WO2022103090A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2022103090A1
WO2022103090A1 PCT/KR2021/016086 KR2021016086W WO2022103090A1 WO 2022103090 A1 WO2022103090 A1 WO 2022103090A1 KR 2021016086 W KR2021016086 W KR 2021016086W WO 2022103090 A1 WO2022103090 A1 WO 2022103090A1
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substituted
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carbon atoms
monocyclic
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Korean (ko)
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조혜민
금수정
이우철
김명곤
김경희
이호중
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주식회사 엘지화학
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Priority to CN202180069286.7A priority Critical patent/CN116326241A/zh
Publication of WO2022103090A1 publication Critical patent/WO2022103090A1/fr

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    • 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
    • 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
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • 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

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Condensed rings of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
  • Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • At least one of R1 to R3 is a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic group; or -NR11R12, the remainder being hydrogen,
  • R11 and R12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
  • the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.
  • the compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, high color purity, high efficiency, and/or lifespan characteristics may be improved in the organic light emitting device.
  • FIG. 1 and 2 show an organic light emitting diode according to an exemplary embodiment of the present specification.
  • the conventional organic light-emitting device to which a boron-based compound is applied has better efficiency than an organic light-emitting device to which a pyrene-based compound is applied, but has a short lifespan.
  • the compound represented by Formula 1 includes a boron core including a 5-membered ring differently from a conventional boron core including a 6-membered ring, the energy band gaps of HOMO and LUMO are similar or smaller. It has an appropriate value for use as a fluorescent dopant.
  • the first triplet excitation energy of Formula 1 is lowered, the difference between the first singlet excitation energy and the first triplet excitation energy increases. Accordingly, by suppressing triplet quenching, an organic light emitting device including the same is increased in device lifetime and efficiency in a host-dopant system.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; alkenyl group; haloalkyl group; haloalkoxy group; an arylalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • that two or more substituents are connected means that the hydrogen of any one substituent is connected with the other substituent.
  • substituents when two substituents are connected, a phenyl group and a naphthyl group are connected. or It can be a substituent of
  • (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1) include
  • a phenyl group, a naphthyl group and an isopropyl group are connected , , or It can be a substituent of
  • the above definition applies equally to a case in which 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 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, and the like, but is not limited thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the haloalkoxy group means that at least one halogen group is substituted for hydrogen of the alkoxy group in the definition of 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 preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
  • the arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and the alkyl group described above may be applied to the aryl group and the alkyl group of the arylalkyl group.
  • the aryloxy group means substituted with an aryl group instead of an alkyl group of the alkoxy group in the definition of the alkoxy group
  • the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy 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-phenane a triloxy group, a 9-phenanthryloxy group, and the like, but is not limited thereto.
  • the alkyl group of the alkylthioxy group is the same as the example of the above-described alkyl group.
  • the alkyl thiooxy group includes, but is not limited to, a methyl thiooxy group, an ethyl thioxy group, a tert-butyl thiooxy group, a hexyl thioxy group, an octyl thiooxy group, and the like.
  • the aryl group in the arylthioxy group is the same as the example of the aryl group described above.
  • the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.
  • the heterocyclic group includes atoms other than carbon and one or more heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, etc., 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 preferably has 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), decahydrobenzocarbazole group, he
  • the silyl group is an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; It may be a heteroarylsilyl group or the like.
  • Examples of the above-described alkyl group may be applied to the alkyl group in the alkylsilyl group
  • the examples of the aryl group may be applied to the aryl group in the arylsilyl group
  • the alkyl group and aryl group in the alkylarylsilyl group may include the alkyl group and the aryl group.
  • the heteroaryl group among the heteroarylsilyl group can be applied to the example of the heterocyclic group.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, and a diphenyl boron group.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like but is not limited thereto.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heterocyclic group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the aforementioned alkyl group and heterocyclic group.
  • 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 including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time.
  • the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.
  • the alkyl group in the N-alkylarylamine group, the alkylthioxy group, and the N-alkylheteroarylamine group is the same as the above-described alkyl group.
  • the alkyl thiooxy group includes, but is not limited to, a methyl thiooxy group, an ethyl thioxy group, a tert-butyl thiooxy group, a hexyl thioxy group, an octyl thiooxy group, and the like.
  • the aryl group in the aryloxy group, the arylthioxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the above-described aryl group.
  • the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy 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-phenanthryloxy group, 9-phenanthryloxy group, and the like
  • the arylthioxy group includes phenylthioxy group, 2- a methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, but is not limited thereto.
  • 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, aryl group, and combinations thereof.
  • the hydrocarbon ring group is a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo [2.2.1] heptyl group, a bicyclo [2.2.1] octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene group, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, but is not limited thereto.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, except that the cycloalkyl group, the aryl group, and combinations thereof It may be selected from among examples, and the hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo [2.2.1] heptane, bicyclo [2.2.1] octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, and the like, but are not limited thereto.
  • the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups except that it is not monovalent. there is.
  • the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but is not limited thereto.
  • At least one of the hydrogens in the substitutable positions of Formula 1 is substituted with deuterium.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • X1 and X2 are the same as or different from each other, and each independently O or S,
  • A11 and A21 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Condensed rings of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
  • Z1 to Z4, Y1 to Y5 and T1 to T4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group, or a substituted or
  • Chemical Formula 1-2 is represented by the following Chemical Formula 1-2-1 or 1-2-2.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • Chemical Formula 1-2 is represented by any one of the following Chemical Formulas 1-2-3 to 1-2-6.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • A21, Z1 to Z4, and Y1 to Y5 are the same as defined in Formula 1-2 above.
  • Chemical Formula 1-3 is represented by Chemical Formula 1-3-1 or 1-3-2.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • Chemical Formula 1-3 is represented by any one of the following Chemical Formulas 1-3-3 to 1-3-6.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • A11, T1 to T4, and Y1 to Y5 are the same as those defined in Formula 1-3.
  • Chemical Formula 1-4 is represented by any one of the following Chemical Formulas 1-4-1 to 1-4-4.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • A11, A21, X1, X2, and Y1 to Y5 are the same as those defined in Formula 1-4.
  • Chemical Formula 1-4 is represented by any one of the following Chemical Formulas 1-4-5 to 1-4-20.
  • R1 to R3 are the same as those defined in Formula 1 above,
  • A11, A21, and Y1 to Y5 are the same as those defined in Formula 1-4.
  • At least one of R1 to R3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group 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; A substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or -NR11R12, and the remainder is hydrogen.
  • At least one of R1 to R3 is deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and any one or more unsubstituted or substituted C6 to 30 carbon atoms selected from combinations thereof a monocyclic or polycyclic aryl group; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkenyl group having 2 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms
  • At least one of R1 to R3 is a phenyl group unsubstituted or substituted with any one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof; biphenyl group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; a tetrahydronaphthyl group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a carbazole group; a hexahydrocarbazole group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophene group; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms,
  • At least one of R1 to R3 is a phenyl group unsubstituted or substituted with any one or more selected from deuterium, a methyl group, and combinations thereof; biphenyl group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; a carbazole group; hexahydrocarbazole group unsubstituted or substituted with a methyl group; dibenzofuran; dibenzothiophene group; Deuterium, F, cyano group, methyl group, tert-butyl group, vinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, fluorene group, spirobifluorene group, pyrene group, pyridine
  • any one of R1 to R3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group 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; A substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or -NR11R12, and the remainder is hydrogen.
  • any one of R1 to R3 is deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and any one or more unsubstituted or substituted C6 to 30 carbon atoms selected from combinations thereof a monocyclic or polycyclic aryl group; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkenyl group having 2 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • any one of R1 to R3 is a phenyl group unsubstituted or substituted with any one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof; biphenyl group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; a tetrahydronaphthyl group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a carbazole group; a hexahydrocarbazole group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophene group; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a
  • any one of R1 to R3 is a phenyl group unsubstituted or substituted with any one or more selected from deuterium, a methyl group, and combinations thereof; biphenyl group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; a carbazole group; hexahydrocarbazole group unsubstituted or substituted with a methyl group; dibenzofuran; dibenzothiophene group; Deuterium, F, cyano group, methyl group, tert-butyl group, vinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, fluorene group, spirobifluorene group, pyrene group, pyridine group
  • R11 and R12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R11 and R12 are the same as or different from each other, and each independently deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with any one or more selected from combinations thereof; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl
  • R11 and R12 are the same as or different from each other, and each independently deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a phenyl group unsubstituted or substituted with any one or more selected from combinations thereof; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; naphthyl group; phenanthrene group; a fluorene group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran group; dibenzothiophene group; or a carbazole group unsubsti
  • R11 and R12 are the same as or different from each other, and each independently substituted or unsubstituted with any one or more selected from deuterium, a methyl group, a tert-butyl group, a cyclohexyl group, and combinations thereof.
  • phenyl group a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; naphthyl group; phenanthrene group; a fluorene group unsubstituted or substituted with a methyl group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • A1 and A2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, 6 to carbon atoms 30 monocyclic or polycyclic aryl group, monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polypolylene
  • A1 and A2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, 6 to carbon atoms 30 monocyclic or polycyclic aryl group, monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof benzene; naphthalene; fluorene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthalene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzofuran unsubstituted or substituted with a linear or branched alkyl group having 1
  • A1 and A2 are the same as or different from each other, and each independently a methyl group, isopropyl group, tert-butyl group, cyclohexyl group, phenyl group, diphenylamine group, dibiphenylamine group, benzene unsubstituted or substituted with any one or more selected from a dinaphthylamine group, a hexahydrocarbazole group, and combinations thereof; naphthalene; fluorene unsubstituted or substituted with a methyl group; tetrahydronaphthalene unsubstituted or substituted with a methyl group; tetrahydrobenzofuran unsubstituted or substituted with a methyl group; tetrahydrobenzothiophene unsubstituted or substituted with a methyl group; tetrahydronaphthothiophene un
  • Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 is a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and these A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with any one or more selected from a combination of; A monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms unsubstituted or substituted with any one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof a condensed ring group of a ring and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycycl
  • Ar1 is a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and these a phenyl group unsubstituted or substituted with any one or more selected from a combination of; a biphenyl group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; a fluorene group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl group unsubstituted or substituted with any one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl
  • Ar1 is a phenyl group unsubstituted or substituted with any one or more selected from a methyl group, isopropyl group, tert-butyl group, cyclohexyl group, phenyl group, and combinations thereof; a biphenyl group unsubstituted or substituted with a tert-butyl group; naphthyl group; a fluorene group unsubstituted or substituted with a methyl group; a tetrahydronaphthyl group unsubstituted or substituted with any one or more selected from a methyl group, a phenyl group, and combinations thereof; tetrahydrobenzofuran group unsubstituted or substituted with a methyl group; tetrahydrobenzothiophene group unsubstituted or substituted with a methyl group; benzofuran group; benzothiophene group;
  • any one of R1 to R3 is deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and any one or more unsubstituted or substituted C6 to 30 carbon atoms selected from combinations thereof a monocyclic or polycyclic aryl group; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkenyl group having 2 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R11 and R12 are the same as or different from each other, and each independently substituted with any one or more selected from deuterium, a linear or branched chain alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and combinations thereof or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • A1 and A2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, A monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and a monocyclic or polycyclic group having 6 to 30 carbon atoms unsubstituted or substituted with any one or more selected from combinations thereof ring aromatic hydrocarbon ring; a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1
  • Ar1 is a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and any one or more selected from combinations thereof or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms;
  • Z1 to Z4 are the same as or different from each other, and each independently a substituted or unsubstituted hydrogen; heavy hydrogen; a linear 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 diarylamine group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms combined with an adjacent group; Or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon
  • Z1 to Z4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain alkyl group having 1 to 30 carbon atoms bonded to an adjacent group and substituted with an alkyl group having 1 to 30 carbon atoms or an un
  • Z1 to Z4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; a diphenylamine group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibiphenylamine group; dinaphthylamine group; phenyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; cyclohexane unsubstituted or substituted with a C1-C30 linear or branched alkyl group; benzofuran;
  • Z1 to Z4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; a diphenylamine group unsubstituted or substituted with a tert-butyl group; dibiphenylamine group; dinaphthylamine group; phenyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a methyl group; Cyclohexane unsubstituted or substituted with a C methyl group; benzofuran; or benzothiophene.
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms combined with an adjacent group; Or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain alkyl group having 1 to 30 carbon atoms bonded to an adjacent group and substituted with an alkyl group having 1 to 30 carbon atoms or an un
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; a diphenylamine group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibiphenylamine group; dinaphthylamine group; phenyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; cyclohexane unsubstituted or substituted with a C1-C30 linear or branched alkyl group; benzofuran;
  • T1 to T4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; a diphenylamine group unsubstituted or substituted with a tert-butyl group; dibiphenylamine group; dinaphthylamine group; phenyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a methyl group; Cyclohexane unsubstituted or substituted with a C methyl group; benzofuran; or benzothiophene.
  • Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms combined with an adjacent group; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
  • Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a straight-chain or branched chain alkyl group having 1 to 30 carbon atoms in combination with an adjacent group, and a carbon number a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with any one or more selected from a monocyclic or polycyclic aryl group having 6 to 30; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is un
  • Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; or a phenyl group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; cyclohexane unsubstituted or substituted with at least one selected from a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzofuran; or benzothiophene.
  • Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; tert-butyl group; cyclohexyl group; or a phenyl group unsubstituted or substituted with a tert-butyl group, or benzene by bonding to an adjacent group; indene unsubstituted or substituted with a methyl group; Cyclohexane unsubstituted or substituted with any one or more selected from a methyl group and a phenyl group; benzofuran; or benzothiophene.
  • X1 is O.
  • X1 is S.
  • X2 is O.
  • X2 is S.
  • A11 and A21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a fused 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.
  • A11 and A21 are the same as or different from each other, and each independently a monocyclic or polycyclic aliphatic having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • hydrocarbon ring A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • A11 and A21 are the same as or different from each other, and each independently a cyclohexane substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or tetrahydronaphthalene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • A11 and A21 are the same as or different from each other, and each independently a methyl group substituted or unsubstituted cyclohexane; benzene unsubstituted or substituted with a methyl group unsubstituted or substituted with deuterium, or a tert-butyl group; Or tetrahydronaphthalene unsubstituted or substituted with a methyl group.
  • Formula 1 is any one selected from the following compounds.
  • triplet energy can be measured using a method known in the art, and specifically, it was measured at 77K using a commercially available F-4500 (manufactured by Hitachi). Measurement of triplet energy is performed as follows. First, a sample in which a solution in which a compound to be measured is dissolved in an appropriate solvent is sealed in a quartz glass tube is prepared.
  • a phosphorescence spectrum (vertical axis: phosphorescence intensity, abscissa: wavelength) is measured at a low temperature (77 K), a tangent line is drawn from the short wavelength side of the phosphorescence spectrum, and the wavelength value ⁇ at the intersection of the tangent line and the abscissa axis Based on edge (nm), triplet energy was calculated by substituting into the following conversion equation.
  • the singlet energy can be measured using a method known in the art, specifically, a 1 ⁇ 10 -5 mol/L toluene solution of the compound to be measured is prepared, and placed in a quartz cell at room temperature (300K) Measure the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample. A tangent line was drawn with respect to the fall on the long-wavelength side of this absorption spectrum, and the wavelength value ⁇ edge (nm) of the intersection of the tangent and the abscissa was substituted into the following conversion formula to calculate the singlet energy.
  • the structure of the ground state is optimized through density functional theory (DFT) calculation, and singlet excitation energy and triplet excitation energy are calculated through time-dependent-density functional theory (TD-DFT) calculation.
  • DFT density functional theory
  • TD-DFT time-dependent-density functional theory
  • the energy level means the size of energy. Therefore, even when the energy level is displayed in the negative (-) direction from the vacuum level, the energy level is interpreted as meaning the absolute value of the corresponding energy value.
  • the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital.
  • the LUMO energy level means the distance from the vacuum level to the lowest unoccupied molecular orbital.
  • the measurement of the HOMO energy level may use UV photoelectron spectroscopy (UPS), which irradiates UV to the surface of the thin film, and detects the electrons protruding at this time to measure the ionization potential of the material.
  • UPS UV photoelectron spectroscopy
  • the measurement of the HOMO energy level may be performed using cyclic voltammetry (CV) in which a measurement target material is dissolved in a solvent together with an electrolyte and then an oxidation potential is measured through a voltage sweep.
  • CV cyclic voltammetry
  • a PYSA Photoemission Yield Spectrometer in Air
  • RKI machine of AC-3
  • the HOMO energy level of the present specification was measured by vacuum-depositing a target material to a thickness of 50 nm or more on an ITO substrate, and then using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3).
  • the LUMO energy level is measured by measuring the absorption spectrum (abs.) and photoluminescence (PL) spectrum of the prepared sample, and then calculating the edge energy of each spectrum and reporting the difference as a band gap (E g ), The LUMO energy level was calculated by subtracting the bandgap difference from the HOMO energy level measured in AC-3.
  • the present specification provides an organic light emitting device including the above-described compound.
  • the 'layer' means compatible with a 'film' mainly used in the present technical field, and refers to a coating covering a desired area.
  • the size of the 'layers' is not limited, and each of the 'layers' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
  • the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.
  • deuterated means that hydrogen at a substitutable position of a compound is replaced with deuterium.
  • X% substitution with deuterium means that X% of hydrogens at substitutable positions in the structure is deuterium it means that it has been
  • the dibenzofuran is "25% substituted with deuterium”
  • the dibenzofuran is "25% deuterated”
  • the dibenzofuran is "25% deuterated”
  • the dibenzofuran is “25% deuterated”
  • the “deuterium substitution rate of 25%” of the dibenzofuran means that two of 8 hydrogens at substitutable positions of the dibenzofuran are substituted with deuterium.
  • the degree of deuteration is nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix assisted laser desorption / ionization Time-of-Flight Mass Spectrometry) ) can be confirmed by a known method.
  • the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Chemical Formula 1 as a blue fluorescent dopant of the emission layer.
  • the organic light emitting device includes a hole injection layer and a hole transport layer. It further includes one or more 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, wherein at least one hydrogen in a substitutable position is substituted with deuterium in the host compound.
  • the host compound when the host compound is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the host compound is substituted with deuterium by 40% or more. In another exemplary embodiment, the host compound is substituted with deuterium by 60% or more. In another exemplary embodiment, the host compound is substituted with deuterium by 80% or more. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
  • the light emitting layer further includes a compound represented by the following formula (H).
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R20 and R21 are the same as or different from each other, and each independently represent hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r21 is an integer of 1 to 7, and when r21 is 2 or more, 2 or more R21 are the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 monocyclic to 4 ring heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofur
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R200 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 linear or branched alkyl group; 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 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 C1-C10 linear or branched alkyl group; 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 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 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 a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.
  • R200 is hydrogen; a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 monocyclic to 4 ring heterocyclic group.
  • R200 is hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted
  • 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 unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclcyclic aryl group having 6 to
  • R200 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; biphenyl group; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.
  • R201 is hydrogen
  • R201 is deuterium
  • the compound represented by Formula H is any one selected from the following compounds.
  • the compound represented by Formula H may be prepared by the following Formula 1, but is not limited thereto.
  • Ar 1 is the same as defined for -L20-Ar20 of Formula H,
  • Ar 2 has the same definition as -L21-Ar21 of Formula H, and R20 and R201 may be further substituted in the anthracene core of Formula 1 above.
  • the compound represented by Formula 1 is used as a dopant in the emission layer, and the compound represented by Formula H is used as a host.
  • the content of the dopant may be selected from 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 are in a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30 by weight, even more preferably 99 It is included 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 heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type and a furan compound, a pyrimidine derivative, or a triazine derivative, and may be a mixture of two or more thereof, but is not limited thereto.
  • the organic material layer includes an emission layer, and the emission layer includes one or more dopants, and a host.
  • the organic material layer includes an emission layer, and the emission layer includes two or more mixed dopants and a host.
  • At least one of the two or more mixed dopants includes Formula 1, and the host includes a compound represented by Formula H.
  • At least one of the two or more types of mixed dopants includes Chemical Formula 1, and for the rest, a dopant material known in the art may be used, but the present invention is not limited thereto.
  • At least one of the two or more mixed dopants includes Formula 1, and the remainder uses at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1
  • the present invention is not limited thereto.
  • the organic material layer includes an emission layer, and the emission layer includes one or more hosts.
  • the organic material layer includes an emission layer, and the emission layer includes two or more types of mixed hosts.
  • At least one of the two or more types of mixed hosts is a compound represented by Formula H.
  • the two or more types of mixed hosts are different from each other and each independently represent a compound represented by Formula H.
  • the organic material layer includes an emission layer, and the emission 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 are represented by Formula H is a compound that becomes
  • the organic material layer includes a light emitting layer, the first host represented by the formula (H); and a second host represented by Formula H, wherein the first host and the second host are different from each other.
  • the first host the second host is included in a weight ratio of 95:5 to 5:95, preferably 70:30 to 30:70 by weight.
  • the organic material layer includes an emission layer, and the emission layer includes at least one host and a dopant.
  • the organic material layer includes a light emitting layer, the light emitting layer includes at least one host and a dopant, the host includes a compound represented by Formula H, and the dopant is a compound represented by Formula H The compound represented by 1 is included.
  • the organic material layer includes an emission layer, and the emission layer includes two or more mixed hosts, and a dopant.
  • At least one of the two or more types of mixed hosts includes the compound represented by Formula H, and the dopant includes the compound represented by Formula 1 above.
  • the two or more types of mixed hosts are different from each other.
  • the organic material layer includes an emission layer, and the emission 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 the compound represented by Formula H, and the dopant includes the compound represented by Formula 1 above.
  • the first host represented by the formula (H); a second host represented by the formula (H); and a dopant represented by Formula 1, wherein the first host and the second host are different from each other.
  • the organic material layer uses at least one host and at least one dopant, the at least one host includes the compound represented by Formula H, and the at least one dopant is and a compound represented by the formula (1).
  • the organic material layer uses two or more types of mixed hosts and two or more types of mixed dopants, and the two or more types of mixed hosts may use the same material as described above, and a mixture of the two or more types The dopant may use the same material as described above.
  • the organic material layer includes an emission layer
  • the emission layer includes a dopant material
  • the dopant material includes the compound of Formula 1 above.
  • the light emitting layer further includes one or more dopants and a host.
  • the at least one dopant may be a dopant material known in the art, but is not limited thereto.
  • the light emitting layer further includes one or more hosts.
  • the at least one host includes a compound represented by Formula (H).
  • the light emitting layer further includes two or more types of mixed hosts. At least one of the two or more types of mixed hosts includes the compound represented by the above formula (H).
  • 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 include a compound represented by Formula (H).
  • the organic light emitting device includes a first electrode; a 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, wherein at least one of the two or more organic material layers includes a compound represented by Formula 1 above.
  • the two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, 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 material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.
  • materials other than the compound represented by Formula 1 may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant those known in the art may be used, for example, a metal or a metal complex may be used.
  • the electron transport layer including the compound represented by 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 represented by Formula 1 above.
  • the compound represented by 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 includes a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 may include
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate the structure of the organic light emitting device according to an exemplary embodiment of the present specification.
  • 1 and 2 illustrate an organic light emitting device, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a 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 hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a first electron transport layer 8, a second
  • the structure of the organic light emitting device in which the electron transport layer 9, the electron injection layer 10, 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 may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by 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 may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO 2 /Al, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material include a condensed aromatic ring derivative or a compound containing a heterocyclic ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
  • an additional compound when included as the dopant material in addition to the compound represented by Formula 1, there may be an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, or a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the light emitting material of the light emitting layer receives holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines them
  • a material capable of emitting light in the visible light region a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxy-quinoline aluminum complex Alq 3
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compounds
  • compounds of the benzoxazole, benzthiazole and benzimidazole series Poly(p-phenylenevinylene) (PPV)-based polymers
  • spiro compounds polyfluorene; and rubrene, but is not limited thereto.
  • the hole injection layer is a layer that injects holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, so that it has a hole injection effect at the first electrode and an excellent hole injection effect on the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection material metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; carbazole-based organics; nitrile-based organics; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; 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 transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material a material capable of transporting holes from the first electrode or the hole injection layer to the light emitting layer and having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of well injecting electrons from the second electrode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives; LiQ, etc., but is not limited thereto.
  • the electron transport layer may be used with any desired first electrode material, as used in accordance with the prior art.
  • suitable first electrode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.
  • the electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has excellent electron transport ability and has excellent electron injection effect from the second electrode and the electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives, and mixtures of two or more of the above examples, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer.
  • a known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that blocks holes from reaching the cathode through the light emitting layer, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but is not limited thereto.
  • the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the compound according to the present specification may act on a principle similar to that applied to an organic light emitting device in an organic light emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and the like.
  • the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.
  • the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
  • Intermediate 12-1 was used instead of Intermediate 1-1 and (4,4,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)boronic acid was used instead of Phenyl boronic aicd. Except for that, intermediate 12-2 was obtained in the same manner as in the preparation method of intermediate 1-2 of Preparation Example 2.
  • Compound 12 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 3, except that Intermediate 11-2 was used instead of Intermediate 1-2.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,400 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermal vacuum deposition of the following HI-A and LG-101 to a thickness of 650 ⁇ and 50 ⁇ , respectively, on the ITO transparent electrode prepared as described above.
  • the following HT-A was vacuum-deposited to a thickness of 600 ⁇ to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • 4 wt% of Compound 1 as a blue light emitting dopant based on the total weight of the light emitting layer and BH-A as a host were vacuum deposited to a thickness of 200 ⁇ to form a light emitting layer.
  • ET-A 50 ⁇ of the following compound ET-A was vacuum-deposited as a first electron transport layer on the light emitting layer, and the following ET-B and LiQ were vacuum-deposited in a 1:1 weight ratio to form an electron transport layer to a thickness of 360 ⁇ .
  • LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer by vacuum deposition to a thickness of 5 ⁇ .
  • aluminum and silver were deposited to a thickness of 220 ⁇ in a weight ratio of 10:1, and aluminum was deposited thereon to a thickness of 1000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the deposition rate of the aluminum of the cathode was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr to manufacture an organic light emitting device.
  • Examples 1-2 to 1-28 were prepared in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the host and dopant compounds of the light emitting layer in Example 1-1. Each organic light emitting device was fabricated.
  • T 95 represents the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%.

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Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/016086 2020-11-13 2021-11-08 Composé et dispositif électroluminescent organique le comprenant WO2022103090A1 (fr)

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CN111574544A (zh) * 2019-02-18 2020-08-25 江苏三月科技股份有限公司 一种含硼的有机化合物及其在有机电致发光器件上的应用
WO2021015417A1 (fr) * 2019-07-23 2021-01-28 에스에프씨 주식회사 Composés électroluminescents organiques et dispositif électroluminescent organique
CN111269250A (zh) * 2020-03-09 2020-06-12 杨曦 一种有机化合物及其在有机电子器件的应用

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