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WO2020050563A1 - Diode électroluminescente organique - Google Patents

Diode électroluminescente organique Download PDF

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Publication number
WO2020050563A1
WO2020050563A1 PCT/KR2019/011245 KR2019011245W WO2020050563A1 WO 2020050563 A1 WO2020050563 A1 WO 2020050563A1 KR 2019011245 W KR2019011245 W KR 2019011245W WO 2020050563 A1 WO2020050563 A1 WO 2020050563A1
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group
substituted
unsubstituted
formula
light emitting
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Korean (ko)
Inventor
허동욱
홍성길
허정오
한미연
이재탁
양정훈
윤희경
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LG Chem Ltd
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LG Chem Ltd
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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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit

Definitions

  • This specification relates to an organic light emitting device.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, 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.
  • aromatic diamine derivatives and aromatic condensed ring diamine derivatives have been known as hole transport materials used in organic EL devices.
  • the applied voltage is mostly high, problems such as deterioration of device life and large power consumption have arisen.
  • a method of doping an electron-accepting compound such as Lewis acid or using a hole injection layer of an organic EL device has been proposed.
  • the above method has shown that there is a limitation in the hole injection and transport, and therefore, the effect of low voltage, high efficiency, and long life time can be achieved by the combination of the material between the hole transport layer or the hole control layer or the material of the hole transport layer and the multilayer hole control layer. I tried to draw.
  • the hole transport layer aromatics were substituted tertiary amines, and the device characteristics found in the combination group of the materials have shown various results. Therefore, there is a continuous demand for the development of new materials for improving device characteristics due to hole transport and carrier control.
  • the present specification is to provide an organic light emitting device.
  • This specification is the first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode.
  • the first organic material layer includes a compound represented by Formula 1,
  • the second organic material layer provides an organic light emitting device comprising a compound represented by the following formula (3).
  • X is O or S
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • At least one of R1 to R4 is represented by the formula (2A) or 2B,
  • n1 to n4 are each independently an integer of 1 to 4,
  • At least one of A1 to A3 is N, and the other is CH or combines with an adjacent group of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
  • Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
  • Ar6 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, a is an integer from 0 to 5,
  • Ar1 and Ar2 each represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Ar3 is a substituted or unsubstituted divalent to tetravalent alkyl group; A substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent cycloalkyl group,
  • At least one of X1 to X3 is N, and the rest are CH;
  • L is a direct bond; Or a substituted or unsubstituted arylene group,
  • n5 is an integer of 2 to 4,
  • the organic light emitting device using the compound according to the exemplary embodiment of the present specification in the hole blocking layer, the electron control layer, the electron transport layer, or the electron injection and transport layer, respectively, can have a low driving voltage, high luminous efficiency, or long life.
  • 1, 3, and 4 show an example of an organic light emitting device in which the substrate 1, the anode 2, the light emitting layer 3, and the cathode 4 are sequentially stacked.
  • the substrate 1, the anode 2, the hole transport layer 5, the light emitting layer 3, the hole blocking layer or the electron control layer 6 electron injection and transport layer 7 and the cathode 4 are sequentially stacked It shows an example of the organic light emitting device.
  • This specification is the first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, wherein the first organic material layer includes a compound represented by Chemical Formula 1, and the second organic material layer is represented by Chemical Formula 3 It provides an organic light emitting device comprising the compound represented.
  • the compound represented by Chemical Formula 1 has an advantage of controlling triplet energy by having the core structure as described above, and may exhibit long life and high efficiency.
  • an organic light emitting device including the compound represented by Chemical Formula 1 in the first organic material layer of the organic light emitting device, and including the compound represented by Chemical Formula 3 as the second organic material layer of the organic light emitting device has an energy relationship of the following Formula 1 Have
  • E Et is the electron affinity of the compound represented by Formula 3 included in the second organic material layer (Electron Affinity (eV))
  • E Ec is represented by Formula 1 included in the first organic material layer
  • the first organic material layer containing the compound may be appropriately controlled to improve the efficiency and lifetime of the organic light emitting device.
  • substitution 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 to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted is hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent having two or more substituents may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60.
  • 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, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto. Does not.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40.
  • 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, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the amine group is selected from the group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group.
  • the carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-60.
  • the polycyclic aryl group may be naphthyl group, anthracene group, phenanthrene group, pyrene group, perylene group, chrysene group, fluorene group and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent substituents may combine with each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, 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, phenanththroline group, isoxazole group, thioph
  • ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
  • the hydrocarbon ring may be an aromatic hydrocarbon, an aliphatic hydrocarbon or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group or the aryl group except for the above-mentioned monovalent.
  • the aromatic hydrocarbon ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S.
  • the heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heterocyclic group except that it is not monovalent.
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.
  • the divalent heterocyclic group refers to a divalent group having two bonding positions in the heterocyclic group.
  • the description of the aforementioned heterocyclic groups can be applied except that they are each divalent.
  • the divalent to tetravalent alkyl group refers to those having two to four bond positions, that is, divalent to tetravalent groups.
  • the description of the aforementioned alkyl groups can be applied except that they are each 2 to 4 valent groups.
  • the divalent to tetravalent aryl group refers to those having two to four bond positions, that is, divalent to tetravalent groups.
  • the description of the aforementioned aryl groups can be applied except that they are each 2 to 4 valent groups.
  • the divalent to tetravalent cycloalkyl group refers to those having two to four bond positions, that is, divalent to tetravalent groups.
  • the description of the cycloalkyl group described above can be applied except that they are each 2 to 4 valent groups.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • a group other than the general formula 2A or 2B of the R1 to R4 is hydrogen or deuterium.
  • At least one of the groups R1 to R4 other than the general formula 2A or 2B is an alkyl group, an aryl group, or an aryl group substituted with an alkyl group, the rest is hydrogen or deuterium.
  • At least one of the groups R1 to R4 other than the following formula A or 2B is a methyl group; n-butyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Naphthyl group; Or a fluorene group substituted with a methyl group, and the remainder is hydrogen or deuterium.
  • n1 is 2, and the adjacent R1 combines with each other to form a substituted or unsubstituted ring.
  • n1 is 2, and the adjacent R1 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • n1 is 2, and the adjacent R1 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • n1 is 2
  • the adjacent R1 is bonded to each other to form a substituted or unsubstituted benzene ring.
  • the n1 is 2, the adjacent R1 is bonded to each other to form a benzene ring.
  • n2 is 2
  • the adjacent R2 combines with each other to form a substituted or unsubstituted ring.
  • n2 is 2 and the adjacent R2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • n2 is 2
  • the adjacent R2 combines with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted benzene ring.
  • n2 is 2, and the adjacent R2 are bonded to each other to form a benzene ring.
  • the n1 is 2, the adjacent R1 is bonded to each other to form a substituted or unsubstituted ring, the n2 is 2, the adjacent R2 is bonded to each other to form a benzene ring. .
  • At least one of the R1 to R4 is represented by the formula 2A or 2B.
  • one of the R1 to R4 is represented by the formula 2A or 2B.
  • two of the R1 to R4 are represented by the formula 2A or 2B.
  • one of the R2 and one of the R3 is represented by the formula 2A or 2B.
  • At least one of A1 to A3 is N, the remainder is CH, or combine with an adjacent group of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylylene group.
  • L3 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Divalent thiophene group; Divalent furan group; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent carbazole groups unsubstituted or substituted with an aryl group or an alkylaryl group; Divalent benzocarbazole groups unsubstituted or substituted with an aryl group or an alkylaryl group; Divalent dibenzosilol groups substituted or substituted with alkyl groups; Divalent phenoxathiine group; Divalent phenoxazine; Divalent phenothiazine group; Divalent pyridine group; A divalent dihydroindenocarbazole group unsubstituted or substituted with an alkyl group; Divalent groups in which dibenzothiophene and a phenyl group are linked; Or a divalent group linked
  • L3 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Divalent thiophene group; Divalent furan group; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent carbazole groups unsubstituted or substituted with a phenyl group or a methylphenyl group; Divalent benzocarbazole groups unsubstituted or substituted with a phenyl group or a methylphenyl group; Divalent dibenzosilol group substituted or substituted with a methyl group; Divalent phenoxathiine group; Divalent phenoxazine; Divalent phenothiazine group; Divalent pyridine group; A divalent dihydroindenocarbazole group unsubstituted or substituted with a methyl group; Divalent groups in which dibenzothiophene and a phenyl group are
  • Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring.
  • Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combined with an adjacent group among A1 to A3 to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.
  • Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.
  • Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.
  • Ar4 and Ar5 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.
  • Ar4 and Ar5 are the same as or different from each other, and each independently CN, alkyl group, alkoxy group, haloalkyl group, haloalkoxy group, alkylsilyl group, aryl group, alkylaryl group or heterocyclic ring
  • Ar4 and Ar5 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a triphenylene group, a phenanthrene group, a fluoranthene group, Phenylene group, carbazole group, benzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, phenoxathiine group, phenoxazine group, phenoxazine group, phenothiazine group, pyridyl group, Dihydroindenocarbazole, an arylsilyl group, an alkylsilyl group, a spirofluorene xanthene group and a group in which one or two or more groups selected from spirofluorene thiox
  • the heterocyclic group as a substituent is a carbazole group, a benzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilol group, a phenoxathiine, a phenoxazine group, a phenothiazine group, It may be a pyridyl group or a dihydroindenocarbazole group, and the aryl group as a substituent may be a phenyl group, a biphenyl group, a naphthyl group, or a triphenylene group.
  • the alkyl group may be a methyl group, or tert-butyl group
  • the alkoxy group may be a methoxy group
  • the haloalkyl group may be a trifluoromethyl group
  • the haloalkoxy group may be a trifluoromethoxy group
  • the silyl group may be a methylsilyl group.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5.
  • X, R1 to R4, L1 to L3, A1 to A3, Ar4, Ar5 and n1 to n4 are the same as defined in Chemical Formulas 1 and 2A, and L1 ', L2', L3 ', A1', A2 'and A3. ', Ar4' and Ar5 'are the same as the definitions of L1, L2, L3, A1, A2, A3, Ar4 and Ar5, respectively.
  • two of A1 to A3 of Formula 2A are N.
  • A1 to A3 of Formula 2A are N.
  • Chemical Formula 2A may be selected from the following structural formulas.
  • Ar6 of Formula 2B is 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 heteroring 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 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • 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 heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with deuterium, CN, a halogen group, an alkyl group, a haloalkyl group, an alkoxy group, or an aryl group; Or a heterocyclic group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, CN, a halogen group, an alkyl group, a haloalkyl group, an alkoxy group, or an aryl group; Biphenyl group; Naphthyl group; Pyridine group; Or a thiophene group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, CN, F, trifluoromethyl group, methyl group, tert-butyl group, methoxy group, or phenyl group Phenyl group; Biphenyl group; Naphthyl group; Pyridine group; Or a thiophene group.
  • n5 is 2.
  • n5 is 2, and the substituents in the parentheses are the same as or different from each other.
  • Ar3 is a substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent cycloalkyl group.
  • Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent cycloalkyl group having 3 to 60 carbon atoms.
  • Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent cycloalkyl group having 3 to 30 carbon atoms.
  • Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted divalent cycloalkyl group having 3 to 15 carbon atoms.
  • Ar3 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent phenanthrene group; Or a substituted or unsubstituted divalent cycloalkyl group.
  • Ar3 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent phenanthrene group; Or a substituted or unsubstituted cyclohexanylene group.
  • Ar3 is a phenylene group; Naphthylene group; Divalent phenanthrene group; Or a cyclohexanylene group.
  • Ar3 is a naphthylene group; Divalent phenanthrene group; Or a cyclohexanylene group.
  • Ar3 is a substituted or unsubstituted divalent tricyclic or more aryl group; Or a substituted or unsubstituted divalent cycloalkyl group.
  • Ar3 is a divalent tricyclic or higher aryl group; Or a divalent cycloalkyl group.
  • Ar3 is a divalent phenanthrene group; Or a cyclohexanylene group
  • Ar3 is a substituted or unsubstituted divalent alkyl group.
  • Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 60 carbon atoms.
  • Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 30 carbon atoms.
  • Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 15 carbon atoms.
  • Ar3 is a divalent alkyl group unsubstituted or substituted with an aryl group.
  • Ar3 is a divalent alkyl group unsubstituted or substituted with a phenyl group.
  • Ar3 is a methylene group unsubstituted or substituted with a phenyl group.
  • At least one of the X1 to X3 is N, the remainder is CH.
  • X1 is N and the others are CH.
  • X2 is N and the others are CH.
  • X3 is N and the others are CH.
  • X1 and X2 are N and the others are CH.
  • X1 and X3 are N and the others are CH.
  • X2 and X3 are N and the others are CH.
  • X1 to X3 are N.
  • L is a direct bond
  • L is a substituted or unsubstituted arylene group.
  • L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • L is a substituted or unsubstituted phenylene group.
  • L is a phenylene group.
  • Chemical Formula 1 is selected from the following structural formulas.
  • Chemical Formula 3 is selected from the following structural formulas.
  • the first and second organic material layers of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layered structure in which two or more organic material layers are stacked.
  • the first organic material layer of the present specification may be composed of 1 to 3 layers.
  • the organic light emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or the like as an organic material layer or a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection and transport layer, and the like.
  • the structure of the organic light emitting device is not limited thereto, and may include more or fewer organic layers.
  • the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.
  • the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer and a hole blocking layer.
  • the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection and transport layer, a hole control layer and an electron control layer.
  • the organic light emitting device may further include an electron charge generating layer.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least two light emitting layers provided between the first electrode and the second electrode.
  • Two or more first and second organic material layers provided between the two or more light emitting layers and the first electrode or between the two or more light emitting layers and the second electrode, wherein the two or more first and second organic material layers Each includes a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 3.
  • the first organic material layer includes a hole blocking layer or an electron control layer
  • the second organic material layer includes an electron transport layer
  • the hole blocking layer or the electron control layer is represented by Chemical Formula 1
  • the electron transport layer may include a compound represented by the formula (3).
  • the first organic material layer includes a hole blocking layer or an electron control layer
  • the second organic material layer includes an electron injection and transport layer
  • the hole blocking layer or the electron control layer is represented by Chemical Formula 1 It includes a compound represented by
  • the electron injection and transport layer may include a compound represented by the formula (3).
  • the first and second organic material layers further include a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer including the compound. .
  • the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic light emitting diode may include two or more light emitting layers.
  • each light emitting layer may independently include a fluorescent dopant or a phosphorescent dopant.
  • one light emitting layer may include a fluorescent dopant, and the other light emitting dopant.
  • the organic light emitting diode may include two or more light emitting layers emitting light of different wavelength bands between the first electrode and the second electrode.
  • the two or more light emitting layers may be provided in the vertical direction of the direction of the second electrode from the first electrode, or may be provided in the horizontal direction.
  • FIG. 2 shows a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or an electron control layer 6, an electron injection and transport layer 7 and a cathode 4 sequentially.
  • the structure of the stacked organic light emitting device is illustrated.
  • another organic light emitting diode may include three or more light emitting layers.
  • another layer may be additionally provided between each light emitting layer and the light emitting layer.
  • each light emitting layer may include a blue fluorescent light emitting layer.
  • the compound represented by Chemical Formula 1 may be included in the hole blocking layer or the electron control layer 6, and the compound represented by Chemical Formula 3 may be included in the electron injection and transport layer 7.
  • the light emitting layer of the three or more layers may be provided in a vertical direction of the direction of the second electrode from the first electrode, or may be provided in the horizontal direction. More specifically, the first electrode may be provided in a horizontal direction in the direction of the second electrode.
  • the blue fluorescent light emitting layer includes a host and a dopant, and the host may be any one selected from the following structures.
  • the organic light emitting device of the present specification is a material and method known in the art, except that at least one layer of the first or second organic material layer includes a compound of the present specification, that is, the compounds represented by Chemical Formulas 1 and 3 above. 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 is a material and method known in the art except that at least one layer of the first or second organic material layer includes the compound, that is, the compound represented by any one of Formulas 1 and 3 above. Can be prepared.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking first electrodes, first and second organic material layers, and second electrodes on a substrate. At this time, using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, metal or conductive metal oxides or alloys thereof are deposited on the substrate to form an anode. And, after forming a hole injection layer, a hole transport layer, an organic material layer including a light emitting layer and an electron transport layer, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • PVD physical vapor deposition
  • the compounds of Formulas 1 and 3 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • an organic material layer and an anode material may be sequentially deposited on a substrate to form an organic light emitting device (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • 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 anode material a material having a large work function is generally preferred to facilitate hole injection.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metal and oxide such as Sb; 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 a material having a small work function to facilitate electron injection.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in a light emitting layer
  • a compound that prevents migration of the excited excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferred. 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
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transport material the hole is transported to the light emitting layer by transporting holes from the anode or the hole injection layer, and the mobility of holes is large.
  • the material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • the electron transporting material is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be an electron control layer to control electrons reaching the light emitting layer.
  • the electron charge generating layer is a layer for generating an electron charge.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
  • a compound represented by Chemical Formula EC7 was prepared by the same method as the preparation method of EC1 of Preparation Example 1, except that each starting material was performed in the same manner as in the above scheme.
  • a compound represented by Chemical Formula EC10 was prepared by the same method as the preparation method of EC1 of Preparation Example 1, except that each starting material was performed in the same manner as in the above scheme.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water was filtered secondly as a filter of Millipore Co. product.
  • ultrasonic washing was repeated 10 times with distilled water twice.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer. 50 ⁇ of the following HAT compound and 60 ⁇ of the following HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the BH compound and the following BD compound were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to form a light emitting layer to form a film thickness of 200 Pa.
  • the compound EC1 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 kHz.
  • the compound ET1 and the following LiQ compound were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa.
  • the cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 1000 ⁇ ⁇ on the electron injection and transport layer sequentially.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
  • the aluminum was 2 ⁇ / sec.
  • An organic light-emitting device was manufactured by maintaining ⁇ 7 to 5 ⁇ 10 ⁇ 5 torr.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Table 1 instead of the compound EC1 and ET1 of Example 1-1.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-18 were measured at a current density of 10 mA / cm 2 , and 20 mA / cm
  • the time T90 of 90% of the initial luminance at the current density of 2 was measured. The results are shown in Table 1 below.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water was filtered secondly as a filter of Millipore Co. product.
  • ultrasonic washing was repeated 10 times with distilled water twice.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a first hole injection layer.
  • the following HAT compound 50 Hz and the following HT-A compound 60 Hz were sequentially vacuum deposited on the first hole injection layer to form a first hole transport layer.
  • a BH compound and a BD compound were vacuum deposited on the first hole transport layer at a film thickness of 200 Pa at a weight ratio of 25: 1 to form a first light emitting layer.
  • the compound EC1 was vacuum-deposited on the first emission layer to form a first hole blocking layer having a thickness of 50 ⁇ s.
  • the compound ET1 and the following LiQ compound were vacuum deposited on the first hole blocking layer in a weight ratio of 1: 1 to form a first electron injection and transport layer at a thickness of 200 ⁇ s.
  • Compound ET-C and a lithium compound were vacuum deposited on the first electron injection and transport layer at a film thickness of 100 Pa to form an electron charge generating layer.
  • a HI-A compound was thermally vacuum-deposited to a thickness of 100 Pa to form a second hole injection layer.
  • the second HAT compound 50 ⁇ s and the following HT-A compound 60 ⁇ s were sequentially vacuum deposited on the second hole injection layer to form a second hole transport layer.
  • a BH compound and a BD compound were vacuum deposited on the second hole transport layer at a film thickness of 200 Pa at a weight ratio of 25: 1 to form a second light emitting layer.
  • Compound EC1 was vacuum deposited on the second light emitting layer to form a hole blocking layer having a thickness of 50 kHz.
  • the compound ET1 and the following LiQ compound were vacuum deposited on the second hole blocking layer at a weight ratio of 1: 1 to form a second electron injection and transport layer at a thickness of 200 ⁇ s.
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 1000 ⁇ on the second electron injection and transport layer sequentially.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
  • the aluminum was 2 ⁇ / sec.
  • An organic light-emitting device was manufactured by maintaining ⁇ 7 to 5 ⁇ 10 ⁇ 5 torr.
  • An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using the compound of Table 1 instead of the compound EC1 and ET1 of Example 2-1.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Examples 2-2 to 2-18 and Comparative Examples 2-1 to 2-18 were measured at a current density of 10 mA / cm 2 , and 20 mA / cm 2.
  • the time T90 of 90% of the initial luminance at the current density of was measured. The results are shown in Table 2 below.
  • Electron Affinity (eV) values according to one embodiment of the present specification are shown in Table 3 below.
  • Electron Affinity was performed using Gaussian 03, a quantum chemistry calculation program manufactured by Gaussian, USA, using density functional theory (DFT), B3LYP, basis function
  • the calculated value was calculated by time dependent density functional theory (TD-DFT) for the structure optimized by using 6-31G * as an electron injection and the compound of Formula 1 used in the hole blocking layer of Table 3
  • TD-DFT time dependent density functional theory
  • the amount of electrons transferred from Formula 3, which is an electron injection and transport compound, in the organic light emitting device having the relationship of E Et > E Ec in the relationship of Electron Affinity (eV) with the compound of Formula 3 used in the transport layer Formula 1, which is a hole blocking layer (or electron control layer) compound, is appropriately controlled to improve efficiency and lifespan of the organic light emitting device.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une diode électroluminescente organique qui comprend : une première électrode ; une seconde électrode placée à l'opposé de la première électrode ; et une première couche organique et une seconde couche organique disposées entre la première électrode et la seconde électrode, la première couche organique comprenant un composé représenté par la formule chimique 1, et la seconde couche organique comprenant un composé représenté par la formule chimique 3.
PCT/KR2019/011245 2018-09-03 2019-09-02 Diode électroluminescente organique Ceased WO2020050563A1 (fr)

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CN114685419B (zh) * 2020-12-29 2024-10-29 北京绿人科技有限责任公司 含螺环结构的有机化合物及有机电致发光器件
CN117177967A (zh) * 2022-03-21 2023-12-05 株式会社Lg化学 含杂环的化合物和包含其的有机发光器件
WO2023195735A1 (fr) * 2022-04-04 2023-10-12 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
CN119678676A (zh) * 2022-12-01 2025-03-21 株式会社Lg化学 有机发光器件
KR20250079495A (ko) * 2023-11-27 2025-06-04 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

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