WO2012043996A2 - Composé dans lequel un dérivé d'amine est substitué par un fluorène, dispositif électro-organique utilisant ledit composé, et terminal associé - Google Patents

Composé dans lequel un dérivé d'amine est substitué par un fluorène, dispositif électro-organique utilisant ledit composé, et terminal associé Download PDF

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WO2012043996A2
WO2012043996A2 PCT/KR2011/006749 KR2011006749W WO2012043996A2 WO 2012043996 A2 WO2012043996 A2 WO 2012043996A2 KR 2011006749 W KR2011006749 W KR 2011006749W WO 2012043996 A2 WO2012043996 A2 WO 2012043996A2
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mmol
substituted
group
unsubstituted
organic
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WO2012043996A3 (fr
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김동하
문성윤
박정철
주진욱
백장열
김원삼
박성진
김은경
최대혁
박정환
홍철광
유한성
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덕산하이메탈(주)
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Priority claimed from KR1020100095402A external-priority patent/KR101035326B1/ko
Priority claimed from KR1020110018801A external-priority patent/KR101298485B1/ko
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Publication of WO2012043996A2 publication Critical patent/WO2012043996A2/fr
Publication of WO2012043996A3 publication Critical patent/WO2012043996A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
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    • 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
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    • 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
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to a compound in which an amine derivative is substituted for fluorene, an organic electric device using the same, and a terminal thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element 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 is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • Embodiments of the present invention to solve the problems of the above-described background, it was found that a compound in which amine derivative is substituted in fluorene, and when the compound is applied to an organic electronic device, the efficiency of the device, the driving voltage drop, It has been found that it can have an increase in life and stability.
  • an object of the present invention is to provide a compound in which an amine derivative is substituted for fluorene, and an organic electric device using the same, an electronic device, or a terminal thereof.
  • the present invention provides a compound of the formula:
  • the present invention is a compound in which an amine derivative is substituted for fluorene, and may be used as a hole injection, hole transport, electron injection, electron transport, light emitting material, and passivation material in organic electronic devices, and in particular, a light emitting material and a host / It can be used as a host or dopant in a dopant, and can be used as a hole injection and hole transport layer.
  • the present invention also provides an organic electronic device using the compound having the above formula, and an electronic device or terminal including the organic electronic device.
  • the present invention is a compound in which an amine derivative is substituted for fluorene, and may be used as a hole injection, hole transport, electron injection, electron transport, light emitting material, and passivation material in organic electronic devices, and in particular, a light emitting material and a host / It can be used as a host or dopant in a dopant, and can be used as a hole injection and hole transport layer.
  • the efficiency of the device may be increased, the driving voltage may be decreased, the lifetime may be increased, and the stability may be increased.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • the present invention provides a compound of Formula 1 below.
  • the Cz group may be a substituted or unsubstituted carbazole derivative which may be represented by the following Chemical Formula 2, but is not limited thereto.
  • R 3 -R 7 which may be substituted on the carbon atom of carbazole in Formula 2 may be the same or different from each other independently, hydrogen atom, deuterium, tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, S, N, O, P and Si Substituted or unsubstituted hetero aryl group having 5 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylcycle having 5 to 60 carbon atoms Amino, substituted or unsubstituted alkoxycarbonyl groups having 5 to 60 carbon atoms, substituted or unsubstituted aryl
  • X may be the same as R 3 -R 7 but is not limited thereto.
  • m may be an integer of 1 to 3, but is not limited thereto.
  • Ar 1 to Ar 3 may be the same as or different from each other, and each independently substituted or unsubstituted aryl group having 3 to 60 nuclear atoms, or at least one of S, N, O, P, and Si.
  • Substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, including a hetero atom of, may be a substituted or unsubstituted alkyl group, but is not limited thereto.
  • Ar 1 ⁇ Ar 3 may be bonded to each other adjacent groups to form a ring (ring).
  • Ar 1 to Ar 3 are specifically substituted or unsubstituted phenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorene group, thiophene group, pyrrole group, furan group, pyridyl group in the group consisting of May be selected but is not limited thereto.
  • R 1 and R 2 , R ′, and R ′′ may be the same as or different from each other, and each independently hydrogen atom, deuterium, tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, S, N, O, P and Si Substituted or unsubstituted hetero aryl group having 5 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms Amino, substituted or unsubstituted alkoxycarbonyl groups having 5 to 60 carbon atoms, substituted or unsubstituted aryl groups having 5 to
  • Substituents of X, R 3 -R 7, R 1 and R 2 , R ', and R''in Formula 1 may be substituted or unsubstituted, and when substituted, hydrogen atom, deuterium, tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, S, N, O, P and Si Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one hetero atom, substituted or unsubstituted A substituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted nuclear C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 aryl cy Amino, substituted or unsubstituted alkoxycarbonyl groups having 5 to 60 carbon atoms, substituted or unsubstit
  • Compounds represented by Formula 1 may be one of the compounds represented by Formula 3 below, but is not limited thereto. At this time, the compounds represented by the formula (1) is substituted with the substituted or unsubstituted substituents of X, R 3 -R 7, R 1 and R 2 , R 'and R''of the formula 1 It is practically difficult to exemplify all compounds in a broad relationship Therefore, exemplary compounds are exemplarily described, but the compounds represented by Formula 1, which are not described in Formula 3, may also form part of the present specification.
  • substituents in Chemical Formulas 1 to 3 may be substituted or unsubstituted again even if not mentioned above, and the substituents may be substituted again.
  • organic electric devices exist in which compounds in which an amine derivative is substituted for fluorene described with reference to Chemical Formulas 1 to 3 are used as the organic material layer.
  • organic electroluminescent devices in which compounds substituted with an amine derivative in fluorene described with reference to Chemical Formulas 1 to 3 may be used include, for example, an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor. And the like (organic TFT).
  • OLED organic electroluminescent device
  • Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formulas 1 to 3 Provided is a light emitting device.
  • an organic electric device including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is represented by Chemical Formulas 1 to 3
  • an organic light emitting display device including a compound in which an amine is substituted for fluorene.
  • the organic material layer includes a hole injection layer, a hole transport layer, and at least one layer of the hole injection and hole transport at the same time, wherein one of the layers is an amine substituted with fluorene represented by the formula (1) It may include.
  • the organic material layer includes at least one layer of a hole injection layer, a hole transport layer, and a layer for simultaneously injecting holes and transporting holes, wherein one of the layers is fluorene represented by Formulas 1 to 3 It may also include a compound substituted with an amine.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include a compound in which an amine is substituted for fluorene represented by Chemical Formulas 1 to 3.
  • the organic material layer may include an electron transport layer
  • the electron transport layer may include a compound in which an amine is substituted with fluorene represented by Chemical Formulas 1 to 3.
  • the organic material layer may include a light emitting auxiliary layer
  • the light emitting auxiliary layer may include a compound in which an amine is substituted for fluorene represented by Chemical Formulas 1 to 3.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • At least one layer of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer is formed to include the compounds of Formulas 1 to 3 above. Except for the above, it may be manufactured in a structure known in the art using conventional manufacturing methods and materials in the art.
  • FIGS. 1 to 6 The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto.
  • reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.
  • the organic light emitting diode may further include a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for preventing the movement of electrons, and a protective layer.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound in which the amine derivative is substituted for fluorene described with reference to Chemical Formulas 1 to 3 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
  • the compound in which the amine derivative is substituted for fluorene described with reference to Chemical Formulas 1 to 3 may include at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a protective layer. It may be used in place of or in combination with them.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • the compound may be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material and a passivation (kepping) material according to the compound in which the amine derivative is substituted for fluorene described with reference to Chemical Formulas 1 to 3, In particular, it can be used alone as a light emitting material and a host or dopant.
  • the organic light emitting device is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • PVD physical vapor deposition
  • An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process in which the amine derivative is substituted with fluorene as described above. .
  • the substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
  • An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • 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), 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] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • Tg glass transition temperature
  • Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene and silicon germanium oxide.
  • NPD or NPB
  • spiro-arylamine compounds perylene-arylamine compounds
  • azacycloheptatriene compounds bis (diphenylvinylphenyl) anthracene
  • silicon germanium oxide silicon germanium oxide
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • 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.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency.
  • an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene.
  • PPV polyphenylene vinylene
  • a polymer such as poly fluorene can be used for
  • the electron transport layer is positioned on the organic light emitting layer.
  • the electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions 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 injection layer is stacked on the electron transport layer.
  • the electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like.
  • the electron injection layer may be formed in a thickness range of 100 ⁇ 300 ⁇ .
  • the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
  • the material used as the cathode it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
  • hole injection materials, hole transport materials, and luminescent materials suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, depending on the compound in which the amine derivative is substituted for fluorene described with reference to Chemical Formulas 1 to 3 It can be used as an electron transport material and an electron injection material, and can be used as a host or dopant material of various colors.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
  • This terminal means a current or future wired or wireless communication terminal.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.
  • intermediate 4 and the intermediate 2 may be reacted to finally synthesize the compounds represented by Chemical Formulas 1 to 3.
  • intermediate 4 may be synthesized through compound 3 in Scheme 1
  • intermediate 2 may be synthesized through compounds 1 and 2. Detailed description thereof will be described below in detail.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), diphenylamine (8.46 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) were synthesized using the synthesis method of 2-2 above. 18.23 g (yield: 60%) of the product were obtained
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), diphenylamine (8.46 g, 50 mmol), Pd 2 ( dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) using 22.68g synthesis using 2-2 (Yield 62%) of the product was obtained.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- phenyl-9,9'-spirobi [fluoren] -2-amine (20.38g, 50 mmol), diphenylamine (8.46 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) were synthesized using the synthesis method of 2-2 above. 23.72 g (yield: 65%) of the product were obtained.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N -phenylpyridin-2 -amine (8.51 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL ) was obtained using the synthesis method of 2-2 above to obtain 18.90 g (yield: 62%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) thiophen-2-amine (14.57 g, 50 mmol), N -phenylthiophen-2 -amine (8.76 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL ) Was obtained using the synthesis method of 2-2 above to obtain 19.52 g (yield: 63%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (28.54g, 100 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were synthesized according to the above-mentioned 2-1 in Scheme 5. ) To give 24.25 g (yield: 67%) of the product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), diphenylamine (8.46 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) were synthesized using the above synthesis method. 23.16 g (yield: 64%) of the product were obtained
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N -9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), 9,9-dimethyl- N -phenyl-9H- fluoren-2-amine (14.27 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) was used in the synthesis of 2-2 to yield 26.28 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), 9,9-dimethyl-N-phenyl- 9H-fluoren-2-amine (14.27 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) , toluene (1050 mL) was obtained using the synthesis method of 2-2 to give 26.22 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (28.64 g, 100 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) were obtained using 23.59 g (yield) using the synthesis method of 2-1. : 65%) of the product was obtained
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) thiphen-2-amine (29.14 g, 100 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) were obtained using 23.18 g (yield) using the above synthesis method. : 63%) of the product was obtained
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-methyl-N-phenylaniline (9.16 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 19.58 g (yield 63%) of product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-methyl-N-phenylaniline (9.16 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 19.89 g (yield: 64%) of product
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N -9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), 4-methyl-N-phenylaniline (9.16 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis yielded 23.12 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-l) thiophen-2-amine (14.57 g, 50 mmol), N -p-tolylthiophen -2-amine (9.46 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene ( 1050 mL) was obtained using the synthesis method of 2-2 above to obtain 19.00 g (yield: 60%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-methoxy- N -phenylaniline (9.96 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL)
  • the synthesis method was used to obtain 20.72 g (yield: 65%) of the product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N -phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-methoxy- N -phenylaniline (9.96 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 19.45 g (yield: 61%) of product
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), 4-methoxy-N-phenylaniline (9.96 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis yielded 23.23 g (yield: 61%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), 4-methoxy-N-phenylaniline (9.96 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Using the synthesis method of 2, 23.06 g (yield: 62%) of the product were obtained.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (4- methoxyphenyl) pyridin-2-amine (10.01 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) , toluene (1050 mL) was obtained using the synthesis method of 2-2 to obtain 19.19 g (yield: 60%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-l) thiophen-2-amine (14.57 g, 50 mmol), N- (4- methoxyphenyl) thiophen-2-amine (10.26 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) , toluene (1050 mL) was obtained using the synthesis method of 2-2 to obtain 19.81 g (yield: 61%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-fluoro- N -phenylaniline (9.36 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 18.77 g (yield: 60%) of product
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), 4-fluoro- N -phenylaniline (9.36 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 18.14 g (yield: 58%) of product
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), 4-fluoro- N -phenylaniline (9.36 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis yielded 22.12 g (yield: 59%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), 4-fluoro- N -phenylaniline (9.36 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) 2. The obtained product was obtained in 21.31 g (yield: 57%).
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (4- fluorophenyl) pyridin-2-amine (9.41 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) , toluene (1050 mL) was obtained using the synthesis method of 2-2 to give 18.20 g (yield: 58%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-l) thiophen-2-amine (14.57 g, 50 mmol), N- (4- fluorophenyl) thiophen-2-amine (9.66 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) , toluene (1050 mL) was obtained using the synthesis method of 2-2 to obtain 19.13 g (yield: 60%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylbiphenyl-4-amine (12.27 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Using the synthesis method of 2 to obtain 23.25 g (yield: 68%) of the product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylbiphenyl-4-amine (12.27 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 21.88 g (yield: 64%) of product
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), N -phenylbiphenyl-4-amine (12.27 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis gave 25.45 g (yield 63%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), N -phenylbiphenyl-4-amine (12.27 g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Using the synthesis method of 2, 25.79 g (yield: 64%) of the product were obtained.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (biphenyl- 4-yl) pyridin-2-amine (12.32 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using the synthesis method of 2-2 to give 21.26 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-l) thiophen-2-amine (14.57 g, 50 mmol), N- (biphenyl- 4-yl) thiophen-2-amine (12.57 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using the synthesis method of 2-2 to give 21.57 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylnaphthalen-1-amine (10.96g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 22.03 g (yield 67%) of product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylnaphthalen-1-amine (10.96g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 21.37 g (yield: 65%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), N -phenylnaphthalen-1-amine (10.96g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis yielded 24.63 g (yield 63%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), N -phenylnaphthalen-1-amine (10.96g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 25.34 g (yield: 65%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (naphthalen- 1-yl) pyridin-2-amine (11.01 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using the synthesis method of 2-2 to give 21.11 g (yield: 64%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) thiophen-2-amine (14.57 g, 50 mmol), N- (naphthalen- 1-yl) thiophen-2-amine (11.27 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol ), toluene (1050 mL) was obtained using the synthesis method of 2-2 above to obtain 20.43 g (yield: 61%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylnaphthalen-2-amine (10.96g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 21.70 g (yield: 66%) of product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N- phenylnaphthalen-2-amine (10.96g , 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis of 2 gave 21.04 g (yield: 64%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), N -phenylnaphthalen-2-amine (10.96g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Synthesis yielded 25.41 g (yield: 65%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (naphthalen- 2-yl) pyridin-2-amine (11.01 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using the synthesis method of 2-2 to give 21.11 g (yield: 64%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) thiophen-2-amine (14.57 g, 50 mmol), N- (naphthalen- 2-yl) thiophen-2-amine (11.27 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol ), toluene (1050 mL) was purified using the synthesis method of 2-2 to yield 20.76 g (yield: 62%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N-phenyldibenzo [b, d] thiophen- 2-amine (13.77g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) was used for the synthesis of 2-2 to yield 23.20 g (yield: 65%) of product.
  • 1,2,4-tribromobenzene (15.74 g, 50 mmol), 9,9-dimethyl- N- phenyl-9H-fluoren-2-amine (14.27 g, 50 mmol), N-phenyldibenzo [b, d] thiophen- 2-amine (13.77g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) was used for the synthesis of 2-2 to yield 22.48 g (yield: 63%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N , 9,9-triphenyl-9H-fluoren-2-amine (20.48 g, 50 mmol), N-phenyldibenzo [b, d] thiophen-2- amine (13.77 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) Using the synthesis method of 2-2 to give 28.07 g (yield: 67%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- phenyl-9,9'-spirobi [fluoren] -2-amine (20.38 g, 50 mmol), N-phenyldibenzo [b, d] thiophen- 2-amine (13.77g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol), toluene (1050 mL) was used to synthesize 27.17 g (yield: 65%) of the product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) pyridin-2-amine (14.32g, 50 mmol), N- (dibenzo [ b, d] thiophen-2-yl) pyridin-2-amine (13.82 g, 50 mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using the synthesis method of 2-2 above to give 21.47 g (yield: 60%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) thiophen-2-amine (14.57 g, 50 mmol), N- (thiophen- 2-yl) dibenzo [b, d] thiophen-2-amine (14.07g, 50mmol), Pd 2 (dba) 3 (4.58 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaO t -Bu (28.84 g, 300 mmol) and toluene (1050 mL) were obtained using 22.86 g (yield: 63%) of the product using the above synthesis method.
  • the final compounds can be analyzed by nuclear magnetic resonance (NMR), mass spectrometry (Mass).
  • NMR nuclear magnetic resonance
  • Mass mass spectrometry
  • the above-mentioned final compounds have many aromatic structures, so the structure was analyzed by mass spectrometry (Mass) rather than nuclear magnetic resonance (NMR).
  • FD-MS means mass spectrometer.
  • mass peaks appear as the final compounds are broken, and m / z means the peak.
  • m / z means the mass spectrometry main peck of the above-mentioned final compounds. This can confirm the presence of the compounds.
  • the compounds represented by the formula (1) is a synthesis of the compounds represented by the formula (3) X or R 3 -R 7, R 1 and R 2 , R 'and R''of the formula or substituted or unsubstituted substituents in a broad relationship Examples are described by way of example, but the compounds represented by Formula 1, which are not described by way of example as synthetic examples, may also form part of the present specification.
  • one of the compounds represented by Formulas 1 to 3 as the hole transport compound was vacuum deposited to a thickness of 30 nm to form a hole transport layer.
  • a light emitting layer doped with 7% of BD-052X (Idemitus) having a thickness of 45 nm on the hole transport layer (where BD-052X was a blue fluorescent dopant) 9,10-di (naphthalene-2-anthracene (AND) was used as the light emitting host material.
  • BAlq (1,1'bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq electron Tris (8-quinolinol) aluminum
  • Alq 3 electron Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
  • an organic electric field having the same structure as in the experimental example was prepared by using a compound represented by the following Chemical Formula 4 (hereinafter abbreviated as NPB) as a hole transport material instead of the compound of the present invention for comparison.
  • NPB Chemical Formula 4
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention has high efficiency and color purity as well as long life blue light emission is obtained as a hole transporting material of the organic electroluminescent device Can be used to significantly improve the low driving voltage, high luminous efficiency and lifetime.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained. .
  • the compounds represented by the formula (1) is a substituted or unsubstituted substituents of X, R 3 -R 7, R 1 and R 2 , R 'and R''of the formula (1).
  • embodiments of the present invention as a hole transport compound (B-1, B-2, B-4, B-5, B-8, C-1, C-2, C-4, C-5, C One of the compounds of -8) was vacuum deposited to a thickness of 30 nm to form a hole transport layer.
  • a light emitting layer doped with 7% of BD-052X (Idemitus) having a thickness of 45 nm on the hole transport layer (where BD-052X was a blue fluorescent dopant) 9,10-di (naphthalene-2-anthracene (AND)) was used as the light emitting host material.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq (2-methyl-8-quinolineoleito) aluminum
  • BAlq 3 Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention is not only high efficiency and color purity but also blue light emission with long life is obtained as a hole transporting material of the organic light emitting device Can be used to significantly improve the low driving voltage, high luminous efficiency and lifetime.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained. .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé dans lequel un dérivé d'amine est substitué par un fluorène, un dispositif électro-organique utilisant ledit composé, et un terminal associé.
PCT/KR2011/006749 2010-09-30 2011-09-09 Composé dans lequel un dérivé d'amine est substitué par un fluorène, dispositif électro-organique utilisant ledit composé, et terminal associé WO2012043996A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2010-0095402 2010-09-30
KR1020100095402A KR101035326B1 (ko) 2010-09-30 2010-09-30 플루오렌에 아민유도체가 치환된 화합물 및 이를 이용한 유기전기소자, 그 단말
KR10-2011-0018801 2011-03-03
KR1020110018801A KR101298485B1 (ko) 2011-03-03 2011-03-03 화합물 및 이를 이용한 유기전기소자, 그 단말

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WO2014061991A1 (fr) * 2012-10-17 2014-04-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique en contenant
WO2014087657A1 (fr) * 2012-12-07 2014-06-12 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique
JP2014111556A (ja) * 2012-12-05 2014-06-19 Samsung Display Co Ltd フッ素置換されたアリール基を有するアミン誘導体、それを含む有機ｅｌ材料及びそれを用いた有機ｅｌ素子
US20150048332A1 (en) * 2013-08-19 2015-02-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
WO2017118238A1 (fr) * 2016-01-07 2017-07-13 广州华睿光电材料有限公司 Dérivé triarylamine deutéré et son application dans des dispositifs électroniques
CN112939787A (zh) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 一种化合物及其应用
CN114516859A (zh) * 2020-11-18 2022-05-20 北京鼎材科技有限公司 一种化合物及其应用
US11437585B2 (en) 2019-02-13 2022-09-06 Samsung Display Co., Ltd. Organic light-emitting device

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WO2014061991A1 (fr) * 2012-10-17 2014-04-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique en contenant
JP2014111556A (ja) * 2012-12-05 2014-06-19 Samsung Display Co Ltd フッ素置換されたアリール基を有するアミン誘導体、それを含む有機ｅｌ材料及びそれを用いた有機ｅｌ素子
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WO2014087657A1 (fr) * 2012-12-07 2014-06-12 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique
KR20150092145A (ko) * 2012-12-07 2015-08-12 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 유기 전계발광소자
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US20150048332A1 (en) * 2013-08-19 2015-02-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US9768388B2 (en) * 2013-08-19 2017-09-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
WO2017118238A1 (fr) * 2016-01-07 2017-07-13 广州华睿光电材料有限公司 Dérivé triarylamine deutéré et son application dans des dispositifs électroniques
US11437585B2 (en) 2019-02-13 2022-09-06 Samsung Display Co., Ltd. Organic light-emitting device
CN112939787A (zh) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 一种化合物及其应用
CN114516859A (zh) * 2020-11-18 2022-05-20 北京鼎材科技有限公司 一种化合物及其应用

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