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WO2013180376A1 - Nouveau matériau de transport d'électrons et dispositif organique électroluminescent l'utilisant - Google Patents

Nouveau matériau de transport d'électrons et dispositif organique électroluminescent l'utilisant Download PDF

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Publication number
WO2013180376A1
WO2013180376A1 PCT/KR2013/001371 KR2013001371W WO2013180376A1 WO 2013180376 A1 WO2013180376 A1 WO 2013180376A1 KR 2013001371 W KR2013001371 W KR 2013001371W WO 2013180376 A1 WO2013180376 A1 WO 2013180376A1
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alkyl
compound
aryl
heteroaryl
electron transport
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PCT/KR2013/001371
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English (en)
Inventor
Hyun Goog Nam
Dae Won Lim
Jae Yong Kim
Sang Mi Park
Seung Hee Jang
Sang Youn Lee
Ju Seok Ham
Kyu Oh Cho
Hyun Don Kim
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Alpha Chem Co., Ltd.
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Priority claimed from KR1020120120910A external-priority patent/KR101474713B1/ko
Application filed by Alpha Chem Co., Ltd. filed Critical Alpha Chem Co., Ltd.
Publication of WO2013180376A1 publication Critical patent/WO2013180376A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • H10K50/16—Electron transporting layers

Definitions

  • the following disclosure relates to a new electron transport material and an organic electroluminescent device using the same.
  • An organic electroluminescent device is a device emitting light while electrons and holes disappear after being coupled in pairs when an electron charge is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode).
  • the organic electroluminescent device has advantages in that the device may be formed on a flexible transparent substrate made of, for example, plastic material, driven at a low voltage (10V or less) as compared with a plasma display panel or an inorganic electroluminescent (EL) display, has relatively low power consumption and excellent color sensation.
  • the organic electroluminescent device has a structure consisting of a substrate, an anode, a hole injection layer receiving a hole from the anode, a hole transport layer transporting the hole, a luminescent layer emitting light while the hole and an electron are bonded, an electron transport layer receiving the electrode from a cathode to transport the electron to the luminescent layer, and the cathode.
  • the luminescent layer may be configured by applying a small amount of a fluorescent or phosphorescent dye to the electron transport layer or the hole transport layer without a separate luminescent layer.
  • one polymer may entirely serve as the hole transport layer, the luminescent layer, and the electron transport layer.
  • Organic thin film layers between two electrodes may be formed by a method such as a vacuum deposition method, a spin coating method, an inkjet printing method, a roll coating method, or the like, and for effective injection of the electron from the cathode, a separate electron injection layer may be inserted.
  • the hole and the electron may be effectively transported to the luminescent layer.
  • the organic electroluminescent device is manufactured to have a multi-layer thin film structure.
  • TPBI which was reported by Kodak in 1996 disclosed in US Patent No. 5,645,948, (See the following structure), is known to be a representative material for electron transport layer having an imidazole group.
  • This material contains three N-phenyl benzimidazole groups at 1, 3, and 5 substitution positions of benzene, and has a function of blocking holes from a luminescent layer as well as transporting electrons.
  • stability of TPBI is too low to be actually used in the device.
  • the material may slightly improve only a driving voltage, or there are problems such as significant deterioration of a device driving lifespan or negative properties such as variation in the device lifespan according to the color, and deterioration of thermal stability, or the like.
  • a fluorescent material was used in the organic electroluminescent device according to the related art, but gradually, phosphorescent material has been mainly used in the organic electroluminescent device. Therefore, in the electron transport material, which is a common material of the organic electroluminescent device, electron mobility appropriate for the phosphorescent material, low driving voltage, and a hole blocking property have been required.
  • An embodiment of the present invention is directed to providing a new electron transport material capable of significantly improving luminescence efficiency, stability and a lifespan of a device.
  • an embodiment of the present invention is directed to providing an organic electroluminescent device capable of having an excellent luminescence property by using the new electron transport material and decreasing consumption power by decreasing driving voltage to induce increase in power efficiency.
  • an electron transport material represented by the following Chemical Formula 1 represented by the following Chemical Formula 1, and an organic electroluminescent device containing the same.
  • the electron transport material according to the present invention is used, such that excellent luminescence property may be obtained, and an increase in power efficiency is induced by decreasing driving voltage, such that the organic electroluminescent device using less consumption power may be manufactured.
  • A, B, C, and D each are independently C-(L 1 ) m -Ar 1 or N, but two of A, B, C, and D are N, the other two are C-(L 1 ) m -Ar 1 , and each of -(L 1 ) m -Ar 1 may be the same as or different from each other, but two -(L 1 ) m -Ar 1 are not hydrogen at the same time;
  • L is (C1-C20)alkylene or (C2-C20)alkenylene
  • R 1 to R 4 each are independently hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, or (C3-C30)heteroaryl;
  • L 1 (s) each are independently a single bond, (C6-C30)arylene, or (C3-C30)heteroarylene;
  • n is an integer of 1 to 3, and in the case in which m is an integer of 2 or more, L 1 (s) each are the same as or different from each other;
  • Ar 1 (s) each are independently hydrogen, (C1-C30)alkyl, (C6-C30)aryl, or (C3-C30)heteroaryl;
  • alkyl, cycloalkyl, aryl, heteroaryl of R 1 to R 4 , alkylene or alkenylene of L, arylene and heteroarylene of L 1 , and aryl and heteroaryl of Ar 1 may be substituted with at least one selected from a group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C6-C30)aryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C3-C30)heteroaryl, (C3-C30)heteroaryl substituted with (C1-C30)alkyl, (C3-C30)heteroaryl substituted with (C6-C30)
  • alkyl alkoxy and other substituents including an “alkyl” part described in the present invention include both of the straight chain type and the branched chain type, and the term “cycloalkyl” includes polycyclic hydrocarbon such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as monocyclic ring system.
  • aryl which is an organic radical derived from aromatic hydrocarbon by the removal of one hydrogen atom, may include a single ring or a fused ring containing, preferably 4 to 7 ring atoms, and more preferably 5 or 6 ring atoms, and include rings in which two or more aryl groups are combined through a single bond(s).
  • aryl include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl, and the like.
  • the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
  • the “heteroaryl”in the present invention may include the structures having one or more heteroaryl group(s) bonded through a single bond.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized, for example, to form N-oxides, quaternary salts, or the like.
  • Specific examples of the heteroaryl group include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like; polycyclic heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl,
  • ‘(C1-C30)alkyl’described herein may be preferably (C1-C20)alkyl, more preferably, (C1-C10)alkyl
  • ‘(C6-C30)aryl’described herein may be preferably (C6-C20)aryl.
  • ‘(C3-C30)heteroaryl’ may be preferably (C3-C20)heteroaryl.
  • ‘(C3-C30)cycloalkyl’ may be preferably (C3-C20)cycloalkyl, more preferably (C3-C7)cycloalkyl.
  • the electron transport material according to the present invention may be represented by the following Chemical Formula 2 or 3.
  • R 1 to R 4 and L each has the same definition in Chemical Formula 1;
  • L 2 and L 3 each are independently a single bond, (C6-C30)arylene, or (C3-C30)heteroarylene;
  • x and y each are independently an integer of 1 to 3, wherein when x is an integer of 2 or more, L 2 (s) are the same as or different from each other, and when y is an integer of 2 or more, L 3 (s) are the same as or different from each other;
  • Ar 2 and Ar 3 each are independently hydrogen, (C1-C30)alkyl, (C6-C30)aryl, or (C3-C30)heteroaryl;
  • Arylene and heteroarylene of L 2 and L 3 , and aryl and heteroaryl of Ar 2 and Ar 3 may be substituted with at least one selected from a group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C6-C30)aryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C3-C30)heteroaryl, (C3-C30)heteroaryl substituted with (C1-C30)alkyl, (C3-C30)heteroaryl substituted with (C6-C30)aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)aryla
  • the electron transport material according to the present invention may be represented by the following Chemical Formulas 4 to 9.
  • R 1 to R 6 each are independently hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, or (C3-C30)heteroaryl;
  • L 2 and L 3 each are independently a single bond, (C6-C30)arylene, or (C3-C30)heteroarylene;
  • x is an integer of 1 to 3, and when x is an integer of 2 or more, L 1 (s) each are the same as or different from each other,
  • Ar 2 and Ar 3 each are independently hydrogen, (C1-C30)alkyl, (C6-C30)aryl, or (C3-C30)heteroaryl; and arylene of L 2 and L 3 and aryl and heteroaryl of Ar 2 and Ar 3 may be further substituted with at least one selected from a group consisting of (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, and (C3-C30)heteroaryl.]
  • L 2 and L 3 each are a single bond, phenylene, biphenylene, 9,9-dimethylfluorenylene, naphthylene, anthrylene, pyridinylene, or pyrimidinylene;
  • Ar 2 and Ar 3 each are independently hydrogen, (C1-C30)alkyl, or selected from the following structure;
  • R', R'', and R'' each may be independently hydrogen, (C1-C30)alkyl, (C6-C30)aryl, (C3-C30)heteroaryl, or (C1-C30)alkyl(C6-C30)aryl.
  • the electron transport material may be, for example, the following compounds, but is not limited thereto.
  • a process of preparing an electron transport material of Chemical Formula 2 when x and y are 1 is represented by the following Reaction Formula 1
  • a process of preparing an electron transport material of Chemical Formula 2 in the case in which x is 3 and y is 1 is represented by the following Reaction Formulas 2 to 4.
  • the electron transport material is not limited thereto, but may be prepared by an organic reaction known in the art.
  • R 1 to R 4 , L, L 2 , L 3 , Ar 2 , and Ar 3 each has the same definition in Chemical Formula 2, X 1 and X 2 are halogen or but are not equal to each other.]
  • an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer interposed between the first and second electrodes, wherein the organic layer includes an electron transport layer containing an electron transport material of Chemical Formula 1.
  • driving voltage may be decreased, such that an increase in power efficiency may be induced, thereby decreasing consumption power.
  • the organic layer may include at least one electron transport layer in which the electron transport material of Chemical Formula 1 is contained and at least one luminescent layer configured of a fluorescent host and a fluorescent dopant or a phosphorescent host and a phosphorescent dopant, wherein the fluorescent host, the fluorescent dopant, the phosphorescent host, or the phosphorescent dopant are not particularly limited.
  • the electron transport material according to the present invention may have the excellent luminescence property and decrease the driving voltage to increase the power efficiency, such that the organic electroluminescent device using less consumption power may be manufactured.
  • FIG. 1 is a graph showing efficiency (cd/A) and luminance (cd/m 2 ) of organic electroluminescent devices manufactured in Examples 7 to 12 and Comparative Example 1.
  • FIG. 2 is a graph showing efficiency (cd/A) and luminance (cd/m 2 ) of organic electroluminescent devices manufactured in Examples 22 to 30 and Comparative Example 1
  • N1-phenylbenzene-1,2-diamine (48g, 260mmol) was completely dissolved in N,N-Dimethyl acetamide (DMAC, 100mL) at 0°C, and then 4-bromobenzoyl chloride (63g, 287mmol) was dropped thereinto and stirred. After 2 hours 30 minutes, pyridine (60mL) and water (100mL) were added thereto. After stirring the mixture for 30 minutes, the prepared solid was filtered while being washed with methanol, thereby obtaining Compound F-1 (95g, 95%) as a white solid.
  • DMAC N,N-Dimethyl acetamide
  • 1,4-dibromonaphthalene 25g, 87.4mmol
  • bis(pinacolato)diboron 46.62g, 184mmol
  • 1,4-dioxane 300mL
  • 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.71g, 0.9mmol)
  • potassium acetate 17.16g, 174.8mmol
  • 1,3-dibromothiophene (10g, 41.3mmol), Compound J (Preparation Example 10, 39.2g, 82.7mmol), THF (200mL), Pd(PPh 3 ) 4 (1.91g, 1.65mmol), K 2 CO 3 (68.6g, 496mmol), and distilled water (100mL) were mixed and stirred under reflux for 18 hours.
  • the reactant was cooled to room temperature. Then, the precipitated solid was filtered and washed with methanol, thereby obtaining Compound 120 (22g, 68.5%).
  • a glass substrate (25mm x 25mm x 0.7mm) having an indium tin oxide (ITO) transparent electrode line having a thickness of 150nm was subjected to ultrasonic cleaning for 10 minutes in distilled water in which a detergent was dissolved and then cleaned with distilled water again for 10 minutes. After washing with distilled water, the substrate was subjected to ultrasonic cleaning with solvents in a sequence of isopropyl alcohol, acetone, and methanol for 10 minutes, respectively, and dried. Thereafter, the substrate was dry cleaned using oxygen/argon plasma, then the glass substrate having the transparent electrode line was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • ITO indium tin oxide
  • a film having a thickness of 60nm was formed on a surface on which the transparent electrode line was formed as a hole injection layer using IDE-406 (the following structure, Idemitsu) so as to cover the transparent electrode.
  • IDE-406 the following structure, Idemitsu
  • a film having a thickness of 30nm was formed on the IDE-406 film as a hole transport layer using H-1 (tetrakis-N-biphenyl-4-yl-benzidine, hereinafter, referred to as the H-1 film ).
  • BD-1 having the following structure and ⁇ -ADN(9,10-di(naphthalene-2-yl)anthracene) were deposited on the H-1 film as a dopant and a luminescent host at a weight ratio of 5%, to thereby form a film having a thickness of 20nm as a luminescent layer.
  • a film having a thickness of 20nm was formed on the luminescent layer as an electron transport layer by depositing Compound 100 according to the present invention. Subsequently, lithium quinolate (Liq) was deposited thereon to form an electron injection layer. Metal aluminum was deposited on this Liq film to form a metal cathode, thereby manufacturing the organic electroluminescent device.
  • Liq lithium quinolate
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 98 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 105 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 106 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 113 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 110 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 114 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 115 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 116 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 117 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 118 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 119 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 120 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 121 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 16 except that Compound 123 was used as an electron transport material instead of Compound 100 in Example 16.
  • An organic electroluminescent device was manufactured by the same process in Example 7 except that Compound ETM-1 having the following structure was used as an electron transport material instead of Compound 100 in Example 7.
  • the material according to the present invention had excellent luminescence properties as compared with the material according to the related art.
  • the organic electroluminescent device using the heteroaromatic cyclic compound according to the present invention as the electron transport layer had an excellent luminescence property and decreased driving current to increase the power efficiency, thereby using less consumption power.

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  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un nouveau matériau de transport d'électrons et un dispositif organique électroluminescent le comprenant. Le matériau de transport d'électrons selon la présente invention peut présenter d'excellentes propriétés de luminescence et réduire la tension d'excitation de manière à augmenter l'efficacité énergétique, ce qui permet de fabriquer un dispositif organique électroluminescent consommant moins d'énergie.
PCT/KR2013/001371 2012-05-30 2013-02-21 Nouveau matériau de transport d'électrons et dispositif organique électroluminescent l'utilisant WO2013180376A1 (fr)

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KR10-2012-0057154 2012-05-30
KR20120057154 2012-05-30
KR10-2012-0120910 2012-10-30
KR1020120120910A KR101474713B1 (ko) 2012-05-30 2012-10-30 신규한 전자 수송 물질 및 이를 이용한 유기 발광 소자

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH599569A5 (en) * 1970-08-11 1978-05-31 Hoechst Ag Photoinitiators
WO1993014080A1 (fr) * 1992-01-15 1993-07-22 E.I. Du Pont De Nemours And Company Fongicides heterocycliques pontes
WO2004039786A1 (fr) * 2002-10-30 2004-05-13 Ciba Specialty Chemicals Holding Inc. Dispositif electroluminescent
KR20120117693A (ko) * 2011-04-15 2012-10-24 에스에프씨 주식회사 신규한 화합물 및 이를 포함하는 유기전계발광소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH599569A5 (en) * 1970-08-11 1978-05-31 Hoechst Ag Photoinitiators
WO1993014080A1 (fr) * 1992-01-15 1993-07-22 E.I. Du Pont De Nemours And Company Fongicides heterocycliques pontes
WO2004039786A1 (fr) * 2002-10-30 2004-05-13 Ciba Specialty Chemicals Holding Inc. Dispositif electroluminescent
KR20120117693A (ko) * 2011-04-15 2012-10-24 에스에프씨 주식회사 신규한 화합물 및 이를 포함하는 유기전계발광소자

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
CHAO, B. ET AL.: "Copper(I)-Mediated Cascade Reactions: An Efficient Approach to the Synthesis of Functionalized Benzofuro[3,2-d]pyrimidines.", ORGANIC LETTERS., vol. 12, no. 9, 26 April 2012 (2012-04-26), pages 2398 - 2401 *
CHETONI, F. ET AL.: "Synthesis of Novel I-Aryl[I]benzoxepino[5,4-c]pyrazole and [1]benzoxepino[5,4-d]pyrimidine Derivatives.", JOURNAL OF HETEROCYCLIC CHEMISTRY., vol. 30, 1993, pages 1653 - 1658 *
HERRERA, A. ET AL.: "The reaction of tetralones with nitriles: a simple approach to the synthesis of new substituted benzo[h]quinazolines, benzo[f]quinazolines and dibenzo[a,i]phenanthridines.", TETRAHEDRON, vol. 62, no. 12, 2006, pages 2799 - 2811 *
KUMAR, A. S. ET AL.: "Synthesis of pyrido[2,3-b]indoles and pyrimidoindoles via Pd-catalyzed amidation and cyclization.", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 26, 25 April 2012 (2012-04-25), pages 5084 - 5093 *
LEONETTI, F. ET AL.: "Design, Snthesis, and 3D QSAR of Novel Potent and Selective Aromatase Inhibitors.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, 2004, pages 6792 - 6803 *
MAMAEV, V. P. ET AL.: "Pyrimidines III. Dehydrogenation of 4-phenylbenzo [h]quinazoline derivatives.", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII., vol. 1, no. 4, 1965, pages 608 - 615 *
MIYASHI, T. ET AL.: "The Intermolecular Nitrene-Type 1,1-Cycloaddition Reaction of Allyl-Substituted Diazomethanes.", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 108, 1986, pages 1617 - 1632 *
ROBBA, M. ET AL.: "Synthese de benzo (1) thieno [2,3-d] pyrimidines et de benzo (1) thieno [3,2-d] pyrimidines.", TETRAHEDRON LETTERS, vol. 13, no. 44, 1972, pages 4549 - 4551 *
ROBEV, S. K. ET AL.: "New sysnthesis of quinazoline and benzoquinazoline derivatives.", TETRAHEDRON LETTERS, vol. 24, no. 40, 1983, pages 4351 - 4354 *
ROBEV, S. K.: "2,4-Disubstituted benzo/h/Quinazolines from N-(l-naphthyl)- amidines.", DOKLADY BOLGARSKOI AKADEMII NAUK., vol. 36, no. 12, 1983, pages 1551 - 1553 *

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EP3878855A1 (fr) 2017-11-28 2021-09-15 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
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US11584763B2 (en) 2017-12-22 2023-02-21 Hibercell, Inc. Chromenopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors
CN110010773B (zh) * 2018-01-05 2023-08-18 固安鼎材科技有限公司 一种调节载流子迁移率的发光层及有机电致发光器件
CN110010773A (zh) * 2018-01-05 2019-07-12 固安鼎材科技有限公司 一种调节载流子迁移率的发光层及有机电致发光器件
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US11498929B2 (en) 2019-06-17 2022-11-15 Hibercell, Inc. Chromenopyrimidine derivatives as phosphatidylinsitol phosphate kinase inhibitors
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KR20210018105A (ko) 2019-08-09 2021-02-17 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 화합물, 발광 디바이스, 발광 장치, 전자 기기, 및 조명 장치
US11690290B2 (en) 2019-08-09 2023-06-27 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device
EP3778614A1 (fr) 2019-08-16 2021-02-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
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CN113214167A (zh) * 2020-02-04 2021-08-06 昱镭光电科技股份有限公司 苯并喹唑啉化合物及有机电致发光元件
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CN116120338A (zh) * 2021-11-11 2023-05-16 烟台显华科技集团股份有限公司 一种稠杂环取代蒽化合物及其应用
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