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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
  • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
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  • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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  • C07—ORGANIC CHEMISTRY
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  • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
  • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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  • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
  • C07F5/02—Boron compounds
  • C07F5/04—Esters of boric acids
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  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
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  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
  • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
• • 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
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  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1007—Non-condensed systems
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  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1011—Condensed systems
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  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—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
  • 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
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

• the present invention relates to an acridine derivative and an organic electroluminescent device including the same, and more particularly, an acridine derivative in which an acridine moiety and an amine moiety are bonded to an aryl moiety or a heteroaryl moiety.
• Compound, and the acridine derivative compound relates to an organic electroluminescent device exhibiting a low driving voltage and high efficiency and an improved lifetime.
• the organic electroluminescence phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
• An organic electroluminescent device using an organic electroluminescence phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
• the organic material layer is often formed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
• the material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
• the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
• a host / dopant system may be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce 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.
• organometallic complexes having relatively high stability and electron transport speed are good candidates as organic monomolecular materials, and Alq3 having high stability and high electron affinity has been reported to be the best. Is being used.
• conventionally known electron transport materials include flavon derivatives published by Sanyo, germanium, and silicon cyclopentadiene derivatives of Chiso. (Japanese Laid-Open Patent Publication No. 1998-017860, Japanese Laid-Open Patent Publication No. 1999-087067).
• the 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, and an electron injection material.
• a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material.
• the development of a stable and efficient organic material for an organic light emitting device has not yet been sufficiently developed, and therefore, the development of new materials is continuously required.
• the present invention can be applied to an organic electroluminescent device, to provide a novel organic compound with improved color purity, luminous efficiency, brightness, power efficiency, heat resistance and the like.
• the present invention is to provide an organic electroluminescent device including the novel organic compound exhibits a low driving voltage and high efficiency and has an improved lifetime.
• the present invention provides a compound represented by the following Chemical Formula 1 as the novel organic compound.
• R 1 to R 4 are each the same or different and each independently C 1 ⁇ C 40 alkyl group of hydrogen, deuterium, halogen, linear or branched, C cycloalkyl group of 3 ⁇ C 40, C 3 ⁇ C 40 heterocycloalkyl groups, fused or unfused C 6 to C 60 aryl groups, fused or unfused C 5 to C 60 heteroaryl groups, straight or branched C 1 to C 40 alkyl Oxyoxy, fused or unfused C 6 -C 60 aryloxy groups, and fused or unfused C 6 -C 60 arylamine groups;
• R 5 to R 7 are the same as or different from each other, and each independently hydrogen, deuterium, a straight or branched C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, Selected from the group consisting of fused or unfused C 6 to C 60 aryl groups, and fused or unfused C 5 to C 60 heteroaryl groups, forming or not forming a ring fused with an adjacent group; ;
• L is a C 6 -C 60 arylene group or a C 5 -C 60 heteroarylene group.
• the present invention also includes (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
• At least one of the one or more organic material layer provides an organic electroluminescent device, characterized in that the organic material layer containing a compound represented by the formula (1) of any one of claims 1 to 3.
• the organic material layer including the compound represented by Chemical Formula 1 in the organic electroluminescent device of the present invention may be at least one selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.
• Compound represented by the formula (1) of the present invention is excellent in brightness, power efficiency, heat resistance, hole transport performance and hole injection performance and can exhibit an increase in color purity and luminous efficiency, and thus, a hole injection layer, a hole transport layer and It can be applied to one or more of the light emitting layers. Therefore, the organic electroluminescent device of the present invention including the compound represented by Chemical Formula 1 exhibits low driving voltage and high efficiency, and thus has a great effect on maximizing performance and improving lifetime in a full color organic EL panel.
• the compound represented by Formula 1 of the present invention is an acridine derivative in which an acridine moiety and an amine moiety are bonded to an aryl moiety or a heteroaryl moiety.
• the compound represented by Formula 1 of the present invention may be applied to the organic electroluminescent device as one or more of a hole injection material, a hole transport material, a light emitting material, an electron transport material and an electron injection material, preferably a hole injection It can be applied to the organic electroluminescent device as one or more of a material, a hole transport material and a light emitting material.
• R 1 to R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, linear or branched C 1 to C 40 alkyl group, C 3 to C 40 Cycloalkyl groups, C 3 to C 40 heterocycloalkyl groups, fused or unfused C 6 to C 60 aryl groups, fused or unfused C 5 to C 60 heteroaryl groups, straight or branched chains A C 1 to C 40 alkyloxy group, a fused or unfused C 6 to C 60 aryloxy group, or a fused or unfused C 6 to C 60 arylamine group, and a ring fused with an adjacent group. It may or may not form.
• R 5 to R 7 of Formula 1 are the same as or different from each other, and each independently hydrogen, deuterium, a straight or branched C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C A 40 heterocycloalkyl group, a fused or unfused C 6 -C 60 aryl group, a fused or unfused C 5 -C 60 heteroaryl group, which does or does not form a fused ring with an adjacent group You may not.
• L in the formula (I) is a heteroaryl group of C 6 ⁇ C 60 arylene group, or a C 5 ⁇ C 60 of.
• L is phenylene, biphenylene, terphenylene, naphthylene, naphthylene, anthracenylene, phenanthrylene, pyrenylene ), Fluorenylene, fluoranthenylene, perylenylene, carbazolylene, N-carbazolephenylene, pyridinylene, quinolinylene )
• isoquinolinylene may be a C 6 ⁇ C 60 arylene group or C 5 ⁇ C 60 hetero arylene group selected from the group consisting of.
• R 1 to R 7 and L of Formula 1 are each independently deuterium, halogen, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 Heterocycloalkyl group, C 6 ⁇ C 60 Aryl group, C 5 ⁇ C 60 Heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group and C 6 ⁇ C 60 Aryl It may be unsubstituted or substituted with one or more substituents selected from the group consisting of amine groups.
• Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.
• the organic electroluminescent device according to the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, At least one of the one or more organic material layers is characterized in that the organic material layer containing a compound represented by the formula (1).
• the organic material layer including the compound represented by Formula 1 of the present invention may be one or more selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
• the organic material layer including the compound represented by Formula 1 is at least one selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.
• the organic material layer other than the organic material layer containing the compound represented by Formula 1 of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and / or an electron injection layer.
• a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the hole injection layer, hole At least one of the transport layer and the light emitting layer includes a compound represented by Chemical Formula 1.
• An electron injection layer may be positioned on the electron transport layer.
• the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.
• the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method.
• the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
• the organic electroluminescent device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. It can be manufactured by.
• a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet may be used as the substrate.
• the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy 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 polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
• 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 polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
• the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
• materials such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer is not particularly limited, and conventional materials known in the art may be used.
• the reaction solution was poured onto a thin pad of silica, subjected to short chromatography, and washed with MC.
• the filtrate was distilled under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (methylene chloride / normal hexane (1/10)) to give 10- (biphenyl-4-yl) -9,10-dihydroacridine compound as an off-white solid. 15.3g (yield 70%) was obtained.
• a hole injection layer was formed by vacuum depositing DS-205 (Doosan Co., Ltd.) at a thickness of 800 kPa on ITO (anode), and vacuum depositing the Cpd 3 compound synthesized in Synthesis Example 2 on the hole injection layer at a thickness of 150 kPa. To form a hole transport layer.
• the compound of Formula 2 was used as a host thereon, and the compound of Formula 3 was doped with 5% as a dopant to be vacuum deposited to a thickness of 300 kPa to form a light emitting layer.
• An electron transport layer was formed by vacuum depositing Alq3, which is an electron transport material, on the light emitting layer to a thickness of 250 kPa.
• LiF an electron injection material
• Alq3 an electron transport material
• Example 1 and C except that Cpd 14, Cpd 36, Cpd 48, Cpd 61, Cpd 81, Cpd 102, Cpd 106, Cpd 113, Cpd 129 and Cpd 131, respectively, were used instead of the Cpd 3 compound in forming the hole transport layer.
• An organic electroluminescent device was manufactured in the same manner.
• An organic electroluminescent device was manufactured in the same manner as in Example 1, except that ⁇ -NPB was used instead of the Cpd 3 compound in forming the hole transport layer.
• the organic electroluminescent devices of Examples 1 to 11 exhibited high luminance.
• the driving voltage was low, the luminance was high, and the color purity was (x, y) was similar to (0.27, 0.63).

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• Electroluminescent Light Sources (AREA)
• Other In-Based Heterocyclic Compounds (AREA)

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• 2009
  • 2009-06-19 KR KR1020090054895A patent/KR101120892B1/ko not_active Expired - Fee Related
• 2010
  • 2010-06-01 JP JP2012515966A patent/JP5690336B2/ja not_active Expired - Fee Related
  • 2010-06-01 WO PCT/KR2010/003526 patent/WO2010147319A2/ko not_active Ceased
  • 2010-06-01 US US13/378,851 patent/US8597802B2/en active Active

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