WO2010093176A2 - Complexe d'iridium et diodes électroluminescentes organiques - Google Patents

Complexe d'iridium et diodes électroluminescentes organiques Download PDF

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WO2010093176A2
WO2010093176A2 PCT/KR2010/000855 KR2010000855W WO2010093176A2 WO 2010093176 A2 WO2010093176 A2 WO 2010093176A2 KR 2010000855 W KR2010000855 W KR 2010000855W WO 2010093176 A2 WO2010093176 A2 WO 2010093176A2
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iridium complex
ring
complex compound
iridium
substituent
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WO2010093176A3 (fr
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Ung-Chan Yoon
Eun-Ah Chae
Dae-Won Cho
Hea-Jung Park
Jung-Hei Choi
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Pusan National University Industry-University Cooperation Foundation
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    • 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
    • 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
    • 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
    • H05B33/26—Light sources with substantially two-dimensional radiating surfaces characterised by the composition or arrangement of the conductive material used as an electrode
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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

Definitions

  • the present invention relates to an iridium complex and an organic light-emitting diode (OLED) comprising the same, and more particularly, to an iridium complex having superior blue light- emitting property and improved phosphorescence quantum yield as compared to existing iridium complexes and an OLED comprising the same .
  • OLED organic light-emitting diode
  • OLED organic light-emitting diode
  • LCD liquid crystal displays
  • OLEDs provide a good viewing angle, consume less power and are capable of processing high-quality images because of remarkably improved response time. Thus, OLEDs are preferred as next-generation display devices.
  • Radiation emitted from an OLED may be either fluorescence or phosphorescence.
  • Fluorescence refers to an emission of light occurring when an- organic molecule in the singlet excited state relaxes to the singlet ground state
  • phosphorescence refers to an emission of light occurring when an organic molecule in the triplet excited state relaxes to the ground state.
  • An organic compound doped in the OLED is formed via carbon-carbon covalent bonding or covalent bonding between carbon and other atom. In the organic molecule, a pair of atomic orbitals is combined to form a bonding molecular orbital and an anti-bonding molecular orbital.
  • the band formed by interaction of a lot of bonding molecular orbitals is called the valence band, and the band formed by a lot of anti-bonding molecular orbitals is called the conduction band.
  • the highest energy level of the valence band is called the highest occupied molecular orbital (HOMO), and the lowest energy level of the conduction band is called the lowest unoccupied molecular orbital (LUMO) .
  • the energy difference between the HOMO and the LUMO is called the band gap.
  • An electron and a hole injected to the LUMO and the HOMO of the organic electroluminescent layer of the OLED respectively are recombined to form an exciton. The electrical energy of the exciton is converted into light.
  • the color of the light is determined by the band gap of the electroluminescent layer where the exciton is formed.
  • singlet excitons with a total spin 0 and triplet excitons with a total spin 1 are produced at a proportion of about 1:3.
  • the spin selection rule for electric dipole transition a transition from the excited state to the ground state accompanying a change in total spin is very difficult to occur. Since the organic molecule in the ground state is in the singlet state, the singlet exciton may be effectively transited and relaxed to the ground state while emitting fluorescence. However, the triplet exciton can not be effectively transited and relaxed to the ground state because the spin quantum number has to be changed.
  • the maximum internal quantum yield of an OLED is limited to ca . 25%. If the spin-orbital coupling can be enhanced significantly, a mixed state of singlet and triplet increases and the efficiency of intersystem crossing between singlet and triplet states increases greatly. As a result, the triplet exciton may efficiently relax to the singlet ground state while emitting phosphorescence. If all of the triplet excitons are able to be used to emit light, the internal quantum yield of the OLED can be improved to 100% in theory.
  • Phosphorescent OLEDs which are capable of improving the emission efficiency of the OLED remarkably were studied and developed by Professor S. R. Forrest at the Princeton University and Professor M. E. Thompson at the USC in 1999.
  • complexes of heavy atoms such as platinum (Pt) , iridium (Ir), europium (Eu) and terbium (Tb) have high efficiency of intersystem crossing and good phosphorescence efficiency.
  • Pt platinum
  • Ir iridium
  • Eu europium
  • Tb terbium
  • the triplet exciton having the lowest energy is the ligand-centered (LC) exciton and has a generally longer lifetime.
  • the triplet exciton having the lowest energy is the metal-to-ligand charge transfer (MLCT) state. Therefore, the iridium complex forms stronger spin-orbital coupling than the platinum complex and, thereby, exhibits high phosphorescence efficiency while having a much shorter triplet exciton lifespan.
  • MLCT metal-to-ligand charge transfer
  • a blue light-emitting phosphorescent material called FIrpic (iridium (III) bis[2,2',4'-difluorophenylpyridinato-N,C 2 ']picolinate) and a red light-emitting phosphorescent material called Ir(btp) 2 (acac) (iridium(III)bis(2-(2'-benzothienyl)pyridinato-
  • electroluminescent layer the electroluminescent materials
  • An object of the present invention is to provide a
  • Another object of the present invention is to provide an
  • electroluminescent material including the iridium complex.
  • Another object of the present invention is to provide an organic compound
  • OLED light-emitting diode
  • Another object of the present invention is to provide a display
  • the present invention provides an iridium complex represented by Chemical Formula I :
  • E 1 represents an aromatic or heteroaromatic ring, which may be further condensed with an aromatic or non-aromatic ring and have one or more substituent ( s ) , the ring E 1 optionally having one or more substituent ( s ) which may selectively form a condensation structure with a ring including E 2 and being coordinated by Ir metal by means of sp 2 -hybridized carbon;
  • E 2 represents a nitrogen-containing aromatic ring, which may be further condensed with an aromatic or non-aromatic ring, the ring E 2 optionally having one or more substituent (s ) which may selectively form a condensation structure with a ring including E 1 and being coordinated by Ir metal by means of sp 2 -hybridized nitrogen;
  • Ri and R 2 independently represent N, NR 4 or CR 4 ;
  • R 3 and R 4 independently represent the same or different electron- donating group selected from a group consisting of H, F, Cl, Br, straight or branched Ci_ 2 o alkyl, C 3-2O cyclic alkyl, straight or branched Ci- 20 alkoxy, straight or branched Ci -2O dialkylamino, C 4 - I4 aryl, C 4-14 heteroaryl, C 4 - I4 aryl with one or more subst ituent ( s ) , C 4-14 heteroaryl with one or more substituent ( s ) ; and n represents an integer 2.
  • present invention provides an electroluminescent material including
  • OLED organic light-emitting diode
  • the iridium complex according to the present invention has
  • electroluminescent material including the iridium complex may be any electroluminescent material including the iridium complex.
  • OLED organic light diode
  • Fig. 1 shows a cross-sectional view of a display device comprising the organic electroluminescent material of the present invention
  • Fig. 2 shows absorption and emission spectra of iridium complex 1
  • Fig. 3 shows absorption and emission spectra of iridium complex 2
  • Fig. 4 shows absorption and emission spectra of iridium complex 3
  • Fig. 5 shows absorption and emission spectra of iridium complex
  • Fig. 6 shows absorption and emission spectra of iridium complex 5
  • Fig. 7 shows absorption and emission spectra of iridium complex 6
  • Figs. 8 to 10 show absorption and emission spectra of iridium
  • Fig. 11 shows cyclic voltammograms of iridium complexes 1 to 6,
  • the present invention provides an iridium complex represented by
  • E 1 represents an aromatic or heteroaromatic ring, which may be further condensed with an aromatic or non-aromatic ring and have one or more substituent (s ) , the ring E 1 optionally having one or more substituent ( s ) which may selectively form a condensation structure with a ring including E 2 and being coordinated by Ir metal by means of sp 2 -hybridized carbon;
  • E 2 represents a nitrogen-containing aromatic ring, which may be further condensed with an aromatic or non-aromatic ring, the ring E 2 optionally having one or more substituent ( s ) which may selectively form a condensation structure with a ring including El and being coordinated by Ir metal by means of sp 2 -hybridized nitrogen;
  • R 1 and R 2 independently represent N, NR 4 or CR 4 ;
  • R 3 and R 4 independently represent the same or different electron- donating group selected from ' a group consisting of H, F, Cl, Br, straight or branched Ci -20 alkyl, C 3 - 2 o cyclic alkyl, straight or branched Ci_ 2 o alkoxy, straight or branched Ci -2O dialkylamino, C 4-I4 aryl, C 4 - I4 heteroaryl, C 4-I4 aryl with one or more subst ituent ( s ) , C 4-14 heteroaryl with one or more substituent (s) ; and n represents an integer 2.
  • the present invention also provides an electroluminescent
  • the present invention further provides an organic light-emitting
  • OLED organic light diode
  • the ligand is selected from
  • the phenylpyridine ligand is selected from the
  • the phenylpyridine ligand is selected from the followings :
  • R 1 may be NR 4
  • R 2 may be CH and n may be 2, or R 1 may be CH, R 2 may be NR 4 and n may be 2 to form an imidazole ligand. In case both R 1 and R 2 are CH, a pyrrole ligand is obtained .
  • the iridium complex may be selected from the f ol l owings :
  • an iridium complex having an imidazole derivative ligand exhibits better absorption and emission properties than one having a pyrrole derivative ligand.
  • the iridium complex having an imidazole derivative or a pyrrole derivative may be used as an electroluminescent material.
  • the iridium complex according to the present invention may be synthesized easily from a reaction of a ⁇ -chloro- bridged iridium dimer comprising two main phenyl pyridines ligands, and an ancillary ligand.
  • the iridium complex according to the present invention may be used as an electroluminescent material in an electroluminescent layer of an OLED. Also, the iridium complex according to the present invention may be used as a phosphorescent material to manufacture an OLED, and may be used as a phosphorescent dopant in a host layer under an appropriate condition. An appropriate host material is selected from those capable of electroluminescence when a voltage is applied to the device.
  • An OLED according to the present invention comprises, as illustrated in Fig. 1, a substrate 1; an anode 2; optionally a hole transport layer (HTL) 3; an electroluminescent layer (EML) 4 ; optionally a hole blocking layer (HBL) 5; an electron transport layer ( ETL ) 6 ; and a cathode 7 .
  • HTL hole transport layer
  • EML electroluminescent layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • the present invention further provides a display device comprising the OLED.
  • the main ligand, 2- ( 2 ' , 4 ' -difluorophenyl ) -4-methylpyridine (9) and 2-(2',4'-difluoro-3- ( trifluoromethyl ) phenyl) -4-methylpyridine (11) were prepared by using Suzuki coupling reaction.
  • the reaction mixture was stirred at room temperature.
  • the mixture was washed with 14% ammonia water (40 mL) and extracted three times with methylene chloride.
  • the organic layer was washed with water (40 mL ) and aqueous NaCl solution (40 mL), dried with anhydrous magnesium sulfate, and then concentrated.
  • the mixture was purified by column chromatography using ethyl acetate and hexane as eluent (yield: 25%) .
  • the cyclometalated iridium ( I II ) - ⁇ -chloro-bridged dimers (12, 13) were synthesized by refluxing IrCl 3 -IiH 2 O with the main ligand (9) and (11) in a 3:1 mixture of 2-ethoxyethanol and water according to the method reported by Nonoyama .
  • Synthesis of the iridium complexes (1 ⁇ 6) was performed by refluxing pyrrole-2-carboxylic acid, imidazole-2-carboxylic acid (8) or imidazole-5-carboxlic acid in 2-ethoxyethanol in the presence of cyclometalated iridium ( III ) - ⁇ -chloro-bridged dimer (12) or (13) .
  • UV absorption and emission properties of iridium ( III ) complex 3 and iridium ( III ) complex 6 were measured in methanol solution.
  • the film for emission property measurement was prepared by spin coating I l Il on a glass plate of the methanol or chloroform solution containing I l Il the iridium complex and polymethyl methacrylate (PMMA) .
  • the iridium(III) complexes showed strong absorption and emission properties.
  • the absorption spectrum exhibited absorption bands in the region between 350 and 470 nm.
  • the absorption spectrum in film state was similar to that in solution state or showed a very slight shift toward shorter wavelength by about 1-2 nm.
  • the material (Ir(tpy) 3 ) was used as reference for the measurement of phosphorescence quantum yield, and quantum yields ( ⁇ ) of iridium complexes 1-6 were obtained as shown in Table 1.
  • Table 1 The result is shown in Table 1.
  • MLCT a means the maximum UV absorption peak for transition to the singlet excited state
  • MLCT b means the maximum absorption peak for transition to the triplet excited state
  • ⁇ c means the quantum yield obtained with the phosphorescence iridium complex
  • ⁇ v (cm ) means the Stokes shift, i.e. the difference in frequency between the maximum absorption peak for transition to the triplet excited state and the maximum phosphorescence peak.
  • Example 7 Measurement of HOMO and LUMP energy level
  • Electrochemical property of an electrochemical cell comprising a platinum electrode (diameter: 2 mm), a platinum wire counter electrode and an Ag/AgCl reference electrode was measured using CHI600 (CH Instruments Inc., USA) .
  • CHI600 CH Instruments Inc., USA
  • electrolyte solution scan rate: 50 mVs "1 )
  • Fig. 11 shows the cyclic voltammograms of the iridium complexes of the present invention.
  • HOMO and LUMO measurement results for iridium complexes 1 to 6 are summarized in Table 2. As seen in Table 2,
  • the HOMO levels for iridium complexes 1 to 6 are -5.55 eV, -5.61 eV, -5.57 eV, -5.71 eV, -5.8 eV and -5.65 eV, respectively, and the
  • LUMO levels are -2.72 eV, -2.73 eV, -2.68 eV, -2.81 eV, -2.85 eV and
  • the iridium complexes of the present invention showed band gap of 2.83 ⁇ 2.98 eV.
  • iridium complexes 5 ⁇ 6 which contain a imidazole carboxylate as an ancillary ligand exhibit their emissions at shorter wavelength in the blue color region (5:458nm 6:459nm) in their film states comprising to ones in solution state.
  • electroluminescent layer of an OLED may be used in a display

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un complexe d'iridium de formule I. Le complexe d'iridium de formule I fournit des matériaux luminescents avec une propriété supérieure d'émission de lumière bleue et améliore nettement le rendement quantique comparé aux complexes d'iridium existants. Le matériau luminescent peut être utilisé dans une couche électroluminescente d'une diode électroluminescente organique et peut être utilisé dans un dispositif d'affichage.
PCT/KR2010/000855 2009-02-13 2010-02-11 Complexe d'iridium et diodes électroluminescentes organiques WO2010093176A2 (fr)

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WO2012142387A1 (fr) * 2011-04-14 2012-10-18 Arizona Board Of Regents Acting For And On Behalf Of Arizona State University Complexes d'iridium (iii) coordinés par pyridine-oxyphényle et procédés de préparation et d'utilisation
WO2014035210A2 (fr) * 2012-08-31 2014-03-06 삼성디스플레이 주식회사 Matériau électroluminescent organique et dispositif électroluminescent organique qui utilise ce dernier
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