WO2021020947A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2021020947A1
WO2021020947A1 PCT/KR2020/010175 KR2020010175W WO2021020947A1 WO 2021020947 A1 WO2021020947 A1 WO 2021020947A1 KR 2020010175 W KR2020010175 W KR 2020010175W WO 2021020947 A1 WO2021020947 A1 WO 2021020947A1
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carbon atoms
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김명곤
허정오
홍완표
김경희
김은호
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주식회사 엘지화학
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Priority to CN202080006746.7A priority Critical patent/CN113196515B/zh
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Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of 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 an organic light emitting device.
  • the present specification is a first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
  • the organic material layer provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 below and a second organic material layer including a compound represented by Formula 2 below.
  • A1, A2, A3, B1 and B2 are the same as or different from each other, and each independently a hydrocarbon ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; Represented by the following formula 3, at least one of R1 to R5 is represented by the following formula 3,
  • the dotted line is a portion connected to A1, A2, A3, B1 or B2,
  • X is C or Si
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • n1 and n5 are each an integer of 0 to 4,
  • n2 and n4 are each an integer of 0 to 5
  • n3 is an integer from 0 to 3
  • n1 + n2 + n3 + n4 + n5 is 1 or more
  • n1 to n5 are 2 or more, the substituents in parentheses are the same as or different from each other,
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring,
  • R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following formula (4), or is bonded to each other with adjacent groups to form a hydrocarbon ring,
  • a31 is an integer from 0 to 8
  • R3-1 is the same as or different from each other
  • the dotted line is a part connected to the core
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • X 1 to X 3 are the same as or different from each other, and each independently N or CR",
  • At least one of X 1 to X 3 is N,
  • R" is hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cyclo An alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heterocyclic group,
  • L 1 to L 3 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 heteroarylene group.
  • the organic light emitting device described in the present specification includes the compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent lifespan.
  • Low driving voltage, high efficiency, and lifespan may be improved by controlling the degree of electron transport through the adjustment of an appropriate HOMO energy level and LUMO energy level.
  • 1, 2, and 8 to 10 show examples of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • 3 to 7 show examples of organic light emitting devices including two or more stacks.
  • hole injection layer/ 4 hole transport layer/ 4a: first hole transport layer/ 4b: second hole transport layer/ 4c: third hole transport layer/ 4d: fourth hole transport layer/ 4e: agent 5 hole transport layer/ 4f: sixth hole transport layer/ 4p: p-doped hole transport layer/ 4R: red hole transport layer/ 4G: green hole transport layer/ 4B: blue hole transport layer/ 5: electron blocking layer/ 6: light emitting layer/ 6a: First emitting layer/6b: second emitting layer 6c: third emitting layer 6BF: blue fluorescent emitting layer 6BFa: first blue fluorescent emitting layer 6BFb: second blue fluorescent emitting layer 6YGP: yellow green phosphorescent emitting layer 6RP: red phosphorescent emitting layer / 6GP: green phosphorescent emission layer/ 7: hole blocking layer/ 8: electron injection and transport layer/ 9: electron transport layer/ 9a: first electron transport layer/ 9b: second electron transport layer/ 9c: third electron transport layer/ 10: electron injection
  • the present specification provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 and a second organic material layer including a compound represented by Formula 2 at the same time.
  • the light-emitting layer containing the compound of Formula 1 has a shallow HOMO level, and the compound of Formula 2 has a deep HOMO and LUMO level, so electrons can be easily transferred to the light-emitting layer, thus exhibiting high efficiency and lifetime.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Alkylthio group; Aryloxy group; Arylthio group; Cycloalkyl group; Aryl group; Amine group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or it means that no substituents are present.
  • connection of two or more substituents means that hydrogen of any one of the substituents is replaced with another substituent.
  • an isopropyl group and a phenyl group are connected or It may be a substituent of.
  • connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections.
  • two phenyl groups and isopropyl groups are connected or It may be a substituent of. The same applies to those in which four or more substituents are connected.
  • substituted with A or B includes not only the case where A is substituted or only B is substituted, but also the case where A and B are substituted.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; Alkynyl group having 2 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; Aryloxy group having 6 to 30 carbon atoms; Arylthio group having 6 to 30 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or not having any substituents.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 6 carbon atoms; An alkenyl group having 2 to 6 carbon atoms; Alkynyl group having 2 to 6 carbon atoms; An alkoxy group having 1 to 6 carbon atoms; An alkylthio group having 1 to 6 carbon atoms; Aryloxy group having 6 to 20 carbon atoms; Arylthio group having 6 to 20 carbon atoms; A cycloalkyl group having 3 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the alkyl group includes a linear or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain.
  • propyl The group includes an n-propyl group and an isopropyl group
  • the butyl group includes an n-butyl group, an isobutyl group and a tert-butyl group.
  • the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10.
  • Cycloalkyl groups include monocyclic groups as well as bicyclic groups such as bridgeheads, fused rings, and spiro rings. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.
  • cycloalkene is a cyclic group that has a double bond in the hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but 3 to 60, 3 to 30, 3 to 20, or 3 to 10 to be.
  • Cycloalkenes include not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, and spiro. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, and cyclohexene, but are not limited thereto.
  • the alkoxy group is an aryl group connected to an oxygen atom
  • an arylthio group is an alkyl group connected to a sulfur atom
  • the above-described description of the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but 6 to 60, 6 to 30, or 6 to 20.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , But is not limited thereto.
  • carbon atom 9 (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, etc., and two substituents may be bonded to each other to form a spiro structure such as cyclopentane and fluorene.
  • the substituted aryl group may include a form in which an aliphatic ring is condensed with an aryl group.
  • a tetrahydronaphthalene group having the following structure is included in a substituted aryl group.
  • one of the carbons of the benzene ring may be linked to another position.
  • an aryloxy group is an aryl group connected to an oxygen atom
  • an arylthio group is an aryl group connected to a sulfur atom
  • the aryl group described above may be applied to the aryl group of the aryloxy group and the arylthio group.
  • the aryl group of the aryloxy group is the same as the aryl group described above.
  • the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but are not limited thereto.
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group includes a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propyl methyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, etc., but is not limited thereto. .
  • the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto.
  • the amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. Can be.
  • the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20.
  • Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group.
  • the aryl group in the arylamine group may be a monocyclic or polycyclic aryl group.
  • Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a bis(tert-butylphenyl)amine group, etc. , But is not limited thereto.
  • heteroarylamine group examples include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted arylheteroarylamine group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group, and descriptions of the aryl group and the heteroaryl group to be described later may be applied.
  • the heterocyclic group is a cyclic group including one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30.
  • the heterocyclic group include a pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene group; Hexahydrocarbazole group; Dihydroacridine group; Dibenzoazacillin group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group; Spiro (dibenzosilol-dibenzoazacillin) group; Spiro (acridine-fluorene) group; Spiro (fluorene-x
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally close to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • the ring formed by bonding adjacent groups refers to a hydrocarbon ring; Or a hetero ring.
  • a 5-membered or 6-membered ring formed by bonding adjacent groups means that the ring including the substituent participating in the ring formation is 5 or 6 members. It may include condensation of an additional ring to the ring including the substituent participating in the ring formation.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring Except that is not monovalent, the above description of the cycloalkyl group may be applied.
  • the aromatic and aliphatic condensed ring include a 1,2,3,4-tetrahydronaphthalene group, and a 2,3-dihydro-1H-indene group, but are not limited thereto.
  • heterocyclic group may be applied, except that the heterocycle is not monovalent.
  • the aromatic hydrocarbon ring refers to a ring in which pi electrons are completely conjugated and planar, and the description of the aryl group described above may be applied except for a divalent group.
  • the aliphatic hydrocarbon ring means all hydrocarbon rings except for an aromatic hydrocarbon ring, and may include a cycloalkyl ring. Except that the cycloalkyl ring is a divalent group, the above description of the cycloalkyl group can be applied.
  • the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • the description of the cycloalkyl group may be applied except that the cycloalkylene group is a divalent group.
  • A1 to A3, B1 and B2 are the same as or different from each other, and each independently a monocyclic or bicyclic hydrocarbon ring.
  • A1 to A3, B1 and B2 are the same as or different from each other, and each independently a benzene ring or a naphthalene ring.
  • A1 to A3 are each a benzene ring.
  • B1 and B2 are each a benzene ring.
  • Formula 1 is represented by the following Formula 1-1.
  • R1 to R5 and n1 to n5 are as defined in Formula 1.
  • R1 to R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group, or is represented by the above formula (3).
  • R1, R2, R4, and R5 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 cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 6 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group' C1-C6 alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; Arylamine group having 6 to 40 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with deuterium; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
  • the heterocyclic group of R1, R2, R4 and R5 includes N as a hetero element.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Fluoro group; Cyano group; A methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a tert-butyl group, or a CD 3 ; Biphenyl group; Naphthyl group; Or a pyridine group.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; It is represented by the following formula (3).
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; At least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or 6 unsubstituted or substituted with a substituent connected with two or more groups selected from the group Arylamine group of to 40; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; An arylamine group having 6 to 40 carbon atoms unsubstituted or substituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, or a triarylamine group having 18 to 60 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
  • the heterocyclic group of R3 includes N as a hetero element.
  • R3 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; tert-butyl group; Diphenylamine group unsubstituted or substituted with deuterium, tert-butyl group, trimethylsilyl group, or triphenylsilyl group; A phenyl group unsubstituted or substituted with deuterium or a fluoro group; Or carbazole group.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or represented by Chemical Formula 3,
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • one of R2 is connected to a position in ortho orientation with respect to N to which B2 is connected.
  • one of R4 is connected to a position in ortho orientation with respect to N to which B2 is connected.
  • n1 is 1 or 2.
  • n2 is 1 to 4. In another exemplary embodiment, n2 is 1 to 3.
  • n3 is 1 or 2.
  • n4 is 1 to 4. In another exemplary embodiment, n4 is 1 to 3.
  • n5 is 1.
  • At least one of R1 to R5 is represented by Chemical Formula 3.
  • R1 to R5 are represented by Chemical Formula 3.
  • R1 to R5 are represented by Chemical Formula 3.
  • R1, R2, R4, and R5 are represented by Chemical Formula 3.
  • R1, R2, R4, and R5 are represented by Chemical Formula 3.
  • R1 is represented by Chemical Formula 3.
  • R2 is represented by Chemical Formula 3.
  • R3 is represented by Chemical Formula 3.
  • R4 is represented by Chemical Formula 3.
  • R5 is represented by Chemical Formula 3.
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group. Or an unsubstituted C6-C30 aryl group.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or a substituted or unsubstituted C6 to C6 group unsubstituted or substituted with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms It is an aryl group of 20.
  • R6 to R8 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
  • X is C, and at least one of R6 to R8 is a substituted or unsubstituted alkyl group.
  • X is C, and at least two of R6 to R8 are substituted or unsubstituted alkyl groups.
  • X is C, and at least one of R6 to R8 is a substituted or unsubstituted aryl group.
  • X is C
  • R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group
  • R8 is a substituted or unsubstituted aryl group.
  • X is Si
  • at least one of R6 to R8 is a substituted or unsubstituted aryl group.
  • X is Si
  • at least two of R6 to R8 are substituted or unsubstituted aryl groups.
  • X is C
  • R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group
  • R8 is a substituted or unsubstituted alkyl group.
  • X is Si
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.
  • Chemical Formula 3 is represented by the following Chemical Formula 3-1 or 3-2.
  • R11 is a substituted or unsubstituted alkyl group
  • R12 is a substituted or unsubstituted aryl group
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R11 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
  • R11 is an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
  • R11 is a methyl group.
  • R12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R12 is at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or two or more selected from the group. It is a substituted or unsubstituted substituted or unsubstituted aryl group having 6 to 20 carbon atoms with a group-linked substituent.
  • R12 is substituted or provided with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms. It is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R12 is a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 , or a trimethylsilyl group.
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R13 to R16 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
  • R13 to R16 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form a ring.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form an aliphatic ring.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or, by bonding to each other to form an aliphatic ring having 3 to 10 carbon atoms.
  • Y31 and Y32 are bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
  • Y31 and Y32 are bonded to each other to form a cyclopentyl ring.
  • Y31 and Y32 are bonded to each other to form a ring in which an aliphatic and aromatic ring having 3 to 10 carbon atoms are fused.
  • Y31 and Y32 are bonded to each other to form a ring in which a cyclopentyl ring and a benzene ring are fused.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Isopropyl group; Terbutyl group; Phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Phenanthrene group; Or an anthracene group,
  • the anthracene group is unsubstituted or substituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, phenanthrene group, or anthracene group.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Naphthyl group; A phenyl group substituted with a methyl group; A naphthyl group substituted with a methyl group; A phenyl group substituted with a naphthyl group; It is a naphthyl group substituted with a phenyl group or is bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
  • R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the formula 4, or an adjacent group and Combined with each other to form a hydrocarbon ring.
  • R3-1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or the above formula (4), or combined with an adjacent group to form a hydrocarbon ring having 3 to 20 carbon atoms.
  • R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; A phenyl group substituted with a methyl group; Biphenyl group; It is a naphthyl group or the above formula (4), or is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; Naphthyl group; Or the formula (4), or by bonding with adjacent groups to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • a31 is an integer of 1 to 8, and at least one R3-1 is Chemical Formula 4.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; Phenothiazine group; Phenoxathiine; Is a trimethylsilyl group,
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Alkyl group; Aryl group; Silyl group; Or substituted or unsubstituted with a heteroaryl group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 30 carbon atoms; An alkylsilyl group having 1 to 10 carbon atoms; Or it is unsubstituted or substituted with a C3-C30 heteroaryl group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Anthracene group; Perylene group; Triphenylene group; Pyren group; Fluoranthene; Thiophene group; Furan group; Pyridine group; Pyrimidine group; Triazine group; Carbazole; It is unsubstituted or substituted with any one or more selected from a dibenzofuran group or a di
  • X 1 to X 3 are N.
  • the above X 1 to X 3 X 1 is N and the others are CR.
  • X 2 of X 1 to X 3 is N, and the rest are CR.
  • X 3 of X 1 to X 3 is N, and the rest are CR.
  • X 1 to X 3 in X 1 is CR, with the remainder being N.
  • X 2 of X 1 to X 3 is CR, and the rest are N.
  • X 3 of X 1 to X 3 is CR, and the rest are N.
  • R is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
  • R is hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
  • R is hydrogen; It is a deuterium or nitrile group.
  • R is hydrogen
  • Formula 2 is represented by the following Formula 2-1.
  • Y is CR111R112, O, or S,
  • R111, R112, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or It is the following formula (4), or combines with an adjacent group to form a hydrocarbon ring,
  • L31 and L32 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
  • a32 is an integer from 0 to 8
  • b33 is an integer from 0 to 8
  • n33 is 0 or 1
  • a33 is 0.
  • a position capable of being substituted with R3-2 is substituted with hydrogen.
  • b33 is 0.
  • a position that can be substituted with R3-3 is substituted with hydrogen.
  • Y is O or S.
  • R3-2 is hydrogen
  • R3-3 is hydrogen
  • a33 is 1.
  • b33 is 1.
  • R3-2 is Formula 6 or 7.
  • R3-3 is the following Chemical Formula 6 or 7.
  • the dotted line is a part connected to the core
  • L4 and L5 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
  • Ar5 and Ar6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • c and d are integers from 0 to 5
  • R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Is a heteroaryl group, Formula 4, Formula 6, or Formula 7.
  • R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted carbon number.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of R3-2 and R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, It is a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group, a triphenylene group, and the phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group,
  • the triphenylene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • a33 is 2, and R3-2 is the same as or different from each other.
  • b33 is 2, and R3-3 is the same as or different from each other.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-2 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy.
  • the ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy.
  • the ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • L 1 to L 5 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 heteroarylene group.
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl
  • overlapped means that two or more substituents are sequentially bonded.
  • the phenylene group and the divalent carbazole group overlap means that -phenylene-divalent carbazole- is sequentially bonded.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 30 carbon atoms; Or a heteroarylene group having 3 to 30 carbon atoms.
  • L 1 to L 3 are direct bonds.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
  • L 3 is a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
  • L 3 is a direct bond or a phenylene group.
  • L31 and L32 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 heteroarylene group.
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl
  • R3-2 is bonded to each other with adjacent groups to form a hydrocarbon ring.
  • R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring.
  • R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-3 is bonded to each other with adjacent groups to form a hydrocarbon ring.
  • R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring.
  • R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • Formula 2-1 is represented by any one of Formulas 2-2 to 2-6 below.
  • R3-4 and R3-5 are the same as R3-3 of Formula 2-1,
  • a34 and a35 are the same as a33 in Chemical Formula 2-1.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted aryl group.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted fluorene group, or a substituted or unsubstituted benzo. It is a fluorene group.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group; Or a benzofluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group.
  • R3-4 and R3-5 are hydrogen.
  • a34 and a35 are 0.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene.
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene.
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstit
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It is a cyclic heteroaryl group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, a dibenzothiophene group, It is a carbazole group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
  • Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstit
  • Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a tricyclic heteroaryl group containing Si, N, O, or S,
  • Tricyclic heteroaryl containing the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S Groups include deuterium, nitrile group, halogen group, methyl group, trifluoromethyl group, trifluoromethoxy group, methoxy group, trimethylsilyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, carbazole group substituted with phenyl group, It is unsubstituted or substituted with one or more substituents selected from dibenzofuran group, dibenzothiophene group, benzocarbazole group, indolocarbazole group, and pyridine group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; A divalent phenothiazine group; Divalent phenoxatiin; Or a trimethylsilyl group,
  • Formula 2 is any one of the following compounds.
  • Chemical Formula 2 is any one of the compounds listed in the following table. In the table below, the dotted line is the position combined with Formula 4.
  • the compound of Formula 1 may be prepared as shown in Scheme 1 below, and the compound of Formula 2 may be prepared as in Scheme 2 below.
  • the following Schemes 1 and 2 describe the synthesis process of some compounds corresponding to Formulas 1 and 2 of the present application, but various compounds corresponding to Formulas 1 and 2 of the present application can be synthesized using a synthesis procedure such as Schemes 1 and 2 below.
  • the substituents may be bonded by methods known in the art, and the type, position and number of the substituents may be changed according to techniques known in the art.
  • R means a substituent connected to the core, and may be R1 to R3, B1 or B2 of the present invention, and the definition of the remaining substituents is as described above.
  • the definition of the substituent is as described above, and can be synthesized by a general coupling reaction. For example, it can be produced using a Suzuki coupling reaction or the like.
  • the organic light emitting device of the present specification except for forming a first organic material layer using the compound represented by Formula 1 and forming a second organic material layer using the compound represented by Formula 2 It can be manufactured by the manufacturing method and material of the light emitting device.
  • the first organic material layer including the compound represented by Formula 1 and the second organic material layer including the compound represented by Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light-emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, but may have a structure in which an additional organic material layer is further included.
  • an additional organic material layer one of a hole injection layer, a hole transport layer, a layer for both hole transport and hole injection, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, and a hole blocking layer. It can be more than one layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first organic material layer is an emission layer
  • the second organic material layer is the second electrode and the first It is provided between the organic material layers. That is, the second organic material layer is provided between the cathode and the emission layer.
  • the first organic material layer is an emission layer.
  • the first organic material layer is an emission layer
  • the compound represented by Formula 1 is included as a dopant of the emission layer.
  • the first organic material layer is an emission layer
  • the compound represented by Chemical Formula 1 is used as a dopant of the emission layer, and further includes a fluorescent host or a phosphorescent host.
  • the dopant in the light emitting layer may be included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host, preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight. When within the above range, energy transfer from the host to the dopant occurs efficiently.
  • the host is an anthracene derivative.
  • the organic material layer includes two or more emission layers, and one of the two or more emission layers includes the compound represented by Formula 1 above.
  • the maximum emission peaks of the two or more emission layers are different from each other.
  • the light emitting layer including the compound represented by Formula 1 has a blue color, and the light emitting layer not including the compound represented by Formula 1 may include a blue, red, or green light emitting compound known in the art.
  • the emission layer including the compound represented by Formula 1 includes a fluorescent dopant, and the emission layer not including the compound represented by Formula 1 includes a phosphorescent dopant.
  • the maximum emission peak of the emission layer including the compound represented by Formula 1 is 400 nm to 500 nm. That is, the emission layer including the compound represented by Formula 1 emits blue light.
  • the organic material layer of the organic light emitting device includes two or more emission layers, the maximum emission peak of one emission layer (light emission layer 1) is 400 nm to 500 nm, and the emission layer of the other layer (light emission layer 2 ) The maximum emission peak of 510 nm to 580 nm; Alternatively, a maximum emission peak of 610 nm and 680 nm may be exhibited.
  • the emission layer 1 includes the compound represented by Chemical Formula 1.
  • the second organic material layer is an electron transport region.
  • the second organic material layer includes at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
  • the second organic material layer includes one or two layers selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
  • the second organic material layer is a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer.
  • the second organic material layer is a hole blocking layer.
  • the second organic material layer is an electron transport layer.
  • the second organic material layer is an electron injection and transport layer.
  • the second organic material layer includes a hole blocking layer and an electron injection and transport layer.
  • the hole blocking layer is provided adjacent to the light emitting layer
  • the electron injection and transport layer is provided adjacent to the cathode.
  • the second organic material layer is provided in contact with the first organic material layer.
  • the second organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
  • the organic alkali metal compound or the organic alkaline earth metal compound When used as an n-type dopant, stability against holes from the light emitting layer can be secured, thereby improving the life of the organic light emitting device.
  • the electron mobility of the electron transport layer may be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the emission layer, thereby increasing luminous efficiency.
  • LiQ is more preferable as the n-type dopant used in the second organic material layer in the present specification.
  • the second organic material layer may include the compound of Formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1.
  • the compound of Formula 2 and the n-type dopant may be included in a ratio of 2:8 to 8:2, more preferably 3:7 to 7:3.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is 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 an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1, 2, and 8, but is not limited thereto.
  • a substrate 1 an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11
  • the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the hole blocking layer 7 or the electron injection and transport layer 8.
  • the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the electron injection and transport layer 8.
  • FIG. 8 shows a substrate 1, an anode 2, a p-doped hole transport layer 4p, a hole transport layer 4R, 4G, 4B, a light emitting layer 6RP, 6GP, 6BF, a first electron transport layer 9a,
  • a structure of an organic light emitting diode in which the second electron transport layer 9b, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in the emission layer (6RP, 6GP, 6BF), and the compound represented by Formula 2 is a first electron transport layer (9a), a second electron transport layer (9b) And one or more layers of the electron injection layer 10.
  • the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series.
  • the tandem structure may be a form in which each organic light emitting device is bonded to a charge generation layer. Since the tandem device can be driven at a lower current than the unit device based on the same brightness, there is an advantage in that the lifespan of the device is greatly improved.
  • the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And at least one charge generation layer provided between the first stack and the second stack.
  • the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And a third stack including one or more emission layers, and between the first stack and the second stack; And one or more charge generation layers, respectively, between the second stack and the third stack.
  • a charge generating layer means a layer in which holes and electrons are generated when a voltage is applied.
  • the charge generation layer may be an N-type charge generation layer or a P-type charge generation layer.
  • the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer
  • the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.
  • the N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed.
  • an NP junction is formed.
  • holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generation layer, and holes are transported toward the cathode through the HOMO level of the P-type organic material layer.
  • Each of the first stack, the second stack, and the third stack includes one or more light emitting layers, and additionally, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole
  • a hole injection layer a layer for simultaneous injection
  • an electron injection layer a layer for simultaneous electron transport and electron injection
  • an electron injection and transport layer a layer for simultaneous electron transport and electron injection
  • FIG. 3 An organic light-emitting device including the first stack and the second stack is illustrated in FIG. 3.
  • a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first emission layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second emission layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked.
  • the structure of the organic light emitting device is illustrated.
  • the compound represented by Formula 1 may be included in the first emission layer 6a or the second emission layer 6b
  • the compound represented by Formula 2 is the first electron transport layer 9a or electron injection. And it may be included in the transport layer (8).
  • Organic light-emitting devices including the first to third stacks are illustrated in FIGS. 4 to 7.
  • the structure of a light emitting device is illustrated.
  • the compound represented by Formula 1 may be included in the first emission layer 6a, the second emission layer 6b, and the third emission layer 6c, and the compound represented by Formula 2 is a first electron It may be included in one or more of the transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.
  • FIG. 5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer.
  • 9a first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), yellow green phosphorescence emission layer (6YGP), green phosphorescence Light-emitting layer (6GP), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e) ,
  • a structure of an organic light-emitting device in which the second blue fluorescent emission layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11 and the capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a.
  • the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
  • FIG. 6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer.
  • 9a) a first N-type charge generation layer (12a), a first P-type charge generation layer (13a), a third hole transport layer (4c), a red phosphorescent layer (6RP), a green phosphorescent layer (6GP), a second electron Transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e, second blue fluorescent light emitting layer 6BFb ), a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked.
  • the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a.
  • the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
  • FIG. 7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, First electron transport layer (9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), fourth hole transport layer (4d), second blue fluorescence Light emitting layer (6BFb), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fifth hole transport layer (4e), sixth hole transport layer (4f) ,
  • a structure of an organic light-emitting device in which a third blue fluorescent emission layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11 and a capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in one or more layers of the first blue fluorescent light emitting layer 6BFa, the second blue fluorescent light emitting layer 6BFb, and the third clean fluorescent light emitting layer 6BFb,
  • the compound represented by Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9c, the third electron transport layer 9c, and the electron injection layer 10.
  • FIG. 9 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer (The structure of an organic light emitting device in which 8) and the cathode 11 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the hole blocking layer 7 or the electron injection and transport layer 8 have.
  • organic light emission in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked.
  • the structure of the device is illustrated.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the electron injection and transport layer 8.
  • the N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-P Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivative And the like, but is not limited thereto.
  • the N-type charge generation layer may include a benzoimidazophenanthrinine derivative and a metal of Li at the same time.
  • the P-type charge generation layer may simultaneously include an arylamine derivative and a compound containing a cyano group.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the organic material layer includes the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light-emitting device according to the present specification forms an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and after forming an organic material layer including the first organic material layer and the second organic material layer described above, It can be manufactured by 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 organic material layer including the first organic material layer and the second organic material layer further includes a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, etc. It may be a multi-layered structure.
  • the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferably used as the anode material to facilitate hole injection into an organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and 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 and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and has a single layer or a multilayer structure of two or more layers.
  • the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole injection layer has a two-layer structure, and each of the layers includes the same or different materials.
  • the hole transport layer may serve to facilitate the transport of holes, and has a single layer or a multilayer structure of two or more layers.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the hole transport layer has a two-layer structure, and each of the layers includes the same or different materials.
  • an arylamine compound is used as the material of the hole transport layer.
  • the hole injection and transport layer is a layer that simultaneously transports and injects holes, and a hole transport layer material and/or a hole injection layer material known in the art may be used.
  • the electron injection and transport layer is a layer that simultaneously transports electrons and injects electrons, and an electron transport layer material and/or an electron injection layer material known in the art may be used.
  • An electron blocking layer may be provided between the hole transport layer and the emission layer. Materials known in the art may be used for the electron blocking layer.
  • the emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum)
  • Alq 3 tris(8-hydroxyquinolino)aluminum
  • the light emitting dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer serves to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable.
  • Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer serves to facilitate injection of electrons.
  • the electron injection material a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to a light emitting layer or a light emitting material, and excellent in thin film formation ability is preferable.
  • Complex compounds and nitrogen-containing 5-membered ring derivatives but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • 2-bromo-1,3-diiodo-5-methylbenzene [2-bromo-1,3-diiodo-5-methylbenzene] 20 g, amine A-2 38 g, sodium tertbutoxide (sodium tert-butoxide) 14 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) 2 ) 0.24 g was added to 450 mL of toluene, heated at 120 o C, and 4 Stir for hours.
  • reaction solution was kept at -78°C and stirred for about 1 hour, and then the organic layer was extracted with methylene chloride, treated with MgSO 4 (anhydrous), and filtered.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer. 50 ⁇ of the HAT compound and 600 ⁇ of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum-deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • BH-1 compound and Compound 1 with a film thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
  • Compound E1 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50 ⁇ .
  • Compound ET and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the materials shown in Table 1 were used as the dopant material and the hole blocking layer material of the emission layer.
  • the Examples 1 to 18 and Comparative Examples 1 to were measured for 8 organic light emitting element driving voltage and luminous efficiency at a current density of 10 mA / cm 2 with respect to the (in terms of efficiency), initially at a current density of 15 mA / cm 2 The time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 1 below.
  • Comparative Examples 1 to 3 used a compound different from the compounds of Formulas 1 and 2 of the present invention as the dopant and hole blocking layer material of the light emitting layer. As compared with Comparative Examples 1 to 3, Examples 1 to 14 show low voltage and high efficiency characteristics, and it can be confirmed that the lifespan is particularly increased to a high width.
  • any one of the dopant of the light emitting layer and the material of the hole blocking layer was used as the compound of the present invention.
  • Example 1 and Comparative Example 4 Example 4 and Comparative Example 5, and Example 12 and Comparative Example 6, respectively, the same material was used as the dopant material of the light emitting layer, but the material used for the hole blocking layer was different. It can be seen that the effect difference appears when applied to the device. It can be seen that Examples 1, 4, and 12 have low voltage, high efficiency, and high lifetime characteristics compared to Comparative Examples 4, 5, and 6.
  • Example 2 Comparative Example 7, Examples 9, 18, and 8 are device data using the same hole blocking material and different dopant materials, respectively. Due to the difference in the dopant material, it can be seen that Examples 2, 9 and 18 have low voltage, high efficiency, and long life characteristics compared to Comparative Examples 7 and 8.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • 50 ⁇ of the following HAT compound and 600 ⁇ of the following HT-A compound were sequentially vacuum-deposited to form a hole transport layer.
  • the BH-2 compound and the following Compound 2 with a film thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
  • LiQ compound E10 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the emission layer to form an electron injection and transport layer with a thickness of 350 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree at the time of deposition was 1 ⁇ 10 -7.
  • an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 19, except that the dopant material of the emission layer and the material of the electron injection and transport layer were used in Table 2 below.
  • Comparative Examples 12 to 14 used the same dopant material as in Examples 19, 20, and 24, respectively, and different materials were used only for the electron injection and transport layers. Examples 19, 20, and 24 show characteristics of low voltage, high efficiency and long life, compared with Comparative Examples 12 to 14.
  • Comparative Examples 15 and 16 used the same electron injection and transport layer materials as Examples 24, 26, 23, and 28, respectively. However, since the dopant materials are different, Examples 24, 26, 23, and 38 are compared with Comparative Examples 15 and 16, respectively, and it can be seen that when applied to a device, more excellent effects are shown.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • 50 ⁇ of the HAT compound and 600 ⁇ of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • a BH-3 compound and Compound 5 with a thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 to form a light emitting layer.
  • Compound E10 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50 ⁇ .
  • Compound E2 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree at the time of deposition was 1 ⁇ 10 -7.
  • an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 29, except that the materials shown in Table 3 below were used as the dopant material, the hole blocking layer material, and the electron injection and transport layer material of the emission layer.
  • Example 29 to 34 and Comparative Examples 17 to 19 was the measurement of driving voltage and light emission efficiency (conversion efficiency) at a current density of 10 mA / cm 2, the organic light emitting device, initially at a current density of 15 mA / cm 2
  • the time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 3 below.
  • Comparative Example 17 is data using a compound other than the chemical formula of the present invention as a dopant material, a hole blocking layer material, an electron injection material, and a transport layer material. Comparative Example 18 uses the same hole blocking layer material as in Example 29, and differs only in the dopant material and the electron injection and transport layer material.
  • Comparative Example 19 the same material for the electron injection and transport layer as in Example 34 was used, and different materials were used for the dopant and the hole blocking layer. Accordingly, it can be confirmed that Examples 29 and 34 have excellent effects of low voltage, high efficiency, and long life compared to Comparative Examples 18 and 19.

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  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant : une première électrode ; une seconde électrode disposée face à la première électrode ; et une couche de substance organique disposée entre la première électrode et la seconde électrode, la couche de substance organique comprenant une couche contenant un composé de formule chimique 1 et une couche contenant un composé de formule chimique 2.
PCT/KR2020/010175 2019-07-31 2020-07-31 Dispositif électroluminescent organique WO2021020947A1 (fr)

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