WO2012091471A2 - Composé et élément électronique organique l'utilisant, et dispositif électronique comprenant l'élément électronique organique - Google Patents

Composé et élément électronique organique l'utilisant, et dispositif électronique comprenant l'élément électronique organique Download PDF

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WO2012091471A2
WO2012091471A2 PCT/KR2011/010267 KR2011010267W WO2012091471A2 WO 2012091471 A2 WO2012091471 A2 WO 2012091471A2 KR 2011010267 W KR2011010267 W KR 2011010267W WO 2012091471 A2 WO2012091471 A2 WO 2012091471A2
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organic
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WO2012091471A3 (fr
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최연희
문성윤
박정환
박정철
김기원
박용욱
박정근
정화순
지희선
이범성
최대혁
김동하
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덕산하이메탈(주)
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    • 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
    • C07C211/54—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 two or three six-membered aromatic rings
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    • 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
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
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    • 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
    • C07C211/59—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 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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    • 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
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • 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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    • 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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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • 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
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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
    • H10K85/636—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • C07C2603/00—Systems containing at least three condensed rings
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound, an organic electronic device using the same, and an electronic device 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 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.
  • the present invention for solving the above problems of the background provides a compound in which a linking group having a substituent is bonded to a triphenyl derivative having a phenyl group substituted with deuterium. Therefore, the compound can be used as a hole injection, hole transport, electron injection, electron transport, light emitting material and passivation (kepping) material in organic electronic devices, in particular can be used alone or as a host or dopant in the light emitting material and host / dopant It can be used as a hole injection, hole transport layer.
  • the present invention provides a compound having a form in which a linking group having a substituent is bonded to a triphenyl derivative connected to a phenyl group substituted with deuterium, an organic electronic device using the same, and an electronic device including the organic electronic device.
  • the present invention provides a compound of the formula:
  • the present invention can provide a compound in which a linking group having a substituent is bonded to a triphenyl derivative having a phenyl group substituted with deuterium, an organic electronic device using the same, and an electronic device including the organic electronic device.
  • the present invention provides a compound in which a linking group having a substituent is bonded to a triphenyl derivative connected to a phenyl group substituted with deuterium, and an organic compound using the same, and shows an effect of increasing efficiency, lowering driving voltage, increasing lifetime, and increasing stability of an organic electronic device. It was.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • substrate 102 anode
  • the present invention can provide a compound represented by the following formula (1).
  • D represents deuterium and a may be an integer of 1 to 5.
  • R 1 to R 2 which may be substituted with a phenyl group are the same as or different from each other, and each independently a hydrogen atom; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or one or more selected from the group consisting of an amino group substituted with an unsubstituted aryl group having 5 to 60 carbon atoms, a halogen
  • R 1 to R 2 may be bonded to groups adjacent to each other to form a substituted or unsubstituted saturated or unsaturated ring.
  • R 1 to R 2 may combine with groups adjacent to each other to form an aliphatic or hetero ring.
  • b to c may be an integer of 1 to 4.
  • L is selected from a substituted or unsubstituted arylene group having 5 to 40 carbon atoms, a substituted or unsubstituted hetero arylene group having 5 to 60 nuclear atoms, and a divalent or trivalent substituted or unsubstituted aliphatic hydrocarbon. It may be, but is not limited to. On the other hand, d may be an integer of 0 to 3.
  • L may be one or more selected from the group consisting of phenyl group, biphenyl group, 1-naphthalyl group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group.
  • Y may be a derivative represented by Chemical Formula 2.
  • Ar 1 ⁇ Ar 3 may be the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 1 to 60 nuclear atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, but It is not limited.
  • Ar 2 to Ar 3 may be a substituted or unsubstituted alkyl group.
  • M may be an integer of 0 to 2.
  • Ar 1 may be one or one or more selected from the group consisting of a substituted or unsubstituted phenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, thiophene group, pyrrole group, furan group, and pyridyl group have.
  • Ar 2 and Ar 3 may be one or more than one selected from the group consisting of functional groups in Table 1 below, but is not limited thereto.
  • the compound having the structural formula may be used in a solution process.
  • the compound may form an organic material layer of an organic electric device, which will be described later, by a soluble process.
  • the organic material layer may be formed by using various polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by the method.
  • the present invention may provide a compound represented by one of the following Chemical Formulas 3 to 13.
  • D in formula 3 to 10 represents deuterium where a is an integer of 1 to 5,
  • R 1 ⁇ R 4 which may be substituted on the phenyl group R1 ⁇ R 2 described in the formulas (2) and (3) may be the same, but is not limited thereto.
  • R 1 to R 4 are the same as or different from each other, and are each independently of the other hydrogen, deuterium, tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or an amino
  • b to e may be integers of 0 to 4.
  • R 1 to R 4 may be bonded to adjacent groups, respectively, to form a substituted or unsubstituted saturated or unsaturated ring.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 1 may each combine with an adjacent group to form a substituted or unsubstituted saturated or unsaturated ring.
  • X in Chemical Formulas 7 to 10 may be C (R 1 ) (R 2 ), N (R 3 ) (R 4 ), S, O, Si, but is not limited thereto.
  • f-i are integers of 0-1.
  • substituents in Chemical Formulas 1 to 11 may be substituted or unsubstituted even if not mentioned above, so that the substituents may be substituted with other substituents or substituents.
  • organic electric devices exist in which compounds in which a linking group is bonded to a triphenyl derivative having a phenyl group substituted with deuterium, described with reference to Chemical Formulas 1 to 11, are used as the organic material layer.
  • organic electric device in which the compounds described with reference to Chemical Formulas 1 to 11 may be used include an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor (organic TFT).
  • OLED organic electroluminescent device
  • the present invention is not limited thereto, and the compounds described above may be applied to various organic electroluminescent devices. .
  • 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 these electrodes, wherein at least one layer of the organic material layer comprises an organic electric field comprising the compounds of Formulas 1 to 11 Provided is a light emitting device.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • the organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 11. It can be prepared as.
  • 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 further includes a hole blocking layer (HBL) that blocks hole movement, an electron blocking layer (EBL) that blocks electrons from moving, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound described with reference to Formulas 1 to 11 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 compounds described with reference to Formulas 1 to 11 may be used in place of one or more 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, a light emitting auxiliary layer, and a protective layer. Or may be used in combination with them.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • it can 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 compounds described with reference to the formulas (1) to 11, 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 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 layer may be formed using a variety of polymer materials, but not by a deposition process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made with a small number of layers.
  • the organic light emitting device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process.
  • 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, 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.
  • Such an electron transport layer requires a material having high electron injection efficiency and efficiently transporting injected electrons from a cathode positioned thereon. 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.
  • electrodes 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.
  • 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.
  • the compounds were synthesized according to the synthesis method described above, and the examples in which the compounds were applied to an organic material layer of an organic electroluminescent device, for example, an organic electroluminescent device, were compared with those of commonly used compounds.
  • Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H 2 O (350 mL) was added to a 2 L round bottom flask, and 4,4 'Dibromo-biphenyl (161 g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh 3 ) 4 (20 g, 17.3 mmol) were added in this order, and the reaction was performed at 80 ° C. for 24 hours.
  • the obtained organic layer was subjected to silicagel column to obtain 65.05 g (60%) of a product.
  • Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H 2 O (350 mL) was added to a 2 L round bottom flask, and 1,4-Dibromobenzene (122.2 g, 518 mmol) and NaOH were dissolved. (42 g, 1035 mmol) and Pd (PPh 3 ) 4 (20 g, 17.3 mmol) were added sequentially, and the reaction proceeds at 80 ° C. for 24 hours.
  • Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H 2 O (350 mL) was added to a 2 L round bottom flask, and 2,7-Dibromo-9-phenyl-carbazole (207g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh 3 ) 4 (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours.
  • the obtained organic layer was silicagel column to give 92.1 g (67%) of the product.
  • the mixture is heated to reflux at 80 ° C to 90 ° C. After the reaction is completed, distilled water is diluted at room temperature. Then, the mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), diphenylamine (8.5 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), P Ph 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 11.3 g (yield: 70%) of product.
  • 1,3,5-tribromobenzene (15.74 g, 50 mmol), diphenylamine (17 g, 100 mmol), Pd 2 (dba) 3 (4.6 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaOt- Bu (28.83 g, 300 mmol) and toluene (525 mL) were obtained using 16.2 g (yield: 66%) of the product using the above synthesis method.
  • 1,2,5-tribromobenzene (15.74 g, 50 mmol), 4-methyl-N-phenylaniline (18.33 g, 100 mmol), Pd 2 (dba) 3 (4.6 g, 5 mmol), PPh 3 (2.62 g, 10 mmol), NaOt-Bu (28.83 g, 300 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to obtain 16.4 g (yield: 63%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylnaphthalen-2-amine (11g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol) , NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13 g (yield: 69%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), dinaphthalen-2-ylamine (13.5 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 15.3 g (yield: 72%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylnaphthalen-1-amine (11 g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13.3 g (yield: 71%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), dinaphthalen-1-ylamine (13.5 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 15.5 g (yield: 73%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), 4-methoxy-N-phenylaniline (10 g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13.3 g (yield: 75%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (4-fluorophenyl) naphthalen-2-amine (11.9g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 ( 1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 12.7 g (yield: 65%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylbiphenyl-4-amine (12.3g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 14.8 g (yield: 74%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) naphthalen-1-amine (14.8g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using 16.2 g (yield: 72%) of the product using the above synthesis method.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), dibiphenyl-4-ylamine (16.1 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 17.4 g (yield: 73%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), bis (9,9-dimethyl-9H-fluoren-2-yl) amine (20.1g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol ), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 19.1 g (yield: 74%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (naphthalen-1-yl) -9H-fluoren-2-amine (16.8g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis method of 2-1 above, 16.7 g (yield: 68 Product)
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N, N-di-m-terphenyl amine (23.7 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g , 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to give 21.1 g (yield: 67%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N-phenyl-Nm-terphenyl amine (16.1 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 16.4 g (yield: 69%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), 4- (naphthalen-1-yl) -N-phenylaniline (14.8g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 15.1 g (yield: 67%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), 4- (naphthalen-2-yl) -N-phenylaniline (14.8g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using 14.2 g (yield: 66%) of the product using the synthesis method 2-1 above.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N, 9,9-triphenyl-9H-fluoren-2-amine (20.5 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 20 g (yield: 71%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.4 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol ), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 19.7 g (yield: 70%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) phenanthren-9-amine (17.3 g, 50 mmol), Pd 2 (dba) 3 (2.3 g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to obtain 17.8 g (yield: 71%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) dibenzo [b, d] furan-3-amine (16.8 g, 50 mmol), Pd 2 (dba) 3 (2.3 g , 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were prepared using 17.9 g (yield: 73%) of the above synthesis method. Obtained the product
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) dibenzo [b, d] thiophen-3-amine (17.6g, 50 mmol), Pd 2 (dba) 3 (2.3g , 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol), toluene (525 mL) were prepared using the synthesis method of 2-1 above in 17.5 g (yield: 69%). Obtained the product
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) pyren-4-amine (18.5g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 19.1 g (yield: 73%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (naphthalen-1-yl) -4-phenylnaphthalen-1-amine (17.3g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol ), PPh 3 (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 18.5 g (yield: 74%) of product.
  • 1,4-dibromobenzene (11.8 g, 50 mmol), N- (6-phenylnaphthalen-2-yl) naphthalen-1-amine (17.3g, 50 mmol), Pd 2 (dba) 3 (2.3g, 2.5 mmol) , PPh 3 (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were prepared using 17.8 g (yield: 71%) of the above-mentioned synthesis method.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the organic substrate to form a thickness of 10 nm.
  • CuPc copper phthalocyanine
  • ⁇ -NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • a light emitting layer in which 45% thick BD-052X (Idemitsu Co., Ltd.) is doped with a 7% doped layer, wherein BD-052X is a blue fluorescent dopant, and the light emitting host material is the compound of the invention or 9, 10-di- (naphthalene- 2-anthracene) AND].
  • the phosphorescent material When measuring the invention compounds as a phosphorescent host material, the phosphorescent material is deposited to form a light emitting layer and at the same time abbreviated as tris (2-phenylpyridine) iridium (hereinafter Ir (ppy) 3 ) as a phosphorescent Ir metal complex dopant. ) was added. At this time, the concentration of Ir (ppy) 3 in the light emitting layer was 10% by weight.
  • BAlq ⁇ (1,1'bisphenyl) -4-oleito ⁇ bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq Tris (8-quinolinol) aluminum
  • Alq3 Tris (8-quinolinol) aluminum
  • LiF an alkyl halide metal
  • 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 above-described compounds of the present invention as a material for an organic electroluminescent device has a high efficiency and a blue color light emission with improved color purity, so that the light emitting host and hole transport of the organic electroluminescent device are obtained. Used as a material, it can significantly improve low driving voltage, high luminous efficiency and lifespan.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, 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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Abstract

La présente invention porte sur un composé et sur un élément électronique organique l'utilisant, et sur un terminal comprenant l'élément électronique organique.
PCT/KR2011/010267 2010-12-28 2011-12-28 Composé et élément électronique organique l'utilisant, et dispositif électronique comprenant l'élément électronique organique WO2012091471A2 (fr)

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