WO2023172110A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2023172110A1
WO2023172110A1 PCT/KR2023/003328 KR2023003328W WO2023172110A1 WO 2023172110 A1 WO2023172110 A1 WO 2023172110A1 KR 2023003328 W KR2023003328 W KR 2023003328W WO 2023172110 A1 WO2023172110 A1 WO 2023172110A1
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substituted
unsubstituted
carbon atoms
monocyclic
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이다정
김명곤
김경희
이우철
황성현
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주식회사 엘지화학
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Priority to CN202380012143.1A priority Critical patent/CN117440960A/en
Publication of WO2023172110A1 publication Critical patent/WO2023172110A1/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
    • 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.
  • A1 is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
  • A2 is a substituted or unsubstituted hydrocarbon ring
  • A1 and A2 are combined with each other to form a substituted or unsubstituted ring, or do not form a substituted or unsubstituted ring,
  • R1 and R2 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(G1)(G2); 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 R1 and R2 combine with each other to form a substituted or unsubstituted ring,
  • Z1 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with Z2 to form a substituted or unsubstituted hydrocarbon ring,
  • Z2 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); 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,
  • G1 to G4 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.
  • 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 substituent.
  • 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.
  • -It can be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.
  • 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 etc., but is not limited to this.
  • 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 6 below.
  • A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
  • R3 to R6 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(G5)(G6); 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 at least one of R3 to R6 combines with A1 to form a substituted or unsubstituted ring,
  • G5 and G6 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r3 is an integer from 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 1 to 6, and when r4 is 2 or more, the 2 or more R4s 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 of 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other.
  • Formula 1 is any one of 7 to 9 below.
  • A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
  • R7 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G5)(G6); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with A1 to form a substituted or unsubstituted ring,
  • G5 and G6 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,
  • r7 is an integer from 1 to 10, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring;
  • Formula 1 is Formula 10 or 11 below.
  • X1 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(G7)(G8); 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,
  • R11 combines with A2 to form a substituted or unsubstituted ring, or
  • R12 combines with A2 to form a substituted or unsubstituted ring, or does not form a substituted or unsubstituted ring,
  • G7 and G8 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 12 to 23 below.
  • X1 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
  • X2 and X3 are the same or different from each other, and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
  • X4 and X5 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, R"'11 and R12 to R28 are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group ; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G9)(G10); Substituted or unsubstituted aryl group; Condensed ring 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, R"'11 and R12 to R28 are bonded to each other and are substituted or unsubstituted. Forms a circular ring,
  • G9 and G10 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 an integer of 1 to 3, and when r"11 is 2 or more, R"11 of 2 or more is the same as 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 Formula 24 or 25 below.
  • A1, A2, R1, r1, R2, r2 and Z1 are the same as those defined in Formula 1 above,
  • R101 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G11)(G12); 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,
  • G11 and G12 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,
  • r101 is an integer of 1 to 4, and when r101 is 2 or more, the 2 or more R101 are the same or different from each other.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof to 30 monocyclic or polycyclic aromatic hydrocarbon rings;
  • the A2 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • A1 and A2 are combined with each other to form 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of straight or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof. Forms or does not form a monocyclic or polycyclic heterocycle,
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to have 1 to 30 carbon atoms.
  • Z1 is a linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with 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 combined with Z2.
  • Z2 When Z2 does not combine with Z1 to form a ring, Z2 is hydrogen
  • G1 to G8 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; 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 substituted or unsubstituted with 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.
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms;
  • it is a monocyclic or polycyclic heterocycle of 2 to 30 carbon atoms that is substituted or unsubstituted and contains at least one of O, N, and S.
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms;
  • it is a monocyclic or polycyclic heterocycle of 6 to 20 carbon atoms that is substituted or unsubstituted and contains at least one of O, N, and S.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof to 30 monocyclic or polycyclic aromatic hydrocarbon rings;
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, monocyclic or polycyclic heterocyclic groups having 6 to 20 carbon atoms, and combinations thereof.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), benzene substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms, and combinations thereof; naphthalene; 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; dibenz
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N(G7)(G8), benzene substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, monocyclic or polycyclic heterocyclic groups having 6 to 20 carbon atoms, and combinations thereof; naphthalene; 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; dibenz
  • A1 is a methyl group, tert-butyl group, cyclohexyl group, trimethylsilyl group, phenyl group, biphenyl group, hexahydrocarbazole group, -N(G7)(G8), and combinations thereof.
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or it is 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.
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or it is 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.
  • A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • A2 is benzene substituted or unsubstituted with a methyl group, tert-butyl group, -N(G5)(G6), or phenyl group; naphthalene; Or it is tetrahydronaphthalene substituted or unsubstituted with a methyl group.
  • A1 and A2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, or do not form.
  • A1 and A2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 6 to 20 carbon atoms, or do not form.
  • A1 and A2 are combined with each other to form at least one 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.
  • a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed or is not formed.
  • A1 and A2 are combined with each other to form at least one selected from a straight-chain 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.
  • a substituted or unsubstituted monocyclic or polycyclic heterocycle having 6 to 20 carbon atoms is formed or is not formed.
  • A1 and A2 are combined with each other to form at least one 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.
  • A1 and A2 are combined with each other to form at least one selected from a straight-chain 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.
  • A1 and A2 are combined with each other and are dihydroacridine substituted or unsubstituted with one or more selected from tert-butyl group, phenyl group, naphthyl group, and combinations thereof; Spiroacridine fluorene; Or, dihydroindenoacridine substituted or unsubstituted with a methyl group is formed or not formed.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon 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 forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon having 6 to 20 carbon atoms.
  • 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, it forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to have 1 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to form a heterocyclic group having 1 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R1 and R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Indene substituted or unsubstituted with a methyl group; Tetrahydronaph
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Alternatively, it forms a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; Alternatively, it forms a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to a straight chain having 1 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to a straight chain having 1 to 20 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to each other and substituted with a straight-chain or branched alkyl group
  • R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to each other and substituted with a straight-chain or branched alkyl group
  • R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R1 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Or, it forms indene substituted or unsubstituted with a methyl group.
  • R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to a substituted or unsubstituted monocyclic or polycyclic 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
  • R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to a substituted or unsubstituted monocyclic or polycyclic 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; A condensed ring of a substituted or unsubstituted monocyclic or
  • R2 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to a straight chain having 1 to 30 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to a straight chain having 1 to 20 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to each other and substituted with a straight-chain or branched alkyl group
  • R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to each other and substituted with a straight-chain or branched alkyl group
  • R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Indene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group
  • R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
  • R1 and R2 are combined with each other to form at least one 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. It forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • R1 and R2 are combined with each other to form at least one selected from a straight-chain 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. It forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
  • R1 and R2 are combined with each other to form at least one 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.
  • R1 and R2 are combined with each other to form at least one selected from a straight-chain 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.
  • R1 and R2 are bonded to each other and are dihydropyridine substituted or unsubstituted with one or more selected from a methyl group, a phenyl group, and a combination thereof; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
  • Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); 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, or is bonded with Z2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); 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 6 to 20 carbon atoms, or is combined with Z2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • Z1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms;
  • Z1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms;
  • Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenox
  • Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenox
  • Z1 is a methyl group substituted or unsubstituted with a phenyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, phenyl group, or biphenyl group; Biphenyl group substituted or unsubstituted with a phenyl group; Terphenyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a methyl group; Or it is a dihydroacridine group substituted or unsubstituted with a methyl group, or it combines with Z
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); 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.
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); 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 6 to 20 carbon atoms.
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A straight-chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atom
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, a straight or branched alkyl group with 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group;
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group;
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group substituted or unsubstituted with a phenyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, phenyl group, or biphenyl group; Biphenyl group substituted or unsubstituted with a phenyl group; Terphenyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a methyl group; Or it is a dihydroacridine group substituted or unsub
  • Z2 when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen.
  • G1 to G8 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; 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.
  • G1 to G8 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; 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.
  • G1 to G8 are the same as or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms; 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 substituted or unsubstituted with 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.
  • G1 to G8 are the same as or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 20 carbon atoms; 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 substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; a phenyl group unsubstituted or substituted 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; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group; Or it is a dibenzothiophene group.
  • G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; a phenyl group unsubstituted or substituted 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; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group; Or it is a dibenzothiophene group.
  • G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; A phenyl group substituted or unsubstituted with a methyl group, tert-butyl group, or phenyl group; Biphenyl group substituted or unsubstituted with a methyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is any one of the following compounds.
  • t-Bu 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 substituted or unsubstituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group; Naphthobenzothiophene group; Or it is a benzobisbenzofuran 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 represented by the 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 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 further 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; Alternatively, 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 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 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 excellent electron transport ability 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.
  • 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.
  • Compound b-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 6-iodo-1,1,4,4-tetramethyl-1,2,3 is used instead of 1-(tert-butyl)-4-iodobenzene.
  • Compound b-1 was synthesized using 4-tetrahydronaphthalene in the same manner as the preparation method for compound a-1.
  • Compound c-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 6-iodo-1,1,4,4-tetramethyl-1,2,3 is used instead of 1-(tert-butyl)-4-iodobenzene.
  • Compound c-1 was synthesized using 4-tetrahydronaphthalene in the same manner as the preparation method for compound a-1.
  • Compound e-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound e-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
  • Compound p-1 was prepared in the same manner as the preparation method for compound a-1, using 6-(tert-butyl)-2-chloro-4-methyl-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole. synthesized.
  • Compound r-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound r-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
  • compound s-1 instead of compound a-1, use compound s-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
  • Compound s was synthesized using the same method as the method for producing compound a.
  • Compound t-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound t-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
  • Compound a-1 was prepared using compound u-2 instead of 2-chloro-4-methyl-9H-carbazole and 5-bromo-2-phenylbenzo[d]oxazole instead of 1-(tert-butyl)-4-iodobenzene.
  • Compound u-1 was synthesized using the same manufacturing method.
  • Compound y-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 3-bromo-5,5,8,8-tetramethyl-5,6,7 is used instead of 1-(tert-butyl)-4-iodobenzene.
  • Compound y-1 was synthesized using 8-tetrahydronaphtho[2,3-b]thiophene in the same manner as the preparation method for compound a-1.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,400 ⁇ was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves.
  • a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • HI-A and HAT-CN were thermally vacuum deposited to a thickness of 650 ⁇ and 50 ⁇ , 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 600 ⁇ to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the aluminum of the cathode was maintained at a deposition rate of 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr.
  • 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.
  • 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.
  • Lifespan T95 refers to the time it takes for luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the organic light-emitting devices of Examples 1 to 25 include a substituent other than hydrogen in Z1, thereby stabilizing the structure to prevent unstable parts, thereby improving the efficiency of the organic light-emitting device. . Therefore, it was confirmed that the driving voltage, luminous efficiency, and lifespan were superior to the organic light-emitting devices of Comparative Examples 1 to 4 using the compound where Z1 was hydrogen.
  • the compounds of Comparative Examples 3 to 5 in which A1 and R1 are bonded to each other to form a ring, have many parts that rapidly degrade, and due to the nature of organic light-emitting devices that rely on intermolecular hopping, the driving voltage is low. It increases.
  • the unstable part such as the compound of Formula 1 of the present specification
  • the injection of electrons and holes is reduced, thereby suppressing quenching and degradation, thereby producing organic light emission.
  • the efficiency of the device increases, the lifespan of the device improves, and the voltage also decreases. 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 3 to 5 in terms of driving voltage, luminous efficiency, and lifespan.

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Abstract

The present specification provides a compound of chemical 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 10-2022-0030805호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0030805 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 demand 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 PCTKR2023003328-appb-img-000001
Figure PCTKR2023003328-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
A1은 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이며,A1 is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
A2는 치환 또는 비치환된 탄화수소고리이고,A2 is a substituted or unsubstituted hydrocarbon ring,
상기 A1 및 A2는 서로 결합하여 치환 또는 비치환된 고리를 형성거나, 형성하지 않고,A1 and A2 are combined with each other to form a substituted or unsubstituted ring, or do not form a substituted or unsubstituted ring,
R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G1)(G2); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 and R2 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(G1)(G2); 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 R1 and R2 combine with each other to form a substituted or unsubstituted ring,
Z1는 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G3)(G4); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, Z2와 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성하고,Z1 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with Z2 to form a substituted or unsubstituted hydrocarbon ring,
상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G3)(G4); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,When Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); 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,
G1 내지 G4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G1 to G4 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 상이하다.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.
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 PCTKR2023003328-appb-img-000002
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2023003328-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 substituent.
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 PCTKR2023003328-appb-img-000003
또는
Figure PCTKR2023003328-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 PCTKR2023003328-appb-img-000005
,
Figure PCTKR2023003328-appb-img-000006
, 또는
Figure PCTKR2023003328-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 PCTKR2023003328-appb-img-000003
or
Figure PCTKR2023003328-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 PCTKR2023003328-appb-img-000005
,
Figure PCTKR2023003328-appb-img-000006
, or
Figure PCTKR2023003328-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 PCTKR2023003328-appb-img-000008
등이 있으나, 이에 한정되지 않는다.Examples of the fluorene group include
Figure PCTKR2023003328-appb-img-000008
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 축합고리 일 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 6 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 2 to 6 below.
[화학식 2][Formula 2]
Figure PCTKR2023003328-appb-img-000009
Figure PCTKR2023003328-appb-img-000009
[화학식 3][Formula 3]
Figure PCTKR2023003328-appb-img-000010
Figure PCTKR2023003328-appb-img-000010
[화학식 4][Formula 4]
Figure PCTKR2023003328-appb-img-000011
Figure PCTKR2023003328-appb-img-000011
[화학식 5][Formula 5]
Figure PCTKR2023003328-appb-img-000012
Figure PCTKR2023003328-appb-img-000012
[화학식 6][Formula 6]
Figure PCTKR2023003328-appb-img-000013
Figure PCTKR2023003328-appb-img-000013
상기 화학식 2 내지 6에 있어서,In Formulas 2 to 6,
A1, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
R3 내지 R6는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G5)(G6); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R3 내지 R6 중 어느 하나 이상은 상기 A1과 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R3 to R6 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(G5)(G6); 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 at least one of R3 to R6 combines with A1 to form a substituted or unsubstituted ring,
G5 및 G6는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리; 또는 치환 또는 비치환된 헤테로고리기이고,G5 and G6 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
r3는 1 내지 4의 정수이며, 상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하고,r3 is an integer from 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
r4는 1 내지 6의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하며,r4 is an integer from 1 to 6, and when r4 is 2 or more, the 2 or more R4s are the same or different from each other,
r5는 1 내지 4의 정수이며, 상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하고,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,
r6은 1 내지 4의 정수이며, 상기 r6가 2 이상인 경우, 상기 2 이상의 R6은 서로 같거나 상이하다.r6 is an integer of 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 7 내지 9 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of 7 to 9 below.
[화학식 7][Formula 7]
Figure PCTKR2023003328-appb-img-000014
Figure PCTKR2023003328-appb-img-000014
[화학식 8][Formula 8]
Figure PCTKR2023003328-appb-img-000015
Figure PCTKR2023003328-appb-img-000015
[화학식 9][Formula 9]
Figure PCTKR2023003328-appb-img-000016
Figure PCTKR2023003328-appb-img-000016
상기 화학식 7 내지 9에 있어서,In Formulas 7 to 9,
A1, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
R7은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G5)(G6); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 A1과 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R7 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G5)(G6); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with A1 to form a substituted or unsubstituted ring,
G5 및 G6는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G5 and G6 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,
r7는 1 내지 10의 정수이며, 상기 r7가 2 이상인 경우, 상기 2 이상의 R7는 서로 같거나 상이하다.r7 is an integer from 1 to 10, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.
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 substituted or unsubstituted and is a heterocycle containing one or more of O, N, S, and Si.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 10 또는 11이다.According to an exemplary embodiment of the present specification, Formula 1 is Formula 10 or 11 below.
[화학식 10][Formula 10]
Figure PCTKR2023003328-appb-img-000017
Figure PCTKR2023003328-appb-img-000017
[화학식 11][Formula 11]
Figure PCTKR2023003328-appb-img-000018
Figure PCTKR2023003328-appb-img-000018
상기 화학식 10 및 11에 있어서,In Formulas 10 and 11,
A2, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A2, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
X1는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X1 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(G7)(G8); 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 형성하고,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(G7)(G8); 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,
상기 R11은 상기 A2와 서로 결합하여 치환 또는 비치환된 고리를 형성하거나, 형성하지 않고,R11 combines with A2 to form a substituted or unsubstituted ring, or
상기 R12는 상기 A2와 서로 결합하여 치환 또는 비치환된 고리를 형성하거나, 형성하지 않고,R12 combines with A2 to form a substituted or unsubstituted ring, or does not form a substituted or unsubstituted ring,
G7 및 G8는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G7 and G8 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 12 내지 23 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 12 to 23 below.
[화학식 12][Formula 12]
Figure PCTKR2023003328-appb-img-000019
Figure PCTKR2023003328-appb-img-000019
[화학식 13][Formula 13]
Figure PCTKR2023003328-appb-img-000020
Figure PCTKR2023003328-appb-img-000020
[화학식 14][Formula 14]
Figure PCTKR2023003328-appb-img-000021
Figure PCTKR2023003328-appb-img-000021
[화학식 15][Formula 15]
Figure PCTKR2023003328-appb-img-000022
Figure PCTKR2023003328-appb-img-000022
[화학식 16][Formula 16]
Figure PCTKR2023003328-appb-img-000023
Figure PCTKR2023003328-appb-img-000023
[화학식 17][Formula 17]
Figure PCTKR2023003328-appb-img-000024
Figure PCTKR2023003328-appb-img-000024
[화학식 18][Formula 18]
Figure PCTKR2023003328-appb-img-000025
Figure PCTKR2023003328-appb-img-000025
[화학식 19][Formula 19]
Figure PCTKR2023003328-appb-img-000026
Figure PCTKR2023003328-appb-img-000026
[화학식 20][Formula 20]
Figure PCTKR2023003328-appb-img-000027
Figure PCTKR2023003328-appb-img-000027
[화학식 21][Formula 21]
Figure PCTKR2023003328-appb-img-000028
Figure PCTKR2023003328-appb-img-000028
[화학식 22][Formula 22]
Figure PCTKR2023003328-appb-img-000029
Figure PCTKR2023003328-appb-img-000029
[화학식 23][Formula 23]
Figure PCTKR2023003328-appb-img-000030
Figure PCTKR2023003328-appb-img-000030
상기 화학식 12 내지 23에 있어서,In Formulas 12 to 23,
A2, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A2, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
X1는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X1 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
X2 및 X3는 서로 같거나 상이하고, 각각 독립적으로 -C(R19)(R20)-; -Si(R21)(R22)-; -O-; 또는 -S-이며,X2 and X3 are the same or different from each other, and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
X4 및 X5은 서로 같거나 상이하고, 각각 독립적으로 -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; 또는 -S-이며,X4 and X5 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, 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(G9)(G10); 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, R"'11 및 R12 내지 R28 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R'2, R"2, R'11, R"11, R"'11 and R12 to R28 are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group ; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G9)(G10); Substituted or unsubstituted aryl group; Condensed ring 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, R"'11 and R12 to R28 are bonded to each other and are substituted or unsubstituted. Forms a circular ring,
G9 및 G10는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G9 and G10 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 내지 3의 정수이고, 상기 r"11이 2 이상인 경우, 상기 2 이상의 R"11은 서로 같거나 상이하며,r"11 is an integer of 1 to 3, and when r"11 is 2 or more, R"11 of 2 or more is the same as 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 24 또는 25이다.According to an exemplary embodiment of the present specification, Formula 1 is Formula 24 or 25 below.
[화학식 24][Formula 24]
Figure PCTKR2023003328-appb-img-000031
Figure PCTKR2023003328-appb-img-000031
[화학식 25][Formula 25]
Figure PCTKR2023003328-appb-img-000032
Figure PCTKR2023003328-appb-img-000032
상기 화학식 24 및 25에 있어서,In Formulas 24 and 25,
A1, A2, R1, r1, R2, r2 및 Z1의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A1, A2, R1, r1, R2, r2 and Z1 are the same as those defined in Formula 1 above,
R101은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G11)(G12); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,R101 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G11)(G12); 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,
G11 및 G12는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G11 and G12 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,
r101은 1 내지 4의 정수이며, 상기 r101이 2 이상인 경우, 상기 2 이상의 R101은 서로 같거나 상이하다.r101 is an integer of 1 to 4, and when r101 is 2 or more, the 2 or more R101 are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기, 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, -N(G7)(G8), 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 단환 또는 다환의 헤테로고리이고,According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof to 30 monocyclic or polycyclic aromatic hydrocarbon rings; 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 straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof, O , is a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms containing one or more of N and S,
상기 A2는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 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 축합고리이며,The A2 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Aromatic hydrocarbon ring; or 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,
상기 A1 및 A2는 서로 결합하여 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 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하거나, 형성하지 않고,A1 and A2 are combined with each other to form 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of straight or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof. Forms or does not form a monocyclic or polycyclic heterocycle,
상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하며,R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to have 1 to 30 carbon atoms. A monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group; 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; 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 monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of 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. forming,
상기 Z1은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하고,Z1 is a linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with 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 combined with Z2. form,
상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소이며,When Z2 does not combine with Z1 to form a ring, Z2 is hydrogen,
상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.G1 to G8 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; 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 substituted or unsubstituted with 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.
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 단환 또는 다환의 헤테로고리이다.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 it is a monocyclic or polycyclic heterocycle of 2 to 30 carbon atoms that is substituted or unsubstituted and contains at least one of O, N, and S.
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 6 내지 20의 단환 또는 다환의 헤테로고리이다.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 it is a monocyclic or polycyclic heterocycle of 6 to 20 carbon atoms that is substituted or unsubstituted and contains at least one of O, N, and S.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기, 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, -N(G7)(G8), 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 단환 또는 다환의 헤테로고리이다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof to 30 monocyclic or polycyclic aromatic hydrocarbon rings; 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 is substituted or unsubstituted with one or more selected from straight or branched alkyl groups having 1 to 30 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof, and O, It is a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms and containing at least one of N and S.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기, 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, -N(G7)(G8), 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 6 내지 20의 단환 또는 다환의 헤테로고리이다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N(G7)(G8), 6 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, monocyclic or polycyclic heterocyclic groups having 6 to 20 carbon atoms, and combinations thereof. to 20 monocyclic or polycyclic aromatic hydrocarbon rings; 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 O, It is a monocyclic or polycyclic heterocycle containing 6 to 20 carbon atoms and containing at least one of N and S.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤젠; 나프탈렌; 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 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 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 알킬기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조퓨란; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조티오펜이다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7)(G8), benzene substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms, and combinations thereof; naphthalene; 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; 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; 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; Benzofuran substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; or benzoti substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof. It's Offen.
본 명세서의 일 실시상태에 따르면, 상기 A1은 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤젠; 나프탈렌; 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 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 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 알킬기, -N(G7)(G8), 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조퓨란; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(G7)(G8), 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조티오펜이다.According to an exemplary embodiment of the present specification, A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N(G7)(G8), benzene substituted or unsubstituted with one or more selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, monocyclic or polycyclic heterocyclic groups having 6 to 20 carbon atoms, and combinations thereof; naphthalene; 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; 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; 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; Benzofuran substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof; or benzoti substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof. It's Offen.
본 명세서의 일 실시상태에 따르면, 상기 A1은 메틸기, tert-부틸기, 시클로헥실기, 트리메틸실릴기, 페닐기, 바이페닐기, 헥사하이드로카바졸기, -N(G7)(G8), 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤젠; 나프탈렌; 메틸기로 치환 또는 비치환된 플루오렌; 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌; 디벤조퓨란; 디벤조티오펜; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 페닐기로 치환 또는 비치환된 벤즈옥사졸; 페닐기로 치환 또는 비치환된 벤조티아졸; 메틸기, 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤즈이미다졸; 메틸기, tert-부틸기, -N(G7)(G8), 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조퓨란; 또는 메틸기, tert-부틸기, -N(G7)(G8), 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 벤조티오펜이다.According to an exemplary embodiment of the present specification, A1 is a methyl group, tert-butyl group, cyclohexyl group, trimethylsilyl group, phenyl group, biphenyl group, hexahydrocarbazole group, -N(G7)(G8), and combinations thereof. benzene substituted or unsubstituted with one or more selected from among; naphthalene; Fluorene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; dibenzofuran; dibenzothiophene; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl 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; Benzofuran substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, -N(G7)(G8), phenyl group, and combinations thereof; or benzothiophene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, -N(G7)(G8), phenyl group, and combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 A2는 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or it is 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.
본 명세서의 일 실시상태에 따르면, 상기 A2는 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리와 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or it is 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.
본 명세서의 일 실시상태에 따르면, 상기 A2는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 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 축합고리이다.According to an exemplary embodiment of the present specification, A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or it is 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.
본 명세서의 일 실시상태에 따르면, 상기 A2는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 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 축합고리이다.According to an exemplary embodiment of the present specification, A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; Or, it is a condensed ring of a monocyclic or polycyclic aromatic 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, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A2는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤젠; 나프탈렌; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌이다.According to an exemplary embodiment of the present specification, A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. benzene; naphthalene; or tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A2는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤젠; 나프탈렌; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌이다.According to an exemplary embodiment of the present specification, A2 is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. benzene; naphthalene; or tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A2는 메틸기, tert-부틸기, -N(G5)(G6), 또는 페닐기로 치환 또는 비치환된 벤젠; 나프탈렌; 또는 메틸기로 치환 또는 비치환된 테트라하이드로나프탈렌이다.According to an exemplary embodiment of the present specification, A2 is benzene substituted or unsubstituted with a methyl group, tert-butyl group, -N(G5)(G6), or phenyl group; naphthalene; Or it is tetrahydronaphthalene substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, or do not form.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리를 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 6 to 20 carbon atoms, or do not form.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 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 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form at least one 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. A substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed or is not formed.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 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 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리를 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form at least one selected from a straight-chain 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. A substituted or unsubstituted monocyclic or polycyclic heterocycle having 6 to 20 carbon atoms is formed or is not formed.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 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 디하이드로아크리딘; 스피로아크리딘플루오렌; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로인데노아크리딘을 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form at least one 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. Substituted or unsubstituted dihydroacridine; Spiroacridine fluorene; Alternatively, it forms or does not form dihydroindenoacridine substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 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 디하이드로아크리딘; 스피로아크리딘플루오렌; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로인데노아크리딘을 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other to form at least one selected from a straight-chain 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. Substituted or unsubstituted dihydroacridine; Spiroacridine fluorene; Alternatively, it forms or does not form dihydroindenoacridine substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A1 및 A2는 서로 결합하여 tert-부틸기, 페닐기, 나프틸기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 디하이드로아크리딘; 스피로아크리딘플루오렌; 또는 메틸기로 치환 또는 비치환된 디하이드로인데노아크리딘을 형성하거나, 형성하지 않는다.According to an exemplary embodiment of the present specification, A1 and A2 are combined with each other and are dihydroacridine substituted or unsubstituted with one or more selected from tert-butyl group, phenyl group, naphthyl group, and combinations thereof; Spiroacridine fluorene; Or, dihydroindenoacridine substituted or unsubstituted with a methyl group is formed or not formed.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms. ring; 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 forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 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 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon having 6 to 20 carbon atoms. ring; 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, it forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to have 1 to 30 carbon atoms. A monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group; 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; 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 monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of 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. forms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to form a heterocyclic group having 1 to 20 carbon atoms. A monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group; A monocyclic or polycyclic aromatic 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; 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 monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a straight-chain 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. forms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로펜타나프탈렌; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌; 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 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Cyclohexene substituted or unsubstituted; benzene; Indene 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; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran; dibenzothiophene; Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dihydropyridine 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; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로펜타나프탈렌; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌; 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 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 and R2 is bonded to each other to form a straight-chain or branched alkyl group having 1 to 20 carbon atoms. Cyclohexene substituted or unsubstituted; benzene; indene 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; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran; dibenzothiophene; Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dihydropyridine 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; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); tert-부틸기로 치환 또는 비치환된 페닐기; tert-부틸기로 치환 또는 비치환된 바이페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오렌기; 또는 메틸기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 메틸기로 치환 또는 비치환된 시클로헥센; 벤젠; 메틸기로 치환 또는 비치환된 인덴; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 메틸기로 치환 또는 비치환된 시클로펜타나프탈렌; 메틸기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 메틸기로 치환 또는 비치환된 플루오렌; 메틸기, 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R1 and R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Indene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a methyl group; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a methyl group; Dibenzofuran; dibenzothiophene; Fluorene substituted or unsubstituted with a methyl group; Dihydropyridine substituted or unsubstituted with one or more selected from methyl groups, phenyl groups, and combinations thereof; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Alternatively, it forms a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; Alternatively, it forms a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to a straight chain having 1 to 30 carbon atoms. or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with a branched alkyl group; Alternatively, it forms 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.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to a straight chain having 1 to 20 carbon atoms. or a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a branched alkyl group; Alternatively, it forms a monocyclic or polycyclic aromatic 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.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R1 is bonded to each other and substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. or unsubstituted cyclohexene; benzene; Alternatively, indene is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R1 is bonded to each other and substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. or unsubstituted cyclohexene; benzene; Alternatively, it forms a substituted or unsubstituted indene with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); tert-부틸기로 치환 또는 비치환된 페닐기; tert-부틸기로 치환 또는 비치환된 바이페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오렌기; 또는 메틸기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R1 중 인접한 어느 한 쌍 이상은 서로 결합하여, 메틸기로 치환 또는 비치환된 시클로헥센; 벤젠; 또는 메틸기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R1 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Or, it forms indene substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to a substituted or unsubstituted monocyclic or polycyclic 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 forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 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 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to a substituted or unsubstituted monocyclic or polycyclic 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; 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 forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to a straight chain having 1 to 30 carbon atoms. or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with a branched alkyl group; 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; 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 monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of 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. forms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G1)(G2); a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to a straight chain having 1 to 20 carbon atoms. or a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a branched alkyl group; A monocyclic or polycyclic aromatic 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; 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 monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a straight-chain 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. forms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로펜타나프탈렌; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or at least one adjacent pair of R2 is bonded to each other and substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. or unsubstituted cyclohexene; benzene; Indene 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; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophene; Alternatively, fluorene is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로헥센; 벤젠; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 시클로펜타나프탈렌; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or at least one adjacent pair of R2 is bonded to each other and substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. or unsubstituted cyclohexene; benzene; indene 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; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; dibenzofuran; dibenzothiophene; Alternatively, fluorene is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G1)(G2); tert-부틸기로 치환 또는 비치환된 페닐기; tert-부틸기로 치환 또는 비치환된 바이페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오렌기; 또는 메틸기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, 상기 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여, 메틸기로 치환 또는 비치환된 시클로헥센; 벤젠; 메틸기로 치환 또는 비치환된 인덴; 메틸기로 치환 또는 비치환된 테트라하이드로나프토퓨란; 메틸기로 치환 또는 비치환된 테트라하이드로나프토티오펜; 나프토퓨란; 나프토티오펜; 메틸기로 치환 또는 비치환된 시클로펜타나프탈렌; 메틸기로 치환 또는 비치환된 테트라하이드로시클로펜타나프탈렌; 디벤조퓨란; 디벤조티오펜; 또는 메틸기로 치환 또는 비치환된 플루오렌을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G1)(G2); A phenyl group substituted or unsubstituted with a tert-butyl group; Biphenyl group substituted or unsubstituted with tert-butyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; or a hexahydrocarbazole group substituted or unsubstituted with a methyl group, or at least one adjacent pair of R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; benzene; Indene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Naphthofuran; Naphthothiophene; Cyclopentanaphthalene substituted or unsubstituted with a methyl group; Tetrahydrocyclopentanaphthalene substituted or unsubstituted with a methyl group; dibenzofuran; dibenzothiophene; Or it forms fluorene substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 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 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form at least one 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. It forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 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 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form at least one selected from a straight-chain 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. It forms a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 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 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form at least one 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. Substituted or unsubstituted dihydropyridine; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 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 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form at least one selected from a straight-chain 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. Substituted or unsubstituted dihydropyridine; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 결합하여 메틸기, 페닐기, 및 이들의 조합 중에서 선택된 1 이상으로 치환 또는 비치환된 디하이드로피리딘; 스피로플루오렌피리딘; 피롤; 옥사진; 또는 디하이드로피라지노인돌을 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are bonded to each other and are dihydropyridine substituted or unsubstituted with one or more selected from a methyl group, a phenyl group, and a combination thereof; spirofluorenepyridine; pyrrole; Oxazine; or forms dihydropyrazinoindole.
본 명세서의 일 실시상태에 따르면, 상기 Z1은 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); 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, or is bonded with Z2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z1은 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); 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 6 to 20 carbon atoms, or is combined with Z2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z1은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with 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 combined with Z2. form
본 명세서의 일 실시상태에 따르면, 상기 Z1은 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, a straight or branched alkyl group with 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms combined with Z2. form
본 명세서의 일 실시상태에 따르면, 상기 Z1은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 터페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로아크리딘기이거나, Z2와 서로 결합하여 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a dihydroacridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or it combines with Z2 to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 Z1은 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 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; 터페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로아크리딘기이거나, Z2와 서로 결합하여 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or, it is a dihydroacridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or it combines with Z2 to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 Z1은 페닐기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 메틸기, tert-부틸기, 페닐기, 또는 바이페닐기로 치환 또는 비치환된 페닐기; 페닐기로 치환 또는 비치환된 바이페닐기; 터페닐기; 메틸기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 메틸기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 메틸기로 치환 또는 비치환된 디하이드로아크리딘기이거나, Z2와 서로 결합하여 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, Z1 is a methyl group substituted or unsubstituted with a phenyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, phenyl group, or biphenyl group; Biphenyl group substituted or unsubstituted with a phenyl group; Terphenyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a methyl group; Or it is a dihydroacridine group substituted or unsubstituted with a methyl group, or it combines with Z2 to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); 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 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); 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 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A straight-chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, a straight or branched alkyl group with 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 터페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로아크리딘기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a dihydroacridine group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 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; 터페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 디하이드로아크리딘기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group substituted or unsubstituted with deuterium, 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; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a dihydroacridine group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 페닐기로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 트리메틸실릴기; -N(G3)(G4); 중수소, 메틸기, tert-부틸기, 페닐기, 또는 바이페닐기로 치환 또는 비치환된 페닐기; 페닐기로 치환 또는 비치환된 바이페닐기; 터페닐기; 메틸기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사진기; 메틸기로 치환 또는 비치환된 헥사하이드로카바졸기; 또는 메틸기로 치환 또는 비치환된 디하이드로아크리딘기이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; A methyl group substituted or unsubstituted with a phenyl group; isopropyl group; tert-butyl group; trimethylsilyl group; -N(G3)(G4); A phenyl group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, phenyl group, or biphenyl group; Biphenyl group substituted or unsubstituted with a phenyl group; Terphenyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Phenoxazine; Hexahydrocarbazole group substituted or unsubstituted with a methyl group; Or it is a dihydroacridine group substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소이다.According to an exemplary embodiment of the present specification, when Z2 does not combine with Z1 to form a ring, Z2 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, G1 to G8 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; 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 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, G1 to G8 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; 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 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, G1 to G8 are the same as or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms; 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 substituted or unsubstituted with 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.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리기이다.According to an exemplary embodiment of the present specification, G1 to G8 are the same as or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 20 carbon atoms; 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 substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 메틸기; tert-부틸기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; a phenyl group unsubstituted or substituted 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; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran group; Or it is a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 메틸기; tert-부틸기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 바이페닐기; 나프틸기; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; a phenyl group unsubstituted or substituted 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; A biphenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran group; Or it is a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 메틸기; tert-부틸기; 메틸기, tert-부틸기, 또는 페닐기로 치환 또는 비치환된 페닐기; 메틸기로 치환 또는 비치환된 바이페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오렌기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, G1 to G8 are the same as or different from each other, and are each independently a methyl group; tert-butyl group; A phenyl group substituted or unsubstituted with a methyl group, tert-butyl group, or phenyl group; Biphenyl group substituted or unsubstituted with a methyl group; naphthyl group; Fluorene group substituted or unsubstituted with a methyl group; Dibenzofuran group; Or it is a dibenzothiophene 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 PCTKR2023003328-appb-img-000033
Figure PCTKR2023003328-appb-img-000033
Figure PCTKR2023003328-appb-img-000034
Figure PCTKR2023003328-appb-img-000034
Figure PCTKR2023003328-appb-img-000035
Figure PCTKR2023003328-appb-img-000035
Figure PCTKR2023003328-appb-img-000036
Figure PCTKR2023003328-appb-img-000036
Figure PCTKR2023003328-appb-img-000037
Figure PCTKR2023003328-appb-img-000037
Figure PCTKR2023003328-appb-img-000038
Figure PCTKR2023003328-appb-img-000038
Figure PCTKR2023003328-appb-img-000039
Figure PCTKR2023003328-appb-img-000039
Figure PCTKR2023003328-appb-img-000040
Figure PCTKR2023003328-appb-img-000040
Figure PCTKR2023003328-appb-img-000041
Figure PCTKR2023003328-appb-img-000041
Figure PCTKR2023003328-appb-img-000042
Figure PCTKR2023003328-appb-img-000042
Figure PCTKR2023003328-appb-img-000043
Figure PCTKR2023003328-appb-img-000043
Figure PCTKR2023003328-appb-img-000044
Figure PCTKR2023003328-appb-img-000044
Figure PCTKR2023003328-appb-img-000045
Figure PCTKR2023003328-appb-img-000045
Figure PCTKR2023003328-appb-img-000046
Figure PCTKR2023003328-appb-img-000046
Figure PCTKR2023003328-appb-img-000047
Figure PCTKR2023003328-appb-img-000047
Figure PCTKR2023003328-appb-img-000048
Figure PCTKR2023003328-appb-img-000048
Figure PCTKR2023003328-appb-img-000049
Figure PCTKR2023003328-appb-img-000049
Figure PCTKR2023003328-appb-img-000050
Figure PCTKR2023003328-appb-img-000050
Figure PCTKR2023003328-appb-img-000051
Figure PCTKR2023003328-appb-img-000051
Figure PCTKR2023003328-appb-img-000052
Figure PCTKR2023003328-appb-img-000052
Figure PCTKR2023003328-appb-img-000053
Figure PCTKR2023003328-appb-img-000053
Figure PCTKR2023003328-appb-img-000054
Figure PCTKR2023003328-appb-img-000054
Figure PCTKR2023003328-appb-img-000055
Figure PCTKR2023003328-appb-img-000055
Figure PCTKR2023003328-appb-img-000056
Figure PCTKR2023003328-appb-img-000056
Figure PCTKR2023003328-appb-img-000057
Figure PCTKR2023003328-appb-img-000057
Figure PCTKR2023003328-appb-img-000058
Figure PCTKR2023003328-appb-img-000058
Figure PCTKR2023003328-appb-img-000059
Figure PCTKR2023003328-appb-img-000059
Figure PCTKR2023003328-appb-img-000060
Figure PCTKR2023003328-appb-img-000060
Figure PCTKR2023003328-appb-img-000061
Figure PCTKR2023003328-appb-img-000061
Figure PCTKR2023003328-appb-img-000062
Figure PCTKR2023003328-appb-img-000062
Figure PCTKR2023003328-appb-img-000063
Figure PCTKR2023003328-appb-img-000063
Figure PCTKR2023003328-appb-img-000064
Figure PCTKR2023003328-appb-img-000064
Figure PCTKR2023003328-appb-img-000065
Figure PCTKR2023003328-appb-img-000065
Figure PCTKR2023003328-appb-img-000066
Figure PCTKR2023003328-appb-img-000066
Figure PCTKR2023003328-appb-img-000067
Figure PCTKR2023003328-appb-img-000067
Figure PCTKR2023003328-appb-img-000068
Figure PCTKR2023003328-appb-img-000068
Figure PCTKR2023003328-appb-img-000069
Figure PCTKR2023003328-appb-img-000069
Figure PCTKR2023003328-appb-img-000070
Figure PCTKR2023003328-appb-img-000070
Figure PCTKR2023003328-appb-img-000071
Figure PCTKR2023003328-appb-img-000071
Figure PCTKR2023003328-appb-img-000072
Figure PCTKR2023003328-appb-img-000072
Figure PCTKR2023003328-appb-img-000073
Figure PCTKR2023003328-appb-img-000073
Figure PCTKR2023003328-appb-img-000074
Figure PCTKR2023003328-appb-img-000074
Figure PCTKR2023003328-appb-img-000075
Figure PCTKR2023003328-appb-img-000075
Figure PCTKR2023003328-appb-img-000076
Figure PCTKR2023003328-appb-img-000076
Figure PCTKR2023003328-appb-img-000077
Figure PCTKR2023003328-appb-img-000077
Figure PCTKR2023003328-appb-img-000078
Figure PCTKR2023003328-appb-img-000078
Figure PCTKR2023003328-appb-img-000079
Figure PCTKR2023003328-appb-img-000079
Figure PCTKR2023003328-appb-img-000080
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Figure PCTKR2023003328-appb-img-000215
상기 화합물에 있어서, t-Bu는 tert-부틸기를 의미한다.In the above compounds, t-Bu 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 PCTKR2023003328-appb-img-000216
Figure PCTKR2023003328-appb-img-000216
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; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조비스벤조퓨란기이다.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; Naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a benzobisbenzofuran 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; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 나프토벤조티오펜기; 또는 벤조비스벤조퓨란기이다.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 substituted or unsubstituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group; Naphthobenzothiophene group; Or it is a benzobisbenzofuran 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 PCTKR2023003328-appb-img-000217
Figure PCTKR2023003328-appb-img-000217
Figure PCTKR2023003328-appb-img-000218
Figure PCTKR2023003328-appb-img-000218
Figure PCTKR2023003328-appb-img-000219
Figure PCTKR2023003328-appb-img-000219
Figure PCTKR2023003328-appb-img-000220
Figure PCTKR2023003328-appb-img-000220
Figure PCTKR2023003328-appb-img-000221
Figure PCTKR2023003328-appb-img-000221
Figure PCTKR2023003328-appb-img-000222
Figure PCTKR2023003328-appb-img-000222
Figure PCTKR2023003328-appb-img-000223
Figure PCTKR2023003328-appb-img-000223
Figure PCTKR2023003328-appb-img-000224
Figure PCTKR2023003328-appb-img-000224
Figure PCTKR2023003328-appb-img-000225
Figure PCTKR2023003328-appb-img-000225
Figure PCTKR2023003328-appb-img-000226
Figure PCTKR2023003328-appb-img-000226
Figure PCTKR2023003328-appb-img-000227
Figure PCTKR2023003328-appb-img-000227
Figure PCTKR2023003328-appb-img-000228
Figure PCTKR2023003328-appb-img-000228
Figure PCTKR2023003328-appb-img-000229
Figure PCTKR2023003328-appb-img-000229
Figure PCTKR2023003328-appb-img-000230
Figure PCTKR2023003328-appb-img-000230
Figure PCTKR2023003328-appb-img-000231
Figure PCTKR2023003328-appb-img-000231
Figure PCTKR2023003328-appb-img-000232
Figure PCTKR2023003328-appb-img-000232
Figure PCTKR2023003328-appb-img-000233
Figure PCTKR2023003328-appb-img-000233
Figure PCTKR2023003328-appb-img-000234
Figure PCTKR2023003328-appb-img-000234
Figure PCTKR2023003328-appb-img-000235
Figure PCTKR2023003328-appb-img-000235
Figure PCTKR2023003328-appb-img-000236
Figure PCTKR2023003328-appb-img-000236
Figure PCTKR2023003328-appb-img-000237
Figure PCTKR2023003328-appb-img-000237
Figure PCTKR2023003328-appb-img-000238
Figure PCTKR2023003328-appb-img-000238
Figure PCTKR2023003328-appb-img-000239
Figure PCTKR2023003328-appb-img-000239
Figure PCTKR2023003328-appb-img-000240
Figure PCTKR2023003328-appb-img-000240
Figure PCTKR2023003328-appb-img-000241
Figure PCTKR2023003328-appb-img-000241
Figure PCTKR2023003328-appb-img-000242
Figure PCTKR2023003328-appb-img-000242
Figure PCTKR2023003328-appb-img-000243
Figure PCTKR2023003328-appb-img-000243
Figure PCTKR2023003328-appb-img-000244
Figure PCTKR2023003328-appb-img-000244
본 명세서의 일 실시상태에 따르면, 상기 화학식 H로 표시되는 화합물은 하기 일반식 1로 제조될 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the compound represented by the formula H may be prepared by the following general formula 1, but is not limited thereto.
[일반식 1][General Formula 1]
Figure PCTKR2023003328-appb-img-000245
Figure PCTKR2023003328-appb-img-000245
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 더포함한다.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 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.
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 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 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 PCTKR2023003328-appb-img-000246
Figure PCTKR2023003328-appb-img-000246
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 PCTKR2023003328-appb-img-000247
Figure PCTKR2023003328-appb-img-000247
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 PCTKR2023003328-appb-img-000248
Figure PCTKR2023003328-appb-img-000248
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 PCTKR2023003328-appb-img-000249
Figure PCTKR2023003328-appb-img-000249
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 PCTKR2023003328-appb-img-000250
Figure PCTKR2023003328-appb-img-000250
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; Alternatively, 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 PCTKR2023003328-appb-img-000251
Figure PCTKR2023003328-appb-img-000251
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 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]
Figure PCTKR2023003328-appb-img-000252
Figure PCTKR2023003328-appb-img-000252
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 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 PCTKR2023003328-appb-img-000253
Figure PCTKR2023003328-appb-img-000253
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 PCTKR2023003328-appb-img-000254
Figure PCTKR2023003328-appb-img-000254
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 PCTKR2023003328-appb-img-000255
Figure PCTKR2023003328-appb-img-000255
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 excellent electron transport ability 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 1Synthesis Example 1
Figure PCTKR2023003328-appb-img-000256
Figure PCTKR2023003328-appb-img-000256
1) 화합물 a-1의 제조1) Preparation of compound a-1
질소 분위기에서 2-chloro-4-methyl-9H-carbazole (100g, 463.6mmol)와 1-(tert-butyl)-4-iodobenzene (120.6g, 463.6mmol), sodium tert-butoxide (89.1g, 927.3mmol)을 toluene 2000ml에 넣고 교반 및 환류하였다. 이 후 bis(tri-tert-butylphosphine)palladium(0) (2.4g, 4.6mmol)을 투입하였다. 3 시간 후 반응이 종결되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 a-1를 120.7g을 얻었다. (수율 75%, MS: [M+H]+= 348)2-chloro-4-methyl-9H-carbazole (100g, 463.6mmol), 1-(tert-butyl)-4-iodobenzene (120.6g, 463.6mmol), and sodium tert-butoxide (89.1g, 927.3mmol) in a nitrogen atmosphere. ) was added to 2000ml of toluene, stirred and refluxed. Afterwards, bis(tri-tert-butylphosphine)palladium(0) (2.4g, 4.6mmol) was added. After 3 hours, the reaction was completed, the reaction was cooled to room temperature, and the solvent was removed under reduced pressure. Afterwards, the compound was completely dissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 120.7 g of compound a-1. (Yield 75%, MS: [M+H]+= 348)
2) 화합물 a의 제조2) Preparation of compound a
화합물 a-1 (120.7g, 346.9mmol)와 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (155.5g, 381.6mmol)를 1,4-dioxane 2414ml에 넣고 교반 및 환류하였다. 이 후 potassim phosphate(220.9g, 1040.8mmol)를 물 663ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (1.8g, 3.5mmol)을 투입하였다. 11시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 a를 100.8g 제조하였다. (수율 49%, MS: [M+H]+= 593) Compound a-1 (120.7g, 346.9mmol) and 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-2-yl)aniline (155.5g, 381.6mmol) was added to 2414ml of 1,4-dioxane, stirred and refluxed. Afterwards, potassim phosphate (220.9g, 1040.8mmol) was dissolved in 663ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (1.8g, 3.5mmol) was added. After reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 100.8 g of compound a. (Yield 49%, MS: [M+H]+= 593)
3) 화합물 1의 제조3) Preparation of Compound 1
질소 분위기에서 화합물 a (20g, 33.7mmol)와 boron triiodide (19.8g, 50.6mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 5시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1을 8.1g 제조하였다. (수율 40%, MS: [M+H]+= 601)In a nitrogen atmosphere, compound a (20g, 33.7mmol) and boron triiodide (19.8g, 50.6mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After 5 hours of reaction, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.1 g of Compound 1. (Yield 40%, MS: [M+H]+= 601)
합성예 2Synthesis Example 2
Figure PCTKR2023003328-appb-img-000257
Figure PCTKR2023003328-appb-img-000257
1) 화합물 b-2의 제조1) Preparation of compound b-2
화합물 a-1 대신 7-bromo-9-chloro-11H-benzo[a]carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 phenylboronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 b-2를 합성했다.Instead of compound a-1, use 7-bromo-9-chloro-11H-benzo[a]carbazole and 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4 Compound b-2 was synthesized in the same manner as for compound a, using phenylboronic acid instead of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 b-1의 제조2) Preparation of compound b-1
2-chloro-4-methyl-9H-carbazole 대신 화합물b-2를 사용하고 1-(tert-butyl)-4-iodobenzene 대신 6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 b-1를 합성했다.Compound b-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 6-iodo-1,1,4,4-tetramethyl-1,2,3 is used instead of 1-(tert-butyl)-4-iodobenzene. Compound b-1 was synthesized using 4-tetrahydronaphthalene in the same manner as the preparation method for compound a-1.
3) 화합물 b의 제조3) Preparation of compound b
화합물 a-1 대신 화합물 b-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 b를 합성했다.Use compound b-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2- Compound b was synthesized using the same method as for compound a using dioxaborolan-2-yl)aniline.
4) 화합물 2의 제조4) Preparation of Compound 2
질소 분위기에서 화합물b (20g, 26.3mmol)와 boron triiodide (15.5g, 39.5mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 4시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 2를 9.3g 제조하였다. (수율 46%, MS: [M+H]+= 767)In a nitrogen atmosphere, compound b (20g, 26.3mmol) and boron triiodide (15.5g, 39.5mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 4 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.3 g of Compound 2. (Yield 46%, MS: [M+H]+= 767)
합성예 3Synthesis Example 3
Figure PCTKR2023003328-appb-img-000258
Figure PCTKR2023003328-appb-img-000258
1) 화합물 c-2의 제조1) Preparation of compound c-2
화합물 a-1 대신 1-bromo-3-chloro-5H-benzo[b]carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 (4-(tert-butyl)phenyl)boronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 c-2를 합성했다.Instead of compound a-1, use 1-bromo-3-chloro-5H-benzo[b]carbazole and 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4 Compound c-2 was prepared in the same manner as for compound a using (4-(tert-butyl)phenyl)boronic acid instead of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. synthesized.
2) 화합물 c-1의 제조2) Preparation of compound c-1
2-chloro-4-methyl-9H-carbazole 대신 화합물c-2를 사용하고 1-(tert-butyl)-4-iodobenzene 대신 6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 c-1를 합성했다.Compound c-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 6-iodo-1,1,4,4-tetramethyl-1,2,3 is used instead of 1-(tert-butyl)-4-iodobenzene. Compound c-1 was synthesized using 4-tetrahydronaphthalene in the same manner as the preparation method for compound a-1.
3) 화합물 c의 제조3) Preparation of compound c
화합물 a-1 대신 화합물 c-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 c를 합성했다.Use compound c-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5 ,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine was used to prepare the compound in the same manner as the method for preparing compound a. c was synthesized.
4) 화합물 3의 제조4) Preparation of Compound 3
질소 분위기에서 화합물c (20g, 21.7mmol)와 boron triiodide (12.7g, 32.5mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 3을 6.9g 제조하였다. (수율 34%, MS: [M+H]+= 932)In a nitrogen atmosphere, compound c (20g, 21.7mmol) and boron triiodide (12.7g, 32.5mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 6.9 g of Compound 3. (Yield 34%, MS: [M+H]+= 932)
합성예 4Synthesis Example 4
Figure PCTKR2023003328-appb-img-000259
Figure PCTKR2023003328-appb-img-000259
1) 화합물 d-2의 제조1) Preparation of compound d-2
2-chloro-4-methyl-9H-carbazole 대신 7-bromo-9-chloro-11H-benzo[a]carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 1-(tert-butyl)-3-iodobenzene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 d-2를 합성했다.Use 7-bromo-9-chloro-11H-benzo[a]carbazole instead of 2-chloro-4-methyl-9H-carbazole and 1-(tert-butyl)- instead of 1-(tert-butyl)-4-iodobenzene. Compound d-2 was synthesized using 3-iodobenzene in the same manner as the method for preparing compound a-1.
2) 화합물 d-1의 제조2) Preparation of compound d-1
2-chloro-4-methyl-9H-carbazole 대신 bis(4-(tert-butyl)phenyl)amine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물d-2을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 d-1을 합성했다.Compound a-1 using bis(4-(tert-butyl)phenyl)amine instead of 2-chloro-4-methyl-9H-carbazole and compound d-2 instead of 1-(tert-butyl)-4-iodobenzene. Compound d-1 was synthesized in the same manner as the preparation method.
3) 화합물 d의 제조3) Preparation of compound d
화합물 a-1 대신 화합물 d-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 d를 합성했다.Instead of compound a-1, use compound d-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Compound d was synthesized using the same method as the method for producing compound a.
4) 화합물 4의 제조4) Preparation of Compound 4
질소 분위기에서 화합물d (20g, 23.5mmol)와 boron triiodide (13.8g, 35.2mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 3시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 4를 8.7g 제조하였다. (수율 43%, MS: [M+H]+= 861)In a nitrogen atmosphere, compound d (20g, 23.5mmol) and boron triiodide (13.8g, 35.2mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 3 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.7 g of Compound 4. (Yield 43%, MS: [M+H]+= 861)
합성예 5Synthesis Example 5
Figure PCTKR2023003328-appb-img-000260
Figure PCTKR2023003328-appb-img-000260
1) 화합물 e-2의 제조1) Preparation of compound e-2
2-chloro-4-methyl-9H-carbazole 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 e-2를 합성했다.Use 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 6-iodo-1,1,4,4- instead of 1-(tert-butyl)-4-iodobenzene. Compound e-2 was synthesized using tetramethyl-1,2,3,4-tetrahydronaphthalene in the same manner as for compound a-1.
2) 화합물 e-1의 제조2) Preparation of compound e-1
2-chloro-4-methyl-9H-carbazole 대신 diphenylamine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물 e-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 e-1을 합성했다.Compound e-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound e-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
3) 화합물 e의 제조3) Preparation of compound e
화합물 a-1 대신 화합물 e-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 e를 합성했다.Instead of compound a-1, use compound e-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5 ,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine was used to prepare the compound in the same manner as the method for preparing compound a. e was synthesized.
4) 화합물 5의 제조4) Preparation of Compound 5
질소 분위기에서 화합물e (20g, 22mmol)와 boron triiodide (12.9g, 33mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물5를 9.5g 제조하였다. (수율 47%, MS: [M+H]+= 917)In a nitrogen atmosphere, compound e (20g, 22mmol) and boron triiodide (12.9g, 33mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.5 g of Compound 5. (Yield 47%, MS: [M+H]+= 917)
합성예 6Synthesis Example 6
Figure PCTKR2023003328-appb-img-000261
Figure PCTKR2023003328-appb-img-000261
1) 화합물 f-1의 제조1) Preparation of compound f-1
2-chloro-4-methyl-9H-carbazole 대신 5-chloro-7H-dibenzo[c,g]carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 1-(tert-butyl)-3-iodobenzene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 f-1을 합성했다.Use 5-chloro-7H-dibenzo[c,g]carbazole instead of 2-chloro-4-methyl-9H-carbazole and 1-(tert-butyl)-3- instead of 1-(tert-butyl)-4-iodobenzene. Compound f-1 was synthesized using iodobenzene in the same manner as the preparation method for compound a-1.
2) 화합물 f의 제조2) Preparation of compound f
화합물 a-1 대신 화합물 f-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(5-(tert-butyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 f를 합성했다.Use compound f-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, N-(5-(tert-butyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5 instead of 2-dioxaborolan-2-yl)aniline Compound f was synthesized using the same method as the preparation method for compound a using ,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine.
3) 화합물 6의 제조3) Preparation of Compound 6
질소 분위기에서 화합물 f (20g, 27.3mmol)와 boron triiodide (16g, 40.9mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 1시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물6을 6.1g 제조하였다. (수율 30%, MS: [M+H]+= 741)In a nitrogen atmosphere, compound f (20g, 27.3mmol) and boron triiodide (16g, 40.9mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 1 hour, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 6.1 g of Compound 6. (Yield 30%, MS: [M+H]+= 741)
합성예 7Synthesis Example 7
Figure PCTKR2023003328-appb-img-000262
Figure PCTKR2023003328-appb-img-000262
1) 화합물 g-1의 제조1) Preparation of compound g-1
2-chloro-4-methyl-9H-carbazole 대신 diphenylamine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 11-bromo-13-chloro-5,5-dimethyl-5H-benzo[a]indolo[3,2,1-de]acridine을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 g-1을 합성했다.Use diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and 11-bromo-13-chloro-5,5-dimethyl-5H-benzo[a]indolo[ instead of 1-(tert-butyl)-4-iodobenzene. Compound g-1 was synthesized using 3,2,1-de]acridine in the same manner as the preparation method of compound a-1.
2) 화합물 g의 제조2) Preparation of compound g
화합물 a-1 대신 화합물 g-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 g를 합성했다.Use compound g-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Compound g was synthesized using the same method as the method for producing compound a.
3) 화합물 7의 제조3) Preparation of compound 7
질소 분위기에서 화합물 g (20g, 27.6mmol)와 boron triiodide (16.2g, 41.4mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 4시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물7을 7.1g 제조하였다. (수율 35%, MS: [M+H]+= 732)In a nitrogen atmosphere, compound g (20 g, 27.6 mmol) and boron triiodide (16.2 g, 41.4 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 4 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.1 g of Compound 7. (Yield 35%, MS: [M+H]+= 732)
합성예 8Synthesis Example 8
Figure PCTKR2023003328-appb-img-000263
Figure PCTKR2023003328-appb-img-000263
1) 화합물 h-1의 제조1) Preparation of compound h-1
2-chloro-4-methyl-9H-carbazole 대신 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 4-bromo-2-chloro-8,8-dimethyl-8H-indolo[3,2,1-de]acridine을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 h-1을 합성했다.Instead of 2-chloro-4-methyl-9H-carbazole, use 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole and instead of 1-(tert-butyl)-4-iodobenzene Compound h-1 was synthesized using 4-bromo-2-chloro-8,8-dimethyl-8H-indolo[3,2,1-de]acridine in the same manner as the method for preparing compound a-1.
2) 화합물 h의 제조2) Preparation of compound h
화합물 a-1 대신 화합물 h-1을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 h를 합성했다.Compound h was synthesized in the same manner as the preparation method for compound a, using compound h-1 instead of compound a-1.
3) 화합물 8의 제조3) Preparation of Compound 8
질소 분위기에서 화합물h (20g, 26.2mmol)와 boron triiodide (15.4g, 39.4mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 8를 6.7g 제조하였다. (수율 33%, MS: [M+H]+= 770)In a nitrogen atmosphere, compound h (20 g, 26.2 mmol) and boron triiodide (15.4 g, 39.4 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 6.7 g of Compound 8. (Yield 33%, MS: [M+H]+= 770)
합성예 9Synthesis Example 9
Figure PCTKR2023003328-appb-img-000264
Figure PCTKR2023003328-appb-img-000264
1) 화합물 i-1의 제조1) Preparation of compound i-1
2-chloro-4-methyl-9H-carbazole 대신 6-(tert-butyl)-2-chloro-4-methyl-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 iodobenzene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 i-1을 합성했다.Use 6-(tert-butyl)-2-chloro-4-methyl-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and iodobenzene instead of 1-(tert-butyl)-4-iodobenzene. Compound i-1 was synthesized in the same manner as the method for producing compound a-1.
2) 화합물 i의 제조2) Preparation of compound i
화합물 a-1 대신 화합물 i-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene]을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 i를 합성했다.Instead of compound a-1, use compound i-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene] Compound i was synthesized using the same method as the method for producing compound a.
3) 화합물 9의 제조3) Preparation of Compound 9
질소 분위기에서 화합물i (20g, 31.1mmol)와 boron triiodide (18.3g, 46.7mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 6시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 9를 8.7g 제조하였다. (수율 43%, MS: [M+H]+= 651)In a nitrogen atmosphere, compound i (20g, 31.1mmol) and boron triiodide (18.3g, 46.7mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 6 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.7 g of Compound 9. (Yield 43%, MS: [M+H]+= 651)
합성예 10Synthesis Example 10
Figure PCTKR2023003328-appb-img-000265
Figure PCTKR2023003328-appb-img-000265
1) 화합물 j-2의 제조1) Preparation of compound j-2
화합물 a-1 대신 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 phenylboronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 j-2를 합성했다.Instead of compound a-1, use 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2- Compound j-2 was synthesized in the same manner as for compound a, using phenylboronic acid instead of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 j-1의 제조2) Preparation of compound j-1
2-chloro-4-methyl-9H-carbazole 대신 화합물j-2를 사용하고 1-(tert-butyl)-4-iodobenzene 대신 2-iododibenzo[b,d]thiophene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 j-1를 합성했다.Method for preparing compound a-1 using compound j-2 instead of 2-chloro-4-methyl-9H-carbazole and 2-iododibenzo[b,d]thiophene instead of 1-(tert-butyl)-4-iodobenzene Compound j-1 was synthesized in the same way.
3) 화합물 j의 제조3) Preparation of compound j
화합물 a-1 대신 화합물 j-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 j를 합성했다.Use compound j-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Compound j was synthesized using the same method as the method for preparing compound a.
4) 화합물 10의 제조4) Preparation of Compound 10
질소 분위기에서 화합물 j (20g, 28.4mmol)와 boron triiodide (16.7g, 42.6mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 10을 10.1g 제조하였다. (수율 50%, MS: [M+H]+= 713)In a nitrogen atmosphere, compound j (20g, 28.4mmol) and boron triiodide (16.7g, 42.6mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 10.1 g of Compound 10. (Yield 50%, MS: [M+H]+= 713)
합성예 11Synthesis Example 11
Figure PCTKR2023003328-appb-img-000266
Figure PCTKR2023003328-appb-img-000266
1) 화합물 k-2의 제조1) Preparation of compound k-2
화합물 a-1 대신 1-bromo-3-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 [1,1'-biphenyl]-2-ylboronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 k-2를 합성했다.Instead of compound a-1, use 1-bromo-3-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole and use 4-(tert-butyl) -N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline instead of [1,1'-biphenyl]- Compound k-2 was synthesized using 2-ylboronic acid in the same manner as for compound a.
2) 화합물 k-1의 제조2) Preparation of compound k-1
2-chloro-4-methyl-9H-carbazole 대신 화합물k-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 k-1를 합성했다.Compound k-1 was synthesized in the same manner as for compound a-1, using compound k-2 instead of 2-chloro-4-methyl-9H-carbazole.
3) 화합물 k의 제조3) Preparation of compound k
화합물 a-1 대신 화합물 k-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 k를 합성했다.Use compound k-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[ [b,d]Compound k was synthesized using the same method as for compound a using furan-2-amine.
4) 화합물 11의 제조4) Preparation of Compound 11
질소 분위기에서 화합물k (20g, 22.9mmol)와 boron triiodide (13.4g, 34.3mmol)를1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 1시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 11를 9.5g 제조하였다. (수율 47%, MS: [M+H]+= 883)In a nitrogen atmosphere, compound k (20 g, 22.9 mmol) and boron triiodide (13.4 g, 34.3 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 1 hour, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.5 g of Compound 11. (Yield 47%, MS: [M+H]+= 883)
합성예 12Synthesis Example 12
Figure PCTKR2023003328-appb-img-000267
Figure PCTKR2023003328-appb-img-000267
1) 화합물 l-2의 제조1) Preparation of compound l-2
화합물 a-1 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 [1,1'-biphenyl]-2-ylboronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 l-2를 합성했다.Instead of compound a-1, use 4-bromo-2-chloro-9H-carbazole and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5 Compound l-2 was synthesized in the same manner as for compound a, using [1,1'-biphenyl]-2-ylboronic acid instead of -tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 l-1의 제조2) Preparation of compound l-1
2-chloro-4-methyl-9H-carbazole 대신 화합물l-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 l-1를 합성했다.Compound l-1 was synthesized in the same manner as the preparation method of compound a-1, using compound l-2 instead of 2-chloro-4-methyl-9H-carbazole.
3) 화합물 l의 제조3) Preparation of compound l
화합물 a-1 대신 화합물 l-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-7,7,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,8,9,10-tetrahydrobenzo[b]naphtho[2,3-d]thiophen-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 l을 합성했다.Instead of compound a-1, use compound l-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-7,7,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3, Compound l was synthesized in the same manner as for compound a using 2-dioxaborolan-2-yl)-7,8,9,10-tetrahydrobenzo[b]naphtho[2,3-d]thiophen-2-amine. did.
4) 화합물 12의 제조4) Preparation of Compound 12
질소 분위기에서 화합물l (20g, 22.4mmol)와 boron triiodide (13.2g, 33.7mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 3시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 12를 7.9g 제조하였다. (수율 39%, MS: [M+H]+= 899)In a nitrogen atmosphere, compound l (20g, 22.4mmol) and boron triiodide (13.2g, 33.7mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 3 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.9 g of Compound 12. (Yield 39%, MS: [M+H]+= 899)
합성예 13Synthesis Example 13
Figure PCTKR2023003328-appb-img-000268
Figure PCTKR2023003328-appb-img-000268
1) 화합물 m-1의 제조1) Preparation of compound m-1
2-chloro-4-methyl-9H-carbazole 대신 9-chloro-11-methyl-7H-benzo[c]carbazole를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 m-1를 합성했다.Compound m-1 was synthesized in the same manner as for compound a-1, using 9-chloro-11-methyl-7H-benzo[c]carbazole instead of 2-chloro-4-methyl-9H-carbazole.
2) 화합물 m의 제조2) Preparation of compound m
화합물 a-1 대신 화합물 m-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-9,9-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-3-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 m를 합성했다.Use compound m-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound m was synthesized using 2-yl)-9H-fluoren-3-amine in the same manner as the preparation method for compound a.
3) 화합물 13의 제조3) Preparation of compound 13
질소 분위기에서 화합물 m (20g, 28.4mmol)와 boron triiodide (16.7g, 42.7mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 3시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 13를 8.7g 제조하였다. (수율 43%, MS: [M+H]+= 711)In a nitrogen atmosphere, compound m (20g, 28.4mmol) and boron triiodide (16.7g, 42.7mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 3 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.7 g of Compound 13. (Yield 43%, MS: [M+H]+= 711)
합성예 14Synthesis Example 14
Figure PCTKR2023003328-appb-img-000269
Figure PCTKR2023003328-appb-img-000269
1) 화합물 n-1의 제조1) Preparation of compound n-1
2-chloro-4-methyl-9H-carbazole 대신 1-(tert-butyl)-3-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 n-1를 합성했다.1-(tert-butyl)-3-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b] instead of 2-chloro-4-methyl-9H-carbazole Compound n-1 was synthesized using carbazole in the same manner as the preparation of compound a-1.
2) 화합물 n의 제조2) Preparation of compound n
화합물 a-1 대신 화합물 n-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-7,7,10,10-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 n를 합성했다.Instead of compound a-1, use compound n-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-7,7,10,10-tetramethyl-2-(4,4,5,5-tetramethyl-1,3, Compound n was synthesized in the same manner as for compound a using 2-dioxaborolan-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine.
3) 화합물 14의 제조3) Preparation of compound 14
질소 분위기에서 화합물 n (20g, 22.5mmol)와 boron triiodide (13.2g, 33.7mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 7시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 14를 8.3g 제조하였다. (수율 41%, MS: [M+H]+= 898)In a nitrogen atmosphere, compound n (20g, 22.5mmol) and boron triiodide (13.2g, 33.7mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 7 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.3 g of Compound 14. (Yield 41%, MS: [M+H]+= 898)
합성예 15Synthesis Example 15
Figure PCTKR2023003328-appb-img-000270
Figure PCTKR2023003328-appb-img-000270
1) 화합물 o-2의 제조1) Preparation of compound o-2
화합물 a-1 대신 1-bromo-3-chloro-5H-benzo[b]carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 phenylboronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 o-2를 합성했다.Instead of compound a-1, use 1-bromo-3-chloro-5H-benzo[b]carbazole and 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4 Compound o-2 was synthesized in the same manner as for compound a, using phenylboronic acid instead of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 o-1의 제조2) Preparation of compound o-1
2-chloro-4-methyl-9H-carbazole 대신 화합물o-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 o-1를 합성했다.Compound o-1 was synthesized in the same manner as for compound a-1, using compound o-2 instead of 2-chloro-4-methyl-9H-carbazole.
3) 화합물 o의 제조3) Preparation of compound o
화합물 a-1 대신 화합물 o-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-3-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 o를 합성했다.Instead of compound a-1, use compound o-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[ [b,d]Compound o was synthesized using the same method as the preparation method for compound a using thiophen-3-amine.
4) 화합물 15의 제조4) Preparation of Compound 15
질소 분위기에서 화합물 o (20g, 26.5mmol)와 boron triiodide (15.6g, 39.7mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 5시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 15를 9.7g 제조하였다. (수율 48%, MS: [M+H]+= 763)In a nitrogen atmosphere, compound o (20 g, 26.5 mmol) and boron triiodide (15.6 g, 39.7 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 5 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.7 g of Compound 15. (Yield 48%, MS: [M+H]+= 763)
합성예 16Synthesis Example 16
Figure PCTKR2023003328-appb-img-000271
Figure PCTKR2023003328-appb-img-000271
1) 화합물 p-1의 제조1) Preparation of compound p-1
2-chloro-4-methyl-9H-carbazole 대신 6-(tert-butyl)-2-chloro-4-methyl-9H-carbazole를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 p-1를 합성했다.Compound p-1 was prepared in the same manner as the preparation method for compound a-1, using 6-(tert-butyl)-2-chloro-4-methyl-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole. synthesized.
2) 화합물 p의 제조2) Preparation of compound p
화합물 a-1 대신 화합물 p-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 p를 합성했다.Use compound p-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound p was synthesized using 2-yl)-9H-fluoren-2-amine in the same manner as the preparation method for compound a.
3) 화합물 16의 제조3) Preparation of compound 16
질소 분위기에서 화합물 p (20g, 28.2mmol)와 boron triiodide (16.6g, 42.3mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 16를 7.7g 제조하였다. (수율 38%, MS: [M+H]+= 717)In a nitrogen atmosphere, compound p (20 g, 28.2 mmol) and boron triiodide (16.6 g, 42.3 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After 2 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.7 g of Compound 16. (Yield 38%, MS: [M+H]+= 717)
합성예 17Synthesis Example 17
Figure PCTKR2023003328-appb-img-000272
Figure PCTKR2023003328-appb-img-000272
1) 화합물 q-1의 제조1) Preparation of compound q-1
2-chloro-4-methyl-9H-carbazole 대신 5-chloro-7H-benzo[c]carbazole를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 q-1를 합성했다.Compound q-1 was synthesized in the same manner as for compound a-1, using 5-chloro-7H-benzo[c]carbazole instead of 2-chloro-4-methyl-9H-carbazole.
2) 화합물 q의 제조2) Preparation of compound q
화합물 a-1 대신 화합물 q-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 q를 합성했다.Use compound q-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound q was synthesized using 2-yl)-9H-fluoren-2-amine in the same manner as the preparation method for compound a.
3) 화합물 17의 제조3) Preparation of compound 17
질소 분위기에서 화합물q (20g, 29mmol)와 boron triiodide (17g, 43.5mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 17를 9.3g 제조하였다. (수율 46%, MS: [M+H]+= 697)In a nitrogen atmosphere, compound q (20g, 29mmol) and boron triiodide (17g, 43.5mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.3 g of Compound 17. (Yield 46%, MS: [M+H]+= 697)
합성예 18Synthesis Example 18
Figure PCTKR2023003328-appb-img-000273
Figure PCTKR2023003328-appb-img-000273
1) 화합물 r-2의 제조1) Preparation of compound r-2
2-chloro-4-methyl-9H-carbazole 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 5-(tert-butyl)-3-iodobenzofuran 을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 r-2를 합성했다.Use 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 5-(tert-butyl)-3-iodobenzofuran instead of 1-(tert-butyl)-4-iodobenzene. Compound r-2 was synthesized in the same manner as the method for producing compound a-1.
2) 화합물 r-1의 제조2) Preparation of compound r-1
2-chloro-4-methyl-9H-carbazole 대신 diphenylamine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물 r-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 r-1을 합성했다.Compound r-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound r-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
3) 화합물 r의 제조3) Preparation of compound r
화합물 a-1 대신 화합물 r-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 r을 합성했다.Instead of compound a-1, use compound r-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Compound r was synthesized using the same method as the method for producing compound a.
4) 화합물 18의 제조4) Preparation of compound 18
질소 분위기에서 화합물 r (20g, 27.4mmol)와 boron triiodide (16.1g, 41.1mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 1시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 18를 8.5g 제조하였다. (수율 42%, MS: [M+H]+= 738)In a nitrogen atmosphere, compound r (20 g, 27.4 mmol) and boron triiodide (16.1 g, 41.1 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 1 hour, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.5 g of Compound 18. (Yield 42%, MS: [M+H]+= 738)
합성예 19Synthesis Example 19
Figure PCTKR2023003328-appb-img-000274
Figure PCTKR2023003328-appb-img-000274
1) 화합물 s-2의 제조1) Preparation of compound s-2
2-chloro-4-methyl-9H-carbazole 대신 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 s-2를 합성했다.Instead of 2-chloro-4-methyl-9H-carbazole, use 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole and instead of 1-(tert-butyl)-4-iodobenzene, use 3-iodo- Compound s-2 was synthesized in the same manner as for compound a-1 using 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene.
2) 화합물 s-1의 제조2) Preparation of compound s-1
2-chloro-4-methyl-9H-carbazole 대신 diphenylamine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물 s-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 s-1을 합성했다.Compound s-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound s-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
3) 화합물 s의 제조3) Preparation of compound s
화합물 a-1 대신 화합물 s-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 s를 합성했다.Instead of compound a-1, use compound s-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Compound s was synthesized using the same method as the method for producing compound a.
4) 화합물 19의 제조4) Preparation of compound 19
질소 분위기에서 화합물 s (20g, 23.4mmol)와 boron triiodide (13.7g, 35mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 3시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 19를 8.3g 제조하였다. (수율 41%, MS: [M+H]+= 864)In a nitrogen atmosphere, compound s (20g, 23.4mmol) and boron triiodide (13.7g, 35mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 3 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 8.3 g of Compound 19. (Yield 41%, MS: [M+H]+= 864)
합성예 20Synthesis Example 20
Figure PCTKR2023003328-appb-img-000275
Figure PCTKR2023003328-appb-img-000275
1) 화합물 t-2의 제조1) Preparation of compound t-2
2-chloro-4-methyl-9H-carbazole 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 3-iodo-5-phenylbenzo[b]thiophene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 t-2를 합성했다.Use 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 3-iodo-5-phenylbenzo[b]thiophene instead of 1-(tert-butyl)-4-iodobenzene. Compound t-2 was synthesized using the same method as the method for producing compound a-1.
2) 화합물 t-1의 제조2) Preparation of compound t-1
2-chloro-4-methyl-9H-carbazole 대신 diphenylamine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물 t-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 t-1을 합성했다.Compound t-1 was prepared in the same manner as the method for preparing compound a-1, using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound t-2 instead of 1-(tert-butyl)-4-iodobenzene. was synthesized.
3) 화합물 t의 제조3) Preparation of compound t
화합물 a-1 대신 화합물 t-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-6,6,9,9,11,11-hexamethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,8,9,11-tetrahydro-6H-benzo[b]fluoren-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 t를 합성했다.Instead of compound a-1, use compound t-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-6,6,9,9,11,11-hexamethyl-3-(4,4,5,5-tetramethyl- Compound t was synthesized in the same manner as for compound a using 1,3,2-dioxaborolan-2-yl)-7,8,9,11-tetrahydro-6H-benzo[b]fluoren-2-amine. did.
4) 화합물 20의 제조4) Preparation of Compound 20
질소 분위기에서 화합물t (20g, 20.2mmol)와 boron triiodide (11.8g, 30.2mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 20를 7.5g 제조하였다. (수율 37%, MS: [M+H]+= 1000)In a nitrogen atmosphere, compound t (20g, 20.2mmol) and boron triiodide (11.8g, 30.2mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.5 g of Compound 20. (Yield 37%, MS: [M+H]+= 1000)
합성예 21Synthesis Example 21
Figure PCTKR2023003328-appb-img-000276
Figure PCTKR2023003328-appb-img-000276
1) 화합물 u-2의 제조1) Preparation of compound u-2
화합물 a-1 대신 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 (4-(tert-butyl)phenyl)boronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 u-2를 합성했다.Instead of compound a-1, use 4-bromo-6-(tert-butyl)-2-chloro-9H-carbazole and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2- Compound a was prepared in the same manner as for compound a using (4-(tert-butyl)phenyl)boronic acid instead of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. u-2 was synthesized.
2) 화합물 u-1의 제조2) Preparation of compound u-1
2-chloro-4-methyl-9H-carbazole 대신 화합물u-2를 사용하고 1-(tert-butyl)-4-iodobenzene 대신 5-bromo-2-phenylbenzo[d]oxazole를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 u-1를 합성했다.Compound a-1 was prepared using compound u-2 instead of 2-chloro-4-methyl-9H-carbazole and 5-bromo-2-phenylbenzo[d]oxazole instead of 1-(tert-butyl)-4-iodobenzene. Compound u-1 was synthesized using the same manufacturing method.
3) 화합물 u의 제조3) Preparation of compound u
화합물 a-1 대신 화합물 u-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 7,7,10,10-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 u를 합성했다.Instead of compound a-1, use compound u-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, use 7,7,10,10-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5 Compound a using ,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine Compound u was synthesized using the same method as the preparation method.
4) 화합물 21의 제조4) Preparation of Compound 21
질소 분위기에서 화합물 u (20g, 19.5mmol)와 boron triiodide (11.4g, 29.2mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 5시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 21를 9.9g 제조하였다. (수율 49%, MS: [M+H]+= 1035)In a nitrogen atmosphere, compound u (20 g, 19.5 mmol) and boron triiodide (11.4 g, 29.2 mmol) were added to 200 ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 5 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 9.9 g of Compound 21. (Yield 49%, MS: [M+H]+= 1035)
합성예 22Synthesis Example 22
Figure PCTKR2023003328-appb-img-000277
Figure PCTKR2023003328-appb-img-000277
1) 화합물 v-1의 제조1) Preparation of compound v-1
2-chloro-4-methyl-9H-carbazole 대신 9-chloro-11-methyl-7H-benzo[c]carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 3-bromo-5-phenylbenzofuran를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 v-1을 합성했다.Use 9-chloro-11-methyl-7H-benzo[c]carbazole instead of 2-chloro-4-methyl-9H-carbazole and 3-bromo-5-phenylbenzofuran instead of 1-(tert-butyl)-4-iodobenzene. Compound v-1 was synthesized using the same method as the method for producing compound a-1.
2) 화합물 v의 제조2) Preparation of compound v
화합물 a-1 대신 화합물 v-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N1,N1-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,3-diamine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 v를 합성했다.Use compound v-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N 1 ,N 1 -diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N 3 -(5, Compound v was synthesized in the same manner as for compound a using 5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,3-diamine.
3) 화합물 22의 제조3) Preparation of Compound 22
질소 분위기에서 화합물 v (20g, 23mmol)와 boron triiodide (13.5g, 34.6mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 4시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 22를 6.9g 제조하였다. (수율 34%, MS: [M+H]+= 876)In a nitrogen atmosphere, compound v (20g, 23mmol) and boron triiodide (13.5g, 34.6mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 4 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 6.9 g of Compound 22. (Yield 34%, MS: [M+H]+= 876)
합성예 23Synthesis Example 23
Figure PCTKR2023003328-appb-img-000278
Figure PCTKR2023003328-appb-img-000278
1) 화합물 w-2의 제조1) Preparation of compound w-2
2-chloro-4-methyl-9H-carbazole 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 2-iododibenzo[b,d]thiophene을 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 w-2를 합성했다.Use 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 2-iododibenzo[b,d]thiophene instead of 1-(tert-butyl)-4-iodobenzene. Compound w-2 was synthesized in the same manner as the preparation method of compound a-1.
2) 화합물 w-1의 제조2) Preparation of compound w-1
2-chloro-4-methyl-9H-carbazole 대신 10H-phenoxazine을 사용하고 1-(tert-butyl)-4-iodobenzene 대신 화합물 w-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 w-1을 합성했다.Compound w was prepared in the same manner as for compound a-1, using 10H-phenoxazine instead of 2-chloro-4-methyl-9H-carbazole and compound w-2 instead of 1-(tert-butyl)-4-iodobenzene. -1 was synthesized.
3) 화합물 w의 제조3) Preparation of compound w
화합물 a-1 대신 화합물 w-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 w를 합성했다.Use compound w-1 instead of compound a-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Same method as for preparing compound a using 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole instead of 2-dioxaborolan-2-yl)aniline Compound w was synthesized.
4) 화합물 23의 제조4) Preparation of compound 23
질소 분위기에서 화합물 w (20g, 28.7mmol)와 boron triiodide (16.9g, 43.1mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 2시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 23를 7.5g 제조하였다. (수율 37%, MS: [M+H]+= 704)In a nitrogen atmosphere, compound w (20g, 28.7mmol) and boron triiodide (16.9g, 43.1mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 2 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.5 g of Compound 23. (Yield 37%, MS: [M+H]+= 704)
합성예 24Synthesis Example 24
Figure PCTKR2023003328-appb-img-000279
Figure PCTKR2023003328-appb-img-000279
1) 화합물 x-2의 제조1) Preparation of compound x-2
화합물 a-1 대신 7-bromo-9-chloro-11H-benzo[a]carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 (phenyl-d5)boronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 x-2를 합성했다.Instead of compound a-1, use 7-bromo-9-chloro-11H-benzo[a]carbazole and 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4 Compound x-2 was synthesized in the same manner as for compound a, using (phenyl-d 5 )boronic acid instead of ,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 x-1의 제조2) Preparation of compound x-1
2-chloro-4-methyl-9H-carbazole 대신 화합물x-2를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 x-1를 합성했다.Compound x-1 was synthesized in the same manner as for compound a-1, using compound x-2 instead of 2-chloro-4-methyl-9H-carbazole.
3) 화합물 x의 제조3) Preparation of compound x
화합물 a-1 대신 화합물 x-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 x를 합성했다.Instead of compound a-1, use compound x-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound x was synthesized using 2-yl)-9H-fluoren-2-amine in the same manner as the preparation method for compound a.
4) 화합물 24의 제조4) Preparation of compound 24
질소 분위기에서 화합물 x (20g, 26mmol)와 boron triiodide (15.3g, 39mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 5시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 24를 6.7g 제조하였다. (수율 33%, MS: [M+H]+= 778)In a nitrogen atmosphere, compound After reaction for 5 hours, it was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 6.7 g of Compound 24. (Yield 33%, MS: [M+H]+= 778)
합성예 25Synthesis Example 25
Figure PCTKR2023003328-appb-img-000280
Figure PCTKR2023003328-appb-img-000280
1) 화합물 y-2의 제조1) Preparation of compound y-2
화합물 a-1 대신 4-bromo-2-chloro-9H-carbazole을 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 (phenyl-d5)boronic acid를 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 y-2를 합성했다.Instead of compound a-1, use 4-bromo-2-chloro-9H-carbazole and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5 Compound y-2 was synthesized in the same manner as for compound a, using (phenyl-d 5 )boronic acid instead of -tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
2) 화합물 y-1의 제조2) Preparation of compound y-1
2-chloro-4-methyl-9H-carbazole 대신 화합물y-2를 사용하고 1-(tert-butyl)-4-iodobenzene 대신 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene를 사용하여 화합물 a-1의 제조 방법과 같은 방법으로 화합물 y-1를 합성했다.Compound y-2 is used instead of 2-chloro-4-methyl-9H-carbazole, and 3-bromo-5,5,8,8-tetramethyl-5,6,7 is used instead of 1-(tert-butyl)-4-iodobenzene. Compound y-1 was synthesized using 8-tetrahydronaphtho[2,3-b]thiophene in the same manner as the preparation method for compound a-1.
3) 화합물 y의 제조3) Preparation of compound y
화합물 a-1 대신 화합물 y-1 를 사용하고 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 대신 N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine을 사용하여 화합물 a의 제조 방법과 같은 방법으로 화합물 y를 합성했다.Instead of compound a-1, use compound y-1 and use 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3, Instead of 2-dioxaborolan-2-yl)aniline, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound y was synthesized using 2-yl)-9H-fluoren-2-amine in the same manner as the preparation method for compound a.
4) 화합물 25의 제조4) Preparation of Compound 25
질소 분위기에서 화합물y (20g, 24.1mmol)와 boron triiodide (14.1g, 36.1mmol)를 1,2-dichlorobenzene 200ml에 넣고 160℃에서 교반하였다. 5시간 반응 후 상온으로 식히고 추출 후 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 25를 7.1g 제조하였다. (수율 35%, MS: [M+H]+= 838)In a nitrogen atmosphere, compound y (20g, 24.1mmol) and boron triiodide (14.1g, 36.1mmol) were added to 200ml of 1,2-dichlorobenzene and stirred at 160°C. After reaction for 5 hours, the reaction mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to prepare 7.1 g of Compound 25. (Yield 35%, MS: [M+H]+= 838)
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 반 복하여 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 600 Å의 두께로 진공 증착하여 정공수송층을 형성하였 다. 상기 정공수송층 위에 하기 HT-B를 50 Å의 두께로 진공 증착하여 전자차단층을 형성하였다. 이어서, 상기 전자차단층 위에 청색 발광 도펀트로 상기 합성예 1의 화합물 1을 발광층 100 중량부 기준으로 4 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 360Å의 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 1000Å두께로 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 600 Å to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Next, on the electron blocking layer, 4 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 360 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 aluminum was deposited to a thickness of 1000 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 aluminum of the cathode was maintained at a deposition rate of 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 PCTKR2023003328-appb-img-000281
Figure PCTKR2023003328-appb-img-000281
[비교예 물질][Comparative example material]
Figure PCTKR2023003328-appb-img-000282
Figure PCTKR2023003328-appb-img-000282
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.
비교예 1 내지 비교예 5Comparative Examples 1 to 5
실시예 1의 유기 발광 소자에서 화합물 1 대신 하기 표 1에 기재된 화합물을 각각 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.
상기 실시예 1 내지 실시예 25 및 비교예 1 내지 비교예 5에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 수명을 측정(6000 nit 기준)하고 그 결과를 하기 표 1에 나타냈다. 수명 T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light-emitting devices manufactured in Examples 1 to 25 and Comparative Examples 1 to 5, the voltage, efficiency, and lifespan were measured (based on 6000 nit), and the results are shown in Table 1 below. . Lifespan T95 refers to the time it takes for luminance to decrease from the initial luminance (6000 nit) to 95%.
발광층의 도펀트Dopants in the emitting layer 전압 (V)Voltage (V) 발광효율Luminous efficiency 수명, T95(h)Life, T95(h)
(Cd/A)(Cd/A)
실시예 1Example 1 화합물1 Compound 1 3.463.46 5.885.88 250250
실시예 2Example 2 화합물2 Compound 2 3.53.5 5.925.92 261261
실시예 3Example 3 화합물3 Compound 3 3.443.44 5.875.87 247247
실시예 4Example 4 화합물4 Compound 4 3.533.53 5.785.78 244244
실시예 5Example 5 화합물5 Compound 5 3.423.42 6.036.03 270270
실시예 6Example 6 화합물6 Compound 6 3.573.57 5.75.7 250250
실시예 7Example 7 화합물7 Compound 7 3.553.55 5.665.66 245245
실시예 8Example 8 화합물8Compound 8 3.553.55 5.695.69 243243
실시예 9Example 9 화합물9 Compound 9 3.453.45 5.95.9 258258
실시예10Example 10 화합물10 Compound 10 3.53.5 5.935.93 255255
실시예11Example 11 화합물11 Compound 11 3.483.48 5.765.76 261261
실시예12Example 12 화합물12Compound 12 3.473.47 5.915.91 251251
실시예13Example 13 화합물13Compound 13 3.493.49 5.995.99 247247
실시예14Example 14 화합물14Compound 14 3.393.39 6.086.08 261261
실시예15Example 15 화합물15Compound 15 3.513.51 5.875.87 248248
실시예16Example 16 화합물16Compound 16 3.393.39 6.146.14 270270
실시예17Example 17 화합물17Compound 17 3.383.38 6.26.2 275275
실시예18Example 18 화합물18Compound 18 3.43.4 6.26.2 274274
실시예19Example 19 화합물19Compound 19 3.423.42 6.056.05 275275
실시예20Example 20 화합물20Compound 20 3.443.44 6.186.18 270270
실시예21Example 21 화합물21Compound 21 3.513.51 5.85.8 247247
실시예22Example 22 화합물22Compound 22 3.393.39 6.156.15 273273
실시예23Example 23 화합물23Compound 23 3.553.55 5.75.7 246246
실시예24Example 24 화합물24Compound 24 3.433.43 6.226.22 276276
실시예25Example 25 화합물25Compound 25 3.413.41 6.36.3 278278
비교예1Comparative Example 1 BD-ABD-A 3.643.64 5.035.03 210210
비교예2Comparative example 2 BD-BBD-B 3.623.62 5.135.13 200200
비교예3Comparative example 3 BD-CBD-C 3.73.7 4.374.37 190190
비교예4Comparative example 4 BD-DBD-D 3.773.77 4.984.98 189189
비교예5Comparative Example 5 BD-EBD-E 3.613.61 5.155.15 213213
상기 표 1에 있어서, 본 명세서의 일 실시상태에 따른 유기 발광 소자는 비교예 1 내지 5의 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 device of Comparative Examples 1 to 5 in terms of voltage, luminous efficiency, and lifespan.
구체적으로, 본 명세서의 일 실시상태에 따른 실시예 1 내지 25의 유기 발광 소자는 Z1에 수소 이외의 치환기를 포함하여 불안정한 부분이 생기지 않게 구조를 안정화시켜 유기 발광 소자의 효율 향상을 이끌어 낼 수 있다. 따라서, 상기 Z1이 수소인 화합물을 사용한 비교예 1 내지 4의 유기 발광 소자 보다 구동전압, 발광효율 및 수명이 우수한 것을 확인할 수 있었다.Specifically, the organic light-emitting devices of Examples 1 to 25 according to an exemplary embodiment of the present specification include a substituent other than hydrogen in Z1, thereby stabilizing the structure to prevent unstable parts, thereby improving the efficiency of the organic light-emitting device. . Therefore, it was confirmed that the driving voltage, luminous efficiency, and lifespan were superior to the organic light-emitting devices of Comparative Examples 1 to 4 using the compound where Z1 was hydrogen.
또한, 상기 A1과 R1이 서로 결합하여 고리를 형성하는 비교예 3 내지 5의 화합물은 빠르게 저하(degradation)되는 부분이 많이 존재하게 되어 분자간 호핑(hopping)에 의존하는 유기 발광 소자의 특성상 구동 전압이 증가하게 된다. In addition, the compounds of Comparative Examples 3 to 5, in which A1 and R1 are bonded to each other to form a ring, have many parts that rapidly degrade, and due to the nature of organic light-emitting devices that rely on intermolecular hopping, the driving voltage is low. It increases.
그러나, 본 명세서의 화학식 1의 화합물과 같이 불안정한 부분(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 보다 비교예 3 내지 5 보다 구동전압, 발광효율 및 수명이 우수한 것을 확인할 수 있었다.However, if the unstable part (A1 and R1 are combined 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, thereby suppressing quenching and degradation, thereby producing organic light emission. The efficiency of the device increases, the lifespan of the device improves, and the voltage also decreases. 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 3 to 5 in terms of driving voltage, luminous efficiency, and lifespan.

Claims (15)

  1. 하기 화학식 1의 화합물:Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023003328-appb-img-000283
    Figure PCTKR2023003328-appb-img-000283
    상기 화학식 1에 있어서,In Formula 1,
    A1은 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이며,A1 is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
    A2는 치환 또는 비치환된 탄화수소고리이고,A2 is a substituted or unsubstituted hydrocarbon ring,
    상기 A1 및 A2는 서로 결합하여 치환 또는 비치환된 고리를 형성하거나, 형성하지 않고,A1 and A2 are combined with each other to form a substituted or unsubstituted ring, or do not form a substituted or unsubstituted ring,
    R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G1)(G2); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 and R2 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(G1)(G2); 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 R1 and R2 combine with each other to form a substituted or unsubstituted ring,
    Z1는 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G3)(G4); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, Z2와 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성하고,Z1 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with Z2 to form a substituted or unsubstituted hydrocarbon ring,
    상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G3)(G4); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,When Z2 does not combine with Z1 to form a ring, Z2 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G3)(G4); 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,
    G1 내지 G4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G1 to G4 are the same as 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 상이하다.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.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 내지 6 중 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one of the following formulas 2 to 6:
    [화학식 2][Formula 2]
    Figure PCTKR2023003328-appb-img-000284
    Figure PCTKR2023003328-appb-img-000284
    [화학식 3][Formula 3]
    Figure PCTKR2023003328-appb-img-000285
    Figure PCTKR2023003328-appb-img-000285
    [화학식 4][Formula 4]
    Figure PCTKR2023003328-appb-img-000286
    Figure PCTKR2023003328-appb-img-000286
    [화학식 5][Formula 5]
    Figure PCTKR2023003328-appb-img-000287
    Figure PCTKR2023003328-appb-img-000287
    [화학식 6][Formula 6]
    Figure PCTKR2023003328-appb-img-000288
    Figure PCTKR2023003328-appb-img-000288
    상기 화학식 2 내지 6에 있어서,In Formulas 2 to 6,
    A1, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
    R3 내지 R6는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G5)(G6); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 R3 내지 R6 중 어느 하나 이상은 상기 A1과 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R3 to R6 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(G5)(G6); 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 at least one of R3 to R6 combines with A1 to form a substituted or unsubstituted ring,
    G5 및 G6는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G5 and G6 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,
    r3는 1 내지 4의 정수이며, 상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하고,r3 is an integer from 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
    r4는 1 내지 6의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하며,r4 is an integer from 1 to 6, and when r4 is 2 or more, the 2 or more R4s are the same or different from each other,
    r5는 1 내지 4의 정수이며, 상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하고,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,
    r6은 1 내지 4의 정수이며, 상기 r6가 2 이상인 경우, 상기 2 이상의 R6은 서로 같거나 상이하다.r6 is an integer of 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 7 내지 9 중 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one of the following formulas 7 to 9:
    [화학식 7][Formula 7]
    Figure PCTKR2023003328-appb-img-000289
    Figure PCTKR2023003328-appb-img-000289
    [화학식 8][Formula 8]
    Figure PCTKR2023003328-appb-img-000290
    Figure PCTKR2023003328-appb-img-000290
    [화학식 9][Formula 9]
    Figure PCTKR2023003328-appb-img-000291
    Figure PCTKR2023003328-appb-img-000291
    상기 화학식 7 내지 9에 있어서,In Formulas 7 to 9,
    A1, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A1, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
    R7은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; -N(G5)(G6); 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 A1과 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R7 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G5)(G6); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocyclic group, or combines with A1 to form a substituted or unsubstituted ring,
    G5 및 G6는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G5 and G6 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,
    r7는 1 내지 10의 정수이며, 상기 r7가 2 이상인 경우, 상기 2 이상의 R7는 서로 같거나 상이하다.r7 is an integer from 1 to 10, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.
  4. 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.
  5. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 10 또는 11인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the formula 10 or 11:
    [화학식 10][Formula 10]
    Figure PCTKR2023003328-appb-img-000292
    Figure PCTKR2023003328-appb-img-000292
    [화학식 11][Formula 11]
    Figure PCTKR2023003328-appb-img-000293
    Figure PCTKR2023003328-appb-img-000293
    상기 화학식 10 및 11에 있어서,In Formulas 10 and 11,
    A2, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A2, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
    X1는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X1 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(G7)(G8); 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 형성하고,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(G7)(G8); 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,
    상기 R11은 상기 A2와 서로 결합하여 치환 또는 비치환된 고리를 형성하거나, 형성하지 않고,R11 combines with A2 to form a substituted or unsubstituted ring, or
    상기 R12는 상기 A2와 서로 결합하여 치환 또는 비치환된 고리를 형성하거나, 형성하지 않고,R12 combines with A2 to form a substituted or unsubstituted ring, or does not form a substituted or unsubstituted ring,
    G7 및 G8는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G7 and G8 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.
  6. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 12 내지 23 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 1 is any one of Formulas 12 to 23 below:
    [화학식 12][Formula 12]
    Figure PCTKR2023003328-appb-img-000294
    Figure PCTKR2023003328-appb-img-000294
    [화학식 13][Formula 13]
    Figure PCTKR2023003328-appb-img-000295
    Figure PCTKR2023003328-appb-img-000295
    [화학식 14][Formula 14]
    Figure PCTKR2023003328-appb-img-000296
    Figure PCTKR2023003328-appb-img-000296
    [화학식 15][Formula 15]
    Figure PCTKR2023003328-appb-img-000297
    Figure PCTKR2023003328-appb-img-000297
    [화학식 16][Formula 16]
    Figure PCTKR2023003328-appb-img-000298
    Figure PCTKR2023003328-appb-img-000298
    [화학식 17][Formula 17]
    Figure PCTKR2023003328-appb-img-000299
    Figure PCTKR2023003328-appb-img-000299
    [화학식 18][Formula 18]
    Figure PCTKR2023003328-appb-img-000300
    Figure PCTKR2023003328-appb-img-000300
    [화학식 19][Formula 19]
    Figure PCTKR2023003328-appb-img-000301
    Figure PCTKR2023003328-appb-img-000301
    [화학식 20][Formula 20]
    Figure PCTKR2023003328-appb-img-000302
    Figure PCTKR2023003328-appb-img-000302
    [화학식 21][Formula 21]
    Figure PCTKR2023003328-appb-img-000303
    Figure PCTKR2023003328-appb-img-000303
    [화학식 22][Formula 22]
    Figure PCTKR2023003328-appb-img-000304
    Figure PCTKR2023003328-appb-img-000304
    [화학식 23][Formula 23]
    Figure PCTKR2023003328-appb-img-000305
    Figure PCTKR2023003328-appb-img-000305
    상기 화학식 12 내지 23에 있어서,In Formulas 12 to 23,
    A2, R1, R2, r1, r2, Z1 및 Z2의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of A2, R1, R2, r1, r2, Z1 and Z2 are the same as those defined in Formula 1 above,
    X1는 -C(R13)(R14)-; -Si(R15)(R16)-; -O-; 또는 -S-이며,X1 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
    X2 및 X3는 서로 같거나 상이하고, 각각 독립적으로 -C(R19)(R20)-; -Si(R21)(R22)-; -O-; 또는 -S-이며,X2 and X3 are the same or different from each other, and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
    X4 및 X5은 서로 같거나 상이하고, 각각 독립적으로 -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; 또는 -S-이며,X4 and X5 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, 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(G9)(G10); 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, R"'11 및 R12 내지 R28 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R'2, R"2, R'11, R"11, R"'11 and R12 to R28 are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group ; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(G9)(G10); Substituted or unsubstituted aryl group; Condensed ring 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, R"'11 and R12 to R28 are bonded to each other and are substituted or unsubstituted. Forms a circular ring,
    G9 및 G10는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리기; 또는 치환 또는 비치환된 헤테로고리기이고,G9 and G10 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 내지 3의 정수이고, 상기 r"11이 2 이상인 경우, 상기 2 이상의 R"11은 서로 같거나 상이하며,r"11 is an integer of 1 to 3, and when r"11 is 2 or more, R"11 of 2 or more is the same as 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.
  7. 청구항 1에 있어서, 상기 A1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, -N(G7)(G8), 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기, 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, -N(G7)(G8), 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 단환 또는 다환의 헤테로고리이고,The method of claim 1, wherein A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N(G7 ) (G8), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and a combination thereof, substituted or unsubstituted with one or more selected from the group consisting of a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms Or a polycyclic 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 straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(G7)(G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof, O , is a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms containing one or more of N and S,
    상기 A2는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, -N(G5)(G6), 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 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 축합고리이며,The A2 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, -N(G5)(G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Aromatic hydrocarbon ring; or 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,
    상기 A1 및 A2는 서로 결합하여 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 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성거나, 형성하지 않고,A1 and A2 are combined with each other to form 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of straight or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof. Forms or does not form a monocyclic or polycyclic heterocycle,
    상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G1)(G2); 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, 상기 R1 및 R2 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 지방족 탄화수소고리; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 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 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하며,R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G1)(G2); 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to have 1 to 30 carbon atoms. A monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group; 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; 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 monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of 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. forming,
    상기 Z1은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기; -N(G3)(G4); 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기이거나, Z2와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하고,Z1 is a linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; -N(G3)(G4); a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, 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; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with 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 combined with Z2. form,
    상기 Z2가 Z1과 서로 결합하여 고리를 형성하지 않는 경우, Z2는 수소이며,When Z2 does not combine with Z1 to form a ring, Z2 is hydrogen,
    상기 G1 내지 G8은 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기인 것인 화합물.G1 to G8 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; 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 substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a compound that is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  8. 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 PCTKR2023003328-appb-img-000306
    Figure PCTKR2023003328-appb-img-000306
    Figure PCTKR2023003328-appb-img-000307
    Figure PCTKR2023003328-appb-img-000307
    Figure PCTKR2023003328-appb-img-000308
    Figure PCTKR2023003328-appb-img-000308
    Figure PCTKR2023003328-appb-img-000309
    Figure PCTKR2023003328-appb-img-000309
    Figure PCTKR2023003328-appb-img-000310
    Figure PCTKR2023003328-appb-img-000310
    Figure PCTKR2023003328-appb-img-000311
    Figure PCTKR2023003328-appb-img-000311
    Figure PCTKR2023003328-appb-img-000312
    Figure PCTKR2023003328-appb-img-000312
    Figure PCTKR2023003328-appb-img-000313
    Figure PCTKR2023003328-appb-img-000313
    Figure PCTKR2023003328-appb-img-000314
    Figure PCTKR2023003328-appb-img-000314
    Figure PCTKR2023003328-appb-img-000315
    Figure PCTKR2023003328-appb-img-000315
    Figure PCTKR2023003328-appb-img-000316
    Figure PCTKR2023003328-appb-img-000316
    Figure PCTKR2023003328-appb-img-000317
    Figure PCTKR2023003328-appb-img-000317
    Figure PCTKR2023003328-appb-img-000318
    Figure PCTKR2023003328-appb-img-000318
    Figure PCTKR2023003328-appb-img-000319
    Figure PCTKR2023003328-appb-img-000319
    Figure PCTKR2023003328-appb-img-000320
    Figure PCTKR2023003328-appb-img-000320
    Figure PCTKR2023003328-appb-img-000321
    Figure PCTKR2023003328-appb-img-000321
    Figure PCTKR2023003328-appb-img-000322
    Figure PCTKR2023003328-appb-img-000322
    Figure PCTKR2023003328-appb-img-000323
    Figure PCTKR2023003328-appb-img-000323
    Figure PCTKR2023003328-appb-img-000324
    Figure PCTKR2023003328-appb-img-000324
    Figure PCTKR2023003328-appb-img-000325
    Figure PCTKR2023003328-appb-img-000325
    Figure PCTKR2023003328-appb-img-000326
    Figure PCTKR2023003328-appb-img-000326
    Figure PCTKR2023003328-appb-img-000327
    Figure PCTKR2023003328-appb-img-000327
    Figure PCTKR2023003328-appb-img-000328
    Figure PCTKR2023003328-appb-img-000328
    Figure PCTKR2023003328-appb-img-000329
    Figure PCTKR2023003328-appb-img-000329
    Figure PCTKR2023003328-appb-img-000330
    Figure PCTKR2023003328-appb-img-000330
    Figure PCTKR2023003328-appb-img-000331
    Figure PCTKR2023003328-appb-img-000331
    Figure PCTKR2023003328-appb-img-000332
    Figure PCTKR2023003328-appb-img-000332
    Figure PCTKR2023003328-appb-img-000333
    Figure PCTKR2023003328-appb-img-000333
    Figure PCTKR2023003328-appb-img-000334
    Figure PCTKR2023003328-appb-img-000334
    Figure PCTKR2023003328-appb-img-000335
    Figure PCTKR2023003328-appb-img-000335
    Figure PCTKR2023003328-appb-img-000336
    Figure PCTKR2023003328-appb-img-000336
    Figure PCTKR2023003328-appb-img-000337
    Figure PCTKR2023003328-appb-img-000337
    Figure PCTKR2023003328-appb-img-000338
    Figure PCTKR2023003328-appb-img-000338
    Figure PCTKR2023003328-appb-img-000339
    Figure PCTKR2023003328-appb-img-000339
    Figure PCTKR2023003328-appb-img-000340
    Figure PCTKR2023003328-appb-img-000340
    Figure PCTKR2023003328-appb-img-000341
    Figure PCTKR2023003328-appb-img-000341
    Figure PCTKR2023003328-appb-img-000342
    Figure PCTKR2023003328-appb-img-000342
    Figure PCTKR2023003328-appb-img-000343
    Figure PCTKR2023003328-appb-img-000343
    Figure PCTKR2023003328-appb-img-000344
    Figure PCTKR2023003328-appb-img-000344
    Figure PCTKR2023003328-appb-img-000345
    Figure PCTKR2023003328-appb-img-000345
    Figure PCTKR2023003328-appb-img-000346
    Figure PCTKR2023003328-appb-img-000346
    Figure PCTKR2023003328-appb-img-000347
    Figure PCTKR2023003328-appb-img-000347
    Figure PCTKR2023003328-appb-img-000348
    Figure PCTKR2023003328-appb-img-000348
    Figure PCTKR2023003328-appb-img-000349
    Figure PCTKR2023003328-appb-img-000349
    Figure PCTKR2023003328-appb-img-000350
    Figure PCTKR2023003328-appb-img-000350
    Figure PCTKR2023003328-appb-img-000351
    Figure PCTKR2023003328-appb-img-000351
    Figure PCTKR2023003328-appb-img-000352
    Figure PCTKR2023003328-appb-img-000352
    Figure PCTKR2023003328-appb-img-000353
    Figure PCTKR2023003328-appb-img-000353
    Figure PCTKR2023003328-appb-img-000354
    Figure PCTKR2023003328-appb-img-000354
    Figure PCTKR2023003328-appb-img-000355
    Figure PCTKR2023003328-appb-img-000355
    Figure PCTKR2023003328-appb-img-000356
    Figure PCTKR2023003328-appb-img-000356
    Figure PCTKR2023003328-appb-img-000357
    Figure PCTKR2023003328-appb-img-000357
    Figure PCTKR2023003328-appb-img-000358
    Figure PCTKR2023003328-appb-img-000358
    Figure PCTKR2023003328-appb-img-000359
    Figure PCTKR2023003328-appb-img-000359
    Figure PCTKR2023003328-appb-img-000360
    Figure PCTKR2023003328-appb-img-000360
    Figure PCTKR2023003328-appb-img-000361
    Figure PCTKR2023003328-appb-img-000361
    Figure PCTKR2023003328-appb-img-000362
    Figure PCTKR2023003328-appb-img-000362
    Figure PCTKR2023003328-appb-img-000363
    Figure PCTKR2023003328-appb-img-000363
    Figure PCTKR2023003328-appb-img-000364
    Figure PCTKR2023003328-appb-img-000364
    Figure PCTKR2023003328-appb-img-000365
    Figure PCTKR2023003328-appb-img-000365
    Figure PCTKR2023003328-appb-img-000366
    Figure PCTKR2023003328-appb-img-000366
    Figure PCTKR2023003328-appb-img-000367
    Figure PCTKR2023003328-appb-img-000367
    Figure PCTKR2023003328-appb-img-000368
    Figure PCTKR2023003328-appb-img-000368
    Figure PCTKR2023003328-appb-img-000369
    Figure PCTKR2023003328-appb-img-000369
    Figure PCTKR2023003328-appb-img-000370
    Figure PCTKR2023003328-appb-img-000370
    Figure PCTKR2023003328-appb-img-000371
    Figure PCTKR2023003328-appb-img-000371
    Figure PCTKR2023003328-appb-img-000372
    Figure PCTKR2023003328-appb-img-000372
    Figure PCTKR2023003328-appb-img-000373
    Figure PCTKR2023003328-appb-img-000373
    Figure PCTKR2023003328-appb-img-000374
    Figure PCTKR2023003328-appb-img-000374
    Figure PCTKR2023003328-appb-img-000375
    Figure PCTKR2023003328-appb-img-000375
    Figure PCTKR2023003328-appb-img-000376
    Figure PCTKR2023003328-appb-img-000376
    Figure PCTKR2023003328-appb-img-000377
    Figure PCTKR2023003328-appb-img-000377
    Figure PCTKR2023003328-appb-img-000378
    Figure PCTKR2023003328-appb-img-000378
    Figure PCTKR2023003328-appb-img-000379
    Figure PCTKR2023003328-appb-img-000379
    Figure PCTKR2023003328-appb-img-000380
    Figure PCTKR2023003328-appb-img-000380
    Figure PCTKR2023003328-appb-img-000381
    Figure PCTKR2023003328-appb-img-000381
    Figure PCTKR2023003328-appb-img-000382
    Figure PCTKR2023003328-appb-img-000382
    Figure PCTKR2023003328-appb-img-000383
    Figure PCTKR2023003328-appb-img-000383
    Figure PCTKR2023003328-appb-img-000384
    Figure PCTKR2023003328-appb-img-000384
    Figure PCTKR2023003328-appb-img-000385
    Figure PCTKR2023003328-appb-img-000385
    Figure PCTKR2023003328-appb-img-000386
    Figure PCTKR2023003328-appb-img-000386
    Figure PCTKR2023003328-appb-img-000387
    Figure PCTKR2023003328-appb-img-000387
    Figure PCTKR2023003328-appb-img-000388
    Figure PCTKR2023003328-appb-img-000388
    Figure PCTKR2023003328-appb-img-000389
    Figure PCTKR2023003328-appb-img-000389
    Figure PCTKR2023003328-appb-img-000390
    Figure PCTKR2023003328-appb-img-000390
    Figure PCTKR2023003328-appb-img-000391
    Figure PCTKR2023003328-appb-img-000391
    Figure PCTKR2023003328-appb-img-000392
    Figure PCTKR2023003328-appb-img-000392
    Figure PCTKR2023003328-appb-img-000393
    Figure PCTKR2023003328-appb-img-000393
    Figure PCTKR2023003328-appb-img-000394
    Figure PCTKR2023003328-appb-img-000394
    Figure PCTKR2023003328-appb-img-000395
    Figure PCTKR2023003328-appb-img-000395
    Figure PCTKR2023003328-appb-img-000396
    Figure PCTKR2023003328-appb-img-000396
    Figure PCTKR2023003328-appb-img-000397
    Figure PCTKR2023003328-appb-img-000397
    Figure PCTKR2023003328-appb-img-000398
    Figure PCTKR2023003328-appb-img-000398
    Figure PCTKR2023003328-appb-img-000399
    Figure PCTKR2023003328-appb-img-000399
    Figure PCTKR2023003328-appb-img-000400
    Figure PCTKR2023003328-appb-img-000400
    Figure PCTKR2023003328-appb-img-000401
    Figure PCTKR2023003328-appb-img-000401
    Figure PCTKR2023003328-appb-img-000402
    Figure PCTKR2023003328-appb-img-000402
    Figure PCTKR2023003328-appb-img-000403
    Figure PCTKR2023003328-appb-img-000403
    Figure PCTKR2023003328-appb-img-000404
    Figure PCTKR2023003328-appb-img-000404
    Figure PCTKR2023003328-appb-img-000405
    Figure PCTKR2023003328-appb-img-000405
    Figure PCTKR2023003328-appb-img-000406
    Figure PCTKR2023003328-appb-img-000406
    Figure PCTKR2023003328-appb-img-000407
    Figure PCTKR2023003328-appb-img-000407
    Figure PCTKR2023003328-appb-img-000408
    Figure PCTKR2023003328-appb-img-000408
    Figure PCTKR2023003328-appb-img-000409
    Figure PCTKR2023003328-appb-img-000409
    Figure PCTKR2023003328-appb-img-000410
    Figure PCTKR2023003328-appb-img-000410
    Figure PCTKR2023003328-appb-img-000411
    Figure PCTKR2023003328-appb-img-000411
    Figure PCTKR2023003328-appb-img-000412
    Figure PCTKR2023003328-appb-img-000412
    Figure PCTKR2023003328-appb-img-000413
    Figure PCTKR2023003328-appb-img-000413
    Figure PCTKR2023003328-appb-img-000414
    Figure PCTKR2023003328-appb-img-000414
    Figure PCTKR2023003328-appb-img-000415
    Figure PCTKR2023003328-appb-img-000415
    Figure PCTKR2023003328-appb-img-000416
    Figure PCTKR2023003328-appb-img-000416
    Figure PCTKR2023003328-appb-img-000417
    Figure PCTKR2023003328-appb-img-000417
    Figure PCTKR2023003328-appb-img-000418
    Figure PCTKR2023003328-appb-img-000418
    Figure PCTKR2023003328-appb-img-000419
    Figure PCTKR2023003328-appb-img-000419
    Figure PCTKR2023003328-appb-img-000420
    Figure PCTKR2023003328-appb-img-000420
    Figure PCTKR2023003328-appb-img-000421
    Figure PCTKR2023003328-appb-img-000421
    Figure PCTKR2023003328-appb-img-000422
    Figure PCTKR2023003328-appb-img-000422
    Figure PCTKR2023003328-appb-img-000423
    Figure PCTKR2023003328-appb-img-000423
    Figure PCTKR2023003328-appb-img-000424
    Figure PCTKR2023003328-appb-img-000424
    Figure PCTKR2023003328-appb-img-000425
    Figure PCTKR2023003328-appb-img-000425
    Figure PCTKR2023003328-appb-img-000426
    Figure PCTKR2023003328-appb-img-000426
    Figure PCTKR2023003328-appb-img-000427
    Figure PCTKR2023003328-appb-img-000427
    Figure PCTKR2023003328-appb-img-000428
    Figure PCTKR2023003328-appb-img-000428
    Figure PCTKR2023003328-appb-img-000429
    Figure PCTKR2023003328-appb-img-000429
    Figure PCTKR2023003328-appb-img-000430
    Figure PCTKR2023003328-appb-img-000430
    Figure PCTKR2023003328-appb-img-000431
    Figure PCTKR2023003328-appb-img-000431
    Figure PCTKR2023003328-appb-img-000432
    Figure PCTKR2023003328-appb-img-000432
    Figure PCTKR2023003328-appb-img-000433
    Figure PCTKR2023003328-appb-img-000433
    Figure PCTKR2023003328-appb-img-000434
    Figure PCTKR2023003328-appb-img-000434
    Figure PCTKR2023003328-appb-img-000435
    Figure PCTKR2023003328-appb-img-000435
    Figure PCTKR2023003328-appb-img-000436
    Figure PCTKR2023003328-appb-img-000436
    Figure PCTKR2023003328-appb-img-000437
    Figure PCTKR2023003328-appb-img-000437
    Figure PCTKR2023003328-appb-img-000438
    Figure PCTKR2023003328-appb-img-000438
    Figure PCTKR2023003328-appb-img-000439
    Figure PCTKR2023003328-appb-img-000439
    Figure PCTKR2023003328-appb-img-000440
    Figure PCTKR2023003328-appb-img-000440
    Figure PCTKR2023003328-appb-img-000441
    Figure PCTKR2023003328-appb-img-000441
    Figure PCTKR2023003328-appb-img-000442
    Figure PCTKR2023003328-appb-img-000442
    Figure PCTKR2023003328-appb-img-000443
    Figure PCTKR2023003328-appb-img-000443
    Figure PCTKR2023003328-appb-img-000444
    Figure PCTKR2023003328-appb-img-000444
    Figure PCTKR2023003328-appb-img-000445
    Figure PCTKR2023003328-appb-img-000445
    Figure PCTKR2023003328-appb-img-000446
    Figure PCTKR2023003328-appb-img-000446
    Figure PCTKR2023003328-appb-img-000447
    Figure PCTKR2023003328-appb-img-000447
    Figure PCTKR2023003328-appb-img-000448
    Figure PCTKR2023003328-appb-img-000448
    Figure PCTKR2023003328-appb-img-000449
    Figure PCTKR2023003328-appb-img-000449
    Figure PCTKR2023003328-appb-img-000450
    Figure PCTKR2023003328-appb-img-000450
    Figure PCTKR2023003328-appb-img-000451
    Figure PCTKR2023003328-appb-img-000451
    Figure PCTKR2023003328-appb-img-000452
    Figure PCTKR2023003328-appb-img-000452
    Figure PCTKR2023003328-appb-img-000453
    Figure PCTKR2023003328-appb-img-000453
    Figure PCTKR2023003328-appb-img-000454
    Figure PCTKR2023003328-appb-img-000454
    Figure PCTKR2023003328-appb-img-000455
    Figure PCTKR2023003328-appb-img-000455
    Figure PCTKR2023003328-appb-img-000456
    Figure PCTKR2023003328-appb-img-000456
    Figure PCTKR2023003328-appb-img-000457
    Figure PCTKR2023003328-appb-img-000457
    Figure PCTKR2023003328-appb-img-000458
    Figure PCTKR2023003328-appb-img-000458
    Figure PCTKR2023003328-appb-img-000459
    Figure PCTKR2023003328-appb-img-000459
    Figure PCTKR2023003328-appb-img-000460
    Figure PCTKR2023003328-appb-img-000460
    Figure PCTKR2023003328-appb-img-000461
    Figure PCTKR2023003328-appb-img-000461
    Figure PCTKR2023003328-appb-img-000462
    Figure PCTKR2023003328-appb-img-000462
    Figure PCTKR2023003328-appb-img-000463
    Figure PCTKR2023003328-appb-img-000463
    Figure PCTKR2023003328-appb-img-000464
    Figure PCTKR2023003328-appb-img-000464
    Figure PCTKR2023003328-appb-img-000465
    Figure PCTKR2023003328-appb-img-000465
    Figure PCTKR2023003328-appb-img-000466
    Figure PCTKR2023003328-appb-img-000466
    Figure PCTKR2023003328-appb-img-000467
    Figure PCTKR2023003328-appb-img-000467
    Figure PCTKR2023003328-appb-img-000468
    Figure PCTKR2023003328-appb-img-000468
    Figure PCTKR2023003328-appb-img-000469
    Figure PCTKR2023003328-appb-img-000469
    Figure PCTKR2023003328-appb-img-000470
    Figure PCTKR2023003328-appb-img-000470
    Figure PCTKR2023003328-appb-img-000471
    Figure PCTKR2023003328-appb-img-000471
    Figure PCTKR2023003328-appb-img-000472
    Figure PCTKR2023003328-appb-img-000472
    Figure PCTKR2023003328-appb-img-000473
    Figure PCTKR2023003328-appb-img-000473
    Figure PCTKR2023003328-appb-img-000474
    Figure PCTKR2023003328-appb-img-000474
    Figure PCTKR2023003328-appb-img-000475
    Figure PCTKR2023003328-appb-img-000475
    Figure PCTKR2023003328-appb-img-000476
    Figure PCTKR2023003328-appb-img-000476
    Figure PCTKR2023003328-appb-img-000477
    Figure PCTKR2023003328-appb-img-000477
    Figure PCTKR2023003328-appb-img-000478
    Figure PCTKR2023003328-appb-img-000478
    Figure PCTKR2023003328-appb-img-000479
    Figure PCTKR2023003328-appb-img-000479
    Figure PCTKR2023003328-appb-img-000480
    Figure PCTKR2023003328-appb-img-000480
    Figure PCTKR2023003328-appb-img-000481
    Figure PCTKR2023003328-appb-img-000481
    Figure PCTKR2023003328-appb-img-000482
    Figure PCTKR2023003328-appb-img-000482
    Figure PCTKR2023003328-appb-img-000483
    Figure PCTKR2023003328-appb-img-000483
    Figure PCTKR2023003328-appb-img-000484
    Figure PCTKR2023003328-appb-img-000484
    Figure PCTKR2023003328-appb-img-000485
    Figure PCTKR2023003328-appb-img-000485
    Figure PCTKR2023003328-appb-img-000486
    Figure PCTKR2023003328-appb-img-000486
    Figure PCTKR2023003328-appb-img-000487
    Figure PCTKR2023003328-appb-img-000487
    Figure PCTKR2023003328-appb-img-000488
    Figure PCTKR2023003328-appb-img-000488
    상기 화합물에 있어서, t-Bu는 tert-부틸기를 의미한다.In the above compounds, t-Bu refers to a tert-butyl group.
  9. 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 8 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 8. Light-emitting device.
  10. 청구항 9에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 9, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.
  11. 청구항 9에 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 9, 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.
  12. 청구항 9에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 H의 화합물을 더 포함하는 것인 유기 발광 소자:The organic light-emitting device of claim 9, 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 PCTKR2023003328-appb-img-000489
    Figure PCTKR2023003328-appb-img-000489
    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.
  13. 청구항 11에 있어서, 상기 발광층은 1종 이상의 도펀트 및 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the light emitting layer further includes one or more types of dopants and a host.
  14. 청구항 11에 있어서, 상기 발광층은 1 종 이상의 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the light emitting layer further includes one or more types of hosts.
  15. 청구항 11에 있어서, 상기 발광층은 2종 이상의 혼합 호스트를 더 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the light emitting layer further includes two or more types of mixed hosts.
PCT/KR2023/003328 2022-03-11 2023-03-10 Compound and organic light-emitting device comprising same WO2023172110A1 (en)

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