WO2023172111A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes

Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • This specification provides a compound and an organic light-emitting device containing the same.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • X1 and X2 are the same or different from each other and are each independently -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-
  • A1 is a substituted or unsubstituted hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle, or combines with R3 to form a substituted or unsubstituted ring,
  • n 0 or 1
  • n 0 or 1
  • At least one of n and m is 1,
  • R1 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R)(R'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R2 to R10 combine with each other to form a substituted or unsubstituted ring,
  • R and R' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r1 is an integer from 1 to 5, and when r1 is 2 or more, the 2 or more R1 are the same or different from each other,
  • r2 is an integer of 1 to 4, and when r2 is 2 or more, the 2 or more R2s are the same or different from each other,
  • r3 is 1 to 4, and when r3 is 2 or more, the 2 or more R3s are the same or different from each other,
  • r4 is an integer from 0 to 2, and when r4 is 2, the two R4 are the same or different from each other,
  • r5 is an integer from 1 to 4, and when r5 is 2 or more, the 2 or more R5 are the same or different from each other,
  • r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other,
  • r4 is 1 or 2.
  • the present specification includes a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the one or more organic material layers contain the compound.
  • the compound according to an exemplary embodiment of the present specification can be used as a material for the organic layer of an organic light-emitting device, and by using it, high color purity, high efficiency, and/or improved lifespan characteristics can be achieved in the organic light-emitting device.
  • FIG. 1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
  • An exemplary embodiment of the present specification relates to the compound of Formula 1 above.
  • Organic light-emitting devices using conventional boron-based compounds have better efficiency than organic light-emitting devices using pyrene-based compounds, but have the disadvantage of having a shorter lifespan.
  • the compound of Formula 1 has a narrow half width, and organic light emitting devices containing it have the advantage of increased efficiency and lifespan. It maintains a narrow half width due to the hexagonal ring of boron and amine, but fills the missing electrons of boron through direct bonding between boron and amine on the other side, thereby increasing the stability of the core in the unstable polaron state. The lifespan increases, and the polaron transitions to the exciton state easily, thereby increasing the efficiency of the organic light-emitting device containing it.
  • the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, It means including one or more selected from the group consisting of.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; alkenyl group; Haloalkyl group; Haloalkoxy group; Arylalkyl group; silyl group; boron group; Amine group; Aryl group; A condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or is substituted with a substituent in which two or more of the substituents exemplified above are linked, or does not have any substituents.
  • linking two or more substituents means that the hydrogen of one substituent is linked to another substituent.
  • a phenyl group and a naphthyl group are connected. or It can be a substituent of .
  • connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group, and an isopropyl group are connected, , or It can be a substituent of .
  • the above definition equally applies to those in which 4 or more substituents are connected.
  • halogen groups include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, bicyclo [2.2.1]heptyl group, bicyclo[2.2.1]octyl group, norbornyl group, etc., but are not limited thereto.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the haloalkoxy group means that in the definition of the alkoxy group, at least one halogen group is substituted for hydrogen in the alkoxy group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • fluorene group examples include
  • an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • an arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and alkyl group described above may be applied.
  • an aryloxy group refers to an aryl group being substituted for the alkyl group of the alkoxy group in the above definition of alkoxy group, and the aryloxy group includes phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenene Triloxy group, 9-phenanthryloxy group, etc. are included, but are not limited thereto.
  • alkyl group of the alkylthioxy group is the same as the example of the alkyl group described above.
  • alkylthioxy groups include methylthioxy group, ethylthioxy group, tert-butylthioxy group, hexylthioxy group, octylthioxy group, etc., but are not limited thereto.
  • the aryl group in the arylthioxy group is the same as the example of the aryl group described above.
  • the arylthioxy group includes phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenylthioxy group, but is not limited thereto.
  • the heterocyclic group includes one or more non-carbon atoms and heteroatoms.
  • the heterocyclic group may include one or more atoms selected from the group consisting of O, N, Se, and S, etc., Includes an aromatic heterocyclic group or an aliphatic heterocyclic group.
  • the aromatic heterocyclic group may be represented by a heteroaryl group.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and acridine group.
  • pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group isoquinoline group, indole group, carbazole group, benzyl group.
  • the silyl group is an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; It may be a heteroarylsilyl group, etc.
  • the alkyl group described above may be applied to the alkyl group among the alkylsilyl groups
  • examples of the aryl group described above may be applied to the aryl group among the arylsilyl group
  • examples of the alkyl group and aryl group in the alkylarylsilyl group include the alkyl group and the aryl group.
  • Examples of may be applied, and examples of the heterocyclic group may be applied to the heteroaryl group among the heteroarylsilyl groups.
  • the boron group may be -BR 100 R 101 , where R 100 and R 101 are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • the alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.
  • N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as examples of the aryl group and heterocyclic group described above.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heterocyclic group described above.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a straight-chain or branched alkyl group.
  • the alkylamine group containing two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group.
  • the alkyl group in the alkylamine group may be selected from the examples of alkyl groups described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of heterocyclic groups described above.
  • the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, an aryl group, and combinations thereof.
  • the hydrocarbon ring group includes phenyl group, cyclohexyl group, adamantyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.1]octyl group, tetrahydronaphthalene group, tetrahydroanthracene group, 1,2, Examples include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene group and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group.
  • the meaning of “adjacent” in “joining with adjacent groups to form a ring” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for the non-monovalent ones, the cycloalkyl group, the aryl group, and combinations thereof.
  • hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, These include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.
  • the aliphatic hydrocarbon ring includes a single bond hydrocarbon ring, a hydrocarbon ring containing a non-aromatic multiple bond, or a ring in the form of a condensation of a ring containing a single bond and a multiple bond.
  • the ring consisting of a single bond among the aliphatic hydrocarbon rings may be selected from the examples of cycloalkyl groups above, except that it is not a monovalent group, and includes cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, Hydrocarbon rings that contain single and double bonds but are not aromatic rings, such as cyclononene, cyclodecene, and cyclonorbornene, also belong to aliphatic hydrocarbon rings.
  • a heterocycle includes one or more non-carbon atoms and heteroatoms.
  • the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be an aromatic heterocycle; Aliphatic heterocycle; A condensed ring of an aromatic heterocycle and an aliphatic heterocycle; It may be a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic group, or a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocyclic group, except that the aromatic heterocycle is not monovalent. It may be selected from examples of heteroaryl groups.
  • an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms.
  • the aliphatic heterocycle includes a single bond aliphatic ring, an aliphatic ring containing multiple bonds, or an aliphatic ring in the form of a condensed ring containing a single bond and a multiple bond.
  • Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine.
  • thiocane tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.
  • the portion in Formula 1 where a substituent is not indicated may mean that hydrogen has been substituted.
  • Formula 1 is any one of Formulas 2 to 4 below.
  • A1, X1, X2, R1 to R6, and r1 to r6 are the same as those defined in Formula 1 above.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring;
  • it is a heterocycle that is substituted or unsubstituted and contains one or more of O, N, S, and Si.
  • the formula 1 is the formula 5 or 6 below.
  • X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
  • R11 to R16 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R11 to R16 are combined with each other to form a substituted or unsubstituted ring,
  • R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r11 is an integer from 1 to 4, and when r11 is 2 or more, the 2 or more R11 are the same or different from each other,
  • r12 is an integer of 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other.
  • Formula 1 is any one of Formulas 7 to 16 below.
  • X3 is -C(R13)(R14)-; -Si(R15)(R16)-; -O-; or -S-,
  • X4 and X5 are the same or different from each other and are each independently -C(R19)(R20)-; -Si(R21)(R22)-; -O-; or -S-,
  • X6 and X7 are the same or different from each other and are each independently -C(R23)(R24)-; -Si(R25)(R26)-; -N(R27); -O-; or -S-,
  • Y1 to Y4 are the same or different from each other and are each independently -C(R28)- or N,
  • R'2, R"2, R'11, R"11 and R12 to R28 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; -N(R")(R"'); Substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or one or more adjacent pairs of R'2, R"2, R'11, R"11 and R12 to R28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.
  • R" and R"' are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; A condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • r'11 is an integer of 1 to 4, and when r'11 is 2 or more, 2 or more R'11 are the same or different from each other,
  • r"11 is 1 or 2, and when r"11 is 2, the two R"11 are the same or different from each other,
  • r'2 is an integer of 1 to 4, and when r'2 is 2 or more, R'2 of 2 or more is the same or different,
  • r"2 is 1 or 2, and when r"2 is 2, the two R"2 are the same or different from each other,
  • r12 is an integer from 1 to 4, and when r12 is 2 or more, the 2 or more R12s are the same or different from each other,
  • r17 is an integer of 1 to 4, and when r17 is 2 or more, the 2 or more R17 are the same or different from each other,
  • r18 is an integer of 1 to 4, and when r18 is 2 or more, the 2 or more R18s are the same or different from each other.
  • Formula 1 is the following Formula 1-1.
  • A1, R2 to R6, r2 to r6, n, m, X1 and X2 are the same as those defined in Formula 1.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with -N(R")(R"');
  • a heterocycle having 2 to 30 carbon atoms is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S Forming a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms,
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms;
  • R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms,
  • R5 and R6 are hydrogen
  • R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R, R', R", and R"' are the same or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
  • m is 1 and n is 0.
  • m is 0 and n is 1.
  • n 1
  • X1 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
  • X1 is -C(R7)(R8)-.
  • X1 is -Si(R9)(R10)-.
  • X1 is -O-.
  • X1 is -S-.
  • X2 is -C(R7)(R8)-, -Si(R9)(R10)-, -O-, or -S-.
  • X2 is -C(R7)(R8)-.
  • X2 is -Si(R9)(R10)-.
  • X2 is -O-.
  • X2 is -S-.
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms;
  • A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms;
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic group having 6 to 30 carbon atoms substituted or unsubstituted with -N(R")(R"') Ring aromatic hydrocarbon ring;
  • ⁇ is a heterocycle having 2 to 30 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 30 carbon atoms.
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic group having 6 to 20 carbon atoms substituted or unsubstituted with -N(R")(R"').
  • Ring aromatic hydrocarbon ring A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; or substituted or unsubstituted with one or more selected from a straight or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and combinations thereof, and includes one or more of O, N, and S.
  • ⁇ is a heterocycle having 2 to 20 carbon atoms, or is bonded to R3 and is substituted or unsubstituted with a straight or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, N, O or S It forms a monocyclic or polycyclic heterocycle containing 6 to 20 carbon atoms.
  • A1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group
  • A1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocycl
  • A1 is a tert-butyl group, or benzene substituted or unsubstituted with -N(R")(R"'); Fluorene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Dibenzofuran; dibenzothiophene; Benzofuran substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzothiophene substituted or unsubstituted with a tert-butyl group or a phenyl group; Benzoxazole substituted or unsubstituted with a phenyl group; Benzothiazole substituted or unsubstituted with a phenyl group; Benzimidazole substituted or unsubstituted with one or more selected from methyl group, phenyl
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or at least one adjacent pair of R2 and R3 is bonded to a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms; It is substituted or unsubstit
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 30 carbon atoms and 3 to 30 carbon atoms.
  • Aliphatic hydrocarbon ring A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, -N(R")(R"'), and combinations thereof ;
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); A straight or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs of R2 and R3 are bonded to each other to form a substituted or unsubstituted straight-chain or branched alkyl group of 1 to 20 carbon atoms.
  • Aliphatic hydrocarbon ring A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with one or more selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms, -N(R")(R"'), and combinations thereof ;
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substitute
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substitute
  • R1 to R3 are the same as or different from each other, and are each independently hydrogen; -N(R)(R'); methyl group; tert-butyl group; or a phenyl group, or at least one adjacent pair of R2 and R3 is bonded to benzene; Cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, or -N(R)(R') methyl group;
  • R1 is hydrogen; or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 is hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 is hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R1 is hydrogen; methyl group; tert-butyl group; Or it is a phenyl group.
  • R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; A condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or, it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 30 carbon atoms including N, O or S.
  • R2 is hydrogen; -N(R)(R'); or a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms;
  • it is substituted or unsubstituted and forms a monocyclic or polycyclic heterocycle containing 2 to 20 carbon atoms including N, O or S.
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or an adjacent pair of R2 is bonded to a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Tetrahydron
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or a pair of adjacent R2 is bonded to each other to form a substituted or unsubstituted cyclohexene with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms;
  • R2 is hydrogen; -N(R)(R'); or a tert-butyl group, or any pair of adjacent R2s are bonded to each other to form cyclohexene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; Tetrahydronaphthofuran substituted or unsubstituted with a methyl group; Tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; Tetrahydronaphthalene substituted or unsubstituted with a methyl group; benzodioxin; indene substituted or unsubstituted with one or more selected from methyl group, tert-butyl group, -N(R")(R"'), and combinations thereof; Benzofuran substituted or unsubstituted with a tert-
  • R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or any pair of adjacent R3s are combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or any pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a pair of adjacent R3 is bonded to each other to form an aliphatic hydrocarbon ring having 6 to 20 carbon atoms, substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Alternatively, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.
  • R3 is hydrogen; -N(R)(R'); Or, it is a tert-butyl group, or any pair of adjacent R3s are combined with each other to form cyclohexene substituted or unsubstituted with a methyl group.
  • R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; Or it is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 30 carbon atoms.
  • R4 is hydrogen; Or it is a straight or branched alkyl group having 1 to 20 carbon atoms.
  • R4 is hydrogen; Or it is a methyl group.
  • R5 and R6 are hydrogen.
  • R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R7 to R10 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R7 to R10 are the same or different from each other, and are each independently a straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R7 to R10 are the same as or different from each other, and are each independently a straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R7 to R10 are methyl groups; Or it is a phenyl group.
  • R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R, R', R", and R"' are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R, R', R", and R"' are the same or different from each other, and are each independently substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms and 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 30 to 30 members.
  • R, R', R", and R"' are the same or different from each other, and each independently is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted with 6 carbon atoms. It is a monocyclic or polycyclic aryl group of 20 to 20 members.
  • R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. .
  • R, R', R", and R"' are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. .
  • R, R', R", and R"' are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a tert-butyl group.
  • R3 is hydrogen
  • R4 is hydrogen
  • Formula 1 includes at least one tert-butyl group.
  • Formula 1 is any one of the following compounds.
  • tBu refers to a tert-butyl group.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area.
  • the size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
  • a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
  • deuterated As used herein, “deuterated,” “substituted with deuterium,” or “deuterated” means that hydrogen at a replaceable position in a compound is replaced with deuterium.
  • X% substitution with deuterium means that It means that it has been dented.
  • the dibenzofuran is “25% substituted with deuterium,” the dibenzofuran is “25% deuterated,” the dibenzofuran is “deuterated by 25%,” or
  • the “deuterium substitution rate of 25%” of the dibenzofuran means that two of the eight hydrogens at the replaceable positions of the dibenzofuran are replaced with deuterium.
  • the degree of deuteration is determined by nuclear magnetic resonance spectroscopy ( 1H NMR), Thin-Layer Chromatography/Mass Spectrometry (TLC/MS), or Matrix assisted laser desorption/ionization Time-of-Flight Mass Spectrometry (MALDI-TOF MS). ) can be confirmed by known methods such as.
  • This specification includes: a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc.
  • the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes the compound of Formula 1 as a dopant of the light-emitting layer.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes the compound of Formula 1 as a blue fluorescent dopant of the light-emitting layer.
  • the organic light emitting device is a hole injection layer or a hole transport layer. It further includes one or two layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the light emitting layer further includes a host compound.
  • the light-emitting layer further includes a host compound, and the host compound is one in which at least one hydrogen at a replaceable position is replaced with deuterium.
  • the host compound when the host compound is substituted with deuterium, more than 30% of the host compound is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by more than 40% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 60% with deuterium. In another exemplary embodiment, the host compound is substituted by more than 80% with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
  • the light-emitting layer further includes a compound of the following formula (H).
  • L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R200 and R201 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer from 1 to 7, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted
  • Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R200 is hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; heavy hydrogen; fluorine; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • R200 is hydrogen; A substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • R200 is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran
  • R200 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A naphthyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon
  • R200 is hydrogen; heavy hydrogen; Phenyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Biphenyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • R201 is hydrogen
  • R201 is deuterium
  • the compound of formula H when the compound of formula H is substituted with deuterium, more than 30% of the hydrogen at the replaceable position is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 40% of hydrogen at replaceable positions is replaced with deuterium. In another exemplary embodiment, in the structure of Formula H, more than 60% of hydrogen at replaceable positions is replaced with deuterium.
  • the compound of formula H is any one selected from the following compounds.
  • the compound of formula H may be prepared by the following general formula 1, but is not limited thereto.
  • Ar 1 is the same as defined for -L20-Ar20 in Formula H above,
  • Ar 2 is the same as the definition of -L21-Ar21 in Formula H, and R200 and R201 may be additionally substituted in the anthracene core of Formula 1.
  • the compound of Formula 1 is used as a dopant and the compound of Formula H is used as a host in the light emitting layer.
  • the content of the dopant may be selected in the range of 0.01 to 10 parts by weight based on 100 parts by weight of the light-emitting layer, but is not limited thereto.
  • the light-emitting layer includes a host and a dopant, and the host and the dopant have a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30, and even more preferably 99:99. It is contained in a weight ratio of :1 to 90:10.
  • the light-emitting layer may further include a host material, and the host may be a condensed aromatic ring derivative or a heterocycle-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds.
  • furan compounds, pyrimidine derivatives, triazine derivatives, etc. and may be a mixture of two or more types thereof, but are not limited thereto.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of dopants and a host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed dopants and a host.
  • At least one of the two or more mixed dopants includes the formula (1), and the host includes a compound of the formula (H).
  • At least one of the two or more types of mixed dopants may include Formula 1, and the remaining dopant materials known in the art may be used, but are not limited thereto.
  • At least one of the two or more mixed dopants includes Formula 1, and the remainder includes at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1.
  • the remainder includes at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1.
  • it is not limited to this.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes one or more types of hosts.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer further includes two or more types of mixed hosts.
  • At least one of the two or more mixed hosts is a compound of formula H.
  • the two or more mixed hosts are different from each other and are each independently a compound of the formula H.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes two types of mixed hosts
  • the two types of mixed hosts are different from each other
  • the two types of hosts include the compound of Formula H am.
  • the organic material layer includes a light-emitting layer, and includes a first host of the formula H; and a second host of formula H, wherein the first host and the second host are different from each other.
  • the first host and the second host are included at a weight ratio of 95:5 to 5:95, and preferably at a weight ratio of 70:30 to 30:70.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes one or more types of hosts and a dopant.
  • the organic layer includes a light-emitting layer, the light-emitting layer includes one or more hosts, and a dopant, the host includes a compound of formula H, and the dopant includes a compound of formula (1) Contains compounds.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed hosts and a dopant.
  • At least one of the two or more types of mixed hosts includes a compound of Formula H, and the dopant includes a compound of Formula 1.
  • the two or more mixed hosts are different from each other.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes two types of mixed hosts and a dopant.
  • the two types of mixed hosts are different from each other and each independently includes a compound of Formula H, and the dopant includes a compound of Formula 1.
  • a first host of Formula H a second host of formula H; and a dopant of Formula 1, wherein the first host and the second host are different from each other.
  • the organic material layer uses one or more types of hosts and one or more dopants
  • the one or more hosts include a compound of the formula H
  • the one or more dopants have the formula (1) Contains compounds of
  • the organic material layer uses two or more types of mixed hosts and two or more types of mixed dopants, the two or more types of mixed hosts may use the same materials as described above, and the two or more types of mixed hosts may be used.
  • the dopant may be the same material as described above.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes a dopant material
  • the dopant material includes the compound of Formula 1.
  • the light emitting layer further includes one or more types of dopants and a host.
  • the one or more types of dopants may be conventionally known dopant materials, but are not limited thereto.
  • the light emitting layer further includes one or more types of hosts.
  • the one or more hosts include compounds of formula H above.
  • the light emitting layer further includes two or more types of mixed hosts. At least one of the two or more mixed hosts includes a compound of formula H above.
  • the light emitting layer further includes two or more types of mixed hosts.
  • the two types of mixed hosts are different from each other, and each independently includes a compound of formula H.
  • the organic light emitting device includes a first electrode; second electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound of Formula 1.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer that simultaneously performs hole transport and hole injection, and an electron blocking layer.
  • the organic light emitting device may include two or more electron transport layers, but is not limited thereto.
  • the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound of Formula 1.
  • the compound of Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the materials of each of the two or more electron transport layers may be the same or different from each other.
  • the organic light emitting device may include two or more hole injection layers, but is not limited thereto.
  • the materials of each of the two or more hole injection layers may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant may be one known in the art, for example, a metal or a metal complex.
  • the electron transport layer containing the compound of Formula 1 may further include lithium quinolate (LiQ).
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound of Formula 1.
  • the compound of Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • the organic material layer may further include a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound of Formula 1. You can.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, a first electrode 2, a light-emitting layer 3, and a second electrode 4 are sequentially stacked.
  • the compound may be included in the light-emitting layer 3.
  • FIG. 2 shows a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, and a light emitting layer 3.
  • the structure of an organic light-emitting device in which the first electron transport layer 9, the second electron transport layer 10, the electron injection layer 11, and the second electrode 4 are sequentially stacked is illustrated.
  • the compound may be included in the light-emitting layer 3.
  • the organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound of Formula 1 above.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or conductive metal oxide or alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode.
  • PVD physical vapor deposition
  • It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited to this.
  • the first electrode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
  • the second electrode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • metals or alloys thereof for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the light-emitting material of the light-emitting layer transmits holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines them to emit visible light.
  • a material capable of emitting light in a range a material with good quantum efficiency for fluorescence or phosphorescence is desirable.
  • 8-hydroxy-quinoline aluminum complex Alq 3
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Spiro compounds polyfluorene
  • rubrene but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
  • the dopant material includes additional compounds in addition to the compound of Formula 1, it includes aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group.
  • a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the hole injection layer is a layer that injects holes from an electrode.
  • the hole injection material preferably has the ability to transport holes and has an excellent hole injection effect in the first electrode and an excellent hole injection effect in the light-emitting layer or light-emitting material. Additionally, a material having an excellent ability to prevent movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Carbazole-based organic substances; Nitrile-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, or mixtures of two or more of the above examples, but are not limited thereto.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • R301 to R306 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • L301 and L302 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.
  • R301 and R302 are the same or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R301 and R302 are methyl groups.
  • R301 and R302 are combined with each other to form a substituted or unsubstituted heterocycle.
  • R301 and R302 are combined with each other to form a substituted or unsubstituted dihydroacridine ring; Or, it forms a substituted or unsubstituted indoloacridine ring.
  • R301 and R302 are combined with each other to form a dihydroacridine ring substituted or unsubstituted with a phenyl group; Or, it forms an indoloacridine ring.
  • L301 and L302 are a direct bond.
  • R303 to R306 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • R303 to R306 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R303 to R306 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
  • the formula HI-1 is represented by the following compound, but is not limited thereto.
  • the hole injection layer includes a compound represented by the following formula HI-2.
  • At least one of X'1 to X'6 is N, and the remainder is CH,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • the formula HI-2 is represented by the following compound.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material is preferably a material that can transport holes from the first electrode or the hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
  • the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
  • R'314, R315 and R316 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same or different from each other.
  • R'314 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R'314 is a carbazole group; phenyl group; Biphenyl group; It is any one selected from the group consisting of naphthyl groups and combinations thereof.
  • R315 and R316 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an alkyl group, or an aromatic hydrocarbon substituted or unsubstituted with an aryl group. forms a ring
  • R315 and R316 are the same or different from each other, and are each independently a phenyl group, or are combined with adjacent groups to form benzene; Or, it forms indene substituted or unsubstituted with a phenyl group or a methyl group.
  • the formula HT-1 is represented by the following compound.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transport material is a material that can easily receive electrons from the second electrode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complex; triazine derivatives; LiQ, etc., but is not limited thereto.
  • the electron transport layer can be used with any desired first electrode material, as used according to the prior art.
  • suitable first electrode materials are conventional materials with a low work function, followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron transport layer includes a compound represented by the following formula ET-1.
  • At least one of X'7 to X'8 is N, and the rest are CH,
  • R317 to R322 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • L'1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • r322 is an integer from 1 to 7, and when r322 is 2 or more, R322 is the same as or different from each other,
  • l'1 is an integer from 1 to 5, and when l'1 is 2 or more, L'1 is the same or different from each other.
  • R317 to R322 are the same or different from each other, and are each independently hydrogen; Or it is a substituted or unsubstituted aryl group, and adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R317 to R322 are the same or different from each other, and are each independently hydrogen; phenyl group; Or it is a naphthyl group, or adjacent groups combine with each other to form benzene.
  • L'1 is a substituted or unsubstituted arylene group.
  • L'1 is a phenylene group.
  • the ET-1 is selected from the following compounds.
  • the electron transport layer includes a compound represented by the following formula ET-2.
  • T1 to T3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of substituted or unsubstituted heteroaryl groups, and combinations thereof, or combines with adjacent groups to form a substituted or unsubstituted ring,
  • t1 is an integer from 1 to 4, and when t1 is 2 or more, 2 or more T1 are the same or different from each other,
  • t2 is an integer from 1 to 4, and when t2 is 2 or more, 2 or more T2 are the same or different from each other,
  • t3 is an integer from 1 to 10, and when t3 is 2 or more, 2 or more T3 are the same or different from each other.
  • T1 to T3 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl groups, and combinations thereof.
  • T1 to T3 are the same or different from each other, and are each independently hydrogen; carbazole group; phenyl group; Biphenyl group; triazine group; and any one selected from the group consisting of combinations thereof.
  • the ET-2 is selected from the following compounds.
  • the electron transport layer may further include a metal complex.
  • the metal may be a metal used in the industry.
  • the electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has an excellent ability to transport electrons and has an excellent electron injection effect from the second electrode and an excellent electron injection effect to the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is desirable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
  • the electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer.
  • Known materials can be used without limitation, and can be formed between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
  • the electron blocking layer is represented by the formula HT-1.
  • the hole blocking layer is a layer that prevents holes from passing through the light emitting layer and reaching the cathode, and can generally be formed under the same conditions as the electron injection layer.
  • oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, etc. are included, but are not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.
  • the compounds according to the present specification may function in organic light-emitting devices, including organic phosphorescent devices, organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.
  • the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.
  • the organic light emitting device can be included and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • the organic light emitting device of the present specification can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

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Abstract

La présente invention concerne un composé de formule 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2023/003330 2022-03-11 2023-03-10 Composé et dispositif électroluminescent organique le comprenant WO2023172111A1 (fr)

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US20180114929A1 (en) * 2016-10-24 2018-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US20190067577A1 (en) * 2017-08-22 2019-02-28 Chuanjun Xia Boron containing heterocyclic compound for oleds, an organic light-emitting device, and a formulation comprising the boron-containing heterocyclic compound
WO2020135953A1 (fr) * 2018-12-28 2020-07-02 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
WO2021214310A1 (fr) * 2020-04-23 2021-10-28 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
WO2021255698A1 (fr) * 2020-06-19 2021-12-23 Idemitsu Kosan Co., Ltd. Composé hétérocyclique et dispositif électroluminescent organique comprenant le composé hétérocyclique

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Publication number Priority date Publication date Assignee Title
JPS5935199U (ja) 1982-08-30 1984-03-05 櫻木　光男 波動推進装置

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Publication number Priority date Publication date Assignee Title
US20180114929A1 (en) * 2016-10-24 2018-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US20190067577A1 (en) * 2017-08-22 2019-02-28 Chuanjun Xia Boron containing heterocyclic compound for oleds, an organic light-emitting device, and a formulation comprising the boron-containing heterocyclic compound
WO2020135953A1 (fr) * 2018-12-28 2020-07-02 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
WO2021214310A1 (fr) * 2020-04-23 2021-10-28 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
WO2021255698A1 (fr) * 2020-06-19 2021-12-23 Idemitsu Kosan Co., Ltd. Composé hétérocyclique et dispositif électroluminescent organique comprenant le composé hétérocyclique

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