WO2021107678A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2021107678A1
WO2021107678A1 PCT/KR2020/017069 KR2020017069W WO2021107678A1 WO 2021107678 A1 WO2021107678 A1 WO 2021107678A1 KR 2020017069 W KR2020017069 W KR 2020017069W WO 2021107678 A1 WO2021107678 A1 WO 2021107678A1
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group
substituted
unsubstituted
compound
mmol
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PCT/KR2020/017069
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Korean (ko)
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김선우
홍완표
금수정
김명곤
김경희
조혜민
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주식회사 엘지화학
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Priority claimed from KR1020200060597A external-priority patent/KR20210067844A/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2021539575A priority Critical patent/JP7143570B2/ja
Priority to CN202080009134.3A priority patent/CN113366002B/zh
Priority to US17/428,032 priority patent/US20220089617A1/en
Priority to EP20891826.8A priority patent/EP3909958B1/fr
Publication of WO2021107678A1 publication Critical patent/WO2021107678A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • 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 is a substituted or unsubstituted monocyclic or polycyclic heterocycle including a 5-membered ring including O or S,
  • R1 to R7, R′ and R′′ are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted haloalkyl group; substituted or unsubstituted cyclo Alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted haloalkoxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted
  • 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 described herein may be used as a material for an organic material layer of an organic light emitting device.
  • the compound according to another exemplary embodiment may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.
  • the organic light emitting device according to an exemplary embodiment of the present specification has effects of low driving voltage, high efficiency, or long lifespan.
  • 1 to 3 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
  • FIG. 4 is a diagram illustrating a photoluminescence analysis graph according to Experimental Example 1 of the present specification.
  • thermogravimetric analysis graph of Compound 19 is a diagram showing a thermogravimetric analysis graph of Compound 19 according to Experimental Example 3 of the present specification.
  • thermogravimetric analysis graph of compound BD-A according to Experimental Example 3 of the present specification.
  • thermogravimetric analysis graph of compound BD-C according to Experimental Example 3 of the present specification.
  • Conventional boron compounds have a half width of about 23 to 30 nm, and a wavelength of a basic core structure of about 453 nm, but the stability of the material is relatively lower than that of the amine compound, and thus the lifespan is lowered. Therefore, there is a need for a method for securing a long lifespan by increasing the stability of a material while maintaining excellent optical properties by controlling the substituents of the boron compound.
  • the compound of Formula 1 is a compound using electrons abundant in a structure including a monocyclic or polycyclic heterocycle including a 5-membered ring including O or S, in which A1 is substituted or unsubstituted. Structural stability and excellent electrochemical properties can be secured.
  • 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 not limited, and when two or more are 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; Condensed ring groups of aromatic hydrocarbons and aliphatic hydrocarbons; 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 another substituent.
  • a phenyl group and a naphthyl group are connected. or may be a substituent of
  • the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group and an isopropyl group are connected, , or may be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, 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] octyl group, norbornyl group, etc., 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.
  • the "adjacent" group refers to 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 toryloxy group, a 9-phenanthryloxy group, and the like, but is not limited thereto.
  • the alkyl group of the alkyltioxy group is the same as the example of the alkyl group described above.
  • the alkyl thiooxy group includes, but is not limited to, methyl thiooxy group, ethyl thiooxy group, tert-butyl thiooxy group, hexyl thiooxy group, 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 one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms 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, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenoc
  • the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, 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.
  • Examples of can be applied, the heteroaryl group among the heteroarylsilyl group, the examples of the heterocyclic group can be applied.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted 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 includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
  • 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.
  • 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 above-described 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.
  • adjacent two of the substituents combine with each other to form a ring means a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; Or it means to form a substituted or unsubstituted heterocyclic ring.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
  • the hydrocarbon ring group may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring group of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group, an aryl group, and combinations thereof, and the hydrocarbon
  • the cyclic group includes, but is not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a tetrahydronaphthalene group, and a tetrahydroanthracene group.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group, except that it is not monovalent.
  • the hydrocarbon ring may include, but is not limited to, benzene, cyclohexane, adamantane, tetrahydronaphthalene, tetrahydroanthracene, and the like.
  • the heterocycle 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, and the like.
  • the heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heterocyclic group, except that it is not monovalent.
  • 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 are not limited thereto.
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heterocyclic group described above may be applied.
  • Chemical Formula 1 includes at least one condensed aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group.
  • A1 is a substituted or unsubstituted 5-membered monocyclic heterocycle including O, or S; Or a substituted or unsubstituted, O, or a polycyclic heterocycle including a 5-membered heterocycle including S.
  • A1 is a substituted or unsubstituted 5-membered aromatic or aliphatic monocyclic heterocycle including O, or S; Or a substituted or unsubstituted, aromatic, aliphatic, or polycyclic heterocycle of condensed aromatic and aliphatic containing a 5-membered heterocycle containing O, or S.
  • Chemical Formula A1 is represented by the following Chemical Formula A1-1 or A1-2.
  • Y1 and Y3 are the same as or different from each other, and each independently O; or S;
  • G1, G2 and G7 to G10 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted or unsubsti
  • A1 is a structure represented by any one of the following Chemical Formulas A1-3 to Al-5.
  • Y2, Y4 and Y5 are the same as or different from each other, and each independently O; or S;
  • G3 to G6 and G11 to G28 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted or unsub
  • n11 and n12 are each an integer of 0 to 2
  • Chemical Formula A1-1 is represented by the following Chemical Formula A1-1-1 or A1-1-2.
  • Y1 is O; or S;
  • Z1 is O; S; CR201R202; or NR203;
  • G301 to G304 and R201 to R203 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted or unsub
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5.
  • R', R" and R1 to R7 are the same as those defined in Formula 1 above,
  • Y1 to Y5 are the same as or different from each other, and each independently O; or S;
  • G1 to G28 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted sily
  • n11 and n12 are each an integer of 0 to 2
  • Chemical Formula 1 is represented by the following Chemical Formulas 1-1-1, 1-1-2, 1-1-3, 1-1-4, 1-1-5, 1-1-6 , any of 1-2-1, 1-2-2, 1-3-1, 1-3-2, 1-4-1, 1-4-2, 1-5-1, and 1-5-2 displayed as one
  • R', R" and R1 to R7 are the same as those defined in Formula 1 above,
  • Y1 to Y5 are the same as or different from each other, and each independently O; or S;
  • Z1 is O; S; CR201R202; or NR203;
  • G1 to G28, G301 to G304 and R201 to R203 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group;
  • n11 and n12 are each an integer of 0 to 2
  • adjacent groups of R1 to R4 may be bonded to each other to form a substituted or unsubstituted 5-membered monocyclic heterocycle; Or substituted or unsubstituted, to form a polycyclic heterocycle including a 5-membered heterocycle.
  • adjacent groups of R1 to R4 are bonded to each other, a substituted or unsubstituted 5-membered monocyclic heterocycle including N, O, or S; Or substituted or unsubstituted, to form a polycyclic heterocycle including a 5-membered heterocycle including N, O, or S.
  • adjacent groups of R1 to R4 may be bonded to each other, may be substituted or unsubstituted, and may include a 5-membered aromatic or aliphatic monocyclic heterocycle including N, O, or S; Or a substituted or unsubstituted, aromatic, aliphatic, or polycyclic heterocycle containing a 5-membered heterocycle containing N, O, or S is formed by condensation of aromatic and aliphatic.
  • adjacent groups of R1 to R4 are bonded to each other to form a ring represented by the following Chemical Formula B1-1 or B1-2.
  • Y101 and Y103 are the same as or different from each other, and each independently O; S; or NR"';
  • R"', G101, G102, and G107 to G110 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted haloalkyl group; substituted or unsubstituted a cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylalkyl group; substituted or unsubstituted
  • adjacent groups of R1 to R4 are bonded to each other to form a ring represented by any one of Formulas B1-3 to Bl-5.
  • Y102, Y104 and Y105 are the same as or different from each other, and each independently O; S; or NR"';
  • R"', G103 to G106 and G111 to G128 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted haloalkyl group; substituted or unsubstituted a cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylalkyl group; substituted or unsubstituted
  • n111 and n112 are each an integer from 0 to 2
  • Chemical Formula B1-1 is represented by the following Chemical Formula B1-1-1 or B1-1-2.
  • Y101 is O; S; or NR304;
  • Z101 is O; S; CR301R302; or NR303;
  • G401 to G404 and R301 to R304 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 haloalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a substituted or unsub
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-6 to 1-30.
  • R', R" and R1 to R7 are the same as those defined in Formula 1 above,
  • Y1 to Y5 are the same as or different from each other, and each independently O; or S;
  • Y101 to Y105 are the same as or different from each other, and each independently O; S; or NR"';
  • R"', R101, G1 to G28 and G101 to G128 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted haloalkyl group; substituted or an unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkenyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylalkyl group; a
  • n11, n12, n111 and n112 are each an integer from 0 to 2
  • r101 is 1 or 2
  • Y2 is O or S.
  • a group in which adjacent groups of R1 to R4 do not form a substituted or unsubstituted ring with each other is hydrogen.
  • R1 to R4 are hydrogen.
  • R101 is hydrogen
  • R1 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano 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 C1-C30 linear or branched alkylsilyl group; a substituted or unsubstituted C1-C30 linear or branched haloalkyl group; a substituted or unsubstituted C1-C30 linear or branched haloalkoxy group; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms; a substituted or unsubstituted
  • R1 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; 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 linear or branched alkylsilyl group having 1 to 30 carbon atoms; a linear or branched haloalkyl group having 1 to 30 carbon atoms; a linear or branched haloalkoxy group having 1 to 30 carbon atoms; an arylalkyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 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, and the substituents are deuterium, a halogen group,
  • R1 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; methyl group; tert-butyl group; -CD 3 ; -CF 3 ; -OCF 3 ; queuing; trimethylsilyl group; diphenylamine group; cyclohexyl group; phenyl group; adamantyl group; or a carbazole group, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of deuterium, -F, a cyano group, a methyl group, a trimethylsilyl group, a tert-butyl group, and combinations thereof.
  • R6 is deuterium; cyano group; methyl group; tert-butyl group; -CD 3 ; -CF 3 ; -OCF 3 ; queuing; trimethylsilyl group; diphenylamine group; cyclohexyl group; phenyl group; adamantyl group; or a carbazole group, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of deuterium, -F, a cyano group, a methyl group, a trimethylsilyl group, a tert-butyl group, and combinations thereof.
  • R1 to R5 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; methyl group; tert-butyl group; -CD 3 ; -CF 3 ; -OCF 3 ; queuing; trimethylsilyl group; diphenylamine group; cyclohexyl group; phenyl group; adamantyl group; or a carbazole group, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of deuterium, -F, a cyano group, a methyl group, a trimethylsilyl group, a tert-butyl group, and combinations thereof.
  • R1 to R7 are the same as or different from each other, and are each independently a group represented by any one of the structures of Group C below.
  • R10 and R11 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r10 is an integer from 1 to 10
  • r11 is an integer from 1 to 8;
  • r1 is 0 or 1
  • r2 is 0 or 1
  • R1 to R7 are the same as or different from each other, and are each independently a group represented by any one of the structures of Group D below.
  • R100 to R115 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r100, r101, r108 and r109 are each an integer from 1 to 8;
  • r102 and r107 are each an integer from 1 to 12,
  • r103 and r104 are each an integer from 1 to 10,
  • r105 is an integer from 1 to 6
  • r106 and r110 to r113 are each an integer of 1 to 4,
  • r114 is an integer from 1 to 14;
  • r115 is an integer from 1 to 18,
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group.
  • R100 to R115 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 C1-C30 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1-C20 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R100 to R115 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 substituted or unsubstituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; -CD 3 ; tert-butyl group; cyclohexyl group; trimethyl silyl group; Or a phenyl group unsubstituted or substituted with deuterium.
  • adjacent groups of R1 to R4 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle is formed.
  • adjacent groups of R1 to R4 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
  • adjacent groups of R1 to R4 are bonded to each other and include a substituted or unsubstituted monocyclic or polycyclic aliphatic, aromatic, or aliphatic and aromatic condensed hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms is formed.
  • adjacent groups of R1 to R4 are bonded to each other to form a monocyclic or polycyclic aliphatic, aromatic, or aliphatic and aromatic condensed hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, wherein the ring is a linear or branched alkyl group having 1 to 30 carbon atoms, and a linear or branched haloalkyl group having 1 to 30 carbon atoms It is substituted or unsubstituted with one or more selected from the group consisting of.
  • adjacent groups of R1 to R4 are bonded to each other to form a cyclopentane ring; cyclohexane ring; cycloheptane ring; bicyclo[2.2.1]octane ring; norbornane ring; adamantane ring; indene ring; phenanthrene ring; tetrahydrofuran ring; tetrahydrothiophene ring; pyrrolidine ring; tetrahydrobenzofuran ring; tetrahydrobenzothiophene ring; octahydrobenzofuran ring; octahydrobenzothiophene ring; octahydrocycloheptaindole ring; octahydroheptapyrrole ring; octahydroindene ring; benzene ring; phenanthrene ring;
  • R' is a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R' is a linear or branched alkyl group having 1 to 30 carbon atoms; an arylalkyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic hydrocarbon ring group having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, the substituents being deuterium, a halogen group, a cyano group, 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 linear or branched alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 3 to 30 carbon atoms, a linear or branched alkoxy group having 1 to 30 carbon atoms, a linear or branched haloalkyl group having 1 to 30 carbon atoms, a haloalkyl
  • R' is a methyl group; tert-butyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; fluorene group; triphenylene group; dibenzofuran group; cumyl group; adamantyl group; tetrahydronaphthyl group; or a hexahydrodibenzofuran group, and the substituents are deuterium, F, cyano group, methyl group, tert-butyl group, -CD 3 , -CF 3 , -OCF 3 , cyclohexyl group, phenyl group, diphenylamine group, pyridine It is unsubstituted or substituted with one or more selected from the group consisting of a group, a pyrimidine group, a methoxy group, an i-propyl group, a phenoxy group, a triphenyl
  • R" is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; substituted or unsubstituted C3 to 30 monocyclic or polycyclic hydrocarbon ring group, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R" is a linear or branched alkyl group having 1 to 30 carbon atoms; an arylalkyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic hydrocarbon ring group having 3 to 30 carbon atoms; or 2 to carbon atoms 30 is a monocyclic or polycyclic heterocyclic group, and the substituents are deuterium, a halogen group, a cyano group, 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 cycloalkyl group having 1 to 30 carbon atoms.
  • a linear or branched alkylsilyl group an arylsilyl group having 3 to 30 carbon atoms, a straight or branched chain alkoxy group having 1 to 30 carbon atoms, a straight or branched chain haloalkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms
  • a linear or branched haloalkoxy group an aryloxy group having 6 to 30 carbon atoms, a monocyclic or polycyclic arylalkyl group having 6 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic group having 6 to 30 carbon atoms Or a polycyclic aryl group, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic group having 3 to 30 carbon atoms, and a monocyclic or polycyclic aromatic condensed
  • R" is a methyl group; a tert-butyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorene group; a triphenylene group; a dibenzofuran group; a cumyl group; adamantyl group; tetrahydronaphthyl group; or hexahydrodibenzofuran group, wherein the substituents are deuterium, F, cyano group, methyl group, tert-butyl group, -CD 3 , -CF 3 , -OCF 3 , cyclohexyl group , a phenyl group, a diphenylamine group, a pyridine group, a pyrimidine group, a methoxy group, an i-propyl group, a phenoxy group, a triphenyl
  • Y1 is O.
  • Y1 is S.
  • Y2 is O.
  • Y2 is S.
  • Y3 is O.
  • Y3 is S.
  • Y4 is O.
  • Y4 is S.
  • Y5 is O.
  • Y5 is S.
  • Y101 is O.
  • Y101 is S.
  • Y101 is NR"'.
  • Y102 is O.
  • Y102 is S.
  • Y102 is NR"'.
  • Y103 is O.
  • Y103 is S.
  • Y103 is NR"'.
  • Y104 is O.
  • Y104 is S.
  • Y104 is NR"'.
  • Y105 is O.
  • Y105 is S.
  • Y105 is NR"'.
  • R1 and G2 are combined with each other to form a substituted or unsubstituted heterocycle.
  • R1 and G2 are combined with each other to form a heterocycle including substituted or unsubstituted B and N.
  • R1 and G2 are combined with each other to form a 6-membered heterocycle including substituted or unsubstituted B and N.
  • R1 and G2 are combined with each other to form a heterocycle substituted with an aryl group.
  • R1 and G2 are combined with each other to form a heterocycle including B and N substituted with an aryl group.
  • R1 and G2 are combined with each other to form a 6-membered heterocycle including B and Si substituted with a phenyl group.
  • R4 and R' are bonded to each other to form a ring in any one of the structures represented by the following Group A.
  • R10 to R14 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r10 is an integer from 1 to 10
  • r11 is an integer from 1 to 8;
  • r12 is an integer from 1 to 6
  • each of the r10 to r12 is 2 or more, the structures in the two or more parentheses are the same as or different from each other,
  • r1 is 0 or 1
  • r2 is 0 or 1.
  • R4 and R' combine with each other to form a ring in any one of the structures represented by Group B below.
  • R100 to R120 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r100, r101, r108, r109 and r116 to r118 are each an integer of 1 to 8;
  • r102 and r107 are each an integer of 1 to 12,
  • r103 and r104 are each an integer from 1 to 10,
  • r105 is an integer from 1 to 6
  • r106 and r110 to r113 are each an integer of 1 to 4,
  • r114 is an integer from 1 to 14;
  • r115 is an integer from 1 to 18,
  • each of r100 to r118 is two or more, the structures in the two or more parentheses are the same as or different from each other.
  • R100 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group.
  • R100 to R120 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 C1-C30 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R100 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1-C20 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R100 to R120 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 substituted or unsubstituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; -CD 3 ; tert-butyl group; cyclohexyl group; trimethyl silyl group; Or a phenyl group unsubstituted or substituted with deuterium.
  • the G1 to G28 and G101 and G128 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted C1-C30 linear or branched haloalkyl 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 alkylsilyl group; a substituted or unsubstituted monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic diarylamine group having 6 to 30 carbon atom
  • the G1 to G28 and G101 and G128 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; a linear or branched haloalkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; an arylalkyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 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, and the substituent is substituted with
  • the G1 to G28 and G101 and G128 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; methyl group; i-propyl group; tert-butyl group; -CF 3 ; adamantyl group; trimethylsilyl group; triphenylsilyl group; diphenylamine group; phenyl group; naphthyl group; cumyl group; pyridyl group; or a carbazole group, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of deuterium, F, a methyl group, a tert-butyl group, and combinations thereof.
  • R"' is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aliphatic, aromatic, or A condensed hydrocarbon ring group of an aliphatic and an aromatic, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • R"' is a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aliphatic, aromatic, or aliphatic and aromatic condensed hydrocarbon ring group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and the substituents are deuterium, a halogen group, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched chain haloalkyl group having 1 to 30 carbon atoms, and their It is substituted or unsubstituted with one or more selected from the group consisting of combinations.
  • R"' is a tert-butyl group; a phenyl group; a biphenyl group; a tetrahydrobenzofuran group; a pyridine group; or a triazine group
  • the substituents are deuterium, F, -CF 3 , a methyl group , tert- butyl group, and unsubstituted or substituted with one or more selected from the group consisting of combinations thereof.
  • G1 to G28 and G101 and G128 are the same as or different from each other, and are each independently a group represented by any one of the structures of Group C below.
  • R10 and R11 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r10 is an integer from 1 to 10
  • r11 is an integer from 1 to 8;
  • r1 is 0 or 1
  • r2 is 0 or 1
  • G1 to G28 and G101 and G128 are the same as or different from each other, and are each independently a group represented by any one of the structures of Group D below.
  • R100 to R115 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 alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r100, r101, r108 and r109 are each an integer from 1 to 8;
  • r102 and r107 are each an integer from 1 to 12,
  • r103 and r104 are each an integer from 1 to 10,
  • r105 is an integer from 1 to 6
  • r106 and r110 to r113 are each an integer of 1 to 4,
  • r114 is an integer from 1 to 14;
  • r115 is an integer from 1 to 18,
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group.
  • R100 to R115 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 C1-C30 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1-C20 linear or branched alkylsilyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R100 to R115 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 substituted or unsubstituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a linear or branched alkylsilyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R100 to R115 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; -CD 3 ; tert-butyl group; cyclohexyl group; trimethyl silyl group; Or a phenyl group unsubstituted or substituted with deuterium.
  • adjacent groups of G1 to G28 and G101 and G128 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle is formed.
  • adjacent groups of G1 to G28 and G101 and G128 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
  • adjacent groups of G1 to G28 and G101 and G128 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic, aromatic, or aliphatic and aromatic condensed hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms is formed.
  • adjacent groups of G1 to G28 and G101 and G128 are bonded to each other to form a monocyclic or polycyclic aliphatic, aromatic, or aliphatic and aromatic condensed hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms is formed, and the ring is monocyclic or polycyclic having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • adjacent groups of G1 to G28 and G101 and G128 are bonded to each other to form a cyclopentane ring; cyclohexane ring; cycloheptane ring; bicyclo[2.2.1]octane ring; norbornane ring; adamantane ring; indene ring; phenanthrene ring; tetrahydrofuran ring; tetrahydrothiophene ring; tetrahydronaphthofuran ring; tetrahydranaphthothiophene ring; pyrrolidine ring; octahydrobenzofuran ring; octahydrobenzothiophene ring; octahydroindene ring; benzene ring; phenanthrene ring; benzofuran ring; fluorene ring; dihydroanthracene
  • R"' and G102 are combined with each other to form a substituted or unsubstituted heterocycle.
  • the R"' and G102 are combined with each other to form a heterocycle including substituted or unsubstituted B and N.
  • the R"' and G102 are combined with each other to form a 6-membered heterocycle including substituted or unsubstituted B and N.
  • the R"' and G102 are bonded to each other to form a heterocycle.
  • the R"' and G102 are combined with each other to form a heterocycle including B and N.
  • the R"' and G102 are combined with each other to form a 6-membered heterocycle including B and N.
  • Formula 1 is any one selected from the following compounds.
  • Ph means a phenyl group
  • A1 of Formula 1 is benzofuran substituted with a t-butyl group or benzothiophene substituted with a t-butyl group
  • R′ and R′′ are each independently a t-butyl group or iso
  • a compound in which a phenyl group substituted with a propyl group or a biphenyl group substituted with a t-butyl group and R2 or R3 is a t-butyl group or hydrogen, R6 is a terbutyl group, a phenyl group, or an adamantyl group is excluded.
  • A1 of Formula 1 is benzofuran or dibenzofuran
  • a compound that is a diphenylamine group unsubstituted or substituted with a t-butyl group in R2 is excluded.
  • R′ and R′′ are each independently a phenyl group substituted with a t-butyl group, and R3 is a t-butyl group, R6 The compound which is this methyl group or a cyclohexyl group is excluded.
  • A1 of Formula 1 is benzofuran or dibenzofuran
  • R' and R" are each independently a biphenyl group substituted with a t-butyl group
  • R3 is a substituted with a t-butyl group
  • R6 is a methyl group
  • A1 of Formula 1 is benzofuran or dibenzofuran
  • R' and R" are each independently a biphenyl group or a phenyl group substituted with a diphenylamine group
  • R1 to R4 are hydrogen
  • R6 is a cyclohexyl group
  • Formula 1 when A1 of Formula 1 includes a 5-membered aliphatic or aromatic heterocycle, and A1 of Formula 1 includes a 5-membered aromatic heterocycle, Formula 1 is an aliphatic hydrocarbon condensed ring includes at least one.
  • the present specification provides an organic light emitting device including the above-described compound.
  • the 'layer' means compatible with the '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 'layer' 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 D, or iii) ) means all of which are included in one or more C-layers and one or more D-layers, respectively.
  • 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 layer of the organic material layer 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 a 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 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 at a substitutable position is substituted with deuterium in the host compound.
  • the host compound when the host compound is substituted with deuterium, it is substituted with deuterium by 30% or more. 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 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • 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; phenylene group; biphenylrylene group; naphthylene group; 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 monocyclic to 4cyclic heterocyclic group having 6 to 20 carbon atoms.
  • 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 represent 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
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; biphenyl group; a naphthyl group unsubstituted or substituted with deuterium; 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.
  • R 20 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.
  • R 20 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.
  • R 20 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; a naphthyl group unsubstituted or substituted with deuterium or a phenyl group; biphenyl group; dibenzofuran group; or a dibenzothiophene group.
  • the compound represented by Formula H is any one selected from the following compounds.
  • 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 99:1 to 1:99 by weight, 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 include 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 mixed dopants may include 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 at least one host.
  • 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 includes the above formula 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 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 include a compound represented by Formula H, and the dopant includes a compound represented by Formula 1 above.
  • the organic material layer includes a light emitting layer, 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, and the at least one host includes a 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 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, and 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 containing 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 above.
  • a hole injection layer or a hole transport layer containing 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 above. 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 to 3 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 .
  • the compound is included in one or more of the light emitting layer 3 , the hole blocking layer 6 , the electron injection and transport layer 7 , and the hole injection layer 8 .
  • the 3 is a substrate (1), a first electrode (2), a hole injection layer (5), a hole transport layer (8), an electron blocking layer (9), a light emitting layer (3), a first electron transport layer (10), the second
  • 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 a substrate to form an anode.
  • It may 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 heterocyclic compound containing compound.
  • 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.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex, in addition to the compound represented by Formula 1 above.
  • 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 and bonds holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • 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 for injecting holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus 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. Also, 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 ocupied 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 ocupied molecular orbital
  • the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; carbazole-based organics; nitrile-based organics; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic materials; 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 is a material capable of transporting holes from the first electrode or the hole injection layer to the light emitting layer, and a material 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, samarium, and the like, followed by an aluminum layer or a silver layer in each case.
  • the electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has excellent electron transporting ability and has excellent electron injection effect from the second electrode and 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, perylenetetracarboxylic 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 lifetime 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.
  • N 1 , N 1 -bis(phenyl- d 5 ) -N 3 -(4-trimethylsilylphenyl)benzene-1,3-diamine 47.8 mmol, 20 g
  • 1-bromo-3- Chloro-5-methylbenzene 47.8 mmol, 9.82 g
  • toluene 0.2 M, 240 ml
  • sodium terbutoxide 7.17 mmol, 6.89 g
  • bis (tri-terbutylphosphine) palladium (0) 0.478 mmol, 0.244 g
  • N -(4-terbutylphenyl)-5'-methyl-[1,1',3',1''-terphenyl]-2'-amine 76.6 mmol, 30 g
  • 1- Bromo-3-chloro-5-terbutylbenzene 76.6 mmol, 19.0 g
  • toluene 0.2 M, 380 ml
  • sodium terbutoxide 115 mmol, 11.0 g
  • bis(tri-terbutylphosphine) After adding palladium (0) (0.766 mmol, 0.392 g), the mixture was stirred for 12 hours under reflux conditions in an argon atmosphere.
  • N- (4-terphenyl)-1,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 114 mmol, 40 g
  • 1 -Bromo-3-chloro-5-methylbenzene 114 mmol, 23.5 g
  • toluene 0.2 M, 572 ml
  • sodium terbutoxide 172 mmol, 16.5 g
  • bis(tri-terbutylphosphine) After adding palladium (0) (1.14 mmol, 0.585 g), the mixture was stirred for 24 hours under reflux conditions in an argon atmosphere.
  • N,N -bis(2-fluorophenyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro- 1H -carbazol-5-amine (34.1 mmol, 13.8 g) and 1-bromo-3-chloro-5-methylbenzene (34.1 mmol, 7 g) were dissolved in toluene (0.2 M, 170 ml), and sodium terbutoxide (51.1 mmol, 4.91 g), bis(tri -terbutylphosphine)palladium(0) (0.341 mmol, 0.174 g) was added, and the mixture was stirred under reflux conditions in an argon atmosphere for 4 hours.
  • compound 22-b (18.2 mmol, 16.5 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 180 ml), boron triiodide (29.1 mmol, 11.4 g) was added, and argon atmosphere 140 The mixture was stirred at °C for 3 hours. The reaction mass was cooled to 0 °C, N,N-diisopropylethylamine (164 mmol, 21.1 g) was added, and the mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H 2 O.
  • 5-tertbutyl- N- (4-triphenylsilylphenyl)-[1,1'-biphenyl]-2-amine (53.6 mmol, 30 g) and 1-bromo-3-chloro- Dissolve 5-methylbenzene (53.6 mmol, 11.0 g) in toluene (0.2 M, 270 ml), sodium terbutoxide (80.4 mmol, 7.72 g), bis(tri-terbutylphosphine)palladium(0) (0.536 mmol) , 0.274 g), and stirred for 12 hours under reflux conditions in an argon atmosphere.

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Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/017069 2019-11-29 2020-11-27 Composé et dispositif électroluminescent organique le comprenant WO2021107678A1 (fr)

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JP2021539575A JP7143570B2 (ja) 2019-11-29 2020-11-27 化合物およびこれを含む有機発光素子
CN202080009134.3A CN113366002B (zh) 2019-11-29 2020-11-27 化合物和包含其的有机发光器件
US17/428,032 US20220089617A1 (en) 2019-11-29 2020-11-27 Compound and organic light-emitting device comprising same
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