first electrode and an excellent hole injection effect in the light-emitting layer or light-emitting material. Additionally, a material having an excellent ability to prevent movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Carbazole-based organic substances; Nitrile-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, or mixtures of two or more of the above examples, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023003330-appb-img-000379
Figure PCTKR2023003330-appb-img-000379
상기 화학식 HI-1에 있어서,In the formula HI-1,
R301 내지 R306은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R301 to R306 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
L301 및 L302는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2 가의 헤테로고리기이다.L301 and L302 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.
본 명세서의 일시상태에 따르면, 상기 R301 및 R302는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.According to the provisional status of the present specification, R301 and R302 are the same or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 메틸기이다.According to an exemplary embodiment of the present specification, R301 and R302 are methyl groups.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 결합하여 치환 또는 비치환된 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R301 and R302 are combined with each other to form a substituted or unsubstituted heterocycle.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 결합하여 치환 또는 비치환된 디하이드로아크리딘고리; 또는 치환 또는 비치환된 인돌로아크리딘고리를 형성한다.According to an exemplary embodiment of the present specification, R301 and R302 are combined with each other to form a substituted or unsubstituted dihydroacridine ring; Or, it forms a substituted or unsubstituted indoloacridine ring.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 결합하여 페닐기로 치환 또는 비치환된 디하이드로아크리딘고리; 또는 인돌로아크리딘고리를 형성한다.According to an exemplary embodiment of the present specification, R301 and R302 are combined with each other to form a dihydroacridine ring substituted or unsubstituted with a phenyl group; Or, it forms an indoloacridine ring.
본 명세서의 일 실시상태에 따르면, 상기 L301 및 L302는 직접결합이다.According to an exemplary embodiment of the present specification, L301 and L302 are a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 R303 내지 R306은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, R303 to R306 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 R303 내지 R306은 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, R303 to R306 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R303 내지 R306은 서로 같거나 상이하고, 각각 독립적으로 페닐기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, R303 to R306 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물로 표시되나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the formula HI-1 is represented by the following compound, but is not limited thereto.
Figure PCTKR2023003330-appb-img-000380
Figure PCTKR2023003330-appb-img-000380
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-2로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by the following formula HI-2.
[화학식 HI-2][Formula HI-2]
Figure PCTKR2023003330-appb-img-000381
Figure PCTKR2023003330-appb-img-000381
상기 화학식 HI-2에 있어서,In the 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 remainder is 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 or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with 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-2는 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HI-2 is represented by the following compound.
Figure PCTKR2023003330-appb-img-000382
Figure PCTKR2023003330-appb-img-000382
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 제1 전극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 카르바졸 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. The hole transport material is preferably a material that can transport holes from the first electrode or the hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2023003330-appb-img-000383
Figure PCTKR2023003330-appb-img-000383
상기 화학식 HT-1에 있어서,In the formula HT-1,
R'314, R315 및 R316는 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,R'314, R315 and R316 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with 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 or different from each other,
r316는 1 내지 5의 정수이고, 상기 r316가 2 이상인 경우, 2 이상의 상기 R316는 서로 같거나 상이하다.r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R'314는 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, R'314 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R'314는 카바졸기; 페닐기; 바이페닐기; 나프틸기 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R'314 is a carbazole group; phenyl group; Biphenyl group; It is any one selected from the group consisting of naphthyl groups and combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R315 및 R316는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 알킬기, 또는 아릴기로 치환 또는 비치환된된 방향족탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R315 and R316 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an alkyl group, or an aromatic hydrocarbon substituted or unsubstituted with an aryl group. forms a ring
본 명세서의 일 실시상태에 따르면, 상기 R315 및 R316는 서로 같거나 상이하고, 각각 독립적으로 페닐기이거나, 인접한 기와 서로 결합하여 벤젠; 또는 페닐기, 또는 메틸기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R315 and R316 are the same or different from each other, and are each independently a phenyl group, or are combined with adjacent groups to form benzene; Or, it forms indene substituted or unsubstituted with a phenyl group or a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HT-1 is represented by the following compound.
Figure PCTKR2023003330-appb-img-000384
Figure PCTKR2023003330-appb-img-000384
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 전자 수송 물질로는 제2 전극으로부터 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; 트리아진 유도체; LiQ 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 제1 전극 물질과 함께 사용할 수 있다. 특히, 적절한 제1 전극 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 that can easily receive electrons from the second electrode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complex; triazine derivatives; LiQ, etc., but is not limited thereto. The electron transport layer can be used with any desired first electrode material, as used according to the prior art. In particular, suitable first electrode materials are conventional materials with a low work function, followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
본 명세서의 일 실시상태에 따르면, 상기 전자수송층은 하기 화학식 ET-1로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the electron transport layer includes a compound represented by the following formula ET-1.
[화학식 ET-1][Formula ET-1]
[화학식 ET-1][Formula ET-1]
Figure PCTKR2023003330-appb-img-000385
Figure PCTKR2023003330-appb-img-000385
상기 화학식 ET-1에 있어서,In the formula ET-1,
X'7 내지 X'8 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of X'7 to X'8 is N, and the rest are CH,
R317 내지 R322는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R317 to R322 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or combines with adjacent groups to form a substituted or unsubstituted ring,
L'1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L'1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
r322는 1 내지 7의 정수이고, 상기 r322가 2 이상인 경우, 상기 R322는 서로 같거나 상이하고,r322 is an integer from 1 to 7, and when r322 is 2 or more, R322 is the same as or different from each other,
l'1은 1 내지 5의 정수이며, 상기 l'1이 2 이상인 경우, 상기 L'1은 서로 같거나 상이하다.l'1 is an integer from 1 to 5, and when l'1 is 2 or more, L'1 is the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R317 내지 R322는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 아릴기이고, 인접한 기는 서로 결합하여 치환 또는 비치환된 방향족탄화수소 고리를 형성한다.According to an exemplary embodiment of the present specification, R317 to R322 are the same or different from each other, and are each independently hydrogen; Or it is a substituted or unsubstituted aryl group, and adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R317 내지 R322는 서로 같거나 상이하고, 각각 독립적으로 수소; 페닐기; 또는 나프틸기이거나, 인접한 기는 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R317 to R322 are the same or different from each other, and are each independently hydrogen; phenyl group; Or it is a naphthyl group, or adjacent groups combine with each other to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 L'1은 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L'1 is a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L'1은 페닐렌기이다.According to an exemplary embodiment of the present specification, L'1 is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 ET-1는 하기 화합물 중에서 선택된다.According to an exemplary embodiment of the present specification, the ET-1 is selected from the following compounds.
Figure PCTKR2023003330-appb-img-000386
Figure PCTKR2023003330-appb-img-000386
본 명세서의 일 실시상태에 따르면, 상기 전자수송층은 하기 화학식 ET-2로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the electron transport layer includes a compound represented by the following formula ET-2.
[화학식 ET-2][Formula ET-2]
Figure PCTKR2023003330-appb-img-000387
Figure PCTKR2023003330-appb-img-000387
상기 화학식 ET-2에 있어서,In the formula ET-2,
T1 내지 T3는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 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,T1 to T3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of substituted or unsubstituted heteroaryl groups, and combinations thereof, or combines with adjacent groups to form a substituted or unsubstituted ring,
t1은 1 내지 4의 정수이며, 상기 t1이 2 이상인 경우, 2 이상의 상기 T1은 서로 같거나 상이하며,t1 is an integer from 1 to 4, and when t1 is 2 or more, 2 or more T1 are the same or different from each other,
t2는 1 내지 4의 정수이고, 상기 t2가 2 이상인 경우, 2 이상의 상기 T2는 서로 같거나 상이하고, t2 is an integer from 1 to 4, and when t2 is 2 or more, 2 or more T2 are the same or different from each other,
t3는 1 내지 10의 정수이며, 상기 t3가 2 이상인 경우, 2 이상의 상기 T3는 서로 같거나 상이하다.t3 is an integer from 1 to 10, and when t3 is 2 or more, 2 or more T3 are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T3는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로아릴기, 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, T1 to T3 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl groups, and combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T3는 서로 같거나 상이하고, 각각 독립적으로 수소; 카바졸기; 페닐기; 바이페닐기; 트리아진기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, T1 to T3 are the same or different from each other, and are each independently hydrogen; carbazole group; phenyl group; Biphenyl group; triazine group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 ET-2는 하기 화합물 중에서 선택된다.According to an exemplary embodiment of the present specification, the ET-2 is selected from the following compounds.
Figure PCTKR2023003330-appb-img-000388
Figure PCTKR2023003330-appb-img-000388
상기 전자수송층은 금속착물을 더 포함할 수 있다. 상기 금속은 당업계에서 사용하는 금속을 사용할 수 있다.The electron transport layer may further include a metal complex. The metal may be a metal used in the industry.
상기 전자 주입층은 전극으로부터 전자를 주입하는 층이다. 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 여기자가 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 트리아진, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체, 상기 예 중 2 이상의 혼합물 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has an excellent ability to transport electrons and has an excellent electron injection effect from the second electrode and an excellent electron injection effect to the light-emitting layer or 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, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. These include, but are not limited to, their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, and mixtures of two or more of the above examples.
상기 금속 착체 화합물로는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[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.The metal complex compounds 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) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다.The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
본 명세서의 일 실시상태에 따르면, 상기 전자차단층은 상기 화학식 HT-1로 표시된다. According to an exemplary embodiment of the present specification, the electron blocking layer is represented by the formula HT-1.
상기 정공 차단층은 정공이 발광층을 지나 음극으로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex), 피리딘, 피리미딘 또는 트리아진 유도체 등이 있으나, 이에 한정되는 것은 아니다.The hole blocking layer is a layer that prevents holes from passing through the light emitting layer and reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, etc. are included, but are not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In one embodiment of the present specification, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.
본 명세서에 따른 화합물은 유기 인광 소자, 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 발광 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다. 예컨대, 상기 유기 태양 전지는 음극, 양극 및 상기 음극과 양극 사이에 구비된 광활성층을 포함하는 구조일 수 있고, 상기 광활성층은 상기 화합물을 포함할 수 있다.The compounds according to the present specification may function in organic light-emitting devices, including organic phosphorescent devices, organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.
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 can be included 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, etc., but is not limited thereto.
본 명세서의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present specification can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, in order to explain the present specification in detail, examples and comparative examples will be described in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples detailed below. The examples and comparative examples of this specification are provided to more completely explain the present specification to those with average knowledge in the art.
합성예 1. 화합물 1의 합성Synthesis Example 1. Synthesis of Compound 1
1) 중간체 1의 합성1) Synthesis of Intermediate 1
Figure PCTKR2023003330-appb-img-000389
Figure PCTKR2023003330-appb-img-000389
질소 분위기하에서 출발물질 A-1 [11-(tert-butyl)-6-chloro-8H-benzofuro[2,3-c]carbazole] 40 g, 출발물질 B-1 [1-bromo-4-(tert-butyl)benzene] 25 g, 소듐 터트부톡사이드 (NaOtBu) [sodium tert-butoxide] 17 g, 비스(트리-터트부틸포스핀)팔라듐(0) (Pd(P(t-Bu)3)2) 0.6 g을 톨루엔 1.0 L에 넣은 후, 140 ℃에서 가열하고 5시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4(무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 1를 45 g 수득하였다. (수율 82%, Mass [M+]=481)40 g of starting material A-1 [11-(tert-butyl)-6-chloro-8H-benzofuro[2,3-c]carbazole], starting material B-1 [1-bromo-4-(tert) under nitrogen atmosphere. -butyl)benzene] 25 g, sodium tertbutoxide (NaOtBu) [sodium tert-butoxide] 17 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) 2 ) 0.6 g was added to 1.0 L of toluene, heated at 140°C, and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and NH 4 Cl, and then treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 45 g of Intermediate 1. (Yield 82%, Mass [M+]=481)
2) 중간체 2의 합성2) Synthesis of intermediate 2
Figure PCTKR2023003330-appb-img-000390
Figure PCTKR2023003330-appb-img-000390
질소 분위기하에서 출발물질 중간체 1(10 g), 옥타메틸-바이(디옥사보롤레인) (B2Pin2) 9.5 g, 포타슘 아세테이트 (KOAc) [potassium acetate] 6.1g, 비스 (디벤질리덴아세톤)팔라듐 (0) (Pd(dba)2) 0.4 g, 트리시클로헥실포스핀 (PCy3) 0.4 g을 디옥산 0.2 L에 넣은 후, 130 ℃에서 가열하고 12시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물을 가하여 분액한 후 MgSO4(무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정 (헥산)으로 정제하여 중간체 2를 15 g 수득하였다. (수율 84%, Mass [M+]=572)Under nitrogen atmosphere, starting material intermediate 1 (10 g), octamethyl-bi(dioxaborolein) (B 2 Pin 2 ) 9.5 g, potassium acetate (KOAc) [potassium acetate] 6.1 g, bis (dibenzylideneacetone) 0.4 g of palladium (0) (Pd(dba) 2 ) and 0.4 g of tricyclohexylphosphine (PCy 3 ) were added to 0.2 L of dioxane, heated at 130°C, and stirred for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added to separate the layers, and then treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (hexane) to obtain 15 g of Intermediate 2. (Yield 84%, Mass [M+]=572)
3) 중간체 3의 합성3) Synthesis of Intermediate 3
Figure PCTKR2023003330-appb-img-000391
Figure PCTKR2023003330-appb-img-000391
질소 분위기하에서 중간체 2(12 g), C-1 [(2-bromo-N-(4-(tert-butyl)phenyl)dibenzo[b,d]furan-3-amine] 8.3 g, 탄산 칼륨 [potassium carbonate] 4.4 g 디옥산 160 mL와 물 40 mL를 넣은 후 테트라키스(트리페닐포스핀)팔라듐(0) [tetrakis(triphenylhosphine)palladium(0)] Pd(PPh3)4 0.2 g을 첨가한 후, 130 ℃에서 가열하고 3시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물과 톨루엔을 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 3을 12 g 수득하였다. (수율 75%, Mass [M+]=760) Intermediate 2 (12 g), C-1 [(2-bromo-N-(4-(tert-butyl)phenyl)dibenzo[b,d]furan-3-amine] 8.3 g, potassium carbonate [potassium] under nitrogen atmosphere carbonate] After adding 4.4 g of 160 mL of dioxane and 40 mL of water, 0.2 g of tetrakis(triphenylhosphine)palladium(0) [tetrakis(triphenylhosphine)palladium(0)] Pd(PPh 3 ) 4 was added, It was heated at 130 ° C and stirred for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water and toluene were added to separate the liquid, and then treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and recrystallized. Purified with (toluene/hexane), 12 g of Intermediate 3 was obtained. (Yield 75%, Mass [M+]=760)
4) 화합물 1의 합성4) Synthesis of Compound 1
Figure PCTKR2023003330-appb-img-000392
Figure PCTKR2023003330-appb-img-000392
질소 분위기에서 중간체 3(12g), 보론 트리아이오다이드(BI3) [boron triiodide] 7.4 g를 디클로로벤젠 [1,2-dichlorobenzene] 120ml에 넣고 150℃에서 교반하였다. 6시간 반응 후 상온으로 식히고 물과 톨루엔을 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 실리카겔 컬럼 크로마토그래피로 정제하여 화합물 1을 4.5g 수득하였다. (수율 37%, MS: [M+H]+= 767)In a nitrogen atmosphere, Intermediate 3 (12 g) and 7.4 g of boron triiodide (BI3) [boron triiodide] were added to 120 ml of dichlorobenzene [1,2-dichlorobenzene] and stirred at 150°C. After reaction for 6 hours, the mixture was cooled to room temperature, separated by adding water and toluene, and then treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography to obtain 4.5 g of Compound 1. (Yield 37%, MS: [M+H]+= 767)
합성예 2. Compound 2의 합성Synthesis Example 2. Synthesis of Compound 2
1) 중간체 4의 합성1) Synthesis of intermediate 4
Figure PCTKR2023003330-appb-img-000393
Figure PCTKR2023003330-appb-img-000393
출발물질 C-1 대신 C-2(5.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 4 를 10 g 수득하였다. (수율 81%, Mass [M+]=704)10 g of Intermediate 4 was obtained by preparing it in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that C-2 (5.9 g) was used instead of the starting material C-1. (Yield 81%, Mass [M+]=704)
2) 중간체 5의 합성2) Synthesis of intermediate 5
Figure PCTKR2023003330-appb-img-000394
Figure PCTKR2023003330-appb-img-000394
출발물질 중간체 3 대신 중간체 4(10 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 중간체 5 를 3.7 g 수득하였다. (수율 37%, Mass [M+]=712)3.7 g of Intermediate 5 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 4 (10 g) was used instead of the starting material Intermediate 3. (Yield 37%, Mass [M+]=712)
3) 화합물 2의 합성3) Synthesis of Compound 2
Figure PCTKR2023003330-appb-img-000395
Figure PCTKR2023003330-appb-img-000395
출발물질 A-1 대신 중간체 5 (3.7g), 출발물질 B-1 대신 C-3 (1.5 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 화합물 2 를 4.0 g 수득하였다. (수율 80%, Mass [M+]=957)4.0 g of Compound 2 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Intermediate 5 (3.7 g) was used instead of Starting Material A-1 and C-3 (1.5 g) was used instead of Starting Material B-1. did. (Yield 80%, Mass [M+]=957)
합성예 3. 화합물 3의 합성Synthesis Example 3. Synthesis of Compound 3
1) 중간체 6의 합성1) Synthesis of intermediate 6
Figure PCTKR2023003330-appb-img-000396
Figure PCTKR2023003330-appb-img-000396
출발물질 C-1 대신 C-4(7.4 g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 6 를 9.8 g 수득하였다. (수율 71%, Mass [M+]=786)9.8 g of Intermediate 6 was obtained by preparing it in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that C-4 (7.4 g) was used instead of the starting material C-1. (Yield 71%, Mass [M+]=786)
2) 화합물 3의 합성2) Synthesis of Compound 3
Figure PCTKR2023003330-appb-img-000397
Figure PCTKR2023003330-appb-img-000397
출발물질 중간체 3 대신 중간체 6(9.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 3을 4.1 g 수득하였다. (수율 41%, Mass [M+]=793) Compound 3 was prepared in the same amount as 4.1 g of Compound 1 in Synthesis Example 1, except that Intermediate 6 (9.8 g) was used instead of the starting material, Intermediate 3. (Yield 41%, Mass [M+]=793)
합성예 4. 화합물 4의 합성Synthesis Example 4. Synthesis of Compound 4
1) 중간체 7의 합성1) Synthesis of intermediate 7
Figure PCTKR2023003330-appb-img-000398
Figure PCTKR2023003330-appb-img-000398
출발물질 C-1 대신 C-5 (8.0 g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 7 를 12 g 수득하였다. (수율 84%, Mass [M+]=820)12 g of Intermediate 7 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that C-5 (8.0 g) was used instead of the starting material C-1. (Yield 84%, Mass [M+]=820)
2) 중간체 8의 합성2) Synthesis of intermediate 8
Figure PCTKR2023003330-appb-img-000399
Figure PCTKR2023003330-appb-img-000399
출발물질 중간체 3 대신 중간체 7 (12 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 중간체 8 를 4.8 g 수득하였다. (수율 40%, Mass [M+]=828)4.8 g of Intermediate 8 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 7 (12 g) was used instead of the starting material Intermediate 3. (Yield 40%, Mass [M+]=828)
3) 화합물 4의 합성3) Synthesis of Compound 4
Figure PCTKR2023003330-appb-img-000400
Figure PCTKR2023003330-appb-img-000400
출발물질 A-1 대신 중간체 8 (4.8 g), 출발물질 B-1 대신 C-6 (1.0 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 화합물 4 를 4.6 g 수득하였다. (수율 83%, Mass [M+]=961) Compound 4 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Intermediate 8 (4.8 g) was used instead of Starting Material A-1 and C-6 (1.0 g) was used instead of Starting Material B-1 to obtain 4.6 g of Compound 4. did. (Yield 83%, Mass [M+]=961)
합성예 5. 화합물 5의 합성 Synthesis Example 5. Synthesis of Compound 5
1) 중간체 9의 합성1) Synthesis of intermediate 9
Figure PCTKR2023003330-appb-img-000401
Figure PCTKR2023003330-appb-img-000401
출발물질 A-1 (10 g), 출발물질 B-1 대신 B-2 (7.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 9 를 11 g 수득하였다. (수율 71%, Mass [M+]=541)11 g of Intermediate 9 was obtained by preparing it in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that starting material A-1 (10 g) and B-2 (7.9 g) were used instead of starting material B-1. (Yield 71%, Mass [M+]=541)
2) 중간체 10의 합성2) Synthesis of intermediate 10
Figure PCTKR2023003330-appb-img-000402
Figure PCTKR2023003330-appb-img-000402
중간체 1 대신 중간체 9 (11 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 10을 11g 수득하였다. (수율 86%, Mass [M+]=632)11 g of Intermediate 10 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 9 (11 g) was used instead of Intermediate 1. (Yield 86%, Mass [M+]=632)
3) 중간체 11의 합성3) Synthesis of intermediate 11
Figure PCTKR2023003330-appb-img-000403
Figure PCTKR2023003330-appb-img-000403
중간체 2 대신 중간체 10 (11g), C-1 대신 C-4 (7.3g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 11를 9.1 g 수득하였다. (수율 62%, Mass [M+]=846)9.1 g of Intermediate 11 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 10 (11 g) was used instead of Intermediate 2 and C-4 (7.3 g) was used instead of C-1. (Yield 62%, Mass [M+]=846)
4) 화합물 5의 합성4) Synthesis of Compound 5
Figure PCTKR2023003330-appb-img-000404
Figure PCTKR2023003330-appb-img-000404
중간체 3 대신 중간체 11 (9.1 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 5를 3.2 g 수득하였다. (수율 35%, Mass [M+]=853) Compound 5 was prepared in the same amount as 3.2 g of Compound 1 in Synthesis Example 1, except that Intermediate 11 (9.1 g) was used instead of Intermediate 3. (Yield 35%, Mass [M+]=853)
합성예 6. 화합물 6의 합성Synthesis Example 6. Synthesis of Compound 6
1) 중간체 12의 합성1) Synthesis of intermediate 12
Figure PCTKR2023003330-appb-img-000405
Figure PCTKR2023003330-appb-img-000405
출발물질 A-1 (10 g), 출발물질 B-1 대신 B-3 (7.8 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 12 를 12 g 수득하였다. (수율 78%, Mass [M+]=535)12 g of Intermediate 12 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that starting material A-1 (10 g) and B-3 (7.8 g) were used instead of starting material B-1. (Yield 78%, Mass [M+]=535)
2) 중간체 13의 합성2) Synthesis of intermediate 13
Figure PCTKR2023003330-appb-img-000406
Figure PCTKR2023003330-appb-img-000406
중간체 1 대신 중간체 12 (12 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 13을 11g 수득하였다. (수율 78%, Mass [M+]=626)11 g of Intermediate 13 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 12 (12 g) was used instead of Intermediate 1. (Yield 78%, Mass [M+]=626)
3) 중간체 14의 합성3) Synthesis of intermediate 14
Figure PCTKR2023003330-appb-img-000407
Figure PCTKR2023003330-appb-img-000407
중간체 2 대신 중간체 13 (11g), C-1 (6.9g) 을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 14를 10 g 수득하였다. (수율 70%, Mass [M+]=814)10 g of Intermediate 14 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 13 (11 g) and C-1 (6.9 g) were used instead of Intermediate 2. (Yield 70%, Mass [M+]=814)
4) 화합물 6의 합성4) Synthesis of Compound 6
Figure PCTKR2023003330-appb-img-000408
Figure PCTKR2023003330-appb-img-000408
중간체 3 대신 중간체 14 (10 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 6을 3.6 g 수득하였다. (수율 36%, Mass [M+]=821) Compound 6 was prepared in the same amount as 3.6 g of Compound 1 in Synthesis Example 1, except that Intermediate 14 (10 g) was used instead of Intermediate 3. (Yield 36%, Mass [M+]=821)
합성예 7. 화합물 7의 합성Synthesis Example 7. Synthesis of Compound 7
1) 중간체 15의 합성1) Synthesis of intermediate 15
Figure PCTKR2023003330-appb-img-000409
Figure PCTKR2023003330-appb-img-000409
출발물질 A-1 (10 g), 출발물질 B-1 대신 B-4 (9.4 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 15 를 12 g 수득하였다. (수율 71%, Mass [M+]=592)12 g of Intermediate 15 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that starting material A-1 (10 g) and B-4 (9.4 g) were used instead of starting material B-1. (Yield 71%, Mass [M+]=592)
2) 중간체 16의 합성2) Synthesis of intermediate 16
Figure PCTKR2023003330-appb-img-000410
Figure PCTKR2023003330-appb-img-000410
중간체 1 대신 중간체 15 (12 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 16을 10g 수득하였다. (수율 72%, Mass [M+]=683)10 g of Intermediate 16 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 15 (12 g) was used instead of Intermediate 1. (Yield 72%, Mass [M+]=683)
3) 중간체 17의 합성3) Synthesis of intermediate 17
Figure PCTKR2023003330-appb-img-000411
Figure PCTKR2023003330-appb-img-000411
중간체 2 대신 중간체 16 (10g), C-1 (5.8g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 17를 9.2 g 수득하였다. (수율 72%, Mass [M+]=871)9.2 g of Intermediate 17 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 16 (10 g) and C-1 (5.8 g) were used instead of Intermediate 2. (Yield 72%, Mass [M+]=871)
4) 화합물 7의 합성4) Synthesis of Compound 7
Figure PCTKR2023003330-appb-img-000412
Figure PCTKR2023003330-appb-img-000412
중간체 3 대신 중간체 17 (9.2 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 7을 3.1 g 수득하였다. (수율 33%, Mass [M+]=878)3.1 g of compound 7 was obtained in the same manner as the preparation method of compound 1 in Synthesis Example 1, except that intermediate 17 (9.2 g) was used instead of intermediate 3. (Yield 33%, Mass [M+]=878)
합성예 8. 화합물 8의 합성Synthesis Example 8. Synthesis of Compound 8
1) 중간체 18의 합성1) Synthesis of intermediate 18
Figure PCTKR2023003330-appb-img-000413
Figure PCTKR2023003330-appb-img-000413
출발물질 A-1 대신 출발물질 A-2 (10 g), 출발물질 B-1 대신 B-5 (7.3 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 18 를 12 g 수득하였다. (수율 82%, Mass [M+]=592)Intermediate 18 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-2 (10 g) was used instead of Starting Material A-1 and B-5 (7.3 g) was used instead of Starting Material B-1. 12 g was obtained. (Yield 82%, Mass [M+]=592)
2) 중간체 19의 합성2) Synthesis of intermediate 19
Figure PCTKR2023003330-appb-img-000414
Figure PCTKR2023003330-appb-img-000414
중간체 1 대신 중간체 18 (12 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 19을 10.8g 수득하였다. (수율 76%, Mass [M+]=703)10.8 g of Intermediate 19 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 18 (12 g) was used instead of Intermediate 1. (Yield 76%, Mass [M+]=703)
3) 중간체 20의 합성3) Synthesis of intermediate 20
Figure PCTKR2023003330-appb-img-000415
Figure PCTKR2023003330-appb-img-000415
중간체 2 대신 중간체 19 (10.8g), C-1 대신 C-7(6.3g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 20를 9.9 g 수득하였다. (수율 71%, Mass [M+]=907)9.9 g of Intermediate 20 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 19 (10.8 g) was used instead of Intermediate 2 and C-7 (6.3 g) was used instead of C-1. (Yield 71%, Mass [M+]=907)
4) 화합물 8의 합성4) Synthesis of Compound 8
Figure PCTKR2023003330-appb-img-000416
Figure PCTKR2023003330-appb-img-000416
중간체 3 대신 중간체 20 (9.9 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 8을 4.1 g 수득하였다. (수율 41%, Mass [M+]=915)Compound 8 was prepared in the same amount as 4.1 g of Compound 1 in Synthesis Example 1, except that Intermediate 20 (9.9 g) was used instead of Intermediate 3. (Yield 41%, Mass [M+]=915)
합성예 9. 화합물 9의 합성Synthesis Example 9. Synthesis of Compound 9
1) 중간체 21의 합성1) Synthesis of intermediate 21
Figure PCTKR2023003330-appb-img-000417
Figure PCTKR2023003330-appb-img-000417
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 (6.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 21 를 9.9 g 수득하였다. (수율 71%, Mass [M+]=481)9.9 g of Intermediate 21 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) and Starting Material B-1 (6.2 g) were used instead of Starting Material A-1. . (Yield 71%, Mass [M+]=481)
2) 중간체 22의 합성2) Synthesis of intermediate 22
Figure PCTKR2023003330-appb-img-000418
Figure PCTKR2023003330-appb-img-000418
중간체 1 대신 중간체 21 (9.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 22을 9.5g 수득하였다. (수율 81%, Mass [M+]=572)9.5 g of Intermediate 22 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 21 (9.9 g) was used instead of Intermediate 1. (Yield 81%, Mass [M+]=572)
3) 중간체 23의 합성3) Synthesis of intermediate 23
Figure PCTKR2023003330-appb-img-000419
Figure PCTKR2023003330-appb-img-000419
중간체 2 대신 중간체 22 (9.9g), C-1 대신 C-8 (7.9g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 23를 11.1 g 수득하였다. (수율 79%, Mass [M+]=842)11.1 g of Intermediate 23 was obtained by preparing it in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 22 (9.9 g) was used instead of Intermediate 2 and C-8 (7.9 g) was used instead of C-1. (Yield 79%, Mass [M+]=842)
4) 화합물 9의 합성4) Synthesis of compound 9
Figure PCTKR2023003330-appb-img-000420
Figure PCTKR2023003330-appb-img-000420
중간체 3 대신 중간체 23 (11.1 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 9를 4.2 g 수득하였다. (수율 37%, Mass [M+]=849)Compound 9 (4.2 g) was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 23 (11.1 g) was used instead of Intermediate 3. (Yield 37%, Mass [M+]=849)
합성예 10. 화합물 10의 합성Synthesis Example 10. Synthesis of Compound 10
1) 중간체 24의 합성1) Synthesis of intermediate 24
Figure PCTKR2023003330-appb-img-000421
Figure PCTKR2023003330-appb-img-000421
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-2 (7.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 24 를 12.5 g 수득하였다. (수율 81%, Mass [M+]=541)Intermediate 24 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-2 (7.9 g) was used instead of Starting Material B-1. 12.5 g was obtained. (Yield 81%, Mass [M+]=541)
2) 중간체 25의 합성2) Synthesis of intermediate 25
Figure PCTKR2023003330-appb-img-000422
Figure PCTKR2023003330-appb-img-000422
중간체 1 대신 중간체 24 (12.5 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 25을 10.6g 수득하였다. (수율 73%, Mass [M+]=632)10.6 g of Intermediate 25 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 24 (12.5 g) was used instead of Intermediate 1. (Yield 73%, Mass [M+]=632)
3) 중간체 26의 합성3) Synthesis of intermediate 26
Figure PCTKR2023003330-appb-img-000423
Figure PCTKR2023003330-appb-img-000423
중간체 2 대신 중간체 25 (10.6g), C-1 대신 C-9 (6.0g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 26를 10.8 g 수득하였다. (수율 82%, Mass [M+]=786)10.8 g of Intermediate 26 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 25 (10.6 g) was used instead of Intermediate 2 and C-9 (6.0 g) was used instead of C-1. (Yield 82%, Mass [M+]=786)
4) 화합물 10의 합성4) Synthesis of Compound 10
Figure PCTKR2023003330-appb-img-000424
Figure PCTKR2023003330-appb-img-000424
중간체 3 대신 중간체 26 (10.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 10을 3.3 g 수득하였다. (수율 30%, Mass [M+]=793)3.3 g of compound 10 was obtained in the same manner as the preparation method of compound 1 in Synthesis Example 1, except that intermediate 26 (10.8 g) was used instead of intermediate 3. (Yield 30%, Mass [M+]=793)
합성예 11. 화합물 11의 합성Synthesis Example 11. Synthesis of Compound 11
1) 중간체 27의 합성1) Synthesis of intermediate 27
Figure PCTKR2023003330-appb-img-000425
Figure PCTKR2023003330-appb-img-000425
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-6 (7.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 27 를 10.6 g 수득하였다. (수율 72%, Mass [M+]=515)Intermediate 27 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-6 (7.2 g) was used instead of Starting Material B-1. 10.6 g was obtained. (Yield 72%, Mass [M+]=515)
2) 중간체 28의 합성2) Synthesis of intermediate 28
Figure PCTKR2023003330-appb-img-000426
Figure PCTKR2023003330-appb-img-000426
중간체 1 대신 중간체 27 (10.6 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 28을 9.4g 수득하였다. (수율 75%, Mass [M+]=606)9.4 g of Intermediate 28 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 27 (10.6 g) was used instead of Intermediate 1. (Yield 75%, Mass [M+]=606)
3) 중간체 29의 합성3) Synthesis of intermediate 29
Figure PCTKR2023003330-appb-img-000427
Figure PCTKR2023003330-appb-img-000427
중간체 2 대신 중간체 28 (9.4g), C-1 대신 C-10 (6.4g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 29를 9.9 g 수득하였다. (수율 78%, Mass [M+]=814)9.9 g of Intermediate 29 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 28 (9.4 g) was used instead of Intermediate 2 and C-10 (6.4 g) was used instead of C-1. (Yield 78%, Mass [M+]=814)
4) 화합물 11의 합성4) Synthesis of Compound 11
Figure PCTKR2023003330-appb-img-000428
Figure PCTKR2023003330-appb-img-000428
중간체 3 대신 중간체 29 (9.9 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 11을 3.0 g 수득하였다. (수율 30%, Mass [M+]=821)3.0 g of Compound 11 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 29 (9.9 g) was used instead of Intermediate 3. (Yield 30%, Mass [M+]=821)
합성예 12. 화합물 12의 합성Synthesis Example 12. Synthesis of Compound 12
1) 중간체 30의 합성1) Synthesis of intermediate 30
Figure PCTKR2023003330-appb-img-000429
Figure PCTKR2023003330-appb-img-000429
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-7 (10.1g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 30 를 14.2 g 수득하였다. (수율 80%, Mass [M+]=617)Intermediate 30 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-7 (10.1 g) was used instead of Starting Material B-1. 14.2 g was obtained. (Yield 80%, Mass [M+]=617)
2) 중간체 31의 합성2) Synthesis of intermediate 31
Figure PCTKR2023003330-appb-img-000430
Figure PCTKR2023003330-appb-img-000430
중간체 1 대신 중간체 30(14.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 31을 13.5g 수득하였다. (수율 83%, Mass [M+]=708)13.5 g of Intermediate 31 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 30 (14.2 g) was used instead of Intermediate 1. (Yield 83%, Mass [M+]=708)
3) 중간체 32의 합성3) Synthesis of intermediate 32
Figure PCTKR2023003330-appb-img-000431
Figure PCTKR2023003330-appb-img-000431
중간체 2 대신 중간체 31 (13.5g), C-1 (7.5g) 을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 32를 11.4 g 수득하였다. (수율 67%, Mass [M+]=896)11.4 g of Intermediate 32 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 31 (13.5 g) and C-1 (7.5 g) were used instead of Intermediate 2. (Yield 67%, Mass [M+]=896)
4) 화합물 12의 합성4) Synthesis of Compound 12
Figure PCTKR2023003330-appb-img-000432
Figure PCTKR2023003330-appb-img-000432
중간체 3 대신 중간체 32 (11.4 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 12를 3.6 g 수득하였다. (수율 31%, Mass [M+]=9.6)Compound 12 was prepared in the same amount as 3.6 g of Compound 1 in Synthesis Example 1, except that Intermediate 32 (11.4 g) was used instead of Intermediate 3. (Yield 31%, Mass [M+]=9.6)
합성예 13. 화합물 13의 합성Synthesis Example 13. Synthesis of Compound 13
1) 중간체 33의 합성1) Synthesis of intermediate 33
Figure PCTKR2023003330-appb-img-000433
Figure PCTKR2023003330-appb-img-000433
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-8 (7.8 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 33 를 12.1 g 수득하였다. (수율 78%, Mass [M+]=537)Intermediate 33 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-8 (7.8 g) was used instead of Starting Material B-1. 12.1 g was obtained. (Yield 78%, Mass [M+]=537)
2) 중간체 34의 합성2) Synthesis of intermediate 34
Figure PCTKR2023003330-appb-img-000434
Figure PCTKR2023003330-appb-img-000434
중간체 1 대신 중간체 33 (12.1 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 34을 10.8g 수득하였다. (수율 76%, Mass [M+]=628)10.8 g of Intermediate 34 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 33 (12.1 g) was used instead of Intermediate 1. (Yield 76%, Mass [M+]=628)
3) 중간체 35의 합성3) Synthesis of intermediate 35
Figure PCTKR2023003330-appb-img-000435
Figure PCTKR2023003330-appb-img-000435
중간체 2 대신 중간체 34 (10.8g), C-1 대신 C-4 (7.2g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 35를 10 g 수득하였다. (수율 67%, Mass [M+]=842)10 g of Intermediate 35 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 34 (10.8 g) was used instead of Intermediate 2 and C-4 (7.2 g) was used instead of C-1. (Yield 67%, Mass [M+]=842)
4) 화합물 13의 합성4) Synthesis of compound 13
Figure PCTKR2023003330-appb-img-000436
Figure PCTKR2023003330-appb-img-000436
중간체 3 대신 중간체 35(10 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 13을 2.6 g 수득하였다. (수율 26%, Mass [M+]=849)Compound 13 was prepared in the same amount as 2.6 g of Compound 1 in Synthesis Example 1, except that Intermediate 35 (10 g) was used instead of Intermediate 3. (Yield 26%, Mass [M+]=849)
합성예 14. 화합물 14의 합성Synthesis Example 14. Synthesis of Compound 14
1) 중간체 36의 합성1) Synthesis of intermediate 36
Figure PCTKR2023003330-appb-img-000437
Figure PCTKR2023003330-appb-img-000437
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-9 (8.4 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 36 를 12.6 g 수득하였다. (수율 79%, Mass [M+]=557)Intermediate 36 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-9 (8.4 g) was used instead of Starting Material B-1. 12.6 g was obtained. (Yield 79%, Mass [M+]=557)
2) 중간체 37의 합성2) Synthesis of intermediate 37
Figure PCTKR2023003330-appb-img-000438
Figure PCTKR2023003330-appb-img-000438
중간체 1 대신 중간체 36 (12.6 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 37을 11.7g 수득하였다. (수율 80%, Mass [M+]=648)11.7 g of Intermediate 37 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 36 (12.6 g) was used instead of Intermediate 1. (Yield 80%, Mass [M+]=648)
3) 중간체 38의 합성3) Synthesis of intermediate 38
Figure PCTKR2023003330-appb-img-000439
Figure PCTKR2023003330-appb-img-000439
중간체 2 대신 중간체 38 (11.7g), C-1 대신 C-11 (9.1g) 을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 38를 12.2 g 수득하였다. (수율 71%, Mass [M+]=946)12.2 g of Intermediate 38 was obtained by preparing it in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 38 (11.7 g) was used instead of Intermediate 2 and C-11 (9.1 g) was used instead of C-1. (Yield 71%, Mass [M+]=946)
4) 화합물 14의 합성4) Synthesis of compound 14
Figure PCTKR2023003330-appb-img-000440
Figure PCTKR2023003330-appb-img-000440
중간체 3 대신 중간체 38(12.2 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 14를 4.0 g 수득하였다. (수율 33%, Mass [M+]=954)4.0 g of compound 14 was obtained in the same manner as the preparation method of compound 1 in Synthesis Example 1, except that intermediate 38 (12.2 g) was used instead of intermediate 3. (Yield 33%, Mass [M+]=954)
합성예 15. 화합물 15의 합성Synthesis Example 15. Synthesis of Compound 15
1) 중간체 39의 합성1) Synthesis of intermediate 39
Figure PCTKR2023003330-appb-img-000441
Figure PCTKR2023003330-appb-img-000441
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-10 (7.4 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 39 를 11.1 g 수득하였다. (수율 74%, Mass [M+]=521)Intermediate 39 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-10 (7.4 g) was used instead of Starting Material B-1. 11.1 g was obtained. (Yield 74%, Mass [M+]=521)
2) 중간체 40의 합성2) Synthesis of intermediate 40
Figure PCTKR2023003330-appb-img-000442
Figure PCTKR2023003330-appb-img-000442
중간체 1 대신 중간체 39 (11.1 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 40을 10.5g 수득하였다. (수율 80%, Mass [M+]=612)10.5 g of Intermediate 40 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 39 (11.1 g) was used instead of Intermediate 1. (Yield 80%, Mass [M+]=612)
3) 중간체 41의 합성3) Synthesis of intermediate 41
Figure PCTKR2023003330-appb-img-000443
Figure PCTKR2023003330-appb-img-000443
중간체 2 대신 중간체 40 (10.5g), C-1 대신 C-10 (7.1g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 41를 10.4 g 수득하였다. (수율 74%, Mass [M+]=820)10.4 g of Intermediate 41 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 40 (10.5 g) was used instead of Intermediate 2 and C-10 (7.1 g) was used instead of C-1. (Yield 74%, Mass [M+]=820)
4) 화합물 15의 합성4) Synthesis of Compound 15
Figure PCTKR2023003330-appb-img-000444
Figure PCTKR2023003330-appb-img-000444
중간체 3 대신 중간체 41(10.4 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 15를 2.8 g 수득하였다. (수율 27%, Mass [M+]=827)Compound 15 was prepared in the same amount as 2.8 g of Compound 1 in Synthesis Example 1, except that Intermediate 41 (10.4 g) was used instead of Intermediate 3. (Yield 27%, Mass [M+]=827)
합성예 16. 화합물 16의 합성Synthesis Example 16. Synthesis of Compound 16
1) 중간체 42의 합성1) Synthesis of intermediate 42
Figure PCTKR2023003330-appb-img-000445
Figure PCTKR2023003330-appb-img-000445
출발물질 A-1 대신 출발물질 A-3 (10 g), 출발물질 B-1 대신 B-11 (8.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 42 를 13.3 g 수득하였다. (수율 81%, Mass [M+]=575)Intermediate 42 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-3 (10 g) was used instead of Starting Material A-1 and B-11 (8.9 g) was used instead of Starting Material B-1. 13.3 g was obtained. (Yield 81%, Mass [M+]=575)
2) 중간체 43의 합성2) Synthesis of intermediate 43
Figure PCTKR2023003330-appb-img-000446
Figure PCTKR2023003330-appb-img-000446
중간체 1 대신 중간체 42 (13.3 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 43을 12.2g 수득하였다. (수율 79%, Mass [M+]=666)12.2 g of Intermediate 43 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 42 (13.3 g) was used instead of Intermediate 1. (Yield 79%, Mass [M+]=666)
3) 중간체 44의 합성3) Synthesis of intermediate 44
Figure PCTKR2023003330-appb-img-000447
Figure PCTKR2023003330-appb-img-000447
중간체 2 대신 중간체 43 (12.2g), C-1 대신 C-4 (7.7g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 44를 12.9 g 수득하였다. (수율 80%, Mass [M+]=880)12.9 g of Intermediate 44 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 43 (12.2 g) was used instead of Intermediate 2 and C-4 (7.7 g) was used instead of C-1. (Yield 80%, Mass [M+]=880)
4)화합물 16의 합성4) Synthesis of Compound 16
Figure PCTKR2023003330-appb-img-000448
Figure PCTKR2023003330-appb-img-000448
중간체 3 대신 중간체 44 (12.9 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 16을 4.2 g 수득하였다. (수율 32%, Mass [M+]=887)Compound 16 was prepared in the same amount as 4.2 g of Compound 1 in Synthesis Example 1, except that Intermediate 44 (12.9 g) was used instead of Intermediate 3. (Yield 32%, Mass [M+]=887)
합성예 17. 화합물 17의 합성Synthesis Example 17. Synthesis of Compound 17
1) 중간체 45의 합성1) Synthesis of intermediate 45
Figure PCTKR2023003330-appb-img-000449
Figure PCTKR2023003330-appb-img-000449
출발물질 A-1 대신 출발물질 A-4 (10 g), 출발물질 B-1 (5.4 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 45 를 9.7 g 수득하였다. (수율 73%, Mass [M+]=535)9.7 g of Intermediate 45 was obtained by preparing it in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-4 (10 g) and Starting Material B-1 (5.4 g) were used instead of Starting Material A-1. . (Yield 73%, Mass [M+]=535)
2) 중간체 46의 합성2) Synthesis of intermediate 46
Figure PCTKR2023003330-appb-img-000450
Figure PCTKR2023003330-appb-img-000450
중간체 1 대신 중간체 45 (9.7 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 46을 8.5g 수득하였다. (수율 75%, Mass [M+]=626)8.5 g of Intermediate 46 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 45 (9.7 g) was used instead of Intermediate 1. (Yield 75%, Mass [M+]=626)
3) 중간체 47의 합성3) Synthesis of intermediate 47
Figure PCTKR2023003330-appb-img-000451
Figure PCTKR2023003330-appb-img-000451
중간체 2 대신 중간체 46 (8.5g), C-1 대신 C-12(6.9g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 47를 8.8 g 수득하였다. (수율 71%, Mass [M+]=924)8.8 g of Intermediate 47 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 46 (8.5 g) was used instead of Intermediate 2 and C-12 (6.9 g) was used instead of C-1. (Yield 71%, Mass [M+]=924)
4) 화합물 17의 합성4) Synthesis of compound 17
Figure PCTKR2023003330-appb-img-000452
Figure PCTKR2023003330-appb-img-000452
중간체 3 대신 중간체 47 (8.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 17을 3.6 g 수득하였다. (수율 41%, Mass [M+]=932)Compound 17 was prepared in the same amount as 3.6 g of Compound 1 in Synthesis Example 1, except that Intermediate 47 (8.8 g) was used instead of Intermediate 3. (Yield 41%, Mass [M+]=932)
합성예 18. 화합물 18의 합성Synthesis Example 18. Synthesis of Compound 18
1) 중간체 48의 합성1) Synthesis of intermediate 48
Figure PCTKR2023003330-appb-img-000453
Figure PCTKR2023003330-appb-img-000453
출발물질 A-1 대신 출발물질 A-4 (10 g), 출발물질 B-1 대신 B-3 (6.7 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 48 를 9.2 g 수득하였다. (수율 63%, Mass [M+]=589)Intermediate 48 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-4 (10 g) was used instead of Starting Material A-1 and B-3 (6.7 g) was used instead of Starting Material B-1. 9.2 g was obtained. (Yield 63%, Mass [M+]=589)
2) 중간체 49의 합성2) Synthesis of intermediate 49
Figure PCTKR2023003330-appb-img-000454
Figure PCTKR2023003330-appb-img-000454
중간체 1 대신 중간체 48 (9.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 49을 7.5g 수득하였다. (수율 71%, Mass [M+]=680)7.5 g of Intermediate 49 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 48 (9.2 g) was used instead of Intermediate 1. (Yield 71%, Mass [M+]=680)
3) 중간체 50의 합성3) Synthesis of intermediate 50
Figure PCTKR2023003330-appb-img-000455
Figure PCTKR2023003330-appb-img-000455
중간체 2 대신 중간체 49 (7.5g), C-1 대신 C-10 (4.6g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 50를 7.7 g 수득하였다. (수율 79%, Mass [M+]=888)7.7 g of Intermediate 50 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 49 (7.5 g) was used instead of Intermediate 2 and C-10 (4.6 g) was used instead of C-1. (Yield 79%, Mass [M+]=888)
4) 화합물 18의 합성4) Synthesis of compound 18
Figure PCTKR2023003330-appb-img-000456
Figure PCTKR2023003330-appb-img-000456
중간체 3 대신 중간체 50 (7.7 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 18을 2.5 g 수득하였다. (수율 32%, Mass [M+]=896)2.5 g of Compound 18 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 50 (7.7 g) was used instead of Intermediate 3. (Yield 32%, Mass [M+]=896)
합성예 19. 화합물 19의 합성Synthesis Example 19. Synthesis of Compound 19
1) 중간체 51의 합성1) Synthesis of intermediate 51
Figure PCTKR2023003330-appb-img-000457
Figure PCTKR2023003330-appb-img-000457
출발물질 A-1 대신 출발물질 A-5 (10 g), 출발물질 B-1 (5.8 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 51 를 13.3 g 수득하였다. (수율 85%, Mass [M+]=589)13.3 g of Intermediate 51 was obtained in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-5 (10 g) and Starting Material B-1 (5.8 g) were used instead of Starting Material A-1. . (Yield 85%, Mass [M+]=589)
2) 중간체 52의 합성2) Synthesis of intermediate 52
Figure PCTKR2023003330-appb-img-000458
Figure PCTKR2023003330-appb-img-000458
중간체 1 대신 중간체 51 (13.3 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 52을 10.8g 수득하였다. (수율 80%, Mass [M+]=598)10.8 g of Intermediate 52 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 51 (13.3 g) was used instead of Intermediate 1. (Yield 80%, Mass [M+]=598)
3) 중간체 53의 합성3) Synthesis of intermediate 53
Figure PCTKR2023003330-appb-img-000459
Figure PCTKR2023003330-appb-img-000459
중간체 2 대신 중간체 52 (10.8g), C-1 대신 C-13 (7.2g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 53를 8.9 g 수득하였다. (수율 63%, Mass [M+]=786)8.9 g of Intermediate 53 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 52 (10.8 g) was used instead of Intermediate 2 and C-13 (7.2 g) was used instead of C-1. (Yield 63%, Mass [M+]=786)
4) 화합물 19의 합성4) Synthesis of compound 19
Figure PCTKR2023003330-appb-img-000460
Figure PCTKR2023003330-appb-img-000460
중간체 3 대신 중간체 53 (8.9 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 19를 3.1 g 수득하였다. (수율 34%, Mass [M+]=793)3.1 g of Compound 19 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 53 (8.9 g) was used instead of Intermediate 3. (Yield 34%, Mass [M+]=793)
합성예 20. 화합물 20의 합성Synthesis Example 20. Synthesis of Compound 20
1) 중간체 54의 합성1) Synthesis of intermediate 54
Figure PCTKR2023003330-appb-img-000461
Figure PCTKR2023003330-appb-img-000461
출발물질 A-1 대신 출발물질 A-6 (10 g), 출발물질 B-1 대신 B-12 (7.3 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 54 를 11.3 g 수득하였다. (수율 75%, Mass [M+]=547)Intermediate 54 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-6 (10 g) was used instead of Starting Material A-1 and B-12 (7.3 g) was used instead of Starting Material B-1. 11.3 g was obtained. (Yield 75%, Mass [M+]=547)
2) 중간체 55의 합성2) Synthesis of intermediate 55
Figure PCTKR2023003330-appb-img-000462
Figure PCTKR2023003330-appb-img-000462
중간체 1 대신 중간체 54 (11.3 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 55을 9.6g 수득하였다. (수율 73%, Mass [M+]=638)9.6 g of Intermediate 55 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 54 (11.3 g) was used instead of Intermediate 1. (Yield 73%, Mass [M+]=638)
3) 중간체 56의 합성3) Synthesis of intermediate 56
Figure PCTKR2023003330-appb-img-000463
Figure PCTKR2023003330-appb-img-000463
중간체 2 대신 중간체 55 (9.6g), C-1 대신 C-14(6.3g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 56를 8.8 g 수득하였다. (수율 69%, Mass [M+]=852)8.8 g of Intermediate 56 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 55 (9.6 g) was used instead of Intermediate 2 and C-14 (6.3 g) was used instead of C-1. (Yield 69%, Mass [M+]=852)
4) 화합물 20의 합성4) Synthesis of Compound 20
Figure PCTKR2023003330-appb-img-000464
Figure PCTKR2023003330-appb-img-000464
중간체 3 대신 중간체 56 (8.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 20을 2.2 g 수득하였다. (수율 25%, Mass [M+]=859)Compound 20 (2.2 g) was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 56 (8.8 g) was used instead of Intermediate 3. (Yield 25%, Mass [M+]=859)
합성예 21. 화합물 21의 합성Synthesis Example 21. Synthesis of Compound 21
1) 중간체 57의 합성1) Synthesis of intermediate 57
Figure PCTKR2023003330-appb-img-000465
Figure PCTKR2023003330-appb-img-000465
출발물질 A-1 대신 출발물질 A-7 (10 g), 출발물질 B-1 대신 B-2 (6.6 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 57 를 12.2 g 수득하였다. (수율 80%, Mass [M+]=557)Intermediate 57 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-7 (10 g) was used instead of Starting Material A-1 and B-2 (6.6 g) was used instead of Starting Material B-1. 12.2 g was obtained. (Yield 80%, Mass [M+]=557)
2) 중간체 58의 합성2) Synthesis of intermediate 58
Figure PCTKR2023003330-appb-img-000466
Figure PCTKR2023003330-appb-img-000466
중간체 1 대신 중간체 57 (12.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 58을 11.1g 수득하였다. (수율 78%, Mass [M+]=648)11.1 g of Intermediate 58 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 57 (12.2 g) was used instead of Intermediate 1. (Yield 78%, Mass [M+]=648)
3) 중간체 59의 합성3) Synthesis of intermediate 59
Figure PCTKR2023003330-appb-img-000467
Figure PCTKR2023003330-appb-img-000467
중간체 2 대신 중간체 58 (11.1g), C-1 대신 C-10 (7.1g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 59를 10.8 g 수득하였다. (수율 74%, Mass [M+]=856)10.8 g of Intermediate 59 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 58 (11.1 g) was used instead of Intermediate 2 and C-10 (7.1 g) was used instead of C-1. (Yield 74%, Mass [M+]=856)
4) 화합물 21의 합성4) Synthesis of Compound 21
Figure PCTKR2023003330-appb-img-000468
Figure PCTKR2023003330-appb-img-000468
중간체 3 대신 중간체 59 (10.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 21을 3.6 g 수득하였다. (수율 33%, Mass [M+]=864)3.6 g of Compound 21 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 59 (10.8 g) was used instead of Intermediate 3. (Yield 33%, Mass [M+]=864)
합성예 22. 화합물 22의 합성Synthesis Example 22. Synthesis of Compound 22
1) 중간체 60의 합성1) Synthesis of intermediate 60
Figure PCTKR2023003330-appb-img-000469
Figure PCTKR2023003330-appb-img-000469
출발물질 A-1 대신 출발물질 A-8(10 g), 출발물질 B-1 대신 B-6 (8.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 60 를 11.9 g 수득하였다. (수율 77%, Mass [M+]=472)Intermediate 60 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-8 (10 g) was used instead of Starting Material A-1 and B-6 (8.2 g) was used instead of Starting Material B-1. 11.9 g was obtained. (Yield 77%, Mass [M+]=472)
2) 중간체 61의 합성2) Synthesis of intermediate 61
Figure PCTKR2023003330-appb-img-000470
Figure PCTKR2023003330-appb-img-000470
중간체 1 대신 중간체 60 (11.9 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 61을 10.6g 수득하였다. (수율 75%, Mass [M+]=564)10.6 g of Intermediate 61 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 60 (11.9 g) was used instead of Intermediate 1. (Yield 75%, Mass [M+]=564)
3) 중간체 62의 합성3) Synthesis of intermediate 62
Figure PCTKR2023003330-appb-img-000471
Figure PCTKR2023003330-appb-img-000471
중간체 2 대신 중간체 61 (10.6g), C-1 대신 C-14 (6.7g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 62를 8.8 g 수득하였다. (수율 66%, Mass [M+]=711)8.8 g of Intermediate 62 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 61 (10.6 g) was used instead of Intermediate 2 and C-14 (6.7 g) was used instead of C-1. (Yield 66%, Mass [M+]=711)
4) 화합물 22 의 합성4) Synthesis of Compound 22
Figure PCTKR2023003330-appb-img-000472
Figure PCTKR2023003330-appb-img-000472
중간체 3 대신 중간체 62(8.8 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 22를 3.5 g 수득하였다. (수율 39%, Mass [M+]=719)3.5 g of Compound 22 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 62 (8.8 g) was used instead of Intermediate 3. (Yield 39%, Mass [M+]=719)
합성예 23. 화합물 23의 합성Synthesis Example 23. Synthesis of Compound 23
1) 중간체 63의 합성1) Synthesis of intermediate 63
Figure PCTKR2023003330-appb-img-000473
Figure PCTKR2023003330-appb-img-000473
출발물질 A-1 대신 출발물질 A-9 (10 g), 출발물질 B-1 대신 B-10 (8.8 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 63 를 9.2 g 수득하였다. (수율 58%, Mass [M+]=464)Intermediate 63 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-9 (10 g) was used instead of Starting Material A-1 and B-10 (8.8 g) was used instead of Starting Material B-1. 9.2 g was obtained. (Yield 58%, Mass [M+]=464)
2) 중간체 64의 합성2) Synthesis of intermediate 64
Figure PCTKR2023003330-appb-img-000474
Figure PCTKR2023003330-appb-img-000474
중간체 1 대신 중간체 63 (9.2 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 64을 8.7g 수득하였다. (수율 79%, Mass [M+]=556)8.7 g of Intermediate 64 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 63 (9.2 g) was used instead of Intermediate 1. (Yield 79%, Mass [M+]=556)
3) 중간체 65의 합성3) Synthesis of intermediate 65
Figure PCTKR2023003330-appb-img-000475
Figure PCTKR2023003330-appb-img-000475
중간체 2 대신 중간체 64 (8.7g), C-1 (6.2g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 65를 8.5 g 수득하였다. (수율 73%, Mass [M+]=743)8.5 g of Intermediate 65 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 64 (8.7 g) and C-1 (6.2 g) were used instead of Intermediate 2. (Yield 73%, Mass [M+]=743)
4) 화합물 23의 합성4) Synthesis of Compound 23
Figure PCTKR2023003330-appb-img-000476
Figure PCTKR2023003330-appb-img-000476
중간체 3 대신 중간체 65 (8.5 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 23을 2.2 g 수득하였다. (수율 26%, Mass [M+]=751)Compound 23 (2.2 g) was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 65 (8.5 g) was used instead of Intermediate 3. (Yield 26%, Mass [M+]=751)
합성예 24. 화합물 24의 합성Synthesis Example 24. Synthesis of Compound 24
1) 중간체 66의 합성1) Synthesis of intermediate 66
Figure PCTKR2023003330-appb-img-000477
Figure PCTKR2023003330-appb-img-000477
출발물질 A-1 대신 출발물질 A-10 (10 g), 출발물질 B-1 대신 B-6 (6.1 g)을 사용한 것을 제외하고 합성예 1의 중간체 1의 제조법과 동일하게 제조하여 중간체 66 를 11 g 수득하였다. (수율 78%, Mass [M+]=575)Intermediate 66 was prepared in the same manner as the preparation method of Intermediate 1 in Synthesis Example 1, except that Starting Material A-10 (10 g) was used instead of Starting Material A-1 and B-6 (6.1 g) was used instead of Starting Material B-1. 11 g was obtained. (Yield 78%, Mass [M+]=575)
2) 중간체 67의 합성2) Synthesis of intermediate 67
Figure PCTKR2023003330-appb-img-000478
Figure PCTKR2023003330-appb-img-000478
중간체 1 대신 중간체 66 (11 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 67을 9.5g 수득하였다. (수율 74%, Mass [M+]=666)9.5 g of Intermediate 67 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that Intermediate 66 (11 g) was used instead of Intermediate 1. (Yield 74%, Mass [M+]=666)
3) 중간체 68의 합성3) Synthesis of intermediate 68
Figure PCTKR2023003330-appb-img-000479
Figure PCTKR2023003330-appb-img-000479
중간체 2 대신 중간체 67 (9.5g), C-1 대신 C-10(5.9g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 68를 8.1 g 수득하였다. (수율 65%, Mass [M+]=874)8.1 g of Intermediate 68 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 67 (9.5 g) was used instead of Intermediate 2 and C-10 (5.9 g) was used instead of C-1. (Yield 65%, Mass [M+]=874)
4) 화합물 24의 합성4) Synthesis of compound 24
Figure PCTKR2023003330-appb-img-000480
Figure PCTKR2023003330-appb-img-000480
중간체 3 대신 중간체 68 (8.1 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 24를 2.8 g 수득하였다. (수율 34%, Mass [M+]=881)2.8 g of Compound 24 was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 68 (8.1 g) was used instead of Intermediate 3. (Yield 34%, Mass [M+]=881)
합성예 25. 화합물 25의 합성Synthesis Example 25. Synthesis of Compound 25
1) 중간체 69의 합성1) Synthesis of intermediate 69
Figure PCTKR2023003330-appb-img-000481
Figure PCTKR2023003330-appb-img-000481
중간체 1 대신 출발물질 A-11 (10 g)을 사용한 것을 제외하고 합성예 1의 중간체 2 제조법과 동일하게 제조하여 중간체 69을 8.5g 수득하였다. (수율 71%, Mass [M+]=570)8.5 g of Intermediate 69 was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that starting material A-11 (10 g) was used instead of Intermediate 1. (Yield 71%, Mass [M+]=570)
2) 중간체 70의 합성2) Synthesis of intermediate 70
Figure PCTKR2023003330-appb-img-000482
Figure PCTKR2023003330-appb-img-000482
중간체 2 대신 중간체 69 (8.5g), C-1 대신 C-4 (6.3g)을 사용한 것을 제외하고 합성예 1의 중간체 3의 제조법과 동일하게 제조하여 중간체 70를 6.2 g 수득하였다. (수율 53%, Mass [M+]=784)6.2 g of Intermediate 70 was obtained in the same manner as the preparation method of Intermediate 3 in Synthesis Example 1, except that Intermediate 69 (8.5 g) was used instead of Intermediate 2 and C-4 (6.3 g) was used instead of C-1. (Yield 53%, Mass [M+]=784)
3) 화합물 25의 합성3) Synthesis of compound 25
Figure PCTKR2023003330-appb-img-000483
Figure PCTKR2023003330-appb-img-000483
중간체 3 대신 중간체 70 (6.2 g)을 사용한 것을 제외하고 합성예 1의 화합물 1의 제조법과 동일하게 제조하여 화합물 25를 2.4 g 수득하였다. (수율 38%, Mass [M+]=791)Compound 25 (2.4 g) was obtained in the same manner as the preparation method of Compound 1 in Synthesis Example 1, except that Intermediate 70 (6.2 g) was used instead of Intermediate 3. (Yield 38%, Mass [M+]=791)
실시예 Example
ITO(indium tin oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(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 a thin film of ITO (indium tin oxide) with a thickness of 1,400 Å was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에 하기 HI-A와 HAT-CN을 각각 650 Å, 50 Å의 두께로 열 진공증착하여 제1 및 제2 정공주입층을 형성하였다. 상기 정공 주입층 위에 하기 HT-A를 700 Å의 두께로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 HT-B를 100 Å의 두께로 진공 증착하여 전자차단층을 형성하였다. 이어서, 상기 전자차단층 위에 청색 발광 도펀트로 상기 합성예 1의 화합물 1을 발광층 100 중량부 기준으로 3 중량부, 호스트로 하기 BH-A 를 200Å의 두께로 진공 증착하여 발광층을 형성하였다. 그 다음에 상기 발광층 위에 제1 전자수송층으로 하기 화합물 ET-A 50Å을 진공 증착하고, 연이어 하기 ET-B 및 LiQ 를 1:1 중량비로 진공증착하여 250Å의 두께로 제2 전자수송층을 형성하였다. 상기 제2 전자수송층 위에 LiQ를 진공 증착하여 5Å의 두께로 진공증착하여 전자주입층을 형성하였다. 상기 전자주입층 위에 220Å두께로 알루미늄과 은을 10:1의 중량 비로 증착하고 그 위에 알루미늄을 800Å두께로 증착하여 음극을 형성하였다.On the ITO transparent electrode prepared as above, HI-A and HAT-CN were thermally vacuum deposited to a thickness of 650 Å and 50 Å, respectively, to form first and second hole injection layers. The following HT-A was vacuum deposited on the hole injection layer to a thickness of 700 Å to form a hole transport layer. The following HT-B was vacuum deposited on the hole transport layer to a thickness of 100 Å to form an electron blocking layer. Next, on the electron blocking layer, 3 parts by weight of Compound 1 of Synthesis Example 1 as a blue light-emitting dopant, based on 100 parts by weight of the light-emitting layer, and the following BH-A as a host were vacuum deposited to a thickness of 200 Å to form a light-emitting layer. Next, 50 Å of the following compound ET-A was vacuum deposited as a first electron transport layer on the light emitting layer, and then ET-B and LiQ were vacuum deposited at a 1:1 weight ratio to form a second electron transport layer with a thickness of 250 Å. LiQ was vacuum deposited on the second electron transport layer to a thickness of 5Å to form an electron injection layer. Aluminum and silver were deposited on the electron injection layer to a thickness of 220 Å at a weight ratio of 10:1, and then aluminum was deposited to a thickness of 800 Å to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 음극의 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 ~ 5 × 10-8 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of aluminum on the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 × 10 -7 ~ 5 × 10 -8 torr. By maintaining this, an organic light emitting device was manufactured.
Figure PCTKR2023003330-appb-img-000484
Figure PCTKR2023003330-appb-img-000484
실시예 2 내지 실시예 25Examples 2 to 25
상기 실시예 1에서 발광층의 도펀트로 상기 화합물 1 대신 하기 표 1의 화합물을 각각 사용한 것을 제외하고는 동일하게 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as the dopant of the light-emitting layer.
Figure PCTKR2023003330-appb-img-000485
Figure PCTKR2023003330-appb-img-000485
Figure PCTKR2023003330-appb-img-000486
Figure PCTKR2023003330-appb-img-000486
비교예 1 내지 비교예 4Comparative Examples 1 to 4
실시예 1의 유기 발광 소자에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조했다. An organic light emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 in the organic light emitting device of Example 1.
[비교예 물질][Comparative example material]
Figure PCTKR2023003330-appb-img-000487
Figure PCTKR2023003330-appb-img-000487
상기 실시예 1 내지 실시예 25 및 비교예 1 내지 비교예 4의 유기 발광 소자에 10 mA/cm2의 전류 밀도를 인가할 때의 전압, 효율(cd/A) 및 20 mA/cm2의 전류 밀도를 인가할 때의 수명(T95)을 측정하고, 그 결과를 하기 표 1에 나타내었다. 수명 T95는 전류 밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소되는데 소요되는 시간을 의미한다.Voltage, efficiency ( cd /A), and current of 20 mA/cm 2 when applying a current density of 10 mA/cm 2 to the organic light-emitting devices of Examples 1 to 25 and Comparative Examples 1 to 4 The lifespan (T 95 ) when density was applied was measured, and the results are shown in Table 1 below. Lifespan T 95 refers to the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is set to 100%.
　 도판트dopant 전압 (V)Voltage (V) 발광효율Luminous efficiency 수명, T95(h)Life, T95(h)
(Cd/A)(Cd/A)
실시예 1Example 1 화합물1 Compound 1 3.543.54 5.665.66 242242
실시예 2Example 2 화합물2 Compound 2 3.543.54 6.166.16 256256
실시예 3Example 3 화합물3 Compound 3 3.543.54 5.965.96 242242
실시예 4Example 4 화합물4 Compound 4 3.543.54 6.066.06 238238
실시예 5Example 5 화합물5 Compound 5 3.543.54 5.815.81 236236
실시예 6Example 6 화합물6 Compound 6 3.543.54 5.765.76 244244
실시예 7Example 7 화합물7 Compound 7 3.543.54 5.965.96 250250
실시예 8Example 8 화합물8Compound 8 3.583.58 5.565.56 222222
실시예 9Example 9 화합물9 Compound 9 3.543.54 5.965.96 236236
실시예10Example 10 화합물10 Compound 10 3.53.5 5.715.71 232232
실시예11Example 11 화합물11 Compound 11 3.503.50 5.865.86 236236
실시예12Example 12 화합물12Compound 12 3.543.54 5.665.66 230230
실시예13Example 13 화합물13Compound 13 3.473.47 5.865.86 242242
실시예14Example 14 화합물14Compound 14 3.473.47 5.815.81 246246
실시예15Example 15 화합물15Compound 15 3.473.47 5.765.76 238238
실시예16Example 16 화합물16Compound 16 3.473.47 5.865.86 238238
실시예17Example 17 화합물17Compound 17 3.543.54 6.066.06 242242
실시예18Example 18 화합물18Compound 18 3.543.54 6.166.16 238238
실시예19Example 19 화합물19Compound 19 3.543.54 5.865.86 230230
실시예20Example 20 화합물20Compound 20 3.613.61 5.565.56 226226
실시예21Example 21 화합물21Compound 21 3.613.61 5.715.71 222222
실시예22Example 22 화합물22Compound 22 3.583.58 5.615.61 234234
실시예23Example 23 화합물23Compound 23 3.583.58 5.665.66 226226
실시예24Example 24 화합물24Compound 24 3.543.54 5.765.76 236236
실시예25Example 25 화합물25Compound 25 3.583.58 5.615.61 230230
비교예1Comparative Example 1 BD-ABD-A 3.653.65 4.854.85 160160
비교예2Comparative example 2 BD-BBD-B 3.653.65 5.055.05 200200
비교예3Comparative Example 3 BD-CBD-C 4.024.02 4.654.65 150150
비교예4Comparative Example 4 BD-DBD-D 3.833.83 4.754.75 156156
상기 표 1에 있어서, 본 명세서의 일 실시상태에 따른 유기 발광 소자는 비교예 1 내지 4의 유기 발광 소자 보다 전압, 발광효율 및 수명이 우수한 것을 알 수 있었다.In Table 1, it was found that the organic light-emitting device according to an exemplary embodiment of the present specification was superior to the organic light-emitting devices of Comparative Examples 1 to 4 in terms of voltage, luminous efficiency, and lifespan.
구체적으로, 상기 본 명세서의 화학식 1의 R1 및 R2에 대응되는 치환기가 서로 결합하여 고리를 형성하는 화합물을 포함하는 비교예 1 내지 3 및 본 명세서의 화학식 1의 A1 및 R1이 서로 결합하여 고리를 형성하는 화합물을 포함하는 비교예 4는 빠르게 저하(degradation)되는 부분이 많이 존재하게 되어 분자간 호핑(hopping)에 의존하는 유기 발광 소자의 특성상 구동 전압이 증가하게 된다. Specifically, Comparative Examples 1 to 3 including compounds in which the substituents corresponding to R1 and R2 of Formula 1 of the present specification are bonded to each other to form a ring, and A1 and R1 of Chemical Formula 1 of the present specification are bonded to each other to form a ring. In Comparative Example 4, which includes the forming compound, there are many parts that rapidly degrade, so the driving voltage increases due to the nature of organic light-emitting devices that rely on intermolecular hopping.
그러나, 본 명세서의 화학식 1의 화합물과 같이 불안정한 부분(R1과 R2가 서로 결합하여 고리를 형성, 및 A1과 R1이 서로 결합하여 고리를 형성)을 없애 주면 전자와 정공의 주입이 줄어들게되어 퀸칭(Quenching) 및 저하(degradation)를 억제시켜 유기 발광 소자의 효율이 상승하고 소자의 수명이 향상되며 전압 또한 줄어 들게 된다. 따라서, 본 명세서의 일 실시상태에 따른 실시예 1 내지 25의 유기 발광 소자는 비교예 1 내지 4 보다 구동전압, 발광효율 및 수명이 우수한 것을 확인할 수 있었다.However, if the unstable part (R1 and R2 combine with each other to form a ring, and A1 and R1 combine with each other to form a ring), such as the compound of Formula 1 of the present specification, is removed, the injection of electrons and holes is reduced, resulting in quenching ( By suppressing quenching and degradation, the efficiency of the organic light emitting device increases, the lifespan of the device is improved, and the voltage is also reduced. Accordingly, it was confirmed that the organic light emitting devices of Examples 1 to 25 according to an exemplary embodiment of the present specification were superior to those of Comparative Examples 1 to 4 in terms of driving voltage, luminous efficiency, and lifespan.

Claims (14)

  1. 하기 화학식 1의 화합물:Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023003330-appb-img-000488
    Figure PCTKR2023003330-appb-img-000488
    상기 화학식 1에 있어서,In Formula 1,
    X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 -C(R7)(R8)-, -Si(R9)(R10)-, -O-, 또는 -S-이고,X1 and X2 are the same or different from each other and are each independently -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-
    A1은 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이거나, R3와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,A1 is a substituted or unsubstituted hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle, or combines with R3 to form a substituted or unsubstituted ring,
    n은 0 또는 1이고,n is 0 or 1,
    m은 0 또는 1이며,m is 0 or 1,
    상기 n 및 m 중 적어도 하나는 1이고,At least one of n and m is 1,
    R1 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R)(R'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R2 내지 R10 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R)(R'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R2 to R10 combine with each other to form a substituted or unsubstituted ring,
    R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R and R' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
    r1은 1 내지 5의 정수이며, 상기 r1이 2 이상인 경우, 상기 2 이상의 R1은 서로 같거나 상이하며,r1 is an integer from 1 to 5, and when r1 is 2 or more, the 2 or more R1 are the same or different from each other,
    r2는 1 내지 4의 정수이고, 상기 r2가 2 이상인 경우, 상기 2 이상의 R2는 서로 같거나 상이하고,r2 is an integer of 1 to 4, and when r2 is 2 or more, the 2 or more R2s are the same or different from each other,
    r3는 1 내지 4이고, 상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하며,r3 is 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
    r4는 0 내지 2의 정수이며, 상기 r4가 2인 경우, 상기 2개의 R4는 서로 같거나 상이하고, r4 is an integer from 0 to 2, and when r4 is 2, the two R4 are the same or different from each other,
    r5는 1 내지 4의 정수이며, 상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하며,r5 is an integer from 1 to 4, and when r5 is 2 or more, the 2 or more R5 are the same or different from each other,
    r6는 1 내지 4의 정수이며, 상기 r6가 2 이상인 경우, 상기 2 이상의 R6는 서로 같거나 상이하며,r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other,
    상기 n이 1 인 경우, 상기 r3는 1 또는 2이고,When n is 1, r3 is 1 or 2,
    상기 n이 0 인 경우, 상기 r3는 1 내지 4이며,When n is 0, r3 is 1 to 4,
    상기 m이 1 인 경우, 상기 r4는 0이며, When m is 1, r4 is 0,
    상기 m이 0 인 경우, 상기 r4는 1 또는 2이다.When m is 0, r4 is 1 or 2.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 내지 4 중 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one of the following formulas 2 to 4:
    [화학식 2][Formula 2]
    Figure PCTKR2023003330-appb-img-000489
    Figure PCTKR2023003330-appb-img-000489
    [화학식 3][Formula 3]
    Figure PCTKR2023003330-appb-img-000490
    Figure PCTKR2023003330-appb-img-000490
    [화학식 4][Formula 4]
    Figure PCTKR2023003330-appb-img-000491
    Figure PCTKR2023003330-appb-img-000491
    상기 화학식 2 내지 4에 있어서,In Formulas 2 to 4,
    A1, X1, X2, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하다.The definitions of A1, X1, X2, R1 to R6, and r1 to r6 are the same as those defined in Formula 1 above.
  3. 청구항 1에 있어서, 상기 A1은 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환되고, O, N, S, 및 Si 중 1 이상을 포함하는 헤테로고리인 것인 화합물.The method according to claim 1, wherein A1 is a substituted or unsubstituted aromatic hydrocarbon ring; A condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a compound that is substituted or unsubstituted and is a heterocycle containing one or more of O, N, S, and Si.
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 5 또는 6인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the formula 5 or 6:
    [화학식 5][Formula 5]
    Figure PCTKR2023003330-appb-img-000492
    Figure PCTKR2023003330-appb-img-000492
    [화학식 6][Formula 6]
    Figure PCTKR2023003330-appb-img-000493
    Figure PCTKR2023003330-appb-img-000493
    상기 화학식 5 및 6에 있어서,In Formulas 5 and 6,
    X1, X2, m, n, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1, X2, m, n, R1 to R6 and r1 to r6 are the same as those defined in Formula 1 above,
    X3는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
    R11 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R")(R"'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R11 내지 R16 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R11 to R16 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R11 to R16 are combined with each other to form a substituted or unsubstituted ring,
    R" 및 R"'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
    r11은 1 내지 4의 정수이고, 상기 r11이 2 이상인 경우, 상기 2 이상의 R11은 서로 같거나 상이하며,r11 is an integer from 1 to 4, and when r11 is 2 or more, the 2 or more R11 are the same or different from each other,
    r12는 1 내지 4의 정수이며, 상기 r12가 2 이상인 경우, 상기 2 이상의 R12는 서로 같거나 상이하다.r12 is an integer of 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other.
  5. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 7 내지 16 중 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one of the following formulas 7 to 16:
    [화학식 7][Formula 7]
    Figure PCTKR2023003330-appb-img-000494
    Figure PCTKR2023003330-appb-img-000494
    [화학식 8][Formula 8]
    Figure PCTKR2023003330-appb-img-000495
    Figure PCTKR2023003330-appb-img-000495
    [화학식 9][Formula 9]
    Figure PCTKR2023003330-appb-img-000496
    Figure PCTKR2023003330-appb-img-000496
    [화학식 10][Formula 10]
    Figure PCTKR2023003330-appb-img-000497
    Figure PCTKR2023003330-appb-img-000497
    [화학식 11][Formula 11]
    Figure PCTKR2023003330-appb-img-000498
    Figure PCTKR2023003330-appb-img-000498
    [화학식 12][Formula 12]
    Figure PCTKR2023003330-appb-img-000499
    Figure PCTKR2023003330-appb-img-000499
    [화학식 13][Formula 13]
    Figure PCTKR2023003330-appb-img-000500
    Figure PCTKR2023003330-appb-img-000500
    [화학식 14][Formula 14]
    Figure PCTKR2023003330-appb-img-000501
    Figure PCTKR2023003330-appb-img-000501
    [화학식 15][Formula 15]
    Figure PCTKR2023003330-appb-img-000502
    Figure PCTKR2023003330-appb-img-000502
    [화학식 16][Formula 16]
    Figure PCTKR2023003330-appb-img-000503
    Figure PCTKR2023003330-appb-img-000503
    상기 화학식 7 내지 16에 있어서,In Formulas 7 to 16,
    X1, X2, m, n, R1 내지 R6 및 r1 내지 r6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of X1, X2, m, n, R1 to R6 and r1 to r6 are the same as those defined in Formula 1 above,
    X3는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
    X4 및 X5는 서로 같거나 상이하고, 각각 독립적으로 -C(R19)(R20)-; -Si(R21)(R22)-; -O-; 또는 -S-이며,X4 and X5 are the same or different from each other and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
    X6 및 X7은 서로 같거나 상이하고, 각각 독립적으로 -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; 또는 -S-이며,X6 and X7 are the same or different from each other and are each independently -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; or -S-,
    Y1 내지 Y4는 서로 같거나 상이하고, 각각 독립적으로 -C(R28)- 또는 N이고,Y1 to Y4 are the same or different from each other and are each independently -C(R28)- or N,
    R'2, R"2, R'11, R"11 및 R12 내지 R28은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(R")(R"'); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R'2, R"2, R'11, R"11 및 R12 내지 R28 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리를 형성하며,R'2, R"2, R'11, R"11 and R12 to R28 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R'2, R"2, R'11, R"11 and R12 to R28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring. forming,
    R" 및 R"'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
    r'11은 1 내지 4의 정수이고, 상기 r'11이 2 이상인 경우, 상기 2 이상의 R'11은 서로 같거나 상이하며,r'11 is an integer of 1 to 4, and when r'11 is 2 or more, 2 or more R'11 are the same or different from each other,
    r"11은 1 또는 2이고, 상기 r"11이 2인 경우, 상기 2개의 R"11은 서로 같거나 상이하고,r"11 is 1 or 2, and when r"11 is 2, the two R"11 are the same or different from each other,
    r'2은 1 내지 4의 정수이고, 상기 r'2이 2 이상인 경우, 상기 2 이상의 R'2은 서로 같거나 상이하며,r'2 is an integer of 1 to 4, and when r'2 is 2 or more, R'2 of 2 or more is the same or different,
    r"2은 1 또는 2이고, 상기 r"2이 2인 경우, 상기 2개의 R"2은 서로 같거나 상이하고,r"2 is 1 or 2, and when r"2 is 2, the two R"2 are the same or different from each other,
    r12는 1 내지 4의 정수이며, 상기 r12가 2 이상인 경우, 상기 2 이상의 R12는 서로 같거나 상이하며,r12 is an integer from 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other,
    r17는 1 내지 4의 정수이며, 상기 r17가 2 이상인 경우, 상기 2 이상의 R17는 서로 같거나 상이하고,r17 is an integer of 1 to 4, and when r17 is 2 or more, the 2 or more R17 are the same or different from each other,
    r18는 1 내지 4의 정수이며, 상기 r18가 2 이상인 경우, 상기 2 이상의 R18는 서로 같거나 상이하다.r18 is an integer of 1 to 4, and when r18 is 2 or more, the 2 or more R18s are the same or different from each other.
  6. 청구항 1에 있어서, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환되고, O, N 및 S 중 1 이상을 포함하는 탄소수 2 내지 30의 헤테로고리이거나, R3와 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 6 내지 30의 단환 또는 다환의 헤테로고리를 형성하고,The method of claim 1, wherein A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with -N(R")(R"'). ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or substituted or unsubstituted with one or more selected from a straight or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof, and includes one or more of O, N, and S. is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S Forming a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms,
    상기 R1은 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이며,R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
    상기 R2는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R2는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(R")(R"'), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 -N(R")(R"')로 치환 또는 비치환되고, N, O 또는 S를 포함하는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하고,R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic hetero alkyl group having 2 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"'), and containing N, O or S. forming a ring,
    상기 R3는 수소; -N(R)(R'); 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이거나, 인접한 어느 한 쌍의 R3는 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리를 형성하며,R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. forming,
    상기 R4는 수소; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이고,R4 is hydrogen; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms,
    상기 R5 및 R6은 수소이고,R5 and R6 are hydrogen,
    상기 R7 내지 R10은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이고,R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
    R, R', R" 및 R"'은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기인 것인 화합물.R, R', R", and R"' are the same or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Phosphorus compounds.
  7. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one of the following compounds:
    Figure PCTKR2023003330-appb-img-000504
    Figure PCTKR2023003330-appb-img-000504
    Figure PCTKR2023003330-appb-img-000505
    Figure PCTKR2023003330-appb-img-000505
    Figure PCTKR2023003330-appb-img-000506
    Figure PCTKR2023003330-appb-img-000506
    Figure PCTKR2023003330-appb-img-000507
    Figure PCTKR2023003330-appb-img-000507
    Figure PCTKR2023003330-appb-img-000508
    Figure PCTKR2023003330-appb-img-000508
    Figure PCTKR2023003330-appb-img-000509
    Figure PCTKR2023003330-appb-img-000509
    Figure PCTKR2023003330-appb-img-000510
    Figure PCTKR2023003330-appb-img-000510
    Figure PCTKR2023003330-appb-img-000511
    Figure PCTKR2023003330-appb-img-000511
    Figure PCTKR2023003330-appb-img-000512
    Figure PCTKR2023003330-appb-img-000512
    Figure PCTKR2023003330-appb-img-000513
    Figure PCTKR2023003330-appb-img-000513
    Figure PCTKR2023003330-appb-img-000514
    Figure PCTKR2023003330-appb-img-000514
    Figure PCTKR2023003330-appb-img-000515
    Figure PCTKR2023003330-appb-img-000515
    Figure PCTKR2023003330-appb-img-000516
    Figure PCTKR2023003330-appb-img-000516
    Figure PCTKR2023003330-appb-img-000517
    Figure PCTKR2023003330-appb-img-000517
    Figure PCTKR2023003330-appb-img-000518
    Figure PCTKR2023003330-appb-img-000518
    Figure PCTKR2023003330-appb-img-000519
    Figure PCTKR2023003330-appb-img-000519
    Figure PCTKR2023003330-appb-img-000520
    Figure PCTKR2023003330-appb-img-000520
    Figure PCTKR2023003330-appb-img-000521
    Figure PCTKR2023003330-appb-img-000521
    Figure PCTKR2023003330-appb-img-000522
    Figure PCTKR2023003330-appb-img-000522
    Figure PCTKR2023003330-appb-img-000523
    Figure PCTKR2023003330-appb-img-000523
    Figure PCTKR2023003330-appb-img-000524
    Figure PCTKR2023003330-appb-img-000524
    Figure PCTKR2023003330-appb-img-000525
    Figure PCTKR2023003330-appb-img-000525
    Figure PCTKR2023003330-appb-img-000526
    Figure PCTKR2023003330-appb-img-000526
    Figure PCTKR2023003330-appb-img-000527
    Figure PCTKR2023003330-appb-img-000527
    Figure PCTKR2023003330-appb-img-000528
    Figure PCTKR2023003330-appb-img-000528
    Figure PCTKR2023003330-appb-img-000529
    Figure PCTKR2023003330-appb-img-000529
    Figure PCTKR2023003330-appb-img-000530
    Figure PCTKR2023003330-appb-img-000530
    Figure PCTKR2023003330-appb-img-000531
    Figure PCTKR2023003330-appb-img-000531
    Figure PCTKR2023003330-appb-img-000532
    Figure PCTKR2023003330-appb-img-000532
    Figure PCTKR2023003330-appb-img-000533
    Figure PCTKR2023003330-appb-img-000533
    Figure PCTKR2023003330-appb-img-000534
    Figure PCTKR2023003330-appb-img-000534
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    Figure PCTKR2023003330-appb-img-000760
    Figure PCTKR2023003330-appb-img-000761
    Figure PCTKR2023003330-appb-img-000761
    Figure PCTKR2023003330-appb-img-000762
    Figure PCTKR2023003330-appb-img-000762
    Figure PCTKR2023003330-appb-img-000763
    Figure PCTKR2023003330-appb-img-000763
    Figure PCTKR2023003330-appb-img-000764
    Figure PCTKR2023003330-appb-img-000764
    Figure PCTKR2023003330-appb-img-000765
    Figure PCTKR2023003330-appb-img-000765
    Figure PCTKR2023003330-appb-img-000766
    Figure PCTKR2023003330-appb-img-000766
    Figure PCTKR2023003330-appb-img-000767
    Figure PCTKR2023003330-appb-img-000767
    Figure PCTKR2023003330-appb-img-000768
    Figure PCTKR2023003330-appb-img-000768
    Figure PCTKR2023003330-appb-img-000769
    Figure PCTKR2023003330-appb-img-000769
    Figure PCTKR2023003330-appb-img-000770
    Figure PCTKR2023003330-appb-img-000770
    Figure PCTKR2023003330-appb-img-000771
    Figure PCTKR2023003330-appb-img-000771
    Figure PCTKR2023003330-appb-img-000772
    Figure PCTKR2023003330-appb-img-000772
    Figure PCTKR2023003330-appb-img-000773
    Figure PCTKR2023003330-appb-img-000773
    Figure PCTKR2023003330-appb-img-000774
    Figure PCTKR2023003330-appb-img-000774
    Figure PCTKR2023003330-appb-img-000775
    Figure PCTKR2023003330-appb-img-000775
    Figure PCTKR2023003330-appb-img-000776
    Figure PCTKR2023003330-appb-img-000776
    Figure PCTKR2023003330-appb-img-000777
    Figure PCTKR2023003330-appb-img-000777
    Figure PCTKR2023003330-appb-img-000778
    Figure PCTKR2023003330-appb-img-000778
    Figure PCTKR2023003330-appb-img-000779
    Figure PCTKR2023003330-appb-img-000779
    Figure PCTKR2023003330-appb-img-000780
    Figure PCTKR2023003330-appb-img-000780
    Figure PCTKR2023003330-appb-img-000781
    Figure PCTKR2023003330-appb-img-000781
    Figure PCTKR2023003330-appb-img-000782
    Figure PCTKR2023003330-appb-img-000782
    Figure PCTKR2023003330-appb-img-000783
    Figure PCTKR2023003330-appb-img-000783
    Figure PCTKR2023003330-appb-img-000784
    Figure PCTKR2023003330-appb-img-000784
    Figure PCTKR2023003330-appb-img-000785
    Figure PCTKR2023003330-appb-img-000785
    Figure PCTKR2023003330-appb-img-000786
    Figure PCTKR2023003330-appb-img-000786
    Figure PCTKR2023003330-appb-img-000787
    Figure PCTKR2023003330-appb-img-000787
    Figure PCTKR2023003330-appb-img-000788
    Figure PCTKR2023003330-appb-img-000788
    Figure PCTKR2023003330-appb-img-000789
    Figure PCTKR2023003330-appb-img-000789
    Figure PCTKR2023003330-appb-img-000790
    Figure PCTKR2023003330-appb-img-000790
    Figure PCTKR2023003330-appb-img-000791
    Figure PCTKR2023003330-appb-img-000791
    Figure PCTKR2023003330-appb-img-000792
    Figure PCTKR2023003330-appb-img-000792
    Figure PCTKR2023003330-appb-img-000793
    Figure PCTKR2023003330-appb-img-000793
    Figure PCTKR2023003330-appb-img-000794
    Figure PCTKR2023003330-appb-img-000794
    Figure PCTKR2023003330-appb-img-000795
    Figure PCTKR2023003330-appb-img-000795
    Figure PCTKR2023003330-appb-img-000796
    Figure PCTKR2023003330-appb-img-000796
    Figure PCTKR2023003330-appb-img-000797
    Figure PCTKR2023003330-appb-img-000797
    Figure PCTKR2023003330-appb-img-000798
    Figure PCTKR2023003330-appb-img-000798
    Figure PCTKR2023003330-appb-img-000799
    Figure PCTKR2023003330-appb-img-000799
    Figure PCTKR2023003330-appb-img-000800
    Figure PCTKR2023003330-appb-img-000800
    Figure PCTKR2023003330-appb-img-000801
    Figure PCTKR2023003330-appb-img-000801
    Figure PCTKR2023003330-appb-img-000802
    Figure PCTKR2023003330-appb-img-000802
    Figure PCTKR2023003330-appb-img-000803
    Figure PCTKR2023003330-appb-img-000803
    Figure PCTKR2023003330-appb-img-000804
    Figure PCTKR2023003330-appb-img-000804
    Figure PCTKR2023003330-appb-img-000805
    Figure PCTKR2023003330-appb-img-000805
    Figure PCTKR2023003330-appb-img-000806
    Figure PCTKR2023003330-appb-img-000806
    Figure PCTKR2023003330-appb-img-000807
    Figure PCTKR2023003330-appb-img-000807
    Figure PCTKR2023003330-appb-img-000808
    Figure PCTKR2023003330-appb-img-000808
    Figure PCTKR2023003330-appb-img-000809
    Figure PCTKR2023003330-appb-img-000809
    Figure PCTKR2023003330-appb-img-000810
    Figure PCTKR2023003330-appb-img-000810
    Figure PCTKR2023003330-appb-img-000811
    Figure PCTKR2023003330-appb-img-000811
    Figure PCTKR2023003330-appb-img-000812
    Figure PCTKR2023003330-appb-img-000812
    Figure PCTKR2023003330-appb-img-000813
    Figure PCTKR2023003330-appb-img-000813
    Figure PCTKR2023003330-appb-img-000814
    Figure PCTKR2023003330-appb-img-000814
    Figure PCTKR2023003330-appb-img-000815
    Figure PCTKR2023003330-appb-img-000815
    Figure PCTKR2023003330-appb-img-000816
    Figure PCTKR2023003330-appb-img-000816
    Figure PCTKR2023003330-appb-img-000817
    Figure PCTKR2023003330-appb-img-000817
    Figure PCTKR2023003330-appb-img-000818
    Figure PCTKR2023003330-appb-img-000818
    Figure PCTKR2023003330-appb-img-000819
    Figure PCTKR2023003330-appb-img-000819
    Figure PCTKR2023003330-appb-img-000820
    Figure PCTKR2023003330-appb-img-000820
    Figure PCTKR2023003330-appb-img-000821
    Figure PCTKR2023003330-appb-img-000821
    Figure PCTKR2023003330-appb-img-000822
    Figure PCTKR2023003330-appb-img-000822
    Figure PCTKR2023003330-appb-img-000823
    Figure PCTKR2023003330-appb-img-000823
    Figure PCTKR2023003330-appb-img-000824
    Figure PCTKR2023003330-appb-img-000824
    Figure PCTKR2023003330-appb-img-000825
    Figure PCTKR2023003330-appb-img-000825
    Figure PCTKR2023003330-appb-img-000826
    Figure PCTKR2023003330-appb-img-000826
    Figure PCTKR2023003330-appb-img-000827
    Figure PCTKR2023003330-appb-img-000827
    Figure PCTKR2023003330-appb-img-000828
    Figure PCTKR2023003330-appb-img-000828
    Figure PCTKR2023003330-appb-img-000829
    Figure PCTKR2023003330-appb-img-000829
    Figure PCTKR2023003330-appb-img-000830
    Figure PCTKR2023003330-appb-img-000830
    Figure PCTKR2023003330-appb-img-000831
    Figure PCTKR2023003330-appb-img-000831
    상기 화합물에 있어서, tBu는 tert-부틸기를 의미한다.In the above compounds, tBu refers to a tert-butyl group.
  8. 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 7 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.first electrode; second electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 7. Light-emitting device.
  9. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.
  10. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 도펀트 물질을 포함하며, 상기 도펀트 물질은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a dopant material, and the dopant material includes the compound.
  11. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 H의 화합물을 더 포함하는 것인 유기 발광 소자:The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer further includes a compound of the formula H:
    [화학식 H][Formula H]
    Figure PCTKR2023003330-appb-img-000832
    Figure PCTKR2023003330-appb-img-000832
    상기 화학식 H에 있어서,In the formula H,
    L20 및 L21은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar20 및 Ar21은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar20 and Ar21 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    R200 및 R201은 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R200 and R201 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    r201은 1 내지 7의 정수이며, 상기 r201이 2 이상인 경우, 2 이상의 R201은 서로 같거나 상이하다.r201 is an integer from 1 to 7, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  12. 청구항 10에 있어서, 상기 발광층은 1종 이상의 도펀트 및 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 10, wherein the light emitting layer further includes one or more types of dopants and a host.
  13. 청구항 10에 있어서, 상기 발광층은 1 종 이상의 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 10, wherein the light emitting layer further includes one or more types of hosts.
  14. 청구항 10에 있어서, 상기 발광층은 2종 이상의 혼합 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 10, wherein the light emitting layer further includes two or more types of mixed hosts.
PCT/KR2023/003330 2022-03-11 2023-03-10 Compound and organic light-emitting device comprising same WO2023172111A1 (en)

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US20180114929A1 (en) * 2016-10-24 2018-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US20190067577A1 (en) * 2017-08-22 2019-02-28 Chuanjun Xia Boron containing heterocyclic compound for oleds, an organic light-emitting device, and a formulation comprising the boron-containing heterocyclic compound
WO2020135953A1 (en) * 2018-12-28 2020-07-02 Cynora Gmbh Organic molecules for optoelectronic devices
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WO2021255698A1 (en) * 2020-06-19 2021-12-23 Idemitsu Kosan Co., Ltd. Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound

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US20180114929A1 (en) * 2016-10-24 2018-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US20190067577A1 (en) * 2017-08-22 2019-02-28 Chuanjun Xia Boron containing heterocyclic compound for oleds, an organic light-emitting device, and a formulation comprising the boron-containing heterocyclic compound
WO2020135953A1 (en) * 2018-12-28 2020-07-02 Cynora Gmbh Organic molecules for optoelectronic devices
WO2021214310A1 (en) * 2020-04-23 2021-10-28 Cynora Gmbh Organic molecules for optoelectronic devices
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