WO2020180005A1 - Composé binaphtalène et dispositif électroluminescent organique le comprenant - Google Patents

Composé binaphtalène et dispositif électroluminescent organique le comprenant Download PDF

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WO2020180005A1
WO2020180005A1 PCT/KR2020/000806 KR2020000806W WO2020180005A1 WO 2020180005 A1 WO2020180005 A1 WO 2020180005A1 KR 2020000806 W KR2020000806 W KR 2020000806W WO 2020180005 A1 WO2020180005 A1 WO 2020180005A1
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차용범
양정훈
홍성길
이재구
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주식회사 엘지화학
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Priority to CN202080006914.2A priority Critical patent/CN113195458A/zh
Publication of WO2020180005A1 publication Critical patent/WO2020180005A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/02—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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present specification relates to a binaphthalene compound and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure made of different materials.
  • the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification is to provide a binaphthalene compound and an organic light emitting device including the same.
  • A1 to A6 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, represented by the following formula (2),
  • A1, A3, A4 and A5 are represented by the following formula (2),
  • R1 to R8 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar1 and Ar2 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,
  • L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • X1 to X3 are the same as or different from each other, and each independently CH or N,
  • At least one of X1 to X3 is N.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a binaphthalene compound represented by Formula 1 above. Provides.
  • the compound according to the exemplary embodiment of the present specification is used in an organic light-emitting device, so that a driving voltage of the organic light-emitting device may be lowered and light efficiency may be improved. In addition, it is possible to improve the life characteristics of the device by the thermal stability of the compound.
  • 1 to 3 illustrate examples of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • the compound represented by Formula 1 is a compound in which a nitrogen-containing 6-membered substituent is connected to binaphthalene, and has long life and high efficiency characteristics when used as a hole blocking layer, an electron transport layer, or an electron injection layer of an organic light-emitting device.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Alkyl group; Silyl group; Aryl group; And a heteroaryl group containing at least one of N, O, and S atoms, substituted with one or two or more substituents selected from the group consisting of, or substituted with a substituent to which two or more substituents are connected, or have any substituents. Means not.
  • connection of two or more substituents means that hydrogen of any one substituent is connected with another substituent.
  • an isopropyl group and a phenyl group are connected or It can be a substituent of.
  • connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections.
  • two phenyl groups and isopropyl groups are connected or It may be a substituent of. The same applies to those in which four or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR 201 R 202 R 203 , R 201 to R 203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, methyldiphenylsilyl group, t- Butyldiphenylsilyl group, phenylsilyl group, and the like, but are not limited thereto.
  • an aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative.
  • an aromatic hydrocarbon refers to a compound in which pi electrons are completely conjugated and includes a planar ring
  • a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon.
  • the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other.
  • the aryl group is not particularly limited, but includes 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the substituted fluorenyl group when the fluorenyl group may be substituted, includes all compounds in which the substituents of the pentagonal rings of fluorene are spied to each other to form an aromatic hydrocarbon ring.
  • the substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited thereto.
  • the heterocyclic group is an atom other than carbon and includes one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, and S.
  • the number of carbon atoms is not particularly limited, the number of carbon atoms is 2 to 50; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13.
  • heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazino-pyrazine group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxadiazole
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic, and may be selected from examples of the heterocyclic group.
  • the heteroaryl group refers to a monovalent aromatic heterocycle.
  • the aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and refers to a group including at least one of N, O, and S in the ring as a hetero atom.
  • the aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring.
  • the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms are connected to each other. 2 to 50 carbon atoms of the heteroaryl group; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13.
  • an 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.
  • a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • I can.
  • 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 to each other.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent one.
  • the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • a 6-membered nitrogen-containing substituent is connected to two or more carbons in the group consisting of carbons 3, 7, 3'and 7'of binaphthalene.
  • the nitrogen-containing 6-membered substituent includes triazine, pyrimidine, and pyridine, and the nitrogen-containing 6-membered substituent may be substituted with an aryl group or heteroaryl group.
  • the compound of Formula 1 is a nitrogen-containing 6 member at the 2nd, 4th, 5th, 6th, 8th, 2', 4', 5', 6'or/and 8'times of binaphthalene Device performance is better than when a substituent is connected.
  • a nitrogen-containing 6-membered substituent is connected to carbon 3 and 3'of binaphthalene.
  • 6-membered nitrogen-containing substituents are connected to carbons 7 and 7'of binaphthalene.
  • A1 to A6 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, represented by Formula 2, and at least two of A1, A3, A4, and A5 are represented by Formula 2.
  • A1 and A6 are the same as or different from each other, and each independently is represented by Formula 2 above.
  • A3 and A4 are the same as or different from each other, and each independently is represented by Formula 2 above.
  • A1 to A6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, represented by Formula 2, and at least two of A1, A3, A4, and A5 are represented by Formula 2.
  • A2 and A5 are the same as or different from each other, and each independently hydrogen or deuterium.
  • A2 and A5 are hydrogen.
  • R1 to R8 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • two of A1, A3, A4, and A5 are represented by Formula 2, and the remaining four and R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
  • two of A1, A3, A4, and A5 are represented by Formula 2, and the remaining four and R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.
  • R1 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.
  • R1 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.
  • R1 and R8 are the same.
  • R2 to R7 are each hydrogen.
  • Ar1 and Ar2 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.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or bicyclic aryl group; Or a substituted or unsubstituted monocyclic or bicyclic heteroaryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted chrysenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group;
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar1 and Ar2 are a phenyl group; Biphenyl group; Or a naphthyl group.
  • L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroarylene group.
  • L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroarylene group.
  • L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent carbazole group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • L1 is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.
  • L1 is a direct bond; Or an arylene group having 6 to 20 carbon atoms.
  • L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L1 is a direct bond; Phenylene group; Or a biphenylene group.
  • L1 is a direct bond.
  • L1 is any one selected from the following structures.
  • the structure is deuterium; Halogen group; Nitrile group; Alkyl group; Silyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, or does not have any substituents.
  • X1 to X3 are the same as or different from each other, and each independently CH or N, and at least one of X1 to X3 is N.
  • X1 is N
  • X2 and X3 are CH.
  • X2 is N
  • X1 and X3 are CH.
  • X3 is N, and X1 and X2 are CH.
  • X1 and X2 are N, and X3 is CH.
  • X1 and X3 are N, and X2 is CH.
  • X2 and X3 are N, and X1 is CH.
  • X1 to X3 are N.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 101 or 103.
  • A1 to A6, R1 to R8, L1, X1 to X3, Ar1 and Ar2 are as defined in Formula 1,
  • Ar3 and Ar4 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,
  • L2 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • X4 to X6 are the same as or different from each other, and each independently CH or N,
  • At least one of X4 to X6 is N.
  • Ar3 and Ar4 may be described with respect to Ar1 and Ar2 described above.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • the compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. If necessary, a substituent may be added or removed, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, and the like can be changed based on techniques known in the art.
  • the compound represented by Formula 1 may have a core structure as shown in Formula 1 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. Substituents may be combined as shown in the following general formula 1, but are not limited thereto.
  • R1, R8, L1, X1 to X3, Ar1 and Ar2 are the same as those defined in Chemical Formula 1.
  • A1 to A6 and R2 to R7 are not shown in the general formula 1, A1 to A6 and R2 using a reactant in which A1 to A6 and R2 to R7 are substituted, or using a method known for the compound prepared above. To R7 may be substituted to obtain a desired compound.
  • the present specification provides an organic light-emitting device including the above-described compound.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers 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'layer' is meant to be compatible with the'film' mainly used in the present technical field, and means a coating covering a desired area.
  • the size of the'layer' is not limited, and each'layer' may be the same or different in size. In one embodiment, the size of the'layer' may be the same as the entire device, may correspond to the size of a specific functional region, and may be as small as a single sub-pixel.
  • the meaning that a specific A material is included in the B layer means that i) one or more A material is included in one layer B, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B Includes all those included in one or more of the floors.
  • the meaning that a specific A material is included in the C layer or the D layer means i) is included in one or more of the C layers, ii) is included in one or more of the D layers, or iii ) It means both included in one or more layers C and one or more layers D.
  • the organic light-emitting device may include an additional organic material layer in addition to the emission layer.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer 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 emission layer, and the emission layer includes a binaphthalene compound represented by Chemical Formula 1.
  • the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the binaphthalene compound represented by Formula 1 above. .
  • the organic material layer includes an electron injection layer, a hole blocking layer, or an electron transport layer, and the electron injection layer, the electron transport layer, or the hole blocking layer includes the binaphthalene compound represented by Formula 1 above. .
  • the organic material layer includes an electron injection layer, and the electron injection layer includes a binaphthalene compound represented by Formula 1 above.
  • the organic material layer includes an electron transport layer
  • the electron transport layer includes the binaphthalene compound represented by Chemical Formula 1.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes a binaphthalene compound represented by Formula 1 above.
  • the organic material layer including the binaphthalene compound represented by Formula 1 is in contact with the emission layer.
  • the organic material layer including the binaphthalene compound represented by Formula 1 is a hole blocking layer, and the hole blocking layer is provided in contact with the emission layer.
  • the organic material layer is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; An emission layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the emission layer and the first electrode, or between the emission layer and the second electrode.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 to 3. 1 to 3 illustrate an organic light-emitting device, but are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which an anode 102, an emission layer 106, and a cathode 110 are sequentially stacked on a substrate 101.
  • the compound represented by Formula 1 is included in the emission layer.
  • an anode 102 an anode 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, and an electron transport layer 108 on the substrate 101.
  • the structure of an organic light emitting device in which the electron injection layer 109 and the cathode 110 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 is included in the emission layer.
  • the compound represented by Formula 1 is included in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.
  • an anode 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 injection and transport layer on the substrate 101 ( 111) and the cathode 110 are sequentially stacked on the structure of an organic light-emitting device.
  • the compound represented by Formula 1 is included in the emission layer.
  • the compound represented by Formula 1 is included in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.
  • the organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that the emission layer includes the compound.
  • 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 laminating 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 the anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as 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, spray method, 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 preferable 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);
  • a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-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 furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • the host material of the emission layer is an anthracene derivative.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene 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 is selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamine group.
  • the substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the dopant material of the emission layer is a pyrene derivative having an arylamine group.
  • the dopant material of the emission layer is N 1 ,N 6 -bis(6-(tert-butyl)dibenzo[b,d]furan-4-yl)-N 1 ,N 6 -di -m-tolylpyrene-1,6-diamine.
  • the hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Further, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole injection layer is a material in which at least two selected from the group consisting of an arylamine-based organic material and hexanitrile hexaazatriphenylene-based organic material are mixed.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission 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 emission layer, and a material having high mobility for holes 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 a material capable of receiving electrons from the cathode and transferring them to the emission layer is preferable, and a material having high mobility for electrons 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 can be used with any desired negative electrode material, as used according to the prior art.
  • suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a 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 an electrode. It is preferable that the electron-injection material is excellent in the ability to transport electrons, and has an electron-receiving effect from the second electrode and an excellent electron-injection effect on the light emitting layer or the light emitting material. In addition, a material that prevents the 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, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • 8-hydroxyquinolinato lithium bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
  • the electron injection and transport layer includes an alkali metal complex compound.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • Known materials may 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 prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.
  • the hole blocking layer includes the compound represented by Chemical Formula 1.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent
  • distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum depositing a compound of the following compound HI1 and the following compound HI2 to a ratio of 98:2 (molar ratio) to a thickness of 100 ⁇ on the prepared anode ITO transparent electrode.
  • the following compound HT1 (1150 ⁇ ) was vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following compound EB1 was vacuum deposited on the hole transport layer with a film thickness of 50 ⁇ to form an electron blocking layer.
  • a light emitting layer was formed by vacuum depositing a compound represented by the following formula BH and a compound represented by the following formula BD with a film thickness of 200 ⁇ on the electron blocking layer at a weight ratio of 25:1.
  • a hole blocking layer was formed by vacuum depositing a compound represented by Compound 1 synthesized in Preparation Example 1 on the emission layer with a film thickness of 50 ⁇ . Subsequently, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310 ⁇ . Lithium fluoride (LiF) at a thickness of 12 ⁇ and aluminum at a thickness of 1,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the lithium fluoride at the negative electrode maintained a deposition rate of 0.3 ⁇ /sec, and the aluminum at 2 ⁇ /sec, and the vacuum degree during deposition was 2
  • An organic light emitting device was manufactured by maintaining ⁇ 10 -7 torr to 5 ⁇ 10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of the compound of Preparation Example 1.
  • the compounds of HB1, HB2, HB3 and HB4 used in Table 1 are as follows.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • Example 1-1 One 4.56 6.39 (0.146, 0.042) 240
  • Example 1-2 2 4.57 6.34 (0.144, 0.045) 245
  • Example 1-3 3 4.52 6.38 (0.146, 0.046)
  • Example 1-4 7 4.41 6.57 (0.146, 0.042) 255
  • Example 1-5 8 4.42 6.54 (0.144, 0.045) 265
  • Example 1-6 9 4.44 6.58 (0.146, 0.046) 250
  • Example 1-7 10 4.36 6.64 (0.144, 0.045) 275
  • Example 1-8 11 4.37 6.61 (0.146, 0.046) 285
  • Example 1-9 12 4.33 6.65 (0.146, 0.047) 280
  • Example 1-10 16 4.36 6.69 (0.146, 0.047) 285
  • Example 1-11 17 4.32 6.68 (0.146, 0.046) 290
  • Example 1-12 18 4.31 6.69
  • the organic light-emitting device using the compound of the present invention as a hole blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
  • Example 1-1 in the organic light emitting device using the compound of the present invention, 6-membered nitrogen-containing substituents are connected to carbon 4 and 4'of binaphthalene, or 2 and 2'of binaphthalene Comparative Example 1-1 prepared using a substance of HB1, HB2, HB3 and HB4, wherein a nitrogen-containing 6-membered substituent is connected to carbon or a nitrogen-containing 6-membered substituent is connected to carbon 6 and 6'of binaphthalene, Compared to the organic light emitting devices of 1-2, 1-3, and 1-4, it exhibited the characteristics of low voltage, high efficiency, and long life.

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Abstract

La présente invention concerne un composé binaphtalène représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/000806 2019-03-05 2020-01-16 Composé binaphtalène et dispositif électroluminescent organique le comprenant WO2020180005A1 (fr)

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