WO2016105133A1 - Procédé de préparation d'un complexe d'iridium et dispositif électroluminescent organique utilisant un complexe d'iridium ainsi préparé - Google Patents

Procédé de préparation d'un complexe d'iridium et dispositif électroluminescent organique utilisant un complexe d'iridium ainsi préparé Download PDF

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WO2016105133A1
WO2016105133A1 PCT/KR2015/014198 KR2015014198W WO2016105133A1 WO 2016105133 A1 WO2016105133 A1 WO 2016105133A1 KR 2015014198 W KR2015014198 W KR 2015014198W WO 2016105133 A1 WO2016105133 A1 WO 2016105133A1
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group
aryl
alkyl
iridium complex
solvent
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Korean (ko)
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엄민식
백영미
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

Definitions

  • the present invention relates to a method for producing an iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure and an organic electroluminescent device using the iridium complex prepared by the above method.
  • the material used as the organic material layer 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 its function.
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors.
  • yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • phosphorescent dopants include cyclometalated iridium (III) -based compounds. Specifically, Firpic, Ir (ppy) 3 and (acac) Ir (btp) 2 are used as blue, green and red dopant materials, respectively.
  • the iridium complex is a complex formed by coordinating a bidentated ligand submolecule with iridium, which is a central metal, and is divided into facial isomer and merdianal isomer, and when the bidentate ligand is the same, it is called homoleptic, and when the bidentate ligand is not identical, it is called heteroleptic. do.
  • iridium complexes are byproducts produced by third ligands other than the desired product due to the Ligand Scambling phenomenon in the synthesis.
  • the produced iridium complex has different molecular weights, but similar polarity and solubility, in order to purify a desired product with high purity through a column or a recrystallization method, a column purification process is repeatedly performed or a recrystallization process is performed to increase the purity. Or, using expensive and sophisticated column equipment, due to this complicated manufacturing process, there was a problem that the manufacturing cost increases.
  • Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage and high luminous efficiency, including an iridium complex prepared by the above method.
  • the present invention is represented by the formula (C), including the step of reacting the compound represented by the formula (A) and the compound represented by the formula (B) in the presence of a mixed solvent containing a halogen-containing solvent and an alcoholic solvent according to Scheme 1 It provides a process for preparing an iridium complex of heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure:
  • Ar 1 to Ar 4 are the same as or different from each other, each independently selected from the group consisting of hydrogen, a C 1 ⁇ C 40 alkyl group, a C 6 ⁇ C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms; ;
  • R 1 to R 4 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of each other alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and
  • n is an integer from 1 to 3, provided that m + n is 3;
  • X is selected from the group consisting of hexafluorophosphate, triflate, tosylate, trifluoroacetate, and tetrafluoroborate;
  • Sol is a neutral ligand derived from a solvent selected from the group consisting of water (H 2 O), alcohol and acetonitrile (CH 3 CN);
  • the alkyl group, aryl group, heteroaryl group of Ar 1 to Ar 4 the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group of R 1 to R 4 ,
  • Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl group
  • the ratio of the halogen-containing solvent and the alcohol solvent is preferably 20:80 to 80:20 by volume.
  • the use ratio of the compound represented by the said Formula (A) and the compound represented by the formula (B) is 1: 1-5 molar ratio.
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • an organic electroluminescent device comprising an iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by the formula (C) synthesized by Scheme 1.
  • the organic material layer containing the iridium complex is a light emitting layer, and the iridium complex is a phosphorescent dopant of the light emitting layer.
  • the preparation method according to the present invention synthesizes the iridium intermediate and the ligand compound in the presence of a mixed solvent comprising a halogen-containing solvent and an alcoholic solvent, thereby providing heteroleptic fac-Ir (C ⁇ N) with high selectivity and yield without a separate purification process.
  • the iridium complex of the heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure prepared according to the present invention has excellent luminescence performance and structural stability. Therefore, when the iridium complex is used as an organic layer material of OLED, in particular, a phosphorescent dopant material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life can be manufactured, and further, the performance and lifespan of the full Color display panels can also be manufactured.
  • the present invention provides a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure of the iridium complex represented by the formula C, in the presence of a mixed solvent containing a halogen-containing solvent and an alcohol-based solvent And reacting the compound represented by Formula A with the compound represented by Formula B.
  • C ⁇ N means a cyclometalated ligand.
  • the present invention by using a halogen-containing solvent together with an alcohol-based solvent as a reaction solvent, the halogen-containing solvent can prevent the dissociation of two bidentated ligands already coordinated to the compound of formula A. As a result, Ligand Scambling can be minimized. Therefore, the present invention provides a iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by Chemical Formula C with high selectivity and yield even without a separate purification process such as column or recrystallization. can do.
  • Halogen-containing solvents used in the present invention are solvents containing Group 17 elements of the periodic table, such as F, Cl, Br, and the like, examples of which are dichloromethane, trichloromethane, and tetrachloromethane.
  • alcohol solvents examples include methanol, ethanol, propan-1-ol, butan-1-ol, pentan-1-ol, hexane-1-ol, heptane-1-ol, octane-1-ol, and nonane -1-ol, decan-1-ol, undecane-1-ol, dodecane-1-ol, tridecane-1-ol, tetradecane-1-ol, pentadecane-1-ol, hexadecane-1 -Ol, heptadecan-1-ol, octadecane-1-ol, nonadecan-1-ol, icosane-1-ol, henic acid-1-ol, docosan-1-ol, tricosan-1 -Ol, tetracoic acid-1-ol, pentacoic acid-1-ol, hexacoic acid-1-ol, hept
  • the use ratio of the halogen-containing solvent and the alcohol-based solvent is not particularly limited, but in the case of 20:80 to 80:20 volume ratio, preferably 25:75 to 75:25 volume ratio, Ligand Scambling without a separate purification process The phenomenon is minimized so that the iridium complex represented by Formula C can be synthesized with high selectivity of 99% or more.
  • Ar 1 to Ar 4 are the same as or different from each other, and each independently hydrogen, a C 1 to C 20 alkyl group, a C 6 to C 20 aryl group, and a heteroaryl group having 5 to 30 nuclear atoms may be selected from the group consisting of and, and an aryl group of C 6 ⁇ C 60 is more preferable, it is more preferable that an aryl group of C 6 ⁇ C 20.
  • R 1 to R 4 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, an alkenyl group, nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 of, C 2 ⁇ C An alkynyl group of 20 , a cycloalkyl group of C 3 to C 20 , a heterocycloalkyl group of 3 to 20 nuclear atoms, an aryl group of C 6 to C 20 , a heteroaryl group of 5 to 40 nuclear atoms, and C 1 to C 20 Alkyloxy group, C 6 ⁇ C 30 aryloxy group, C 1 ⁇ C 20 alkylsilyl group, C 6 ⁇ C 30 arylsilyl group, C 1 ⁇ C 20 alkyl boron group, C 6 ⁇ C 30 that of the arylboronic group, C 6 ⁇ C 30 aryl phosphine group, C 6 ⁇ C 30 aryl phosphine
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and It may be selected from the group consisting of heteroaryl groups having 5 to 60 nuclear atoms, even more preferably each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 30 It may be selected from the group consisting of an aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.
  • the alkyl group, aryl group, heteroaryl group of Ar 1 to Ar 4 the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group of R 1 to R 4 ,
  • An aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an arylamine group are each independently a C 1 to C 40 alkyl group (preferably, C 1 ⁇ C 20 alkyl group), C 2 ⁇ C 40 alkenyl group (preferably, C 2 ⁇ C alkenyl group of 20), C alkynyl group of 2 ⁇ C 40 alkynyl group (preferably, C 2 ⁇ C 20 in) , A C 3 to C 40 cycloalkyl group
  • the compound represented by the formula (A) used in the present invention is a solvent-coordinated cationic iridium intermediate, which may be prepared by the following method, but is not limited thereto.
  • the compound represented by the formula (A) is a iridium dimer represented by the formula (D) in the presence of a mixed solvent of a second halogen-containing solvent and a second alcohol-based solvent, according to Scheme 2 below It can obtain by making it react with the compound represented by.
  • R 1 , R 2 , Ar 1 , Ar 2 , and Sol are each as defined in Scheme 1 above;
  • Y is halogen, preferably F, Cl, Br or I, more preferably Cl;
  • M is a + monovalent metal, preferably Ag
  • X is selected from the group consisting of hexafluorophosphate, triflate, tosylate, trifluoroacetate, and tetrafluoroborate, preferably hexafluorophosphate.
  • Examples of the second alcohol solvent are as described in the above-described alcohol solvent.
  • the use ratio of the second halogen-containing solvent and the second alcohol-based solvent is not particularly limited, and may be, for example, 1 to 5: 1 by volume.
  • the use ratio of the iridium dimer represented by the formula (D) and the compound represented by the formula (E) is not particularly limited, but may be, for example, 1: 1 to 4 molar ratio.
  • the compound represented by Chemical Formula D may be synthesized by the reaction of the compound represented by Chemical Formula G and the compound represented by Chemical Formula F in a mixed solvent of a third alcohol solvent and water, according to Scheme 3, but is not limited thereto. .
  • Y is halogen, preferably F, Cl, Br or I, more preferably Cl;
  • R 1 , R 2 , Ar 1 and Ar 2 are the same as defined in Scheme 1, respectively.
  • the use ratio of the compound of Formula G and the compound of Formula F is not particularly limited, and may be, for example, 1: 1 to 5 molar ratio.
  • the use ratio of the third alcohol solvent and water is not particularly limited, but may be, for example, 1 to 5: 1 volume ratio.
  • Examples of the third alcohol solvent are as described above in the alcohol solvent.
  • the use ratio of the compound represented by Formula A and the compound represented by Formula B is not particularly limited, and may be, for example, 1: 1 to 5 molar ratio.
  • the iridium complex prepared by the above-described preparation method is a compound having a Heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by Chemical Formula C, and has a low purity due to minimization of Ligand Scambling during manufacture. Higher than 99%
  • the iridium complex may be embodied as the following Compounds 1 to 125, but is not limited thereto.
  • Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycloalkyl monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • unsubstituted alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
  • unsubstituted aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms
  • Unsubstituted arylphosphine group means a phosphine group substituted with aryl having 1 to 60 carbon atoms
  • unsubstituted arylphosphine oxide group means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides an organic electroluminescent device (organic EL device) comprising an iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by the formula (C) to provide.
  • organic EL device organic electroluminescent device
  • the purity of the iridium complex is 99% or more.
  • the organic electroluminescent device comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes an iridium complex of the heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by the formula (C).
  • the compound may be used alone, or two or more may be used in combination.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is a heteroleptic fac-Ir ( C ⁇ N) 2 (C ⁇ N) 'structure of iridium complex.
  • the light emitting layer comprises an iridium complex of the heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by the formula (C).
  • the light emitting layer of the present invention includes a host and a dopant, wherein the dopant, preferably a phosphorescent dopant, comprises an iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by Formula C. Include.
  • the dopant preferably a phosphorescent dopant
  • the dopant comprises an iridium complex having a heteroleptic fac-Ir (C ⁇ N) 2 (C ⁇ N) 'structure represented by Formula C.
  • the content of the iridium complex is not particularly limited, but when it is about 1 to 30% by weight based on the total weight of the light emitting layer material, the color purity and efficiency of the light may be increased, so that the luminous efficiency and lifetime characteristics of the device may be further improved. Can be.
  • the host usable in the present invention can be used without particular limitation as long as it is known in the art.
  • the structure of the organic EL device according to the present invention is not particularly limited.
  • an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer. It may be a structure.
  • the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate.
  • an electron injection layer may be positioned between the electron transport layer and the cathode.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include the iridium complex, preferably the hole transport layer or the light emitting layer may include the iridium complex.
  • a light emission auxiliary layer may be selectively inserted between the hole transport layer and the light emitting layer.
  • at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the iridium complex, preferably a hole transport layer, electron blocking layer, light emission
  • At least one of the auxiliary layer and the light emitting layer may include the iridium complex.
  • the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the iridium complex.
  • the organic material layer 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 substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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 or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the light emitting layer, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • Iridium was prepared in the same manner as in ⁇ Step 2> of Synthesis Example 1, except that 7.0 g (41.4 mmol) of 4-Methyl-2-phenylpyridine was used instead of 2-phenylpyridine used in ⁇ Step 2> of Synthesis Example 1. dimer D3 (7.55 g, yield: 97%) was obtained.

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Abstract

La présente invention concerne : un procédé pour préparer, avec une sélectivité et un rendement élevés, un complexe d'iridium ayant une structure fac-Ir(C^N)2(C^N) hétéroleptique, par réaction d'un intermédiaire contenant de l'iridium et d'un composé ligand en présence d'un mélange de solvants comprenant un solvant halogéné et un solvant à base d'alcool; et un dispositif électroluminescent organique employant un complexe d'iridium préparé par ce procédé.
PCT/KR2015/014198 2014-12-24 2015-12-23 Procédé de préparation d'un complexe d'iridium et dispositif électroluminescent organique utilisant un complexe d'iridium ainsi préparé WO2016105133A1 (fr)

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KR20140052418A (ko) * 2012-10-24 2014-05-07 주식회사 두산 유기 전계 발광 소자
KR20140074726A (ko) * 2012-12-10 2014-06-18 주식회사 두산 이리듐(ⅲ) 착화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014094964A1 (fr) * 2012-12-18 2014-06-26 Merck Patent Gmbh Dispositifs électroluminescents organiques

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