WO2021125813A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2021125813A1
WO2021125813A1 PCT/KR2020/018494 KR2020018494W WO2021125813A1 WO 2021125813 A1 WO2021125813 A1 WO 2021125813A1 KR 2020018494 W KR2020018494 W KR 2020018494W WO 2021125813 A1 WO2021125813 A1 WO 2021125813A1
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허동욱
홍성길
한미연
이재탁
윤정민
윤희경
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주식회사 엘지화학
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    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K50/18—Carrier blocking layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • A1 is a direct bond; O; or S;
  • R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring substituted or unsubstituted with -L1-Ar1,
  • R3 to R10 are the same as or different from each other, and each independently hydrogen; or -L1-Ar1;
  • R1 and R2 are combined with each other to form a ring substituted with -L1-Ar1, R3 to R10 are hydrogen;
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or when combined with each other to form an unsubstituted ring, any one of R3 to R10 is -L1-Ar1 and the rest is hydrogen;
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 is a group represented by any one of the following formulas 2-1 to 2-7,
  • Y1 is a group represented by the following formula (3),
  • At least two of X1 to X3 are N, the rest are CH,
  • At least one of X4 and X5 is N, the other is CH,
  • At least one of X6 and X7 is N, the other is CH,
  • X8 is N, Z1 is N or C, or X8 is CH, Z1 is N,
  • X9 is N, Z2 is N or C, or X9 is CH, Z2 is N,
  • X10 is N, Z3 is N or C, or X10 is CH, Z3 is N,
  • X11 is N, Z4 is N or C, or X11 is CH, Z4 is N,
  • Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,
  • y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,
  • y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,
  • y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,
  • y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,
  • y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other,
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group,
  • one to four of Q1 to Q5 are N, the others are CR,
  • At least one of R is a substituted or unsubstituted aryl group, the rest are the same as or different from each other, and each independently hydrogen; or deuterium,
  • Ar1 is in Formula 2-1 and L2 in Formula 3 is a direct bond, at least two of R are substituted or unsubstituted aryl groups.
  • the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.
  • the compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using it, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
  • 1 to 3 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
  • the compound according to the exemplary embodiment of the present specification has a non-linear structure, and thus it is possible to improve efficiency, low driving voltage, and lifespan characteristics in an organic light emitting device.
  • the dipole moment of the molecule can be increased.
  • the efficiency and lifespan of the organic light emitting device including the compound represented by Chemical Formula 1 can be improved by smoothly controlling the electron mobility during the fabrication of the device.
  • R1 and R2 of Formula 1 form a ring
  • steric hindrance due to the spiro-type structure prevents crystallization occurring during film formation, and maintains high thermal stability, so that it has a very stable effect even at a high deposition temperature. Accordingly, in the organic light emitting device including the compound according to the exemplary embodiment of the present specification, 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 replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent.
  • a phenyl group and a naphthyl group are connected. or can be a substituent of
  • the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group and an isopropyl group are connected , , or can be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 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 thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenoc
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like.
  • Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group
  • the examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group
  • the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like but is not limited thereto.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a straight-chain or branched alkyl group.
  • the alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time.
  • the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • adjacent two of the substituents combine with each other to form a ring means a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; Or it means to form a substituted or unsubstituted heterocyclic ring.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from the examples of the cycloalkyl group or the aryl group except for the non-monovalent.
  • the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, or combine with each other to form a hydrocarbon ring substituted or unsubstituted with -L1-Ar1.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms, or combine with each other to form an aromatic hydrocarbon ring substituted or unsubstituted with -L1-Ar1.
  • R1 and R2 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, or combine with each other to form a hydrocarbon ring unsubstituted or substituted with -L1-Ar1.
  • R1 and R2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combine with each other to form -L1-Ar1 A substituted or unsubstituted aromatic hydrocarbon ring is formed.
  • R1 and R2 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, or combine with each other to form -L1-Ar1 A substituted or unsubstituted aromatic hydrocarbon ring is formed.
  • R1 and R2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, or combine with each other to form -L1-Ar1 A substituted or unsubstituted aromatic hydrocarbon ring is formed.
  • R1 and R2 are phenyl groups, or combine with each other to form a fluorene ring unsubstituted or substituted with -L1-Ar1.
  • R1 and R2 are phenyl groups.
  • R1 and R2 are combined with each other to form a fluorene ring unsubstituted or substituted with -L1-Ar1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • G1 and G2 are the same as or different from each other, and each is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
  • R3 to R10 is -L1-Ar1, the rest is hydrogen,
  • any one of R3 to R10 and R101 to R108 is -L1-Ar1, the rest is hydrogen,
  • L1 and Ar1 are the same as defined in Formula 1 above.
  • G1 and G2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • G1 and G2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • G1 and G2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • G1 and G2 are a phenyl group.
  • L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.
  • L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.
  • L1 is a direct bond; phenylene group; biphenylrylene group; or a naphthylene group.
  • L1 is a direct bond.
  • L1 is a phenylene group.
  • L1 is a biphenylrylene group.
  • L1 is a naphthylene group.
  • Ar1 is a group represented by any one of the following structures.
  • Y1 is a group represented by Formula 3,
  • Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,
  • y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,
  • y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,
  • y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,
  • y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,
  • y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other.
  • Y2 is a substituted or unsubstituted aryl group.
  • Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.
  • Y2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • Y2 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms.
  • Y2 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 10 carbon atoms.
  • Y2 is a phenyl group unsubstituted or substituted with a methyl group; biphenyl group; or a naphthyl group.
  • Y3 is hydrogen
  • Y4 is hydrogen
  • Y5 is hydrogen
  • Y6 is hydrogen
  • Y7 is hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
  • Y7 is hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Y7 is hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Y7 is hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • Y7 is hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Y7 is hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Y7 is hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • Y7 is hydrogen; methyl group; or a phenyl group.
  • Y8 is hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
  • Y8 is hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Y8 is hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Y8 is hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • Y8 is hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Y8 is hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Y8 is hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • Y8 is hydrogen; methyl group; or a phenyl group.
  • Ar1 is a group represented by any one of the following structures.
  • Y1 is a group represented by the above formula (3).
  • Chemical Formula 3 is a group represented by any one of the following structures.
  • L2 is the same as defined in Formula 3 above,
  • At least one of Ra1 to Ra4 is a substituted or unsubstituted aryl group, the rest are the same as or different from each other, and each independently hydrogen; or deuterium,
  • At least one of Rb1 to Rb3 is a substituted or unsubstituted aryl group, the rest are the same as or different from each other, and each independently hydrogen; or deuterium,
  • At least one of Rc1 and Rc2 is a substituted or unsubstituted aryl group, and the remainder is hydrogen; or deuterium,
  • Rd1 is a substituted or unsubstituted aryl group.
  • L2 is a direct bond.
  • L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.
  • L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L2 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L2 is a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.
  • L2 is a phenylene group; or a biphenylrylene group.
  • At least one of Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Ra1 to Ra4 is a phenyl group; biphenyl group; or a naphthyl group, the rest being the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rb1 to Rb3 is a phenyl group; biphenyl group; or a naphthyl group, the rest being the same as or different from each other, and each independently hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, and the remainder is hydrogen; or deuterium.
  • At least one of Rc1 and Rc2 is a phenyl group; biphenyl group; or a naphthyl group, the remainder being hydrogen; or deuterium.
  • Rd1 is a substituted or unsubstituted aryl group.
  • Rd1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Rd1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Rd1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.
  • Rd1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Rd1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Rd1 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.
  • Rd1 is a phenyl group; biphenyl group; or a naphthyl group.
  • Rd1 is a phenyl group.
  • Rd1 is a biphenyl group.
  • Rd1 is a naphthyl group.
  • Formula 1 is selected from the following compounds.
  • the present specification provides an organic light emitting device including the compound represented by Formula 1 above.
  • the 'layer' means compatible with the 'film' mainly used in the present technical field, and refers to a coating covering a desired area.
  • the size of the 'layers' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
  • the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of D, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.
  • the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
  • the organic material layer includes a light emitting layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
  • the organic material layer includes an electron blocking layer.
  • 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 and an electron blocking layer. It further comprises one or more floors selected from.
  • the organic light emitting device includes a first electrode; a second electrode provided to face 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 material 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 and an electron blocking layer. Two or more may be selected from the group.
  • two or more hole transport layers are 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 negative electrode or an anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 to 3 illustrate an organic light emitting device, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102 , an organic material layer 111 , and a second electrode 110 are sequentially stacked on a substrate 101 .
  • the compound represented by Formula 1 is included in the organic layer.
  • FIG. 2 shows a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer ( 108 ), the electron injection layer 109 , and the second electrode 110 are sequentially stacked.
  • the structure of the organic light emitting device is exemplified. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the electron injection layer, the electron transport layer, or the hole blocking layer.
  • FIG. 3 shows a first electrode 102, a hole injection layer 103, a first hole transport layer 104-1, a second hole transport layer 104-2, a light emitting layer 106, an electron injection and
  • the structure of the organic light emitting device in which the transport layer 112 and the second electrode 110 are sequentially stacked is exemplified.
  • the compound represented by Formula 1 is included in the electron injection and transport layer.
  • the organic light emitting device of the present specification includes materials known in the art, except that the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer includes the compound, that is, the compound represented by Formula 1 above. method can be prepared.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO 2 /Al, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material having an excellent ability to prevent migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferred. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic materials;
  • polythiophene-based conductive polymers such as anthraquinone and polyaniline, but is not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the emission layer As such, a material having high electron mobility is preferable.
  • Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material, as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver.
  • a layer of aluminum or silver there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.
  • the electron injection layer is a layer that receives electrons from the electrode.
  • the organic light emitting device includes an additional electron injection layer other than the electron injection layer comprising Formula 1
  • the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an electron receiving effect from, and an excellent electron injection effect for the light emitting layer or the 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 formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer.
  • a known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be formed under the same conditions as the electron injection layer in general.
  • the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Formula 1, specifically, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex, and the like, but is not limited thereto.
  • the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • E1-A (20 g, 55.2 mmol) and E1-B (27.4 g, 55.2 mmol) were placed in 400 ml of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.9 g, 165.6 mmol) was dissolved in 23 ml of water and thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.9 g, 1.7 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E10 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • a first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 ⁇ of the HAT compound and 60 ⁇ of the HT-A compound on the hole injection layer.
  • the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to a thickness of 20 nm on the second hole transport layer to form a light emitting layer.
  • the compound E1 prepared in Preparation Example 1-1 and the LiQ compound below were vacuum deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 350 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10 -
  • an organic light emitting device was manufactured.
  • An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that Compounds E2 to 11 described in Table 1 were used instead of Compound E1 of Example 1, respectively.
  • An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that compounds ET-A to ET-S shown in Table 1 were used instead of Compound E1 of Example 1, respectively.
  • the compound represented by Formula 1 according to the present specification may be used in an organic material layer capable of simultaneously injecting and transporting electrons of the organic light emitting device. Comparing Experimental Examples 1 to 11 and Comparative Examples 1 to 6 in Table 1, the organic light emitting device including the compound of Formula 1 according to the present specification has a longer lifespan than the organic light emitting device including the compound not including Y1. It was confirmed that the remarkably excellent properties were shown.
  • the organic light emitting device including Formula 1 according to the present specification includes a compound in which Y1 is an unsubstituted pyridine group or an unsubstituted pyrimidine group It was confirmed that the organic light emitting device showed significantly superior characteristics in terms of efficiency than that of the organic light emitting diode.
  • the organic light emitting device including the compound of Formula 1 according to the present specification is more efficient than the organic light emitting device including the compound in which R1 and R2 are alkyl groups , and it was confirmed that it showed remarkably excellent characteristics in terms of lifespan.
  • Ar1 is Chemical Formula 2-1, and at least two of X1 to X3 are N.
  • Organic light emitting including a compound It can be seen that the device exhibits significantly superior characteristics in terms of driving voltage and efficiency than the organic light emitting device including the compound in which only one of X1 to X3 is N.
  • Ar1 according to the present specification is Formula 2-1, L2 of Formula 3 is a direct bond, and at least two of R are substituted or
  • An organic light emitting device including an unsubstituted aryl group is more efficient than an organic light emitting device including a compound in which Ar1 is Formula 2-1, L2 of Formula 3 is a direct bond, and only one of R is an aryl group, and It was confirmed that it showed remarkably excellent characteristics in terms of life.

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/018494 2019-12-20 2020-12-17 Composé et dispositif électroluminescent organique le comprenant WO2021125813A1 (fr)

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CN113292497B (zh) * 2021-02-09 2023-04-11 长春海谱润斯科技股份有限公司 一种五元杂环衍生物及其有机电致发光器件
CN116969928B (zh) * 2022-06-30 2024-04-19 江苏三月科技股份有限公司 一种含氮杂环结构的化合物及其在有机电致发光器件上的应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150111441A (ko) * 2014-03-24 2015-10-06 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN105601612A (zh) * 2015-12-29 2016-05-25 上海道亦化工科技有限公司 含有吲哚基团的磷光主体化合物及其有机电致发光器件
KR20170101021A (ko) * 2016-02-26 2017-09-05 삼성에스디아이 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20170111802A (ko) * 2016-03-29 2017-10-12 주식회사 엘지화학 유기 발광 소자
KR20180031766A (ko) * 2015-07-30 2018-03-28 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
WO2011005060A2 (fr) * 2009-07-10 2011-01-13 제일모직 주식회사 Composé pour élément photoélectrique organique et élément photoélectrique organique comprenant ce composé
CN104193738B (zh) * 2014-08-21 2016-05-18 上海道亦化工科技有限公司 一种基于苯并咪唑的电子传输化合物
KR102633649B1 (ko) * 2015-11-19 2024-04-17 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180003176A (ko) * 2016-06-30 2018-01-09 주식회사 에스케이씨 전력 계통 모니터링을 이용한 도금 불량 추적 시스템
KR20190009994A (ko) * 2017-07-20 2019-01-30 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
CN109748909B (zh) * 2017-11-02 2022-04-19 江苏三月科技股份有限公司 一种含螺氧杂蒽芴和含氮六元杂环的化合物、其制备方法及其在有机电致发光器件中的应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150111441A (ko) * 2014-03-24 2015-10-06 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20180031766A (ko) * 2015-07-30 2018-03-28 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
CN105601612A (zh) * 2015-12-29 2016-05-25 上海道亦化工科技有限公司 含有吲哚基团的磷光主体化合物及其有机电致发光器件
KR20170101021A (ko) * 2016-02-26 2017-09-05 삼성에스디아이 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20170111802A (ko) * 2016-03-29 2017-10-12 주식회사 엘지화학 유기 발광 소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022131135A1 (fr) * 2020-12-14 2022-06-23 東ソー株式会社 Composé de pyrimidine et élément électroluminescent organique

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