US20160372688A1 - Iridium complex, light-emitting element, display device, electronic device, and lighting device - Google Patents

Iridium complex, light-emitting element, display device, electronic device, and lighting device Download PDF

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US20160372688A1
US20160372688A1 US15/181,605 US201615181605A US2016372688A1 US 20160372688 A1 US20160372688 A1 US 20160372688A1 US 201615181605 A US201615181605 A US 201615181605A US 2016372688 A1 US2016372688 A1 US 2016372688A1
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group
light
carbon atoms
organic compound
emitting element
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Satoshi Seo
Takeyoshi WATABE
Hideko Inoue
Yui Yamada
Satomi Mitsumori
Tatsuyoshi Takahashi
Tomoka HARA
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Semiconductor Energy Laboratory Co Ltd
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Semiconductor Energy Laboratory Co Ltd
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Assigned to SEMICONDUCTOR ENERGY LABORATORY CO., LTD. reassignment SEMICONDUCTOR ENERGY LABORATORY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HARA, TOMOKA, INOUE, HIDEKO, MITSUMORI, SATOMI, TAKAHASHI, Tatsuyoshi, WATABE, TAKEYOSHI, YAMADA, YUI, SEO, SATOSHI
Publication of US20160372688A1 publication Critical patent/US20160372688A1/en
Priority to US16/874,737 priority Critical patent/US20200350503A1/en
Priority to US17/875,925 priority patent/US20230105618A1/en
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    • 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
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • 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
    • H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/121—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements
    • H10K59/1213—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements the pixel elements being TFTs
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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    • 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
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    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H01L2251/552—
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
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    • H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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    • 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
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    • 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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the exciplex preferably has a function of transferring excitation energy to the iridium complex.
  • light emitted from the exciplex preferably has a region overlapping an absorption band on the lowest energy side of the iridium complex.
  • FIGS. 6A and 6B are each a schematic cross-sectional view of a light-emitting element of one embodiment of the present invention.
  • FIG. 46 is a graph showing external quantum efficiency-luminance characteristics of light-emitting elements in Example.
  • FIGS. 48A and 48B are graphs each showing electroluminescence spectra of light-emitting elements in Example.
  • FIG. 62 is a graph showing reliability test results of light-emitting elements in Example.
  • FIG. 85 is a graph showing current efficiency-luminance characteristics of light-emitting elements in Example.
  • Phosphorescence emission energy or a triplet excitation energy can be obtained from a wavelength of a phosphorescence emission peak (including a shoulder) on the shortest wavelength side of phosphorescence emission. Note that the phosphorescence emission can be observed by time-resolved photoluminescence in a low-temperature (e.g., 10 K) environment.
  • a thermally activated delayed fluorescence emission energy can be obtained from a wavelength of an emission peak (including a shoulder) on the shortest wavelength side of thermally activated delayed fluorescence.
  • the light-emitting element 150 includes a pair of electrodes (an electrode 101 and an electrode 102 ) and an EL layer 100 between the pair of electrodes.
  • the EL layer 100 includes at least a light-emitting layer 130 .
  • the HOMO level of the guest material 132 is lower than that of the organic compound 131 _ 2
  • the LUMO level of the guest material 132 is higher than that of the organic compound 131 _ 1 .
  • carriers (holes and electrons) injected from the pair of electrodes (the electrode 101 and the electrode 102 ) holes injected from the anode are easily injected to the organic compound 131 _ 2 and electrons injected from the cathode are easily injected to the organic compound 131 _ 1 in the light-emitting layer 130 .
  • Guest ( 132 ) the guest material 132 (the phosphorescent compound);
  • S PH the S1 level of the host material (the organic compound 131 _ 1 );
  • T PE the T1 level of the exciplex.
  • one of the organic compound 131 _ 1 and the organic compound 131 _ 2 accepts a hole (D + ) and the other accepts an electron (A ⁇ ), whereby the organic compound 131 _ 1 and the organic compound 131 _ 2 form an exciplex ((D ⁇ A)*).
  • a fullerene, a derivative thereof, an acridine derivative such as proflavine, eosin, and the like can be given.
  • a metal-containing porphyrin such as a porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), can be given.
  • a composite material in which an organic compound and an electron donor (donor) are mixed may also be used for the electron-injection layer 119 .
  • Such a composite material is excellent in an electron-injection property and an electron-transport property because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the generated electrons.
  • the above-listed substances for forming the electron-transport layer 118 e.g., the metal complexes and heteroaromatic compounds
  • the electron donor a substance showing an electron-donating property with respect to the organic compound may be used.
  • a compound of one embodiment of the present invention is an iridium complex including, as a ligand, a nitrogen-containing five-membered heterocyclic skeleton to which an aryl group including a cyano group is bonded.
  • the ligand can be easily synthesized with high purity, so that deterioration due to impurities can be suppressed.
  • the number of carbon atoms of the aryl group including a cyano group and being bonded to the nitrogen-containing five-membered heterocyclic skeleton is preferably 6 to 13 in terms of stability and reliability of the element characteristics.
  • the iridium complex can be vacuum-evaporated at a relatively low temperature, and accordingly is unlikely to deteriorate due to pyrolysis or the like at evaporation.
  • Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • the aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group.
  • the aryl group has a substituent, as the substituent, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms can also be selected.
  • the aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group.
  • the aryl group may have a substituent, and substituents of the aryl group may be bonded to form a ring.
  • substituents of the aryl group may be bonded to form a ring.
  • an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms can also be selected.
  • Each of R 1 to R 4 independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
  • alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
  • cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group.
  • alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
  • cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group.
  • the iridium complex described in Embodiment 2 has a function of converting triplet excitation energy into light emission. For this reason, the iridium complex can emit light with energy smaller than the energy difference between the LUMO level and the HOMO level. Accordingly, even in the case where the energy difference between the LUMO level and the HOMO level of the iridium complex is larger than the energy difference between the LUMO level of the organic compound 141 _ 1 and the HOMO level of the organic compound 141 _ 2 , as long as light emission energy or absorption energy of the iridium complex is smaller than an energy difference between the LUMO level of the organic compound 141 _ 1 and the HOMO level of the organic compound 141 _ 2 , excitation energy transfer from an exciplex formed by the organic compound 141 _ 1 and the organic compound 141 _ 2 to the iridium complex is possible and light emission can be obtained from the iridium complex.
  • a silicon oxynitride film refers to a film in which the proportion of oxygen is higher than that of nitrogen.
  • the silicon oxynitride film preferably contains oxygen, nitrogen, silicon, and hydrogen in the ranges of 55 atomic % to 65 atomic %, 1 atomic % to 20 atomic %, 25 atomic % to 35 atomic %, and 0.1 atomic % to 10 atomic %, respectively.
  • a silicon nitride oxide film refers to a film in which the proportion of nitrogen is higher than that of oxygen.
  • optical element 224 B and the optical element 224 G may overlap with each other in a region where they overlap with the light-blocking layer 223 .
  • optical element 224 G and the optical element 224 R may overlap with each other in a region where they overlap with the light-blocking layer 223 .
  • optical element 224 R and the optical element 224 B may overlap with each other in a region where they overlap with the light-blocking layer 223 .
  • the electrode 102 can be formed by stacking a reflective conductive film and a light-transmitting conductive film.
  • the electrode 102 may have a single-layer structure or a stacked-layer structure.
  • FIG. 12A illustrates the structure provided with the light-emitting elements and the coloring layers for the light-emitting elements as an example; however, the structure is not limited thereto.
  • a structure including the red coloring layer 1034 R and the blue coloring layer 1034 B but not including a green coloring layer may be employed to achieve full color display with the three colors of red, green, and blue.
  • the structure as illustrated in FIG. 12A where the light-emitting elements are provided with the coloring layers is effective to suppress reflection of external light.
  • the structure as illustrated in FIG. 12B where the light-emitting elements are provided with the red coloring layer and the blue coloring layer and without the green coloring layer is effective to reduce power consumption because of small energy loss of light emitted from the green light-emitting element.
  • a light-emitting element including the lower electrode 1024 Y preferably has a microcavity structure between the lower electrode and the upper electrode 1026 and the lower electrodes 1024 R, 1024 G, 1024 B, and 1024 Y as in the display device illustrated in FIG. 12A .
  • sealing can be performed with the sealing substrate 1031 on which the coloring layers (the red coloring layer 1034 R, the green coloring layer 1034 G, the blue coloring layer 1034 B, and the yellow coloring layer 1034 Y) are provided.
  • the sealing layer 1029 may have a single-layer or two-layer structure, or four or more sealing layers may be formed as the sealing layer 1029 .
  • the sealing layer has a multilayer structure, the impurities such as water can be effectively prevented from entering the inside of the display device from the outside of the display device.
  • a resin and an organic material are preferably stacked.
  • the shapes of the electrodes 2591 and the electrodes 2592 are not limited thereto and can be any of a variety of shapes.
  • a structure may be employed in which the plurality of electrodes 2591 are arranged so that gaps between the electrodes 2591 are reduced as much as possible, and the electrodes 2592 are spaced apart from the electrodes 2591 with an insulating layer interposed therebetween to have regions not overlapping with the electrodes 2591 .
  • the light-emitting device 3000 has a double sealing structure in which the light-emitting element 3005 is surrounded by the first sealing region 3007 and the second sealing region 3009 .
  • the double sealing structure With the double sealing structure, entry of impurities (e.g., water, oxygen, and the like) from the outside into the light-emitting element 3005 can be favorably suppressed.
  • impurities e.g., water, oxygen, and the like
  • only the first sealing region 3007 may be provided.
  • An electronic device or a lighting device that has a light-emitting region with a curved surface can be obtained with the use of the light-emitting element of one embodiment of the present invention which is manufactured over a substrate having flexibility.
  • Step 1 The obtained white solid was identified as N-4-cyanobenzoyl-N′-2-methylbenzoylhydrazide by nuclear magnetic resonance (NMR) spectroscopy.
  • NMR nuclear magnetic resonance

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US15/181,605 2015-06-17 2016-06-14 Iridium complex, light-emitting element, display device, electronic device, and lighting device Abandoned US20160372688A1 (en)

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US16/874,737 US20200350503A1 (en) 2015-06-17 2020-05-15 Iridium complex, light-emitting element, display device, electronic device, and lighting device
US17/875,925 US20230105618A1 (en) 2015-06-17 2022-07-28 Iridium complex, light-emitting element, display device, electronic device, and lighting device

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JP2016-051311 2016-03-15
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US20180062084A1 (en) * 2016-08-29 2018-03-01 Semiconductor Energy Laboratory Co., Ltd. Light-Emitting Element, Light-Emitting Device, Electronic Device, Lighting Device, and Organometallic Complex
US20190013490A1 (en) * 2016-11-16 2019-01-10 Lg Chem, Ltd. Organic light emitting device
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US10212512B2 (en) 2016-02-22 2019-02-19 Sonos, Inc. Default playback devices
US10224494B2 (en) 2015-08-07 2019-03-05 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
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