WO2009082043A1 - Complexe formé par l'iridium et dispositif organique électroluminescent - Google Patents

Complexe formé par l'iridium et dispositif organique électroluminescent Download PDF

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WO2009082043A1
WO2009082043A1 PCT/KR2007/006757 KR2007006757W WO2009082043A1 WO 2009082043 A1 WO2009082043 A1 WO 2009082043A1 KR 2007006757 W KR2007006757 W KR 2007006757W WO 2009082043 A1 WO2009082043 A1 WO 2009082043A1
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formula
iridium complex
organic electroluminescent
electroluminescent device
group
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PCT/KR2007/006757
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English (en)
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Soo Young Park
Youngmin You
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Dongwoo Fine-Chem Co., Ltd.
Seoul National University Industry Foundation
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Priority to PCT/KR2007/006757 priority Critical patent/WO2009082043A1/fr
Publication of WO2009082043A1 publication Critical patent/WO2009082043A1/fr

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—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
    • 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
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • 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
    • 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
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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

Definitions

  • the present invention relates to an indium complex and an organic electroluminescent device using the same.
  • a liquid crystal display (LCD) that has been recently broadly used is a display device of a non-light emitting type.
  • the liquid crystal display has characteristics such as lightness and low power consumption.
  • a system for driving the LCD is complicate, and characteristics of a response time and contrast are not sufficient.
  • a light-emitting mechanism of the organic electroluminescent device is as follows. A hole injected into a valance band or a HOMO (Highest Occupied Molecular Orbital) of a hole injection layer (HIL) from an anode moves to an emission layer through a hole transporting layer (HTL).
  • HIL hole injection layer
  • the organic electroluminescent device is an active light-emitting disply device using the phenomenon that light is emitted with the exciton transition to a ground state in energy level.
  • the organic electroluminescent device has advantages such as lightness, simple constitutional elements, easy fabrication process, superior image quality, and wide viewing angle. A high color purity and a motion picture may be perfectly realized in the organic electroluminescent device. And, the organic electroluminescent device has an electric characteristic suitable for a portable electronic device because of a low power consumption and a low driving voltage.
  • Materials that may be used to from the emission layer in the organic electroluminescent device are classified into fluorescent materials using a singlet exciton and phosphorescent materials using a triplet exciton according to a light-emitting mechanism.
  • the emission layer may be formed of a fluorescent or phosphorescent material alone, or an appropriate host doped with the fluorescent or phosphorescent material.
  • Singlet excitons and triple excitons may be formed to the host during electronic excitation.
  • a statistical ratio of the single exciton to the triple exciton is 1 to 3.
  • internal quantum efficiency may be 100% when using the phosphorescent material as the material of the emission layer, since both singlet excitons and triplet excitons can be utilized. Thus, four-fold increase in energy and power efficiency may be achieved.
  • a process using a solution state is to be applied to the organic electroluminescent device by improving the solubility, it has long-term merits in terms of scale, structure, coating efficiency and economy through high-resolution printing methods, compared with those of a vapor deposition method used in a current process.
  • the process using the solution may be particularly helpful to a case where a conjugated polymer is used as a host of an emission layer. That is, if the solubility is improved, the efficiency of the device can be improved, the driving voltage can be lowered, and the life span can be increased by using the conjugated polymer.
  • the broadly known phosphorescent material having a complex of an organic metal compound may include an indium based organic metal compound.
  • derivatives of tris(phenylpyridine) complex are known.
  • the compounds reported until now include a phenylpyridine itself, or a phenylpyridine -substituted fluorine, methoxy or mimetic group or benzo-fused phenylpyridine as a ligand, excluding one exception.
  • These compounds have generally low solubility in the conventional solvents.
  • a patent to P.L.Burn et al. only discloses a dendrimer-mimitic derivative having a high solubility (Adv. Master. 2002,14, 975; Appl. Phys. Lett. 2002, 80, 2645).
  • the present invention has been made in an effort to provide an iridium complex and an organic electroluminescent device using the same having advantages of synthesizing a compound having a benzothiophenylpyridine structure by applying a silane providing heat stability through an easy synthetic pathway and improving a solubility in a solvent.
  • a process using a polymer solution may be possible due to the improved solubility, thereby providing an organic electroluminescent device having a high efficiency, a high color purity, and a low driving voltage.
  • the present invention has been made in an effort to provide a red phosphorescent dopant having a maximum light-emitting peak in a wavelength of 600 to 660nm.
  • the present invention provides an iridium complex represented by the following Formula 1 : [Chemical Formula 1 ]
  • R 2 , and R 3 are independently selected from a group consisting of C 1 to Qo aliphatic and aromatic hydrocarbons.
  • R 4 and R 5 are independently selected from a group consisting of hydrogen, a halogen, a cyano, a C 1 to C 20 alkyl, a Ci to C 20 alkoxy, a Ci to C 2 o alkylthio, a Ci to C 20 alkylamino, a Ci to C 2 o heteroalkyl, a Ci to C 20 alkenyl, a C 1 to C 2 o alkynyl, a C 6 to C 3 o aryl, a C 6 to C 3 o arylthio, a C 6 to C 30 aryloxy, a C 6 to C 3 o arylamino, a C 3 to C 3 o heteroaryl, a C 3 to C 30 heteroaryloxy, a C 3 to C 30 heteroarylthio, and a C 3 to C 3
  • Ar 1 is selected from a group consisting of substituted or unsubstituted C 6 to C 30 arylene, and substituted or unsubstituted C 3 to C 30 heteroarylene.
  • Ar 2 is selected from a group consisting of hydrogen, substituted or unsubstituted C 6 to C 30 aryl, and substituted or unsubstituted C 3 to C 30 heteroaryl.
  • X is selected from a group consisting of oxygen (O) and sulfer(S).
  • R 1 , R 2 , R 3 , R 4 , R 5 , Ar 1 and Ar 2 in the above Formula 1-1 are the same as R 1 , R 2 , R 3 , R 4 , R 5 , Ar 1 and Ar 2 in the above Formula 1 , respectively.
  • Ar 1 is selected from a group consisting of arylenes represented by the following Formulae.
  • Ar 2 is selected from a group consisting of hydrogen and (hetero)aryls represented by the following Formulae.
  • the iridium complex has a solubility of 30mg/mL or more in a solvent selected from a group of chlorobenzene, tetrahydrofuran, toluene, xylene, chloroform, and mesitylene at a room temperature.
  • the iridium complex has less than one or no luminescent spot having a maximum length of 20 ⁇ m in an area of 50OjMn X 500 ⁇ m when tested by the following Test Method.
  • a mixture containing 60 ⁇ mol of an iridium complex and Ig of poly-N-vinylcarbazole(PVK) was dissolved in chlorobenzene so that the concentration was 5%.
  • a film having a thickness of lOOnm was formed by spin-coating the chlorobenzene containing the iridium complex and the PVK onto a glass substrate. Then, the film was annealed at a temperature of 150 ° C for ten minutes. Then, the number of luminescent spots and a maximum length of luminescent spots in an area of 500 ⁇ m X 50OjMm were measured in a state excited by a mercury lamp (wavelength: 360 ⁇ 20nm, output: 1 OmW output).
  • the present invention provides an organic electroluminescent device including an anode, an emission layer, and a cathode, wherein the emission layer may include the above iridium complex.
  • the emission layer may have a maximum light-emitting peak in a wavelength of 630 to 660nm.
  • the emission layer may be formed by coating a solution.
  • the emission layer may further include a host.
  • the iridium complex may be included in an amount of 2 to 10 parts by weight based on 100 parts by weight of the host.
  • the host may include a conjugated polymer.
  • An iridium complex of the present invention is represented by the following Formula 1 :
  • Ri, R 2 , and R 3 are independently Ci to Ci 0 aliphatic or aromatic hydrocarbons.
  • R 1 , R 2 , and R 3 maybe a phenyl.
  • R 4 and R 5 are independently hydrogen, a halogen, a cyano, a Ci to C 20 alkyl, a Ci to C 20 alkoxy, a Ci to C 2 o alkylthio, a Ci to C 20 alkylamino, a Ci to C 20 heteroalkyl, a Ci to C 20 alkenyl, a Ci to C 20 alkynyl, a C 6 to C 30 aryl, a C 6 to C 30 arylthio, a C 6 to C 30 aryloxy, a
  • Ari is a substituted or an unsubstituted C 6 to C 3 o arylene, or a substituted or an unsubstituted C 3 to C 30 heteroarylene.
  • Ar 2 is hydrogen, a substituted or an unsubstituted C 6 to C 30 aryl, or a substituted or an unsubstituted C 3 to C 30 heteroaryl.
  • X is oxygen (O) or sulfer(S).
  • the substituent may be independently selected from a group consisting of a halogen (fluorine, chlorine, bromine, iodine), a nitro, a Ci to C 20 alkyl, a C 6 to C 2 o cycloalkyl, a Ci to C 2 o alkoxy, a cyano, and a trifluoromethyl.
  • a halogen fluorine, chlorine, bromine, iodine
  • a nitro a Ci to C 20 alkyl
  • a C 6 to C 2 o cycloalkyl a Ci to C 2 o alkoxy
  • a cyano a trifluoromethyl
  • the above Formula 1 is represented by the following Formulal-1. [Chemical Formula 1-1]
  • Ri, R 2 , R 3 , R 4 , R 5 , Ari and Ar 2 in the above Formula 1-1 are the same as Ri, R 2 , R 3 , R 4 , R 5 , Ar 1 and Ar 2 in the above Formula 1, respectively.
  • Ari is selected from the following Formulae 2 to 9.
  • Ar 2 is selected from the following Formulae 10 to 14.
  • Ar 2 may have a substituent at at least one position of hydrogen.
  • the substituent may be independently selected from a group consisting of a halogen (fluorine, chlorine, bromine, iodine), a nitro, a C 1 to C 20 alkyl, a C 6 to C 20 cycloalkyl, a C 1 to C 20 alkoxy, a cyano, and a trifluoromethyl.
  • a ligand having an organosilane-substituted benzothiophenylpyridine structure and represented by one of the following compounds 1 to 5 is preferable.
  • the iridium complex according to the present invention may be easily synthesized by the following Reaction Scheme 1.
  • the ligand is the above compound 1 as an example.
  • a person of an ordinary skill in the art can easily synthesize the iridium complex represented by the above Formula 1 though the Reaction Scheme 1 using the other compounds. A specific synthesizing method will be described later with reference to Examples.
  • the measured solubility of the iridium complex according to the present invention was 30mg/mL or more in one of chlorobenzene, tetrahydrofuran, toluene, xylene, chloroform, and mesitylene at a room temperature. That is, it can be seen that the solubility significantly increases.
  • the specific example will be described later in detail.
  • the solubility of the iridium complex according to the present invention is greatly increased by applying an arylsilyl, thereby forming a film by using a solution. Finally, a uniform light-emitting surface may be achieved.
  • the iridium complex of the present invention has less than one or no luminescent spot having a maximum length of 20 ⁇ m in an area of 500 ⁇ m X 500 ⁇ m.
  • a mixture containing 60 ⁇ mol of an iridium complex and Ig of poly-N-vinylcarbazole(PVK) was dissolved in chlorobenzene so that the concentration was 5%.
  • a film having a thickness of lOOnm was formed by spin-coating the chlorobenzene containing the iridium complex and the PVK onto a glass substrate. Here, the known spin-coating method was used. Then, the film was annealed at a temperature of 150 ° C for ten minutes. Then, the number of luminescent spots and a maximum length of luminescent spots in an area of 500 ⁇ m X 500/zm were measured in a state excited by a mercury lamp (wavelength: 360 ⁇ 20nm, output: 1OmW).
  • the present invention provides an organic electroluminescent device including a plurality of organic compound layers having an anode, an emission layer, and a cathode.
  • the iridium complex including the ligand having an organosilane-substituted benzothiophenylpyridine structure may be included in one or more of the plurality of organic compound layers.
  • FIG. 1 is a cross-sectional view of an exemplary embodiment of an organic electroluminescent device according to the present invention.
  • the organic electroluminescent device may include a substrate 1, an anode 2, a hole injection layer (HIL) 3, an emission layer 4, and an exciton inhibition layer 5, and a cathode 6.
  • HIL hole injection layer
  • a hole transporting layer (HTL) (not shown) may be further included between the hole injection layer (HIL) 3 and the emission layer 4, and an electron injection layer (EIL) (not shown) may be further included between the exciton inhibition layer 5 and the cathode 6.
  • HTL hole transporting layer
  • EIL electron injection layer
  • the anode 2 may be formed of a metal oxide or a metal nitride such as ITO(indium tin oxide), IZO(indium zinc oxide), tin oxide, zinc oxide, zinc aluminum oxide and titanium nitride; a metal such as gold, platinum, silver, copper, aluminum, nickel, cobalt, lead, molybdenum, tungsten, tantalum, niobium; an alloy including the above metal or an alloy including copper iodide; a conductive polymer such as polyaniline, polythiophene, polypyrrole, polyphenylenevinylene, poly(3-methylthiophene), and polyphenylenesulfide.
  • a metal oxide or a metal nitride such as ITO(indium tin oxide), IZO(indium zinc oxide), tin oxide, zinc oxide, zinc aluminum oxide and titanium nitride
  • a metal such as gold, platinum, silver, copper, aluminum, nickel, cobalt, lead, moly
  • the anode may be formed of only one type of material among the above materials, or may be formed of a mixture of the above materials.
  • the anode may be formed of a plurality of layers.
  • the plurality of layers has the same composition or compositions different from each other.
  • the hole injection layer (HIL) 3 of the present invention may be formed of a material known in the art.
  • the hole injection layer 3 may be formed of PEDOT/PSS or copper phthalocyanine(CuPc),
  • the emission layer 4 may be formed of the above iridium complex.
  • the iridium complex may be added to the emission layer 4 as a dopant.
  • a host may be CBP, TCB, dmCBP, Liq, TPBI, BaIq, BCP, or Alq3 represented by the following constitutional formulare.
  • the host may be deposited by a vacuum thermal evaporation method.
  • a conjugated polymer may be used as a host.
  • PVK poly-N-vinylcarbazole
  • the conjugated polymer is used as a host, a device having flexibility may be easily manufactured, and the durability and the light-emitting characteristic of the device are excellent.
  • the electron transporting layer cannot be formed when an electron transporting material is added to the emission layer 4. In this case, a structure of the device can be simplified.
  • the electron transporting material may be PBD((4-biphenyl) (4-t-butylphenyl)oxidiazole).
  • the emission layer 4 may be formed in a solution state, as stated, by not using a deposition method.
  • spin-coating, casting, micro-gravure coating, gravure coating, bar coating, roll coating, wire bar coating, deep coating, spray coating, screen printing, flexographic printing, offset printing or inkjet printing, nano imprinting methods may be applied. That is, all the known methods for forming a film may be applied to the present invention.
  • the concentration of the dopant is not limited to a specific value. However, considering luminous efficiency, 1 to 20 parts by weight of the dopant based on 100 parts by weight of the host is preferable. From experiments, it can be seen that 2 to 20 parts by weight of the dopant based on 100 parts by weight of the based is preferable. When the concentration of the dopant is below the above numerical value, the luminance is relatively low. When the concentration of the dopant exceeds the above numerical value, quantum efficiency is low.
  • an electron transporting material used to the electron transporting layer may include an aryl-substituted oxadiazole compound, an aryl-substituted triazole compound, an aryl-substituted phenanthroline compound, a benzonxazole compound, or a benzothiazole compound.
  • the electron transporting material may be l,3-bis(N,N-t-butyl-phenyl)-l,3,4-oxadiazole(OXD-7); 3- ⁇ henyl-4- (1 '-naphthyl)-5 -phenyl- 1 ,2,4-triazole(TAZ);
  • the electron transporting material may be (4-biphenyl)(4-t-butylphenyl)oxidiazole(PBD) and tris(8-hydroxyquinolinato)aluminum(III) Alq3.
  • the electron transparent material is preferably (4-biphenyl)(4-t-butylphenyl)oxidiazole(PBD).
  • the exciton inhibition layer 5 may be formed of the known materials in the art.
  • the exciton inhibatation layer may include 2,9-dimethyl-4,7-biphenyl- phenanthroline(basocuproine or BCP) or aluminum(III)-bis(2-methyl-8-hydroxyquinolinato)-4-phenylphenolate(BAlq).
  • BCP 2,9-dimethyl-4,7-biphenyl- phenanthroline
  • BAlq aluminum(III)-bis(2-methyl-8-hydroxyquinolinato)-4-phenylphenolate
  • the present invention is not limited thereto.
  • the exciton inhiation layer is not necessary. Thus, it is possible that the exciton inhibitation layer is not included in some embodiments.
  • the electron injection layer (EIL) and the cathode 6 may be formed of known materials in the art.
  • the electron injection layer may include LiF
  • the cathode 6 may include a metal having a low work function such as Al, Ca, Mg, and Ag.
  • the cathode 6 includes Al.
  • the present invention is not limited thereto.
  • the emission layer has a maximum light-emitting peak in a wavelength of 600 to 660nm.
  • the emission layer has a maximum light emitting peak in a range of 630 to 660nm, which corresponds to deep red emission.
  • the indium complex according to the present invention has an excellent solubility, a film can be formed by solution coating method when an organic electroluminescent device is manufactured.
  • the iridium complex has a maximum light-emitting peak in a wavelength of 600 to 660nm, and thus it can be used as an excellent red light emitting material.
  • the organic electroluminescent device having excellent efficiency, color purity, stability may be provided.
  • FIG. 1 is a view of an exemplary embodiment of an organic electroluminescent device according to the present invention.
  • FIG. 2 is a photography showing a light emitting uniformity of PVK spin-coated films doped with iridium complexes according to an example of the present invention and a comparative example.
  • FIG. 3 shows a PL spectrum and an EL spectrum of iridium complexes according to an example of the present invention and a comparative Example.
  • FIG. 4 is a color coordinate of the organic electroluminescent device according to Exemplary Embodiment of the present invention.
  • FIG. 5 is a graph showing luminance and quantum efficiency measured in the organic electroluminescent device according to Exemplary Embodiment of the present invention. [Best Mode]
  • the red precipitate was sequentially washed with water (10OmL), methanol (5OmL), and ether (5OmL), and purified by silica gel column (using CH 2 Cl 2 ). Then, a dark orange powder was obtained. Finally, the red phosphorescent material (0.13 Ig, 0.0790mmol) was obtained in 48% yield after recrystallization in toluene.
  • the solubility was measured as in Experimental Example 1, except that the following Iridium Complex 2 not having an arylsilyl was used instead of Iridium Complex 1 obtained by Synthesizing Example 4.
  • the solubility was 3.8mg/mL, which was significantly low, compared with that of Iridium Complex 1.
  • Iridium Complex 1 60 ⁇ mol
  • PVK Ig
  • the chlorobenzene containing Iridium Complex 1 and the PVK was spin-coated onto a glass substrate to form a film having a thickness of lOOnm.
  • Iridium Complex 1 was used instead of Iridium Complex 1 obtained by Synthesizing Example 4.
  • a photograph of the film according to Comparative Example 2 is shown in (b) of FIG. 2.
  • Iridium Complex 1 according to the present invention had superior solubility and compatibility with the conjugated polymer, thereby achieving a uniform coating.
  • a light-emitting surface was uniform, and luminescent spots did not exist or only one luminescent spot existed in the present invention.
  • a plurality of luminescent spots having a size of 20 ⁇ m existed in Iridium Complex 2 due to cohesion. It shows that the solubility can be improved and the light emitting uniformity can be increased through application of arylsilyl.
  • Synthesizing Example 4 was dissolved in toluene of an argon atmosphere so that the concentration was 10 ⁇ . The results are shown in FIG. 3 as color-unfilled circles.
  • Iridium Complex 1 obtained by Synthesizing Example 4 was doped in an amount of 7 parts by weight to PVK, and a film having a thickness of lOOnm was formed by using the PVK doped with Iridium Complex. Then, a PL spectrum was measured in the film. The result is shown in FIG. 3 as color-filled circles.
  • Iridium Complex 1 of the present invention can emit a deep red light by applying an arylsilyl, compared with Iridium Complex 2.
  • a spin coater manufactured by Kyowa Riken and an EL evaporation apparatus manufactured by VTS were used.
  • the methods for measuring characteristics of the organic electroluminescent device are as follows.
  • the changes of current density according to the changes of voltage in the organic electroluminescent devices were measured. .
  • the current flowing in a unit device was measured by an ampere-voltage meter (Kethely 273) in a state that the current density gradually increased from 0.1m A/cm to 140m A/cm .
  • the EL spectrum and the color coordinate of the organic electroluminescent device were measured by a luminance meter (PR650) in a state that the current density gradually increased from O.lmA/cm 2 to 140mA/cm 2 .
  • the efficiency was calculated by using the measured luminance and current density.
  • the mercury lamp (wavelength: 360 ⁇ 20nm, output: 1OmW) was used as a light source.
  • the PL spectrum was measured in a wavelength of 380nm to 750nm by using a fluorescence spectrophotometer manufactured by Varian (trade name: Cary Eclipse).
  • the quantum efficiency and the luminance of the organic electroluminescent device were measured while the current density was gradually increased from 0.1mA/cm to 140m A/cm 2 . The results were shown in FIG. 5.
  • the most excellent quantum efficiency was 2.7% when Indium Complex 1 was doped in an amount of 4 parts by weight, and the current density was 0.57 mA/cm 2 .
  • the luminance increased in proportion to the current density.
  • the luminance was most excellent when Indium Complex 1 was doped in an amount of 4 parts by weight and 7 parts by weight.
  • the most excellent luminance was 1018 cd/cm 2 when the current density was 132 mA/cm 2 .
  • the maximum peak was at the wavelength of 640nm, which corresponds to the deep red light emitting.
  • the shoulder peak was shown at the wavelength of 680nm.
  • the color coordinate of the organic electroluminescent device doped with Indium Complex 1 in an amount of 7 parts by weight was measured at the current density of 0.57mA/cm 2 by a luminance meter (PR650). The result is shown in FIG. 4. The color coordinate were (0.69, 0.30), thus providing the deep red light emitting.
  • An indium complex of the present invention has superior solubility, and thus a film can be formed by coating a solution containing the iridium complex.
  • the industry applicability is excellent, in terms of a manufacture method.
  • the iridium complex can be used as a material for an organic electroluminescent device because the iridium complex has excellent characteristics in efficiency, color purity, stability.

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Abstract

L'invention se rapporte à un complexe formé par l'iridium représenté par la formule 1 et qui a une meilleure solubilité. On peut donc former un film par enduction de solution contenant le complexe formé par l'iridium pour fabriquer un dispositif organique électroluminescent. Puisque le complexe formé par l'iridium a une valeur ELmax se situant dans une longueur d'onde de 600 à 660 nm, on peut l'utiliser comme matière pour fabriquer un excellent matériau émetteur de lumière rouge. Le dispositif organique électroluminescent présente une excellente efficacité, une excellente pureté des couleurs et une excellente stabilité notamment lorsqu'on utilise le complexe formé par l'iridium pour fabriquer un dopant phosphorescent rouge destiné à un polymère.
PCT/KR2007/006757 2007-12-21 2007-12-21 Complexe formé par l'iridium et dispositif organique électroluminescent WO2009082043A1 (fr)

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JP2003252888A (ja) * 2001-12-26 2003-09-10 Mitsubishi Chemicals Corp 有機イリジウム錯体およびこれを用いた有機電界発光素子
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WO2012098996A1 (fr) * 2011-01-17 2012-07-26 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique
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