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WO2023182836A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2023182836A1
WO2023182836A1 PCT/KR2023/003876 KR2023003876W WO2023182836A1 WO 2023182836 A1 WO2023182836 A1 WO 2023182836A1 KR 2023003876 W KR2023003876 W KR 2023003876W WO 2023182836 A1 WO2023182836 A1 WO 2023182836A1
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김민준
김재은
문현진
이성재
홍성길
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LG Chem Ltd
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • This specification provides a compound and an organic light-emitting device containing the same.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • A is substituted or unsubstituted benzene; Or substituted or unsubstituted naphthalene,
  • R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and R3 is hydrogen; or deuterium,
  • R3 is an aryl group; or a heteroaryl group, and R1 is hydrogen; or deuterium,
  • R2 and R4 are the same or different from each other and are each independently hydrogen; or deuterium,
  • R5 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
  • L3 is a substituted or unsubstituted arylene group
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r5 is an integer from 1 to 4, and when r5 is 2 or more, the 2 or more R5 are the same or different from each other,
  • R3 is a phenyl group
  • A is benzene
  • R1, R2, R4 and R5 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are biphenyl groups
  • L3 is a phenylene group
  • Ar1 and Ar2 are biphenyl groups
  • 3) A is benzene
  • R1 and R2 , R4 and R5 are hydrogen, L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 is a biphenyl group
  • Ar2 is a fluorene group substituted with a methyl group
  • R3 is a dibenzothiophene group
  • A is benzene
  • R1, R2, R4 and R5 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 is a biphenyl group
  • Ar2 is a phenyl group.
  • R1 is a phenyl group
  • compounds in which A is benzene, R2 to R5 are hydrogen, L1 and L2 are a direct bond, L3 is a phenylene group, and Ar1 and Ar2 are biphenyl groups are excluded.
  • an exemplary embodiment of the present specification includes a first electrode; second electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.
  • the compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device.
  • a compound according to at least one embodiment of the present specification may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.
  • the compounds described in this specification can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, and light emitting materials. Additionally, compared to existing organic light emitting devices, they have the effects of low driving voltage, high efficiency, and/or long lifespan.
  • 1 and 2 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
  • the compound of Formula 1 according to an exemplary embodiment of the present specification has a structure including L3 and a phenylene group including R1 or R3 connecting an amine group to the carbazole (or benzocarbazole) core and is included in the organic material layer of the organic light-emitting device. It is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; alkenyl group; Haloalkyl group; silyl group; boron group; Amine group; Aryl group; It means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • linking two or more substituents means that the hydrogen of one substituent is linked to another substituent.
  • a phenyl group and a naphthyl group are connected. or It can be a substituent of .
  • the connection of three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also that (substituent 2) and (substituent 3) are connected to (substituent 1).
  • phenyl group, naphthyl group and isopropyl group are connected , , or It can be a substituent of .
  • the above definition equally applies to those in which 4 or more substituents are connected.
  • halogen groups include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited to this.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n.
  • -It can be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • fluorene group examples include etc., but is not limited to this.
  • an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • the heteroaryl group includes one or more non-carbon atoms and heteroatoms.
  • the heteroaryl group may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzyl group.
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc.
  • alkylsilyl groups examples of the alkyl group described above may be applied to the alkyl group
  • examples of the aryl group described above may be applied to the aryl group among the arylsilyl groups
  • examples of the heteroaryl group among the heteroarylsilyl groups may apply to the heteroaryl group. can be applied.
  • the boron group may be -BR 100 R 101 , where R 100 and R 101 are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, and diphenyl boron group.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • diphenylamine group ditolylamine group, N-phenyltolylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre
  • Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • the alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.
  • N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heteroaryl group described above.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously.
  • the aryl group in the arylamine group may be selected from the examples of aryl groups described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.
  • an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group.
  • the description of the aryl group described above can be applied, except that each of these is a divalent group.
  • a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a bivalent group.
  • the description of the heteroaryl group described above can be applied, except that each of these is a divalent group.
  • the portion in Formula 1 where a substituent is not indicated may mean that hydrogen has been substituted.
  • R1 is a phenyl group
  • R2 to R5 are hydrogen
  • A is benzene
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other.
  • R3 is a phenyl group
  • A is benzene or naphthalene
  • R1, R2, R4 and R5 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • R3 is a dibenzothiophene group
  • R1, R2, R4 and R5 are hydrogen
  • A is benzene
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 When is a biphenyl group, Ar2 is a biphenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is the following Formula 1-1.
  • R1 is a phenyl group
  • R5 is hydrogen
  • A is benzene
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is the following Formula 1-3.
  • R3 is a phenyl group
  • R5 is hydrogen
  • A is benzene or naphthalene
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or a dibenzothiophene group,
  • R3 is a dibenzothiophene group
  • R5 is hydrogen
  • A is benzene
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 is a biphenyl group
  • Ar2 is a biphenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is the following Formula 1-5 or 1-6.
  • R1, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R6 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6 are the same or different from each other,
  • R1 is a phenyl group
  • R5 and R6 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group,
  • R1, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R7 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is an integer from 1 to 6, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.
  • Formula 1 is any one of the following Formulas 1-6-1 to 1-6-3.
  • R1, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R7 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is an integer from 1 to 6, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.
  • Formula 1 is the following Formula 1-9 or 1-10.
  • R3, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R6 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r6 is an integer from 1 to 4, and when r6 is 2 or more, the 2 or more R6 are the same or different from each other,
  • R3 is a phenyl group
  • R5 and R6 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or a dibenzothiophene group,
  • R3 is a dibenzothiophene group
  • R5 and R6 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 is a biphenyl group
  • Ar2 is a biphenyl group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group,
  • R3, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R7 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is an integer from 1 to 6, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other,
  • R3 is a phenyl group
  • R5 and R6 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; naphthyl group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is any one of the following Formulas 1-10-1 to 1-10-3.
  • R3, R5, r5, L1 to L3, Ar1 and Ar2 are the same as those defined in Formula 1 above,
  • R7 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is an integer from 1 to 6, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other,
  • R3 is a phenyl group
  • R5 and R6 are hydrogen
  • L1 and L2 are a direct bond
  • L3 is a phenylene group
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; naphthyl group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • A is benzene; or naphthalene, and R2, R4, and R5 are the same or different from each other, and are each independently hydrogen; or deuterium, and any one of R1 and R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, the remainder being hydrogen; or deuterium, L3 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, and L1 and L2 are the same or different from each other and are each independently directly bonded; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, wherein Ar1 and Ar2 are the same as or different from each other, and each independently is a monocyclic or polycyclic aryl group
  • A is benzene; or naphthalene, and R2, R4, and R5 are the same or different from each other, and are each independently hydrogen; or deuterium, i) R1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R3 is hydrogen; or deuterium; ii) R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R1 is hydrogen; or deuterium, L3 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, and L1 and L2 are the same or different from each other and are each independently directly bonded; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubsti
  • R2 is hydrogen; Or deuterium.
  • R2 is hydrogen
  • R2 is deuterium
  • R4 is hydrogen; Or deuterium.
  • R4 is hydrogen
  • R4 is deuterium
  • R5 is hydrogen; Or deuterium.
  • R5 is hydrogen
  • R5 is deuterium
  • R6 is hydrogen; Or deuterium.
  • R6 is hydrogen
  • R6 is deuterium
  • R7 is hydrogen; Or deuterium.
  • R7 is hydrogen
  • R7 is deuterium
  • A is benzene; Or naphthalene.
  • A is benzene.
  • A is naphthalene.
  • a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms refers to an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R3 is hydrogen; or deuterium,
  • R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R1 is hydrogen; Or deuterium.
  • R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, and R3 is hydrogen; or deuterium,
  • R3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, and R1 is hydrogen; Or deuterium.
  • R1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R3 is hydrogen; or deuterium,
  • R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R1 is hydrogen; Or deuterium.
  • R1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, and R3 is hydrogen; or deuterium,
  • R3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, and R1 is hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms; or a 3-ring heteroaryl group having 2 to 30 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms; or a three-ring heteroaryl group having 2 to 20 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms including a 6-membered ring; or a 3-ring heteroaryl group having 2 to 30 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms including a 6-membered ring; or a three-ring heteroaryl group having 2 to 20 carbon atoms, the remainder being hydrogen; Or deuterium.
  • any one of R1 and R3 is a phenyl group; Biphenyl group; naphthyl group; phenanthrene group; Dibenzofuran group; or a dibenzothiophene group, and the remainder is hydrogen; Or deuterium.
  • R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • R1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • R1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • R1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms; Or it is a tricyclic heteroaryl group having 2 to 30 carbon atoms.
  • R1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms; Or it is a tricyclic heteroaryl group having 2 to 20 carbon atoms.
  • R1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms including a 6-membered ring; Or it is a tricyclic heteroaryl group having 2 to 30 carbon atoms.
  • R1 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms including a 6-membered ring; Or it is a tricyclic heteroaryl group having 2 to 20 carbon atoms.
  • R1 is a phenyl group; Biphenyl group; naphthyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • R3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • R3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms; Or it is a tricyclic heteroaryl group having 2 to 30 carbon atoms.
  • R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms; Or it is a tricyclic heteroaryl group having 2 to 20 carbon atoms.
  • R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms including a 6-membered ring; Or it is a tricyclic heteroaryl group having 2 to 30 carbon atoms.
  • R3 is a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms including a 6-membered ring; Or it is a tricyclic heteroaryl group having 2 to 20 carbon atoms.
  • R3 is a phenyl group; Biphenyl group; naphthyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • L3 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L3 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L3 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L3 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L3 is a phenylene group; Or it is a naphthylene group.
  • L3 is a phenylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with a phenyl group; Biphenylylene group; Or it is a naphthylene group substituted or unsubstituted with a phenyl group.
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. ; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. ; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic, bicyclic, or tricyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic, bicyclic, or tricyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with a monocyclic aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted by a naphthyl group; Biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Terphenyl group; phenanthrene group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • Formula 1 is any one selected from the following compounds.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area.
  • the size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
  • a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
  • This specification includes: a first electrode; second electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc.
  • the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
  • the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  • the organic material layer includes a hole transport auxiliary layer, and the hole transport auxiliary layer includes the compound.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.
  • the light-emitting layer includes the compound as a host of the light-emitting layer.
  • the light-emitting layer includes the compound as a phosphorescent host of the light-emitting layer.
  • the light-emitting layer includes a dopant, and the dopant is a phosphorescent dopant.
  • the phosphorescent dopant may be any conventionally used material without limitation.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device includes a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, a hole transport auxiliary layer, and an electron transport layer. It further includes one or two layers or more selected from the group consisting of blocking layers.
  • the organic light emitting device includes a first electrode; a second electrode provided opposite to the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.
  • the two or more organic layers include a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, a hole transport auxiliary layer, and Two or more may be selected from the group consisting of electron blocking layers.
  • a hole transport layer of two or more layers is included between the light emitting layer and the first electrode.
  • the two or more hole transport layers may include the same or different materials.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2. 1 illustrates an organic light emitting device and is not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1.
  • the compound is included in the organic layer.
  • FIG. 2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole transport auxiliary layer 7, a light emitting layer 8, a hole blocking layer 9, and an electron injection layer on the substrate 1. and a structure of an organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked.
  • the compound is included in the hole injection layer (5), the hole transport layer (6), or the hole transport auxiliary layer (7).
  • the organic light emitting device of the present specification is a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport auxiliary layer, or a material known in the art, except that the light emitting layer includes the above compound, that is, the compound of Formula 1 above. It can be manufactured using the following method.
  • the hole transport auxiliary layer may be an electron blocking layer.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the manufacturing method is not limited to this.
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
  • the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • metals or alloys thereof for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the light emitting layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
  • the host includes, but is not limited to, a compound represented by the following formula H-1.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R201 is hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R201 is hydrogen; heavy hydrogen; Or it is a phenyl group.
  • the formula H-1 is represented by the following compound.
  • the dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group.
  • a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the dopant material includes, but is not limited to, a compound of the following formula D-1.
  • T1 to T6 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkylsilyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each integers from 1 to 4,
  • t5 is 2 or more, the 2 or more T5 are the same or different from each other,
  • the 2 or more T6s are the same or different from each other.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, cyano group, or a straight or branched alkyl group with 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; isopropyl group; trimethylsilyl group; Phenyl group substituted with deuterium; A phenyl group substituted with a cyano group; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group.
  • Formula D-1 is represented by the following compound.
  • the hole injection layer is a layer that receives holes from the electrode.
  • the hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect to the light emitting layer or light emitting material. Additionally, a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; These include, but are not limited to, polythiophene-based conductive polymers such as anthraquinone and polyaniline.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • R315 to R317 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same or different from each other.
  • R317 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R317 is a carbazole group; phenyl group; Biphenyl group; triphenylene group; and any one selected from the group consisting of combinations thereof.
  • R315 and R316 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R315 and R316 are the same or different from each other and are each independently a phenyl group or a biphenyl group, or are combined with adjacent groups to form an indene substituted with a methyl group.
  • the formula HI-1 is represented by any one of the following compounds.
  • the hole injection layer includes a compound represented by the following formula HI-2, but is not limited thereto.
  • At least one of X'1 to X'6 is N, and the remainder is CH,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • the chemical formula HI-2 may be the following compound, but is not limited thereto.
  • the hole injection layer includes the formulas HI-1 and HI-2.
  • the hole injection layer includes the formulas HI-1 and HI-2 at a weight ratio of 1:99 to 99:1.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material is a hole transport material that receives holes from the anode or hole injection layer and transfers them to the light emitting layer.
  • a material with high mobility for holes is preferred. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
  • the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
  • L501 and L502 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L501 and L502 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L501 and L502 are phenylene groups.
  • R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R501 and Ar501 to Ar504 are phenyl groups; Or it is a naphthyl group.
  • the formula HT-1 is represented by the following compound.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; These include, but are not limited to, hydroxyflavone-metal complexes.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from the electrode.
  • the organic light emitting device includes an additional electron injection layer other than the electron injection layer containing Formula 1
  • the electron injection material has excellent electron transport ability
  • the second electrode It is desirable to have an excellent electron receiving effect from and an excellent electron injection effect with respect to the light emitting layer or light emitting material.
  • a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is desirable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, These include, but are not limited to, metal complex compounds and nitrogen-containing five-membered ring derivatives.
  • the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
  • the electron injection and transport layer is a layer that transports electrons to the light-emitting layer.
  • the electron injection and transport layer may use materials exemplified for the electron transport layer and electron injection layer, but is not limited thereto.
  • the electron injection and transport layer includes a compound represented by the following formula ET-1, but is not limited thereto.
  • At least one of Z11 to Z13 is N, the others are CH,
  • At least one of Z21 to Z23 is N, the others are CH,
  • L601 and L602 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are phenylene groups.
  • Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar601 to Ar604 are phenyl groups.
  • the chemical formula ET-1 may be the following compound, but is not limited thereto.
  • the electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer.
  • the organic light emitting device according to an embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer containing Formula 1, known materials can be used without limitation, and in the description of the hole injection layer, The exemplified materials may be used, but are not limited thereto.
  • the electron blocking layer may be formed between a light-emitting layer and a hole transport layer, between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
  • the hole transport auxiliary layer is a layer that prevents electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer and assists hole transport, and is a layer that can improve the lifespan of the device.
  • the organic light emitting device according to an embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer containing Formula 1, known materials can be used without limitation, and the hole injection layer and the hole transport layer The materials exemplified in the description may be used, but are not limited thereto.
  • the hole transport auxiliary layer may be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.
  • the hole blocking layer includes a compound represented by the following formula HB-1, but is not limited thereto.
  • At least one of Z31 to Z33 is N, and the remainder is CH,
  • L603 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R601 to R603 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or forms a ring by combining with adjacent groups,
  • l603 is an integer from 1 to 3, and when l603 is 2 or more, the 2 or more L603 are the same or different from each other,
  • r601 is an integer from 1 to 4, and when r601 is 2 or more, the 2 or more R601 are the same or different from each other,
  • r602 is an integer from 1 to 4, and when r602 is 2 or more, the 2 or more R602 are the same or different from each other,
  • r603 is an integer of 1 to 3, and when r603 is 2 or more, the 2 or more R603s are the same or different from each other.
  • Z31 to Z33 are N.
  • L603 is a direct bond; Or it is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L603 is a direct bond; phenylene group; naphthylene group; Or it is a biphenylylene group.
  • L603 is a phenylene group; Or it is a naphthylene group.
  • l603 is 2.
  • R601 to R603 are hydrogen.
  • Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. am.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a biphenyl group.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group or a phenyl group substituted or unsubstituted by a naphthyl group; Or it is a biphenyl group.
  • Ar605 and Ar606 are biphenyl groups.
  • Ar605 and Ar606 are phenyl groups.
  • the chemical formula HB-1 may be the following compound, but is not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device can be included and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,400 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following HI-1 compound was formed as a hole injection layer to a thickness of 1150 ⁇ , and the following A-1 compound was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 ⁇ .
  • Compound 1 was then thermally vacuum deposited to a thickness of 150 ⁇ as a hole transport auxiliary layer.
  • BH-1 of the present invention and a compound represented by the formula BD below were vacuum deposited to a thickness of 200 ⁇ at a weight ratio of 25:1.
  • a compound represented by the following chemical formula HB-1 was vacuum deposited to a thickness of 50 ⁇ as a hole blocking layer.
  • a compound represented by the formula ET-1 and a compound represented by LiQ below were thermally vacuum deposited to a thickness of 310 ⁇ at a weight ratio of 1:1.
  • Lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a cathode, thereby manufacturing an organic light-emitting device.
  • the compound of Formula 1 according to an exemplary embodiment of the present specification was used as a hole transport auxiliary layer that serves as an auxiliary role of the blue light-emitting layer of the organic light-emitting device. It was confirmed that compared to the compound of the comparative experiment example, the organic light-emitting device using the compound of the present invention showed improvement effects in driving voltage, efficiency, and lifespan characteristics. Inferred from these results, the compound of the present invention used as a hole transport auxiliary layer appropriately blocks electrons passing into the hole transport layer, achieves good charge balance within the light emitting layer, and contributes to exciton stabilization, thereby increasing the energy from the host to the red dopant. The delivery appears to be going well.

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Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2023/003876 2022-03-23 2023-03-23 Composé et dispositif électroluminescent organique le comprenant Ceased WO2023182836A1 (fr)

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