WO2019168320A1 - Composé et diode électroluminescente organique le comprenant - Google Patents

Composé et diode électroluminescente organique le comprenant Download PDF

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WO2019168320A1
WO2019168320A1 PCT/KR2019/002316 KR2019002316W WO2019168320A1 WO 2019168320 A1 WO2019168320 A1 WO 2019168320A1 KR 2019002316 W KR2019002316 W KR 2019002316W WO 2019168320 A1 WO2019168320 A1 WO 2019168320A1
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group
substituted
unsubstituted
compound
light emitting
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Korean (ko)
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차용범
정민우
홍성길
서상덕
이재구
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주식회사 엘지화학
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Priority to CN201980004957.4A priority Critical patent/CN111201214B/zh
Publication of WO2019168320A1 publication Critical patent/WO2019168320A1/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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • 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]
    • H10K50/17—Carrier injection 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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a compound represented by Formula 1 and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode, and an organic material layer therebetween.
  • the organic material layer has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted fluorene ring,
  • R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
  • a and B is -L1-Ar1, the other is -L2-NAr2Ar3,
  • L 1 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C24 aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a is an integer of 0-6, and when a is 2 or more, R ⁇ 3> is same or different from each other.
  • an exemplary embodiment of the present specification is an organic light emitting device including a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound is included in the organic material layer provided between the anode and the light emitting layer.
  • an organic light emitting device including a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound is included in the organic material layer provided between the anode and the light emitting layer.
  • the organic light emitting device including the compound of the present invention may be improved in efficiency.
  • the organic light emitting device including the compound of the present invention may have a low driving voltage.
  • the organic light emitting device including the compound of the present invention may have improved lifetime characteristics.
  • FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 11, a light emitting layer 6, and a cathode 10.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8.
  • An example of an organic light emitting element comprising an electron injection layer 9 and a cathode 10 is shown.
  • substituted means that a hydrogen atom bonded to a 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 a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Nitrile group; Nitro group; Hydroxyl group; An alkyl group; Aralkyl group; An alkoxy group; Alkenyl groups; Aryloxy group; Aryl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of a heteroaryl group, or two or more substituents of the substituents selected from the group means substituted or unsubstituted.
  • Examples of the group to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, a heteroaryl group substituted with an aryl group substituted with a heteroaryl group, and the like.
  • substituted or unsubstituted is deuterium; An alkyl group; Aralkyl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of aryl groups, or substituted or unsubstituted with a group to which two or more groups from the substituents selected from the group connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkoxy group means a group in which an alkyl group is bonded to an oxygen atom, and the carbon number is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like.
  • the aryloxy group means a group in which an aryl group is bonded to an oxygen atom, and carbon number is not particularly limited, but is preferably 6 to 40. According to an exemplary embodiment, the aryloxy group has 6 to 30 carbon atoms.
  • aryloxy group examples include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, 3-biphenyloxy group, 1- Naphthyloxy group, 2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryl jade There is a period.
  • the alkyl group means a straight or branched hydrocarbon group, and the carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl , tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl,
  • the cyclic alkyl group in the alkyl group is referred to as a cycloalkyl group.
  • carbon number of a cycloalkyl group is not specifically limited, It is preferable that it is 3-60.
  • the cycloalkyl group has 3 to 30 carbon atoms.
  • the cycloalkyl group has 3 to 20 carbon atoms.
  • the cycloalkyl group has 3 to 6 carbon atoms.
  • the alkenyl group represents a straight-chain or pulverized unsaturated hydrocarbon group including a carbon-carbon double bond, and the carbon number is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl.
  • the aralkenyl group means an alkenyl group substituted with an aryl group.
  • an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated.
  • carbon number is not specifically limited, It is preferable that it is C6-C60, It may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 40 carbon atoms.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group has 6 to 20 carbon atoms.
  • Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto.
  • polycyclic aryl group a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heteroaryl group is an aromatic ring group containing at least one of N, O, and S as a hetero atom, and carbon number is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms.
  • heteroaryl group examples include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, tria Genyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, Pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, iso
  • the aryl group described above may be applied to the aryl group in the aralkyl group and the aryloxy group.
  • the arylene group means a divalent aryl group, and the description about the aryl group described above may be applied to the arylene group.
  • An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, or combine with each other to form a substituted or unsubstituted fluorene ring.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a substituted or unsubstituted fluorene ring.
  • R1 and R2 are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-A to 1-C.
  • R 3 A, B and a are the same as defined in the formula (1).
  • R3 is hydrogen or deuterium.
  • Chemical Formula 1 is represented by the following Chemical Formula 2.
  • R1 to R3, L1, L2, Ar1 to Ar3 and a are as defined in the formula (1).
  • Chemical Formula 1 is represented by the following Chemical Formula 3.
  • R1 to R3, L1, L2, Ar1 to Ar3 and a are as defined in the formula (1).
  • -L1-Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • -L1-Ar1 is an aryl group unsubstituted or substituted with an aryl group; Or a heteroaryl group.
  • -L1-Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • -L1-Ar1 is a phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.
  • -L1-Ar1 is a phenyl group; Biphenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or 9,9-dimethylfluorenyl group.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L1 is a direct bond; Or an arylene group having 6 to 12 carbon atoms unsubstituted or substituted with an aryl group.
  • L1 is a direct bond; Or a phenylene group.
  • L1 is a direct bond; Or p-phenylene group.
  • Ar1 is an aryl group which is unsubstituted or substituted with an aryl group; Or a heteroaryl group.
  • Ar1 is a substituted or unsubstituted methyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • Ar1 is a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a 9,9'-spirobifluorenyl group.
  • Ar1 is a phenyl group; [1,1'-biphenyl] -4-yl group; 2-naphthyl group; Dibenzofuranyl group; Or 9,9-dimethylfluorenyl group.
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L2 is a direct bond; Or an arylene group having 6 to 12 carbon atoms unsubstituted or substituted with an aryl group.
  • L2 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L2 is a direct bond
  • L2 is a phenylene group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 6 to 24 carbon atoms.
  • Ar2 and Ar3 are the same as or different from each other, and each independently an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group.
  • Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a 9,9'-spirobifluorenyl group.
  • a is 0.
  • the compound represented by Formula 2 is any one selected from the following compounds.
  • the compound represented by Formula 3 is any one selected from the following compounds.
  • the compound of Formula 1 may be prepared according to the following formula (1).
  • the method for preparing the compound of Formula 1 is not limited to the following Formula 1, and may be prepared by a production method known in the art. In one embodiment, some steps of the manufacturing method of Formula 1 may be performed by another method.
  • a and B are as defined in formula (1).
  • organic light emitting device including the compound represented by Formula 1.
  • an organic light emitting device including a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound of Formula 1 is disposed on the organic material layer provided between the anode and the light emitting layer. It provides an organic light emitting device to be included.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention 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.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the compound of Formula 1 is included in at least one layer of a hole injection layer, a hole transport layer and a hole transport and injection at the same time provided between the anode and the light emitting layer.
  • the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer.
  • the organic light emitting diode includes at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer between the cathode and the light emitting layer.
  • the organic light emitting device further includes a layer for simultaneously injecting and transporting electrons between the cathode and the light emitting layer.
  • the organic light emitting diode further includes a hole blocking layer between the cathode and the light emitting layer.
  • the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer, and further includes a hole transport layer between the electron blocking layer and the anode.
  • the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer, and further includes a hole injection layer between the electron blocking layer and the anode.
  • the organic light emitting diode may be an organic light emitting diode having a normal 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 organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 11, a light emitting layer 6, and a cathode 10.
  • the organic layer 11 includes a hole transport layer, a hole injection layer, at least one layer of a hole transport and injection at the same time, and an electron blocking layer, the hole transport layer, hole injection layer, hole transport and At least one of the layer to be injected at the same time and the electron blocking layer includes the compound described above.
  • the compound described above is included in the electron blocking layer.
  • an organic light emitting element comprising an electron injection layer 9 and a cathode 10 is shown.
  • the compound described above is included in the electron blocking layer.
  • the compound described above is included in the hole injection layer.
  • the compound described above is included in the hole transport layer.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a cathode, an organic material layer and an anode on a substrate, or sequentially stacking an anode, an organic material layer and a cathode on a substrate.
  • PVD physical vapor deposition
  • sputtering e-beam evaporation
  • a metal or conductive metal oxide or alloys thereof on the substrate
  • It can be prepared by forming an anode, 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 of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material.
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is generally a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the cathode materials 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 layer is a layer for injecting holes from an electrode.
  • the hole injection material has a capability of transporting holes to a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect to a light emitting layer or a light emitting material, and is produced in a light emitting layer.
  • the compound which prevents the movement of an exciton to an electron injection layer or an electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole injection layer is provided between the anode and the hole transport layer.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transporting material a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable.
  • Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together.
  • the hole transport layer is provided between the hole injection layer and the light emitting layer.
  • the hole transport layer is provided between the hole injection layer and the electron blocking layer.
  • the electron blocking layer is a layer for preventing excess electrons passing through the light emitting layer from moving toward the hole transport layer.
  • the electron blocking material is preferably a material having a lower Unoccupied Molecular Orbital (LUMO) level than the hole transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer.
  • LUMO Unoccupied Molecular Orbital
  • an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.
  • the electron blocking layer comprises a compound represented by the above formula (1).
  • the emission layer is a layer that emits light while being converted into photons by combining holes and electrons.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the luminescent material examples include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzothiazole and benzimidazole series compounds examples include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • PSV poly (p-phenylenevinylene)
  • the light emitting layer may include a host material and a dopant material.
  • the host material of the light emitting layer may be a condensed aromatic ring derivative or a hetero ring-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but is not limited thereto.
  • the dopant material of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamine group, and the styrylamine compound may be substituted or unsubstituted.
  • a compound in which at least one arylvinyl group is substituted in the substituted arylamine may be used, and the styrylamine compound may have a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group. May be substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the hole blocking layer serves to prevent holes from flowing into the cathode through the light emitting layer in the driving process of the organic light emitting diode.
  • the hole blocking material it is preferable to use a material having a very high Occupied Molecular Orbital (HOMO) level.
  • the hole blocking material includes TPBi, BCP, CBP, PBD, PTCBI, BPhen, and the like, but is not limited thereto.
  • the hole blocking layer is 2- (3 '-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl] -3-yl) -4 , 6-diphenyl-1,3,5-triazine.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable.
  • Specific examples of the electron transporting material include Al complexes of 8-hydroxyquinoline; Complexes including 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 cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically lithium, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection material has the ability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Moreover, the compound excellent in the thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidenemethane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ 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 filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and 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 compound of the following compound HI1 and the following compound HI2 was thermally vacuum-deposited on the thus prepared ITO transparent electrode (anode) at a molar ratio of 98: 2 to form a hole injection layer (thickness 100 kPa).
  • a compound represented by Chemical Formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer (thickness 1150 Pa).
  • Compound 1 of Preparation Example 1 was vacuum deposited on the hole transport layer to form an electron blocking layer (thickness of 50 GPa).
  • the compound represented by the following formula BH and the compound represented by the following formula BD were vacuum deposited on the electron blocking layer at a weight ratio of 50: 1 to form a light emitting layer (thickness of 200 kPa).
  • a compound represented by the following Chemical Formula HB1 was vacuum deposited on the emission layer to form a hole blocking layer (thickness of 50 kPa).
  • the compound represented by the following formula ET1 and the 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 (thickness: 30 GPa). 12 ⁇ of lithium fluoride (LiF) and 1,000 ⁇ of aluminum were deposited on the electron injection and transport layer sequentially to form a cathode.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ / sec or more and 0.7 ⁇ / sec, and the lithium fluoride of the cathode was 0.3 ⁇ / sec, and the aluminum was maintained at the deposition rate of 2 ⁇ / sec.
  • the organic light emitting device was manufactured by maintaining 2 ⁇ 10 ⁇ 7 torr or more and 5 ⁇ 10 ⁇ 6 torr or less.
  • 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 1 of Preparation Example 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 1 of Preparation Example 1.
  • the compounds of EB1, EB2, EB3, EB4, EB5 and EB6 used in Table 1 below are as follows.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
  • Example 1-3 3 4.15 6.37 (0.140, 0.046)
  • the organic light emitting device using the compound of the present invention as an electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • Examples 1-1 to 1-6 when the amine group was substituted at the carbon position 2 of the fluorene-based core and the aryl group or the heteroaryl group connected at the carbon position 4 was used as the electron blocking layer, the device was low voltage and high efficiency. And long life.
  • the device (Comparative Example 1-2) using a material having an amine group bonded to the carbon position 2 of the fluorene core has a strong service life. It can be seen that the device (Comparative Examples 1-3) using a material having an amine group bonded to the carbon position 4 of the fluorene core has advantages in efficiency.
  • the substituent is further connected to the 2 or 4 carbon position of the fluorene and the amine group is substituted only at the 2 or 4 carbon position of the fluorene-based core, the molecular structure is distorted. As a result, the stability of the device is increased, thereby increasing the life of the device and increasing the efficiency of the device.
  • the compounds used as the electron blocking layer in Examples 1-7 to 1-11 and Comparative Examples 1-3 all have an amine group substituted at the carbon position 4 of fluorene.
  • the device of Examples 1-7 to 1-11 using a compound having an aryl group or a heteroaryl group at position 2 of fluorene is Comparative Example 1- using a compound having no substituent at position 2 of fluorene. Compared with the device of 3, the driving voltage is lower and the life is long, and the efficiency is much improved.
  • Compound EB4 does not have a twisted structure like the compounds of the present invention. Accordingly, the device using the material in which the amine group is bonded to the carbon position 2 of the fluorene core and the substituent is connected to the carbon position 7 (Comparative Example 1-4) is a material having an amine group bonded to the carbon position 2 of the fluorene core The results showed that the voltage and efficiency characteristics were reduced compared to the devices used (Comparative Examples 1-2).
  • Examples 1-5, 6, and 11 wherein R1 and R2 are bonded to form a fluorene ring as an electron blocking layer A comparison using the structure where R1 and R2 are bonded to form a benzofluorene ring as an electron blocking layer Compared with Examples 1-5 and 1-6, the lifespan was significantly improved. When R1 and R2 combine to form a benzofluorene ring, the core of the compound becomes bulky, affecting the flow of electrons, causing a voltage increase and a decrease in efficiency, and a lifetime also decreases.
  • the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.

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

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/002316 2018-02-28 2019-02-26 Composé et diode électroluminescente organique le comprenant WO2019168320A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114555579A (zh) * 2019-10-11 2022-05-27 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102628804B1 (ko) * 2018-07-10 2024-01-24 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기발광 소자
KR102400109B1 (ko) * 2019-12-10 2022-05-19 주식회사 엘지화학 유기 발광 소자
CN114805092A (zh) * 2022-04-21 2022-07-29 南京高光半导体材料有限公司 一种化合物及有机电致发光器件
KR102611998B1 (ko) * 2023-10-05 2023-12-11 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140018789A (ko) * 2012-07-31 2014-02-13 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자
KR101555155B1 (ko) * 2014-09-30 2015-09-22 머티어리얼사이언스 주식회사 신규한 스피로바이플루오렌 타입 유기화합물 및 상기 유기화합물을 포함하는 유기전계발광소자
KR20160127429A (ko) * 2015-04-27 2016-11-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20170017701A (ko) * 2015-08-07 2017-02-15 머티어리얼사이언스 주식회사 유기전계발광소자
KR20170075877A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
KR101520955B1 (ko) * 2015-02-10 2015-06-05 덕산네오룩스 주식회사 유기전기소자용 신규 화합물, 이를 이용한 유기전기소자 및 그 전자장치
KR102283231B1 (ko) * 2015-03-16 2021-07-30 덕산네오룩스 주식회사 유기전기소자용 신규 화합물, 이를 이용한 유기전기소자 및 그 전자장치
KR20180112962A (ko) * 2017-04-05 2018-10-15 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140018789A (ko) * 2012-07-31 2014-02-13 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자
KR101555155B1 (ko) * 2014-09-30 2015-09-22 머티어리얼사이언스 주식회사 신규한 스피로바이플루오렌 타입 유기화합물 및 상기 유기화합물을 포함하는 유기전계발광소자
KR20160127429A (ko) * 2015-04-27 2016-11-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20170017701A (ko) * 2015-08-07 2017-02-15 머티어리얼사이언스 주식회사 유기전계발광소자
KR20170075877A (ko) * 2015-12-23 2017-07-04 삼성디스플레이 주식회사 유기 발광 소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114555579A (zh) * 2019-10-11 2022-05-27 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备
EP4043431A4 (fr) * 2019-10-11 2023-11-01 Idemitsu Kosan Co., Ltd Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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