WO2022053905A1 - 有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置 - Google Patents

有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置 Download PDF

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WO2022053905A1
WO2022053905A1 PCT/IB2021/057893 IB2021057893W WO2022053905A1 WO 2022053905 A1 WO2022053905 A1 WO 2022053905A1 IB 2021057893 W IB2021057893 W IB 2021057893W WO 2022053905 A1 WO2022053905 A1 WO 2022053905A1
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group
carbon atoms
light emitting
emitting device
layer
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English (en)
French (fr)
Japanese (ja)
Inventor
吉安唯
高畑正利
吉住英子
河野優太
渡部剛吉
瀬尾哲史
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Semiconductor Energy Laboratory Co Ltd
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Semiconductor Energy Laboratory Co Ltd
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Priority to US18/025,112 priority Critical patent/US20230329083A1/en
Priority to CN202180062115.1A priority patent/CN116057148A/zh
Priority to KR1020237007235A priority patent/KR20230065246A/ko
Priority to JP2022548257A priority patent/JPWO2022053905A1/ja
Publication of WO2022053905A1 publication Critical patent/WO2022053905A1/ja
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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
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • 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
    • C07F15/0046—Ruthenium compounds
    • 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
    • C07F15/0086—Platinum 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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
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    • 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
    • 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

  • One aspect of the invention relates to organometallic complexes.
  • it relates to an organometallic complex capable of converting energy in a triplet excited state into light emission.
  • the present invention also relates to a light emitting device, a light emitting device, an electronic device, and a lighting device using an organometallic complex.
  • one aspect of the present invention is not limited to the above technical fields.
  • the technical field of one aspect of the invention disclosed in the present specification and the like relates to a product, a method, or a manufacturing method.
  • one aspect of the invention relates to a process, machine, manufacture, or composition (composition of matter).
  • the technical field of one aspect of the present invention disclosed in the present specification is a semiconductor device, a display device, a liquid crystal display device, a power storage device, a storage device, a method for driving them, or a method thereof.
  • the manufacturing method thereof can be given as an example.
  • a light emitting device also called an organic EL element having an organic compound which is a light emitting substance between a pair of electrodes has characteristics such as thinness and light weight, high speed response, and low voltage drive. Therefore, a display to which these are applied is the next generation. It is attracting attention as a flat panel display.
  • the light emitting device When a voltage is applied, the light emitting device recombines electrons and holes injected from the electrode, whereby the luminescent substance becomes an excited state, and when the excited state returns to the ground state, it emits light.
  • S * : T * 1: 3.
  • a compound capable of converting energy in a singlet excited state into light emission is called a fluorescent compound (fluorescent material), and it is possible to convert energy in a triplet excited state into light emission.
  • fluorescent compound fluorescent material
  • Compounds are called phosphorescent compounds (phosphorescent materials).
  • the theoretical limit of the internal quantum efficiency (ratio of photons generated to the injected carriers) in the light emitting device using each of the above luminescent substances is the case where a fluorescent material is used. Is 25%, and 100% when a phosphorescent material is used.
  • a light emitting device using a phosphorescent material can obtain higher efficiency than a light emitting device using a fluorescent material. Therefore, in recent years, various types of phosphorescent materials have been actively developed.
  • an organic metal complex having iridium or the like as a central metal has attracted attention because of its high phosphorescence quantum yield (for example, Patent Document 1).
  • a novel organometallic complex is provided. Further, in another aspect of the present invention, a novel organometallic complex exhibiting good red emission is provided. Further, in another aspect of the present invention, a novel organometallic complex having an emission spectrum having a narrow half-value width is provided. Further, in one aspect of the present invention, a novel light emitting device having a good life is provided. Further, in another aspect of the present invention, a novel organometallic complex exhibiting red emission with high quantum efficiency is provided. Further, in another aspect of the present invention, a novel organometallic complex that can be used for the EL layer of a light emitting device is provided.
  • a novel organometallic complex capable of providing a light emitting device having high luminous efficiency is provided.
  • a novel organometallic complex capable of providing a highly reliable light emitting device is provided.
  • a light emitting device having high luminous efficiency is provided.
  • a highly reliable light emitting device is provided.
  • a new light emitting device, a new electronic device, or a new lighting device is provided.
  • One embodiment of the present invention has a ligand containing a pyrazine skeleton, in which iridium and nitrogen at the 1-position of the pyrazine skeleton are bonded, and the 3-position and 6-position of the pyrazine skeleton are independently hydrogen, an alkyl group, or an alkyl group, respectively.
  • the 5-position of the pyrazine skeleton having any one of the alkoxy groups is bonded to an aryl group having a cyano group as a substituent, and the 2-position of the pyrazine skeleton is bonded to an aromatic hydrocarbon group to form an aromatic hydrocarbon group.
  • It is an organic metal complex containing a structure represented by the following general formula (G1) in which a part of carbon contained in the above is bonded to iridium.
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • Another aspect of the present invention is an organometallic complex containing a structure represented by the following general formula (G2).
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • Another aspect of the present invention is an organometallic complex having a structure represented by the following general formula (G3).
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • L represents a monoanionic ligand.
  • Another aspect of the present invention is an organometallic complex having a structure represented by the following general formula (G4).
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • L represents a monoanionic ligand.
  • the monoanionic ligand is a monoanionic bidentate chelate ligand having a ⁇ -diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a phenolic ligand.
  • the monoanionic ligand is preferably any one of the following general formulas (L1) to (L6).
  • R 71 to R 94 are independently hydrogen or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, halogen group, vinyl group, substituted or unsubstituted.
  • a 1 to A 3 independently represent sp 2 mixed carbon that bonds with nitrogen or hydrogen, or sp 2 mixed carbon having a substituent, and the substituent is an alkyl group or a halogen group having 1 to 10 carbon atoms.
  • the substituent is an alkyl group or a halogen group having 1 to 10 carbon atoms.
  • B 1 to B 8 are sp 2 mixed carbons independently bonded to nitrogen or hydrogen, or sp 2 mixed having a substituent. It represents carbon, and the substituent represents any one of an alkyl group having 1 to 10 carbon atoms, a halogen group, a haloalkyl group having 1 to 10 carbon atoms, and a phenyl group.
  • organometallic complex represented by the following general formula (G5).
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted, an aryl group having 6 to 13 carbon atoms substituted or unsubstituted, and a substituted or unsubstituted carbon number. It represents any of 3 to 12 heteroaryl groups and cyano groups, and at least one represents a cyano group.
  • R 71 to R 73 are independently hydrogen or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, halogen group, vinyl group, substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms, substituted or substituted. It represents any one of an unsubstituted alkoxy group having 1 to 10 carbon atoms and a substituted or unsubstituted alkylthio group having 1 to 10 carbon atoms.
  • organometallic complex represented by the following general formula (G6).
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 and R 5 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 13 substituted or unsubstituted carbon atoms, and a hetero with 3 to 12 substituted or unsubstituted carbon atoms. It represents either an aryl group or a cyano group, with at least one representing a cyano group.
  • R 71 to R 73 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a halogen group, a vinyl group, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a carbon number of carbon atoms. Represents any one of 1-10 alkylthio groups.
  • Another aspect of the present invention is an organometallic complex represented by the following general formula (G7).
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 13 substituted or unsubstituted carbon atoms, and a hetero with 3 to 12 substituted or unsubstituted carbon atoms. It represents either an aryl group or a cyano group, and at least one represents a cyano group.
  • organometallic complex represented by the following general formula (G8).
  • R 1 and R 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 and R 5 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 13 substituted or unsubstituted carbon atoms, and a hetero with 3 to 12 substituted or unsubstituted carbon atoms. It represents either an aryl group or a cyano group, and at least one represents a cyano group.
  • organometallic complex represented by the structural formula (100) or the structural formula (101).
  • another aspect of the present invention is a light emitting device using at least one of the above organometallic complexes.
  • the light emitting device according to one aspect of the present invention has an EL layer between a pair of electrodes, and the EL layer has at least one of the above-mentioned organometallic complexes.
  • the EL layer has a light emitting layer, and the light emitting layer has at least one of the above-mentioned organometallic complexes.
  • another aspect of the present invention is a light emitting device having the above-mentioned light emitting device and a transistor or a substrate.
  • another aspect of the present invention is an electronic device having the above-mentioned light emitting device, a microphone, a camera, an operation button, an external connection portion, or a speaker.
  • another aspect of the present invention is an electronic device having the above-mentioned light emitting device and a housing or a touch sensor function.
  • another aspect of the present invention is a lighting device having the above-mentioned light emitting device and a housing, a cover, or a support base.
  • a novel organometallic complex can be provided. Further, in another aspect of the present invention, it is possible to provide a novel organometallic complex exhibiting good red emission. Further, in another aspect of the present invention, it is possible to provide a novel organometallic complex having an emission spectrum having a narrow half width. Further, in one aspect of the present invention, it is possible to provide a novel light emitting device having a good life. Further, in another aspect of the present invention, it is possible to provide a novel organometallic complex exhibiting red emission with high quantum efficiency. Further, in another aspect of the present invention, it is possible to provide a novel organometallic complex that can be used for the EL layer of the light emitting device.
  • a novel organometallic complex capable of providing a light emitting device having high luminous efficiency. Further, in another aspect of the present invention, it is possible to provide a novel organometallic complex which can provide a highly reliable light emitting device. Further, in another aspect of the present invention, it is possible to provide a light emitting device having high luminous efficiency. Further, in another aspect of the present invention, it is possible to provide a highly reliable light emitting device. Further, in another aspect of the present invention, a new light emitting device, a new electronic device, or a new lighting device can be provided.
  • FIG. 1A, 1B and 1C are schematic views of the light emitting device.
  • 2A and 2B are conceptual diagrams of an active matrix type light emitting device.
  • 3A and 3B are conceptual diagrams of an active matrix type light emitting device.
  • FIG. 4 is a conceptual diagram of an active matrix type light emitting device.
  • 5A and 5B are conceptual diagrams of a passive matrix type light emitting device.
  • 6A and 6B are diagrams showing a lighting device.
  • 7A, 7B1, 7B2 and 7C are diagrams representing electronic devices.
  • 8A, 8B and 8C are diagrams representing electronic devices.
  • FIG. 9 is a diagram showing a lighting device.
  • FIG. 10 is a diagram showing a lighting device.
  • FIG. 11 is a diagram showing an in-vehicle display device and a lighting device.
  • FIG. 12A and 12B are diagrams showing electronic devices.
  • 13A, 13B and 13C are diagrams representing electronic devices.
  • FIG. 14 is a 1H NMR chart of [Ir (dmmppr-mCP) 2 (debm)].
  • FIG. 15 is an absorption spectrum and an emission spectrum in a solution state of [Ir (dmmppr-mCP) 2 (debm)].
  • FIG. 16 is a 1H NMR chart of [Ir (tBummppr-mCP) 2 (debm)].
  • FIG. 17 is an absorption spectrum and an emission spectrum of [Ir (tBummppr-mCP) 2 (debm)] in a solution state.
  • FIG. 18 is a diagram illustrating a light emitting device.
  • FIG. 18 is a diagram illustrating a light emitting device.
  • FIG. 19 is a diagram showing current density-luminance characteristics of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 20 is a diagram showing voltage-luminance characteristics of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 21 is a diagram showing the luminance-current efficiency characteristics of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 22 is a diagram showing voltage-current characteristics of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 23 is a diagram showing emission spectra of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 24 is a diagram showing the reliability of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4.
  • FIG. 25 is a diagram showing the current density-luminance characteristic of the light emitting device 5.
  • FIG. 26 is a diagram showing voltage-luminance characteristics of the light emitting device 5.
  • FIG. 27 is a diagram showing the luminance-current efficiency characteristics of the light emitting device 5.
  • FIG. 28 is a diagram showing voltage-current characteristics of the light emitting device 5.
  • FIG. 29 is a diagram showing an emission spectrum of the emission device 5.
  • FIG. 30 is a diagram showing the reliability of the light emitting device 5.
  • membrane and the word “layer” can be interchanged with each other in some cases or depending on the situation. For example, it may be possible to change the term “conductive layer” to the term “conductive layer”. Alternatively, for example, it may be possible to change the term “insulating film” to the term “insulating layer”.
  • the organic metal complex shown in the present embodiment has a central metal, iridium, and a ligand containing a pyrazine skeleton, and iridium and nitrogen at the 1-position of the pyrazine skeleton are bound to each other, and the 3- and 6-positions of the pyrazine skeleton are bonded.
  • each independently has one of hydrogen, an alkyl group, or an alkoxy group
  • the 5-position of the pyrazine skeleton is bonded to an aryl group having a cyano group as a substituent
  • the 2-position of the pyrazine skeleton is aromatic carbonation.
  • the organic metal complex shown in the present embodiment has a first ligand and a second ligand that bind to iridium, which is a central metal, and the first ligand is pyrazine. It contains a skeleton, iridium and nitrogen at the 1-position of the pyrazine skeleton are bonded, and the 3- and 6-positions of the pyrazine skeleton each independently have one of hydrogen, an alkyl group, or an alkoxy group, and 5 of the pyrazine skeleton.
  • the position is bonded to an aryl group having a cyano group as a substituent, the 2-position of the pyrazine skeleton is bonded to an aromatic hydrocarbon group, and a part of the carbon of the aromatic hydrocarbon group is bonded to iridium.
  • the ligand of is an organic metal complex which is a monoanionic ligand.
  • a monoanionic bidentate chelate ligand having a ⁇ -diketone structure a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanion having a phenolic hydroxyland are used.
  • any one of a hydrogen, an alkyl group, or an alkoxy group is independently bonded to the 3-position and the 6-position of the pyrazine skeleton, and the complex is substituted with the 5-position of the pyrazine skeleton.
  • An aryl group having a cyano group as a group is bonded.
  • any one of a hydrogen, an alkyl group, or an alkoxy group is independently provided as a substituent at the 3-position and the 6-position of the pyrazine skeleton.
  • An aryl group is provided at at least one of the 3-position and 6-position of the pyrazine skeleton by independently providing any one of a hydrogen, an alkyl group, or an alkoxy group as a substituent at the 3-position and the 6-position of the pyrazine skeleton.
  • the emission wavelength is shifted by a shorter wavelength. Therefore, the light emission on the long wavelength side having poor visibility is reduced, and the current efficiency can be improved.
  • the sublimation temperature is lower than when the pyrazine skeleton has an aryl group at at least one of the 3-position and the 6-position.
  • any one of a hydrogen, an alkyl group, or an alkoxy group is independently bonded to the 3-position and the 6-position of the pyrazine skeleton, and further, the 5-position of the pyrazine skeleton is further bonded. It is characterized in that the aryl group bonded to has a cyano group as a substituent.
  • the organometallic complex shown in this embodiment is an organometallic complex containing a structure represented by the following general formula (G1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • the organometallic complex shown in this embodiment is an organometallic complex containing a structure represented by the following general formula (G2).
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • the organometallic complex shown in this embodiment is an organometallic complex having a structure represented by the following general formula (G3).
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • L represents a monoanionic ligand.
  • the organometallic complex shown in this embodiment is an organometallic complex having a structure represented by the following general formula (G4).
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • L represents a monoanionic ligand.
  • the monoanionic ligand in each of the above configurations includes a monoanionic bidentate chelate ligand having a ⁇ -diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a phenolic ligand.
  • examples of the monoanionic ligand include any of the following general formulas (L1) to (L6).
  • R 71 to R 94 are independently hydrogen or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, halogen group, vinyl group, substituted or unsubstituted, respectively. It represents a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms substituted or unsubstituted, or an alkylthio group having 1 to 10 carbon atoms substituted or unsubstituted.
  • a 1 to A 3 represent sp 2 mixed carbons independently bonded to nitrogen or hydrogen, or sp 2 mixed carbons having a substituent, and the substituents are alkyl groups and halogen groups having 1 to 6 carbon atoms.
  • B1 to B8 represent sp2 mixed carbons independently bonded to nitrogen or hydrogen, or sp2 mixed carbons having a substituent.
  • the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, and a phenyl group.
  • organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G5).
  • R 1 and R 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 13 substituted or unsubstituted carbon atoms, and a hetero with 3 to 12 substituted or unsubstituted carbon atoms. It represents either an aryl group or a cyano group, and at least one represents a cyano group.
  • R 71 to R 73 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a halogen group, a vinyl group, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a carbon number of carbon atoms. Represents any one of 1-10 alkylthio groups.
  • organometallic complex shown in the present embodiment is an organometallic complex represented by the following general formula (G6).
  • R 1 and R 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 and R 5 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. It represents either a group or a cyano group, and at least one represents a cyano group.
  • R 71 to R 73 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a halogen group, a vinyl group, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. Represents any one of 1-10 alkylthio groups.
  • organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G7).
  • R 1 and R 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 to R 6 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted, an aryl group having 6 to 13 carbon atoms substituted or unsubstituted, and 3 substituted or unsubstituted carbon atoms. It represents any of ⁇ 12 heteroaryl groups and cyano groups, and at least one represents a cyano group.
  • organometallic complex shown in the present embodiment is an organometallic complex represented by the following general formula (G8).
  • R 1 and R 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • R 3 and R 5 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a halogen group, or Represents any one of the trifluoromethyl groups.
  • R 7 to R 11 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted, an aryl group having 6 to 13 carbon atoms substituted or unsubstituted, and 3 substituted or unsubstituted carbon atoms.
  • a substituted or unsubstituted aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms serves as a substituent.
  • the substituent has 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group and a hexyl group.
  • alkyl group or a cycloalkyl group having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 1-norbornyl group and a 2-norbornyl group, or a cycloalkyl group having 6 carbon atoms such as a phenyl group and a biphenyl group. Included are ⁇ 12 aryl groups.
  • alkyl group having 1 to 6 carbon atoms in any of R 1 to R 11 in the above general formulas (G1) to (G8) include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • alkyl group having 1 to 10 carbon atoms in any of R 71 to R 73 in the general formulas (G5) to (G6) include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.
  • Se-butyl group isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl Group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-propylbutyl group, 1-propylpentyl group, 1-butyl Examples thereof include a pentyl group and a trifluoromethyl group.
  • aryl group having 6 to 13 carbon atoms in any of R 3 to R 11 in the general formulas (G2), (G4), and (G5) to (G8) include a phenyl group and a tolyl group.
  • the above-mentioned substituents may be bonded to each other to form a ring.
  • the carbon at the 9-position of the fluorenyl group has two phenyl groups as substituents, and the phenyl group is used. Examples thereof include the case where a spirofluorene skeleton is formed by binding the groups to each other.
  • heteroaryl group having 3 to 12 carbon atoms in any of R 7 to R 11 in the above general formulas (G5) to (G8) include an imidazolyl group, a pyrazolyl group, a pyridyl group, and a pyridadyl group. Examples thereof include a triazil group, a benzoimidazolyl group, a quinolyl group and the like.
  • the alkylthio group having 1 to 10 carbon atoms a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, n.
  • -Pentyroxy group isopentyroxy group, sec-pentyroxy group, tert-pentyroxy group, neopentyroxy group, n-hexyloxy group, isohexyloxy group, sec-hexyloxy group, tert-hexyloxy group, neohexyloxy group, cyclohexyloxy group, 3 -Methylpentyloxy group, 2-methylpentyloxy group, 2-ethylbutoxy group, 1,2-dimethylbutoxy group, 2,3-dimethylbutoxy group, 1-propylbutyl group, 1-propylpentyl group, 1-butyl Examples thereof include a pentyl group, a cyano group, a fluorine, a chlorine, a bromine, an iodine and a trifluoromethyl group.
  • a cyano group at least one of the substituents of the aryl group bonded to the 5-position of the pyrazine skeleton.
  • the organometallic complexes represented by the general formulas (G5) to (G8) it is preferable that at least one of R 7 to R 11 has a cyano group.
  • any one of a hydrogen, an alkyl group, or an alkoxy group is independently provided as a substituent at the 3-position and the 6-position of the pyrazine skeleton.
  • an aryl group is provided at at least one of the 3-position and the 6-position of the pyrazine skeleton.
  • the emission wavelength is shifted to the short wavelength side as compared with the case of providing. Therefore, the light emission on the long wavelength side having poor visibility is reduced, and the current efficiency can be improved.
  • the sublimation temperature is lower than when the pyrazine skeleton has an aryl group at at least one of the 3-position and the 6-position.
  • the organic metal complex according to one aspect of the present invention is independently one of hydrogen, an alkyl group, or an alkoxy group at the 3-position and the 6-position of the pyrazine skeleton in the general formulas (G1) to (G8), respectively.
  • the aryl group bonded to the 5-position of the pyrazine skeleton may have an alkyl group as well as a cyano group. Therefore, in the above general formulas (G5) to (G8), at least one of R 7 to R 11 may be an alkyl group having 1 to 6 carbon atoms. In particular, when at least one of R 7 or R 11 is an alkyl group having 1 to 6 carbon atoms, the peak of the emission spectrum can be prevented from shifting to the long wavelength side, and the visibility can be maintained. That is, in the organometallic complex which is one aspect of the present invention, a deep red color having high color purity and high efficiency can be obtained.
  • the organometallic complex represented by the structural formulas (100) to (137) is a novel substance capable of emitting phosphorescence. These substances may have geometric isomers and steric isomers depending on the type of ligand, but the organic metal complex according to one aspect of the present invention also includes all of these isomers.
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • the pyrazine derivative represented by the general formula (G0) is an intermediate (A-2) by coupling the pyrazine compound (A-1) and the boronic acid (A-2) as shown in the synthetic scheme (A).
  • A-3) can be obtained.
  • the derivative (G0) can be obtained by coupling the intermediate (A-3) and the boronic acid (A-4).
  • a boronic acid ester, a cyclic triol borate salt or the like may be used.
  • X represents a halogen or triflate
  • A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • the organic metal complex according to one aspect of the present invention is characterized by having abundant variations in its ligand.
  • the organic metal complex which is one aspect of the present invention represented by the general formula (G3) contains a pyrazine derivative represented by the general formula (G0) and a halogen as shown in the following synthesis scheme (B-1).
  • No solvent with iridium compound iridium chloride, iridium bromide, iridium iodide, etc.
  • alcohol-based solvent glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol, etc. alone, or one or more alcohol-based solvents.
  • a dinuclear complex (B) which is a kind of organic metal complex having a halogen-crosslinked structure and is a novel substance, can be obtained.
  • the heating means is not particularly limited, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as a heating means.
  • X represents a halogen and A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • the dinuclear complex (B) obtained by the above synthesis scheme (B-1) and the raw material HL of the monoanionic ligand are combined with an inert gas.
  • L formed by desorbing the proton of HL is coordinated to the central metal iridium, so that an organic metal complex represented by the general formula (G3), which is one aspect of the present invention, can be obtained.
  • the heating means is not particularly limited, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as a heating means.
  • L represents a monoanionic ligand and A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.
  • Ar represents an aryl group having at least one cyano group as a substituent and having 6 to 25 carbon atoms.
  • R 1 and R 2 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
  • the present invention is not limited to this, and may be synthesized by any other synthesis method.
  • the above-mentioned organic metal complex can emit phosphorescence, it can be used as a light emitting material or a light emitting substance of a light emitting device.
  • organometallic complex which is one aspect of the present invention, it is possible to realize a light emitting device, a light emitting device, an electronic device, or a lighting device having high luminous efficiency. Further, it is possible to realize a light emitting device, a light emitting device, an electronic device, or a lighting device having low power consumption.
  • one aspect of the present invention has been described. Further, in another embodiment, one aspect of the present invention will be described. However, one aspect of the present invention is not limited to these. That is, since various aspects of the invention are described in this embodiment and other embodiments, one aspect of the present invention is not limited to a specific aspect. For example, as one aspect of the present invention, an example when applied to a light emitting device has been shown, but one aspect of the present invention is not limited thereto. Further, depending on the situation, one aspect of the present invention may be applied to something other than a light emitting device.
  • FIG. 1A shows a diagram showing a light emitting device according to an aspect of the present invention.
  • the light emitting device of one aspect of the present invention has a first electrode 181 and a second electrode 182 and an EL layer 183. Further, the EL layer 183 has the organic compound shown in the first embodiment.
  • the EL layer 183 has a light emitting layer 193, and the light emitting layer 193 contains a light emitting material.
  • a hole injection layer 191 and a hole transport layer 192 are provided between the light emitting layer 193 and the first electrode 181.
  • the organometallic complex according to the first embodiment is preferably used as a light emitting material because it efficiently emits red phosphorescence.
  • the light emitting layer 193 may be configured to include a host material together with the light emitting material.
  • the host material is an organic compound having carrier transportability.
  • the host material may contain not only one kind but also a plurality of kinds.
  • the plurality of organic compounds are an organic compound having an electron transport property and an organic compound having a hole transport property because the carrier balance in the light emitting layer 193 can be adjusted.
  • the plurality of organic compounds may be organic compounds having electron transport properties together, but the electron transport properties in the light emitting layer 193 can be adjusted by different electron transport properties. By appropriately adjusting the carrier balance, it becomes possible to provide a light emitting device having a good life.
  • the configuration may be such that an excitation complex is formed between a plurality of organic compounds which are host materials or between a host material and a light emitting material.
  • an excitation complex having an appropriate emission wavelength, it is possible to realize effective energy transfer to a light emitting material and provide a light emitting device having high efficiency and good lifetime.
  • the EL layer 183 in addition to the light emitting layer 193, the hole injection layer 191 and the hole transport layer 192, the electron transport layer 194 and the electron transport layer 195 are shown, but the configuration of the light emitting device is shown. Is not limited to these. It is not necessary to form any of these layers, or it may have a layer having another function.
  • the light emitting device of one aspect of the present invention has an EL layer 183 composed of a plurality of layers between the pair of electrodes of the first electrode 181 and the second electrode 182, and the EL layer 183. Any portion contains the organic compound disclosed in Embodiment 1.
  • the first electrode 181 is preferably formed by using a metal having a large work function (specifically, 4.0 eV or more), an alloy, a conductive compound, a mixture thereof, or the like.
  • a metal having a large work function specifically, 4.0 eV or more
  • an alloy e.g., aluminum, copper, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium
  • indium oxide-zinc oxide may be formed by a sputtering method using a target in which 1 to 20 wt% zinc oxide is added to indium oxide.
  • Indium oxide (IWZO) containing tungsten oxide and zinc oxide is formed by a sputtering method using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide. You can also do it.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • a nitride of a metallic material for example, titanium nitride
  • Graphene can also be used.
  • the EL layer 183 preferably has a laminated structure, but the laminated structure is not particularly limited, and is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a carrier block layer, and excitons.
  • Various layer structures such as a block layer and a charge generation layer can be applied.
  • FIG. 1A a configuration having an electron transport layer 194 and an electron transport layer 195 in addition to the hole injection layer 191 and the hole transport layer 192 and the light emitting layer 193, and FIG. 1B are shown.
  • two types of configurations having the electron transport layer 194 and the charge generation layer 196 in addition to the hole injection layer 191 and the hole transport layer 192 and the light emitting layer 193 will be described.
  • the materials constituting each layer are specifically shown below.
  • the hole injection layer 191 is a layer containing a substance having acceptability.
  • a substance having acceptability both an organic compound and an inorganic compound can be used.
  • a compound having an electron-withdrawing group (halogen group or cyano group) can be used, and 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane can be used.
  • F4-TCNQ Chloranyl, 2,3,6,7,10,11-Hexaciano-1,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN), 1,3 , 4,5,7,8-Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2- (7-dicyanomethylene-1,3,4,5,6,8,9,10- Octafluoro-7H-pyrene-2-iriden) malononitrile and the like can be mentioned.
  • a compound such as HAT-CN in which an electron-withdrawing group is bonded to a fused aromatic ring having a plurality of complex atoms is thermally stable and preferable.
  • the [3] radialene derivative having an electron-withdrawing group is preferable because it has very high electron acceptability, and specifically, ⁇ , ⁇ ', ⁇ ''-.
  • 1,2,3-Cyclopropanetriylidentris [4-cyano-2,3,5,6-tetrafluorobenzenitrile], ⁇ , ⁇ ', ⁇ ''-1,2,3-cyclopropanetriiridentris [2,6-dichloro-3,5-difluoro-4- (trifluoromethyl) benzenenitrile acetonitrile], ⁇ , ⁇ ', ⁇ ''-1,2,3-cyclopropanetriylidentris [2,3,4 , 5,6-Pentafluorobenzene acetonitrile] and the like.
  • molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide and the like can be used.
  • phthalocyanine-based complex compounds such as phthalocyanine (abbreviation: H2Pc) or copper phthalocyanine (CuPc), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB) ), N, N'-bis ⁇ 4- [bis (3-methylphenyl) amino] phenyl ⁇ -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine (abbreviation: DNTPD) ) Or an aromatic amine compound, or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT /
  • a composite material in which the acceptable substance is contained in a material having a hole transport property can also be used.
  • a material forming an electrode can be selected regardless of the work function. That is, not only a material having a large work function but also a material having a small work function can be used as the first electrode 181.
  • the material having a hole transport property used for the composite material various organic compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a polymer compound (oligomer, dendrimer, polymer, etc.) can be used.
  • the hole-transporting material used for the composite material is preferably a substance having a hole mobility of 1 ⁇ 10 -6 cm 2 / Vs or more. In the following, organic compounds that can be used as materials having hole transport properties in composite materials are specifically listed.
  • DTDPPA N'-di (p-tolyl) -N, N'-diphenyl-
  • carbazole derivative examples include 3- [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1) and 3,6-bis [N-.
  • PCzPCA2 (9-phenylcarbazole-3-yl) -9-phenylamino] -9-phenylcarbazole
  • PCzPCN1 4,4'-di (N-carbazolyl) biphenyl
  • CBP 4,4'-di (N-carbazolyl) biphenyl
  • TCPB 4,4'-di (N-carbazolyl) biphenyl
  • TCPB 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene
  • TCPB 9- [4- (10-phenyl-9-anthrasenyl) phenyl] -9H-carbazole
  • CzPA 1,4-bis [4- (N-carbazolyl) phenyl] -2,3 , 5,6-tetraphenylbenzene and the like
  • aromatic hydrocarbon examples include 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA) and 2-tert-butyl-9,10-di (1-naphthyl).
  • pentacene, coronene and the like can also be used. It may have a vinyl skeleton.
  • aromatic hydrocarbons having a vinyl group include 4,4'-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi) and 9,10-bis [4- (2,2-diphenylvinyl)).
  • Phenyl] Anthracene (abbreviation: DPVPA) and the like can be mentioned.
  • poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- ⁇ N'-[4- (4-diphenylamino)) Phenyl] phenyl-N'-phenylamino ⁇ phenyl) methacrylicamide] (abbreviation: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviation: A polymer compound such as Poly-TPD) can also be used.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N'-[4- (4-diphenylamino) Phenyl] phenyl-N'-phenylamino ⁇ phenyl) methacrylic
  • the hole-transporting material used for the composite material it is more preferable to have any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton.
  • a carbazole skeleton a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton.
  • an aromatic amine having a substituent containing a dibenzofuran ring or a dibenzothiophene ring an aromatic monoamine having a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group.
  • these second organic compounds are substances having an N, N-bis (4-biphenyl) amino group because a light emitting device having a good life can be produced.
  • Specific examples of the second organic compound as described above include N- (4-biphenyl) -6, N-diphenylbenzo [b] naphtho [1,2-d] furan-8-amine (abbreviation: abbreviation:).
  • BnfABP N, N-bis (4-biphenyl) -6-phenylbenzo [b] naphtho [1,2-d] furan-8-amine
  • BBABnf 4,4'-bis (6-phenyl) Benzo [b] naphtho [1,2-d] furan-8-yl) -4''-phenyltriphenylamine
  • BnfBB1BP 4,4'-bis (6-phenyl) Benzo [b] naphtho [1,2-d] furan-8-yl) -4''-phenyltriphenylamine
  • BnfBB1BP N, N-bis (4-biphenyl) benzo [b] naphtho [1] , 2-d] furan-6-amine
  • BBABnf N, N-bis (4-biphenyl) benzo [b] naphtho [1,2-d] furan-8-amine
  • BBABnf (8)
  • the hole-transporting material used for the composite material is more preferably a substance having a relatively deep HOMO level of ⁇ 5.7 eV or more and ⁇ 5.4 eV or less. Since the hole-transporting material used for the composite material has a relatively deep HOMO level, it is easy to inject holes into the hole-transporting layer 192, and a light-emitting device having a good life can be obtained. Becomes easier.
  • the refractive index of the layer can be lowered by further mixing the composite material with a fluoride of an alkali metal or an alkaline earth metal (preferably, the atomic ratio of fluorine atoms in the layer is 20% or more). can. Also by this, a layer having a low refractive index can be formed inside the EL layer 183, and the external quantum efficiency of the light emitting device can be improved.
  • the hole injection layer 191 By forming the hole injection layer 191, the hole injection property is improved, and a light emitting device having a small driving voltage can be obtained. Further, the organic compound having acceptability is an easy-to-use material because it is easy to deposit and form a film.
  • the hole transport layer 192 is formed containing a material having a hole transport property.
  • a material having a hole transport property it is preferable to have a hole mobility of 1 ⁇ 10 -6 cm 2 / Vs or more.
  • the material having a hole transport property include 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and N, N'-bis (3-methylphenyl).
  • mmDBFFLBi-II dibenzofuran
  • the compound having an aromatic amine skeleton and the compound having a carbazole skeleton are preferable because they have good reliability, high hole transportability, and contribute to reduction of driving voltage.
  • the substance mentioned as the material having hole transportability used for the composite material of the hole injection layer 191 can also be suitably used as the material constituting the hole transport layer 192.
  • the light emitting layer 193 has a light emitting substance and a host material.
  • the light emitting layer 193 may contain other materials at the same time. Further, two layers having different compositions may be laminated.
  • the luminescent substance may be a fluorescent luminescent substance, a phosphorescent luminescent substance, a substance exhibiting thermal activated delayed fluorescence (TADF), or another luminescent substance.
  • TADF thermal activated delayed fluorescence
  • Examples of the material that can be used as the fluorescent light emitting substance in the light emitting layer 193 include 5,6-bis [4- (10-phenyl-9-anthryl) phenyl] -2,2'-bipyridine (abbreviation: PAP2BPy).
  • condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn, 1,6 mMlemFLPARn, and 1,6BnfAPrn-03 are preferable because they have high hole trapping properties and excellent luminous efficiency and reliability. Further, other fluorescent light emitting substances can also be used.
  • a phosphorescent luminescent substance is used as the luminescent substance in the light emitting layer 193, as a material that can be used, for example, Tris ⁇ 2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl)) -4H-1,2,4-triazole-3-yl- ⁇ N2] Phenyl- ⁇ C ⁇ Iridium (III) (abbreviation: [Ir (mpptz-dmp) 3 ]), Tris (5-methyl-3,4-diphenyl) -4H-1,2,4-triazolat) Iridium (III) (abbreviation: [Ir (Mptz) 3 ]), Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1,2 , 4-Triazolate] Iridium (III) (abbreviation: [Ir (iPrptz-3b) 3 ]), an organic metal iridium complex having a
  • Tris (4-methyl-6-phenylpyrimidinat) iridium (III) (abbreviation: [Ir (mppm) 3 ]), Tris (4-t-butyl-6-phenylpyrimidinat) iridium (III).
  • organic metal iridium complex having examples thereof include rare earth metal complexes such as tris (acetylacetonato) (monophenanthrolin) terbium (III) (abbreviation: [Tb (acac) 3 (Phen)]). These are compounds that mainly exhibit green phosphorescence and have emission wavelength peaks from 500 nm to 600 nm.
  • the organometallic iridium complex having a pyrimidine skeleton is particularly preferable because it is remarkably excellent in reliability and luminous efficiency.
  • the organometallic iridium complex having a pyrazine skeleton can obtain red light emission with good chromaticity.
  • the organometallic complex of one aspect of the present invention described in the first embodiment is also a substance having good chromaticity and exhibiting highly efficient red light emission.
  • the organometallic complex described in the first embodiment can also be used as a phosphorescent substance.
  • the light emitting device according to one aspect of the present invention preferably uses the metal complex described in the first embodiment. By using the organometallic complex described in the first embodiment, it is possible to provide a light emitting device having good current efficiency and color purity.
  • known phosphorescent luminescent substances may be selected and used.
  • TADF material fullerene and its derivatives, acridine and its derivatives, eosin derivatives and the like can be used.
  • metal-containing porphyrin include a protoporphyrin-tin fluoride complex (SnF2 (Proto IX)), a mesoporphyrin-tin fluoride complex (SnF2 (Meso IX)) and hematoporphyrin-hut represented by the following structural formula.
  • Tinized tin complex SnF2 (Hemato IX)
  • coproporphyrin tetramethyl ester-tin fluoride complex SnF2 (Copro III-4Me)
  • octaethylporphyrin-tin fluoride complex SnF2 (OEP)
  • etioporphyrin-huh examples thereof include a tin complex (SnF2 (Etio I)), an octaethylporphyrin-platinum chloride complex (PtCl 2 OEP), and the like.
  • the heterocyclic compound has a ⁇ -electron excess type heteroaromatic ring and a ⁇ -electron deficiency type heteroaromatic ring, both electron transportability and hole transportability are high, which is preferable.
  • the skeletons having a ⁇ -electron deficient heteroaromatic ring the pyridine skeleton, the diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferable because they are stable and have good reliability.
  • the benzoflopyrimidine skeleton, the benzothienopyrimidine skeleton, the benzoflopyrazine skeleton, and the benzothienopyrazine skeleton are preferable because they have high acceptor properties and good reliability.
  • the skeletons having a ⁇ -electron-rich complex aromatic ring the acridine skeleton, the phenoxazine skeleton, the phenothiazine skeleton, the furan skeleton, the thiophene skeleton, and the pyrrole skeleton are stable and have good reliability, and therefore at least one of the skeletons. It is preferable to have.
  • the furan skeleton is preferably a dibenzofuran skeleton
  • the thiophene skeleton is preferably a dibenzothiophene skeleton.
  • the pyrrole skeleton an indole skeleton, a carbazole skeleton, an indolecarbazole skeleton, a bicarbazole skeleton, and a 3- (9-phenyl-9H-carbazole-3-yl) -9H-carbazole skeleton are particularly preferable.
  • the substance in which the ⁇ -electron-rich heteroaromatic ring and the ⁇ -electron-deficient heteroaromatic ring are directly bonded has both the electron donating property of the ⁇ -electron-rich heteroaromatic ring and the electron acceptability of the ⁇ -electron-deficient heteroaromatic ring. It becomes stronger and the energy difference between the S1 level and the T1 level becomes smaller, which is particularly preferable because the heat-activated delayed fluorescence can be efficiently obtained.
  • an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used.
  • an aromatic amine skeleton, a phenazine skeleton, or the like can be used.
  • a group, an aromatic ring having a cyano group or a heteroaromatic ring, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton and the like can be used.
  • a ⁇ -electron-deficient skeleton and a ⁇ -electron-rich skeleton can be used in place of at least one of the ⁇ -electron-deficient heteroaromatic ring and the ⁇ -electron-rich heteroaromatic ring.
  • the TADF material is a material having a small difference between the S1 level and the T1 level and having a function of converting energy from triplet excitation energy to singlet excitation energy by crossing between inverse terms. Therefore, the triplet excited energy can be up-converted to the singlet excited energy (intersystem crossing) with a small amount of thermal energy, and the singlet excited state can be efficiently generated. In addition, triplet excitation energy can be converted into light emission.
  • an excited complex also referred to as an exciplex, an exciplex or an Exciplex
  • the difference between the S1 level and the T1 level is extremely small, and the triplet excitation energy is the singlet excitation energy. It has a function as a TADF material that can be converted into.
  • a phosphorescence spectrum observed at a low temperature may be used.
  • a tangent line is drawn at the hem on the short wavelength side of the fluorescence spectrum
  • the energy of the wavelength of the extrawire is set to the S1 level
  • a tangent line is drawn at the hem on the short wavelength side of the phosphorescence spectrum, and the extrapolation line is drawn.
  • the difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.
  • the S1 level of the host material is higher than the S1 level of the TADF material. Further, it is preferable that the T1 level of the host material is higher than the T1 level of the TADF material.
  • various carrier transport materials such as a material having an electron transport property, a material having a hole transport property, and the TADF material can be used.
  • an organic compound having an amine skeleton or a ⁇ -electron excess type heteroaromatic ring skeleton is preferable.
  • NPB 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • TPD N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [ 1,1'-biphenyl] -4,4'-diamine
  • TPD 1,1'-biphenyl] -4,4'-diamine
  • Benzene 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl
  • BPAFLP 4-phenyl-4'-(9-phenylfluoren-9-yl) triphenylamine
  • BPAFLP 4-phenyl-3'-(9-phenylfluoren-9-yl) tri Phen
  • Examples of the material having electron transportability include bis (10-hydroxybenzo [h] quinolinato) berylium (II) (abbreviation: BeBq2) and bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum.
  • Examples of the organic compound having a ⁇ -electron-deficient heterocyclic ring skeleton include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD).
  • heterocyclic compounds having a pyridine skeleton such as 5-tri [3- (3-pyridyl) phenyl] benzene (abbreviation: TmPyPB).
  • TmPyPB 5-tri [3- (3-pyridyl) phenyl] benzene
  • the heterocyclic compound having a diazine skeleton, the heterocyclic compound having a triazine skeleton, and the heterocyclic compound having a pyridine skeleton are preferable because they have good reliability.
  • a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has high electron transport properties and contributes to a reduction in driving voltage.
  • the TADF material that can be used as the host material
  • those listed above as the TADF material can also be used in the same manner.
  • the triplet excitation energy generated by the TADF material is converted to singlet excitation energy by crossing between inverse terms, and further energy is transferred to the light emitting material, thereby increasing the light emission efficiency of the light emitting device. be able to.
  • the TADF material functions as an energy donor and the luminescent material functions as an energy acceptor.
  • the S1 level of the TADF material is higher than the S1 level of the fluorescent light emitting substance.
  • the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent light emitting substance. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent light emitting substance.
  • a TADF material that emits light so as to overlap the wavelength of the absorption band on the lowest energy side of the fluorescent light emitting substance.
  • the TADF material in order to efficiently generate singlet excitation energy from triplet excitation energy by reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. Further, it is preferable that the triplet excitation energy generated by the TADF material does not transfer to the triplet excitation energy of the fluorescent light emitting substance.
  • the fluorescent light-emitting substance has a protecting group around the chromophore (skeleton that causes light emission) of the fluorescent light-emitting substance.
  • the protecting group is preferably a substituent having no ⁇ bond, preferably a saturated hydrocarbon, specifically, an alkyl group having 3 or more and 10 or less carbon atoms, or a substituted or unsubstituted cycloalkyl having 3 or more and 10 or less carbon atoms. Examples thereof include a group and a trialkylsilyl group having 3 or more and 10 or less carbon atoms, and it is more preferable that there are a plurality of protecting groups. Substituents that do not have a ⁇ bond have a poor ability to transport carriers, so that the TADF material can be distanced from the chromophore of the fluorescent luminescent material with little effect on carrier transport and carrier recombination.
  • the chromophore refers to an atomic group (skeleton) that causes light emission in a fluorescent luminescent substance.
  • the chromophore preferably has a skeleton having a ⁇ bond, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed complex aromatic ring.
  • Examples of the fused aromatic ring or the condensed heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, and a phenothiazine skeleton.
  • a fluorescent substance having a naphthalene skeleton, anthracene skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, and naphthobisbenzofuran skeleton is preferable because of its high fluorescence quantum yield.
  • a material having an anthracene skeleton is suitable as the host material.
  • a substance having an anthracene skeleton is used as a host material for a fluorescent light emitting substance, it is possible to realize a light emitting layer having good luminous efficiency and durability.
  • a diphenylanthracene skeleton, particularly a substance having a 9,10-diphenylanthracene skeleton is preferable because it is chemically stable.
  • the host material has a carbazole skeleton
  • HOMO is about 0.1 eV shallower than that of carbazole, holes are easily entered, holes are easily transported, and heat resistance is high, which is preferable. ..
  • a substance having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton) at the same time is further preferable as a host material.
  • a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.
  • examples of such substances are 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA), 3- [4- (1-naphthyl)-.
  • Phenyl] -9-Phenyl-9H-carbazole (abbreviation: PCPN), 9- [4- (10-phenyl-9-anthrasenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 7- [4- (10-) Phenyl-9-anthryl) phenyl] -7H-dibenzo [c, g] carbazole (abbreviation: cgDBCzPA), 6- [3- (9,10-diphenyl-2-anthryl) phenyl] -benzo [b] naphtho [1 , 2-d] Fran (abbreviation: 2mBnfPPA), 9-Phenyl-10- ⁇ 4- (9-phenyl-9H-fluoren-9-yl) biphenyl-4'-yl ⁇ anthracene (abbreviation: FLPPA), 9- (1-naphthyl) -10- [4- (2-n
  • the host material may be a material obtained by mixing a plurality of kinds of substances, and when a mixed host material is used, it is preferable to mix a material having an electron transport property and a material having a hole transport property. ..
  • a material having an electron transport property 1: 19 to 19: 1.
  • a phosphorescent substance can be used as a part of the mixed material.
  • the phosphorescent substance can be used as an energy donor to provide excitation energy to the fluorescent substance when the fluorescent substance is used as the light emitting substance.
  • the organometallic complex according to the first embodiment can also be used as the phosphorescent substance.
  • an excited complex may be formed between these mixed materials.
  • At least one of the materials forming the excitation complex may be a phosphorescent substance.
  • the HOMO level of the material having hole transportability is equal to or higher than the HOMO level of the material having electron transportability.
  • the LUMO level of the material having hole transportability is equal to or higher than the LUMO level of the material having electron transportability.
  • the LUMO level and HOMO level of the material can be derived from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV) measurement.
  • the emission spectrum of the material having hole transport property, the emission spectrum of the material having electron transport property, and the emission spectrum of the mixed film in which these materials are mixed are compared, and the emission spectrum of the mixed film is compared.
  • the transient photoluminescence (PL) of the material having hole transportability, the transient PL of the material having electron transportability, and the transient PL of the mixed membrane in which these materials are mixed are compared, and the transient PL lifetime of the mixed membrane is determined.
  • transient PL may be read as transient electroluminescence (EL). That is, the formation of an excited complex can also be formed by comparing the transient EL of the material having hole transportability, the transient EL of the material having electron transportability, and the transient EL of the mixed membrane thereof, and observing the difference in the transient response. You can check.
  • EL transient electroluminescence
  • the electron transport layer 194 is a layer containing a substance having an electron transport property.
  • the substance having electron transporting property the substance listed as the substance having electron transporting property which can be used for the above-mentioned host material can be used.
  • the electron transport layer 194 has an electron mobility of 1 ⁇ 10 -7 cm 2 / Vs or more and 5 ⁇ 10 -5 cm 2 / Vs or less when the square root of the electric field strength [V / cm] is 600. preferable. By reducing the electron transportability in the electron transport layer 194, the amount of electrons injected into the light emitting layer can be controlled, and the light emitting layer can be prevented from being in a state of excess electrons. Further, the electron transport layer preferably contains a material having electron transport properties and an alkali metal or a simple substance, compound or complex of an alkali metal.
  • the hole injection layer is formed as a composite material
  • the HOMO level of the material having hole transportability in the composite material is -5.7 eV or more and -5.4 eV or less, which is a relatively deep HOMO level. It is particularly preferable that the substance has a good life. At this time, it is preferable that the HOMO level of the material having electron transportability is ⁇ 6.0 eV or more.
  • the material having electron transport property is preferably an organic compound having an anthracene skeleton, and more preferably an organic compound containing both an anthracene skeleton and a heterocyclic skeleton.
  • the heterocyclic skeleton is preferably a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton, and these heterocyclic skeletons include a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring. It is particularly preferable to have a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton containing two heteroatoms in the ring.
  • the alkali metal or the simple substance, the compound or the complex of the alkali metal preferably contains an 8-hydroxyquinolinato structure.
  • 8-hydroxyquinolinato-lithium abbreviation: Liq
  • 8-hydroxyquinolinato-sodium abbreviation: Naq
  • a monovalent metal ion complex particularly a lithium complex
  • Liq is more preferable.
  • a methyl-substituted product thereof for example, a 2-methyl-substituted product or a 5-methyl-substituted product
  • the alkali metal or the alkali metal simple substance, the compound or the complex has a concentration difference (including the case where it is 0) in the thickness direction thereof.
  • lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinato-lithium A layer containing an alkali metal or alkaline earth metal such as (abbreviation: Liq) or a compound thereof may be provided.
  • an alkali metal, an alkaline earth metal, or a compound thereof contained in a layer made of a substance having an electron transport property, or an electride may be used. Examples of the electride include a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum.
  • the electron transport layer 195 contains an electron transportable substance (preferably an organic compound having a bipyridine skeleton) containing the alkali metal or alkaline earth metal fluoride in a fine crystal state or more (50 wt% or more). It is also possible to use an alkaline layer. Since the layer has a low refractive index, it is possible to provide a light emitting device having better external quantum efficiency.
  • an electron transportable substance preferably an organic compound having a bipyridine skeleton
  • a charge generation layer 196 may be provided instead of the electron transport layer 195 (FIG. 1B).
  • the charge generation layer 196 is a layer capable of injecting holes into the layer in contact with the cathode side and electrons into the layer in contact with the anode side by applying an electric potential.
  • the charge generation layer 196 includes at least a P-type layer 197.
  • the P-type layer 197 is preferably formed by using the composite material mentioned as a material that can form the hole injection layer 191 described above. Further, the P-type layer 197 may be formed by laminating a film containing the above-mentioned acceptor material and a film containing a hole transport material as a material constituting the composite material.
  • the organic compound according to one aspect of the present invention is an organic compound having a low refractive index, it is possible to obtain a light emitting device having good external quantum efficiency by using it for the P-type layer 197.
  • the charge generation layer 196 preferably has one or both of the electron relay layer 198 and the electron injection buffer layer 199 in addition to the P-type layer 197.
  • the electron relay layer 198 contains at least a substance having electron transportability, and has a function of preventing interaction between the electron injection buffer layer 199 and the P-type layer 197 and smoothly transferring electrons.
  • the LUMO level of the electron-transporting substance contained in the electron relay layer 198 is the LUMO level of the accepting substance in the P-type layer 197 and the substance contained in the layer in contact with the charge generating layer 196 in the electron transporting layer 194. It is preferably between the LUMO level.
  • the specific energy level of the LUMO level in the substance having electron transportability used in the electron relay layer 198 is preferably ⁇ 5.0 eV or higher, preferably ⁇ 5.0 eV or higher and ⁇ 3.0 eV or lower.
  • As the substance having electron transportability used in the electron relay layer 198 it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.
  • the electron injection buffer layer 199 contains alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate, or carbonates such as cesium carbonate). ), Alkaline earth metal compounds (including oxides, halides and carbonates), or rare earth metal compounds (including oxides, halides and carbonates)) and other highly electron-injectable substances may be used. It is possible.
  • the donor substance includes an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (as a donor substance).
  • Alkali metal compounds including oxides such as lithium oxide, halides, lithium carbonate, or carbonates such as cesium carbonate
  • alkaline earth metal compounds including oxides, halides, carbonates
  • rare earth metals in addition to compounds (including oxides, halides, and carbonates), organic compounds such as tetrathianaphthalene (abbreviation: TTN), nickerosen, and decamethyl nickerosen can also be used.
  • TTN tetrathianaphthalene
  • nickerosen nickerosen
  • decamethyl nickerosen can also be used.
  • the substance having electron transportability it can be formed by using the same material as the material constituting the electron transport layer 194 described above.
  • a metal having a small work function (specifically, 3.8 eV or less), an alloy, an electrically conductive compound, a mixture thereof, or the like
  • a cathode material include alkali metals such as lithium (Li) and cesium (Cs), or the first elemental periodic table of elements such as magnesium (Mg), calcium (Ca), and strontium (Sr). Examples thereof include elements belonging to Group 2 or Group 2, rare earth metals such as alloys containing these (MgAg, AlLi), strontium (Eu), and strontium (Yb), and alloys containing these.
  • indium tin oxide containing Al, Ag, ITO, silicon or silicon oxide is provided regardless of the size of the work function.
  • Various conductive materials such as the second electrode 182 can be used as the second electrode 182. These conductive materials can be formed into a film by using a dry method such as a vacuum vapor deposition method and a sputtering method, an inkjet method, a spin coating method, or the like. Further, it may be formed by a wet method using a sol-gel method, or may be formed by a wet method using a paste of a metal material.
  • a method for forming the EL layer 183 various methods can be used regardless of whether it is a dry method or a wet method.
  • a vacuum vapor deposition method, a gravure printing method, an offset printing method, a screen printing method, an inkjet method, a spin coating method, or the like may be used.
  • each electrode or each layer described above may be formed by using a different film forming method.
  • the structure of the layer provided between the first electrode 181 and the second electrode 182 is not limited to the above. However, holes and electrons are located away from the first electrode 181 and the second electrode 182 so that the quenching caused by the proximity of the light emitting region to the metal used for the electrode or carrier injection layer is suppressed. It is preferable to provide a light emitting region that recombines with.
  • the hole transport layer and the electron transport layer in contact with the light emitting layer 193, particularly the carrier transport layer near the recombination region in the light emitting layer 193, have a band gap in order to suppress energy transfer from excitons generated in the light emitting layer.
  • a light emitting device also referred to as a laminated element or a tandem type element having a configuration in which a plurality of light emitting units are laminated
  • This light emitting device is a light emitting device having a plurality of light emitting units between the anode and the cathode.
  • One light emitting unit has almost the same configuration as the EL layer 183 shown in FIG. 1A. That is, it can be said that the light emitting device shown in FIG. 1C is a light emitting device having a plurality of light emitting units, and the light emitting device shown in FIG. 1A or FIG. 1B is a light emitting device having one light emitting unit.
  • a first light emitting unit 511 and a second light emitting unit 512 are laminated between the anode 501 and the cathode 502, and between the first light emitting unit 511 and the second light emitting unit 512. Is provided with a charge generation layer 513.
  • the anode 501 and the cathode 502 correspond to the first electrode 181 and the second electrode 182 in FIG. 1A, respectively, and the same ones described in the description of FIG. 1A can be applied.
  • the first light emitting unit 511 and the second light emitting unit 512 may have the same configuration or different configurations.
  • the charge generation layer 513 has a function of injecting electrons into one light emitting unit and injecting holes into the other light emitting unit when a voltage is applied to the anode 501 and the cathode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 injects electrons into the first light emitting unit 511 and the second light emitting unit. Anything that injects holes into 512 may be used.
  • the charge generation layer 513 is preferably formed with the same configuration as the charge generation layer 196 described with reference to FIG. 1B. Since the composite material of the organic compound and the metal oxide is excellent in carrier injection property and carrier transport property, low voltage drive and low current drive can be realized. When the surface of the light emitting unit on the anode side is in contact with the charge generating layer 513, the charge generating layer 513 can also serve as the hole injection layer of the light emitting unit, so that the light emitting unit uses the hole injection layer. It does not have to be provided.
  • the electron injection buffer layer 199 plays the role of the electron injection layer in the light emitting unit on the anode side, so that the electron injection layer is not necessarily provided in the light emitting unit on the anode side. There is no need to form.
  • FIG. 1C a light emitting device having two light emitting units has been described, but the same can be applied to a light emitting device in which three or more light emitting units are stacked.
  • a light emitting device in which three or more light emitting units are stacked.
  • each light emitting unit by making the emission color of each light emitting unit different, it is possible to obtain light emission of a desired color as the entire light emitting device. For example, in a light emitting device having two light emitting units, a light emitting device that emits white light as a whole by obtaining a red and green light emitting color from the first light emitting unit and a blue light emitting color from the second light emitting unit. It is also possible to get it.
  • each layer such as the EL layer 183, the first light emitting unit 511, the second light emitting unit 512, and the charge generation layer, and the electrodes are, for example, a vapor deposition method (including a vacuum vapor deposition method) or a droplet ejection method. It can be formed by using a method (also referred to as an inkjet method), a coating method, a gravure printing method, or the like. They may also include small molecule materials, medium molecule materials (including oligomers, dendrimers), or polymer materials.
  • FIG. 2A is a top view showing a light emitting device
  • FIG. 2B is a cross-sectional view of FIG. 2A cut by AB and CD.
  • This light emitting device includes a drive circuit unit (source line drive circuit) 601, a pixel unit 602, and a drive circuit unit (gate line drive circuit) 603 shown by dotted lines to control the light emission of the light emitting device.
  • 604 is a sealing substrate
  • 605 is a sealing material
  • the inside surrounded by the sealing material 605 is a space 607.
  • the routing wiring 608 is a wiring for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and is a video signal, a clock signal, and a video signal and a clock signal from the FPC (flexible print circuit) 609 which is an external input terminal. Receives start signal, reset signal, etc. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to the FPC.
  • the light emitting device in the present specification includes not only the light emitting device main body but also a state in which an FPC or PWB is attached to the light emitting device main body.
  • a drive circuit unit and a pixel unit are formed on the element substrate 610, and here, a source line drive circuit 601 which is a drive circuit unit and one pixel in the pixel unit 602 are shown.
  • the element substrate 610 is manufactured by using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc., as well as a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl flolide), polyester, acrylic resin, etc. do it.
  • FRP Fiber Reinforced Plastics
  • PVF polyvinyl flolide
  • polyester acrylic resin, etc. do it.
  • the structure of the transistor used for the pixel and the drive circuit is not particularly limited. For example, it may be an inverted stagger type transistor or a stagger type transistor. Further, a top gate type transistor or a bottom gate type transistor may be used.
  • the semiconductor material used for the transistor is not particularly limited, and for example, silicon, germanium, silicon carbide, gallium nitride and the like can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn-based metal oxide, may be used.
  • the crystallinity of the semiconductor material used for the transistor is not particularly limited, and either an amorphous semiconductor or a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a partially crystalline region). May be used. It is preferable to use a semiconductor having crystallinity because deterioration of transistor characteristics can be suppressed.
  • an oxide semiconductor in addition to the transistors provided in the pixels and the drive circuit, it is preferable to apply an oxide semiconductor to a semiconductor device such as a transistor used in a touch sensor or the like described later. In particular, it is preferable to apply an oxide semiconductor having a wider bandgap than silicon. By using an oxide semiconductor having a wider bandgap than silicon, the current in the off state of the transistor can be reduced.
  • the oxide semiconductor preferably contains at least indium (In) or zinc (Zn). Further, the oxide semiconductor contains an oxide represented by an In—M—Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf). Is more preferable.
  • M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf. Is more preferable.
  • the semiconductor layer has a plurality of crystal portions, and the c-axis of the crystal portion is oriented perpendicular to the surface to be formed of the semiconductor layer or the upper surface of the semiconductor layer, and grain boundaries are formed between adjacent crystal portions. It is preferable to use an oxide semiconductor film that does not have.
  • the transistor having the above-mentioned semiconductor layer can retain the electric charge accumulated in the capacitance through the transistor for a long period of time due to its low off current.
  • the transistor having the above-mentioned semiconductor layer can retain the electric charge accumulated in the capacitance through the transistor for a long period of time due to its low off current.
  • an undercoat film for stabilizing the characteristics of the transistor.
  • an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon nitride film, or a silicon nitride oxide film can be used, and can be produced as a single layer or laminated.
  • the base film is formed by using a sputtering method, a CVD (Chemical Vapor Deposition) method (plasma CVD method, thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. can.
  • the undercoat may not be provided if it is not necessary.
  • the FET 623 represents one of the transistors formed in the source line drive circuit 601.
  • the drive circuit may be formed of various CMOS circuits, epitaxial circuits or MIMO circuits.
  • the driver integrated type in which the drive circuit is formed on the substrate is shown, but it is not always necessary, and the drive circuit can be formed on the outside instead of on the substrate.
  • the pixel unit 602 is formed by a plurality of pixels including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain thereof, but is not limited to 3.
  • a pixel unit may be a combination of two or more FETs and a capacitive element.
  • An insulator 614 is formed so as to cover the end portion of the first electrode 613.
  • it can be formed by using a positive type photosensitive acrylic resin film.
  • a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulating material 614.
  • a positive photosensitive acrylic resin is used as the material of the insulating material 614, it is preferable that only the upper end portion of the insulating material 614 has a curved surface having a radius of curvature (0.2 ⁇ m to 3 ⁇ m).
  • a negative type photosensitive resin or a positive type photosensitive resin can be used as the insulating material 614.
  • An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively.
  • the material used for the first electrode 613 that functions as an anode it is desirable to use a material having a large work function.
  • a laminated structure of a titanium nitride film and a film containing aluminum as a main component, a three-layer structure of a titanium nitride film and a film containing aluminum as a main component, and a titanium nitride film can be used. It should be noted that the laminated structure has low resistance as wiring, good ohmic contact can be obtained, and can further function as an anode.
  • the EL layer 616 is formed by various methods such as a thin-film deposition method using a thin-film deposition mask, an inkjet method, and a spin coating method.
  • the EL layer 616 includes a configuration as described in the second embodiment.
  • a low molecular weight compound or a high molecular weight compound may be used as another material constituting the EL layer 616.
  • the material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode a material having a small work function (Al, Mg, Li, Ca, or an alloy or compound thereof (MgAg, MgIn, etc.) It is preferable to use AlLi etc.)).
  • the second electrode 617 is a thin metal thin film and a transparent conductive film (ITO, 2 to 20 wt% oxidation). It is preferable to use a laminate with indium oxide containing zinc, indium tin oxide containing silicon, zinc oxide (ZnO), etc.).
  • a light emitting device is formed by the first electrode 613, the EL layer 616, and the second electrode 617.
  • the light emitting device is the light emitting device according to the second embodiment. Although a plurality of light emitting devices are formed in the pixel portion, in the light emitting device according to the present embodiment, both the light emitting device according to the second embodiment and the light emitting device having other configurations are mixed. You may be doing it.
  • the sealing substrate 604 by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light emitting device 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605.
  • the space 607 is filled with a filler, and may be filled with an inert gas (nitrogen, argon, etc.) or a sealing material.
  • an epoxy resin, glass frit, or the like for the sealing material 605. Further, it is desirable that these materials are materials that do not allow moisture and oxygen to permeate as much as possible. Further, as the material used for the sealing substrate 604, in addition to the glass substrate or the quartz substrate, a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin or the like can be used.
  • FRP Fiber Reinforced Plastics
  • PVF polyvinyl fluoride
  • polyester acrylic resin or the like
  • a protective film may be provided on the second electrode.
  • the protective film may be formed of an organic resin film or an inorganic insulating film. Further, a protective film may be formed so as to cover the exposed portion of the sealing material 605. Further, the protective film can be provided so as to cover the surface and side surfaces of the pair of substrates, the sealing layer, the insulating layer, and the exposed side surfaces.
  • the protective film a material that does not easily allow impurities such as water to permeate can be used. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.
  • oxides, nitrides, fluorides, sulfides, ternary compounds, metals, polymers and the like can be used, and for example, aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide and oxidation can be used.
  • nitride Materials including hafnium, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride or gallium nitride, nitrides including titanium and aluminum, oxides containing titanium and aluminum, oxides containing aluminum and zinc , A sulfide containing manganese and zinc, a sulfide containing cerium and strontium, an oxide containing erbium and aluminum, an oxide containing yttrium and zirconium, and the like can be used.
  • the protective film is preferably formed by using a film forming method having good step coverage (step coverage).
  • a film forming method having good step coverage is the atomic layer deposition (ALD) method.
  • ALD atomic layer deposition
  • ALD method it is possible to form a protective film having a dense, reduced defects such as cracks and pinholes, or a uniform thickness.
  • damage to the processed member when forming the protective film can be reduced.
  • the protective film using the ALD method, it is possible to form a uniform protective film with few defects on the front surface having a complicated uneven shape, the upper surface, the side surface, and the back surface of the touch panel.
  • a light emitting device manufactured by using the light emitting device according to the second embodiment can be obtained.
  • the light emitting device in the present embodiment uses the light emitting device according to the second embodiment, it is possible to obtain a light emitting device having good characteristics. Specifically, since the light emitting device according to the second embodiment has good luminous efficiency, it can be a light emitting device having low power consumption.
  • FIG. 3 shows an example of a light emitting device in which a light emitting device exhibiting white light emission is formed and a colored layer (color filter) or the like is provided to make it full color.
  • FIG. 3A shows a substrate 1001, an underlying insulating film 1002, a gate insulating film 1003, a gate electrode 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, and a drive.
  • the circuit unit 1041, the first electrode 1024W, 1024R, 1024G, 1024B of the light emitting device, the partition wall 1025, the EL layer 1028, the second electrode 1029 of the light emitting device, the sealing substrate 1031, the sealing material 1032, and the like are shown.
  • the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) is provided on the transparent base material 1033. Further, a black matrix 1035 may be further provided. The transparent base material 1033 provided with the colored layer and the black matrix is aligned and fixed to the substrate 1001. The colored layer and the black matrix 1035 are covered with the overcoat layer 1036. Further, in FIG. 3A, there is a light emitting layer in which light is emitted to the outside without passing through the colored layer and a light emitting layer in which light is transmitted to the outside through the colored layer of each color. Since the light transmitted through the white and colored layers is red, green, and blue, the image can be expressed by the pixels of four colors.
  • FIG. 3B shows an example in which a colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020.
  • the colored layer may be provided between the substrate 1001 and the sealing substrate 1031.
  • the light emitting device has a structure that extracts light to the substrate 1001 side on which the FET is formed (bottom emission type), but has a structure that extracts light to the sealing substrate 1031 side (top emission type). ) May be used as a light emitting device.
  • a cross-sectional view of the top emission type light emitting device is shown in FIG.
  • the substrate 1001 can be a substrate that does not transmit light. It is formed in the same manner as the bottom emission type light emitting device until the connection electrode for connecting the FET and the anode of the light emitting device is manufactured.
  • a third interlayer insulating film 1037 is formed so as to cover the electrode 1022. This insulating film may play a role of flattening.
  • the third interlayer insulating film 1037 can be formed by using the same material as the second interlayer insulating film and other known materials.
  • the first electrodes 1024W, 1024R, 1024G, and 1024B of the light emitting device are used as an anode here, but may be a cathode. Further, in the case of the top emission type light emitting device as shown in FIG. 4, it is preferable that the first electrode is a reflecting electrode.
  • the structure of the EL layer 1028 is the same as that described as the EL layer 183 in the second embodiment, and has an element structure such that white light emission can be obtained.
  • the sealing can be performed by the sealing substrate 1031 provided with the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B).
  • the sealing substrate 1031 may be provided with a black matrix 1035 so as to be located between the pixels.
  • the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) and the black matrix may be covered by the overcoat layer 1036.
  • a substrate having translucency is used as the sealing substrate 1031.
  • an example of performing full-color display with four colors of red, green, blue, and white is shown, but the present invention is not particularly limited, and four colors of red, yellow, green, and blue, or three colors of red, green, and blue are shown. You may display in full color with.
  • the microcavity structure can be preferably applied.
  • a light emitting device having a microcavity structure can be obtained by using a first electrode as a reflective electrode and a second electrode as a semi-transmissive / semi-reflective electrode.
  • An EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light emitting layer serving as a light emitting region is provided.
  • the reflective electrode is a film having a visible light reflectance of 40% to 100%, preferably 70% to 100%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less.
  • the semi-transmissive / semi-reflective electrode is a film having a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less. ..
  • the light emitted from the light emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode and resonates.
  • the light emitting device can change the optical distance between the reflective electrode and the transflective / semi-reflective electrode by changing the thickness of the transparent conductive film, the above-mentioned composite material, the carrier transport material, or the like. As a result, it is possible to intensify the light having a wavelength that resonates between the reflecting electrode and the semi-transmissive / semi-reflective electrode, and to attenuate the light having a wavelength that does not resonate.
  • the light reflected and returned by the reflecting electrode causes large interference with the light directly incident on the semi-transmissive / semi-reflecting electrode from the light emitting layer (first incident light), and is therefore reflected.
  • the EL layer may have a structure having a plurality of light emitting layers or a structure having a single light emitting layer, and may be combined with, for example, the above-mentioned configuration of the tandem type light emitting device.
  • a plurality of EL layers may be provided on one light emitting device with a charge generation layer interposed therebetween, and the present invention may be applied to a configuration in which a single or a plurality of light emitting layers are formed in each EL layer.
  • the microcavity structure By having the microcavity structure, it is possible to enhance the emission intensity in the front direction of a specific wavelength, so that it is possible to reduce power consumption.
  • the microcavity structure that matches the wavelength of each color can be applied to all the sub-pixels in addition to the effect of improving the brightness by yellow light emission. It can be a light emitting device with good characteristics.
  • the light emitting device in the present embodiment uses the light emitting device according to the second embodiment, it is possible to obtain a light emitting device having good characteristics. Specifically, since the light emitting device according to the second embodiment has good luminous efficiency, it can be a light emitting device having low power consumption.
  • FIG. 5 shows a passive matrix type light emitting device manufactured by applying the present invention.
  • 5A is a perspective view showing a light emitting device
  • FIG. 5B is a cross-sectional view of FIG. 5A cut by XY.
  • an EL layer 955 is provided between the electrode 952 and the electrode 956 on the substrate 951.
  • the end of the electrode 952 is covered with an insulating layer 953.
  • a partition wall layer 954 is provided on the insulating layer 953.
  • the side wall of the partition wall layer 954 has an inclination such that the distance between one side wall and the other side wall becomes narrower as it gets closer to the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 is trapezoidal, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is the upper side (the surface of the insulating layer 953). It faces in the same direction as the direction, and is shorter than the side that does not contact the insulating layer 953).
  • the passive matrix type light emitting device also uses the light emitting device according to the second embodiment, and can be a highly reliable light emitting device or a light emitting device having low power consumption.
  • the light emitting device described above can control a large number of minute light emitting devices arranged in a matrix, it is a light emitting device that can be suitably used as a display device for expressing an image.
  • FIG. 6A is a top view of the lighting device
  • FIG. 6B is a sectional view taken along the line EF in FIG. 6A.
  • the first electrode 401 is formed on the translucent substrate 400 which is a support.
  • the first electrode 401 corresponds to the first electrode 181 in the second embodiment.
  • the first electrode 401 is formed of a translucent material.
  • a pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400.
  • the EL layer 403 is formed on the first electrode 401.
  • the EL layer 403 corresponds to the configuration of the EL layer 183 in the second embodiment, or the configuration in which the first light emitting unit 511, the second light emitting unit 512, and the charge generation layer 513 are combined. Please refer to the description for these configurations.
  • a second electrode 404 is formed by covering the EL layer 403.
  • the second electrode 404 corresponds to the second electrode 182 in the second embodiment.
  • the second electrode 404 is formed of a material having high reflectance.
  • the second electrode 404 is connected to the pad 412 to supply a voltage.
  • the lighting device showing the light emitting device having the first electrode 401, the EL layer 403, and the second electrode 404 in the present embodiment is provided. Since the light emitting device is a light emitting device having high luminous efficiency, the lighting device in the present embodiment can be a lighting device having low power consumption.
  • the lighting device is completed by fixing the substrate 400 on which the light emitting device having the above configuration is formed and the sealing substrate 407 using the sealing material 405 and the sealing material 406 and sealing them. Either the sealing material 405 and the sealing material 406 may be used. Further, a desiccant can be mixed with the inner sealing material 406 (not shown in FIG. 6A), whereby moisture can be adsorbed, which leads to improvement in reliability.
  • the pad 412 and a part of the first electrode 401 can be used as an external input terminal.
  • an IC chip 420 or the like on which a converter or the like is mounted may be provided on the IC chip 420.
  • the lighting device according to the present embodiment uses the light emitting device according to the second embodiment for the EL element, and can be a light emitting device having low power consumption.
  • the light emitting device according to the second embodiment is a light emitting device having good luminous efficiency and low power consumption.
  • the electronic device described in the present embodiment can be an electronic device having a light emitting unit having low power consumption.
  • Examples of electronic devices to which the above light emitting device is applied include television devices (also referred to as televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (mobile phones, etc.). (Also referred to as a mobile phone device), a portable game machine, a mobile information terminal, a sound reproduction device, a large game machine such as a pachinko machine, and the like. Specific examples of these electronic devices are shown below.
  • FIG. 7A shows an example of a television device.
  • the display unit 7103 is incorporated in the housing 7101. Further, here, a configuration in which the housing 7101 is supported by the stand 7105 is shown. An image can be displayed by the display unit 7103, and the display unit 7103 is configured by arranging the light emitting devices according to the second embodiment in a matrix.
  • the operation of the television device can be performed by an operation switch provided in the housing 7101 or a separate remote control operation machine 7110.
  • the operation key 7109 included in the remote control operation device 7110 can be used to operate the channel and volume of the television device, and can operate the image displayed on the display unit 7103.
  • the remote controller 7110 may be provided with a display unit 7107 for displaying information output from the remote controller 7110.
  • the television device shall be configured to include a receiver, a modem, and the like.
  • the receiver can receive general television broadcasts, and by connecting to a wired or wireless communication network via a modem, one-way (sender to receiver) or two-way (sender and receiver). It is also possible to perform information communication between (or between receivers, etc.).
  • FIG. 7B1 is a computer, which includes a main body 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like.
  • This computer is manufactured by arranging the light emitting devices according to the second embodiment in a matrix and using them in the display unit 7203.
  • the computer of FIG. 7B1 may have the form shown in FIG. 7B2.
  • the computer of FIG. 7B2 is provided with a second display unit 7210 instead of the keyboard 7204 and the pointing device 7206.
  • the second display unit 7210 is a touch panel type, and input can be performed by operating the input display displayed on the second display unit 7210 with a finger or a dedicated pen.
  • the second display unit 7210 can display not only the input display but also other images. Further, the display unit 7203 may also be a touch panel. By connecting the two screens with a hinge, it is possible to prevent troubles such as damage or damage to the screens during storage or transportation.
  • FIG. 7C shows an example of a mobile terminal.
  • the mobile terminal includes an operation button 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like, in addition to the display unit 7402 incorporated in the housing 7401.
  • the mobile terminal includes a display unit 7402 manufactured by arranging the light emitting devices according to the second embodiment in a matrix.
  • the mobile terminal shown in FIG. 7C may be configured so that information can be input by touching the display unit 7402 with a finger or the like. In this case, operations such as making a phone call or composing an e-mail can be performed by touching the display unit 7402 with a finger or the like.
  • the screen of the display unit 7402 mainly has three modes. The first is a display mode mainly for displaying an image, and the second is an input mode mainly for inputting information such as characters. The third is a display + input mode in which two modes, a display mode and an input mode, are mixed.
  • the display unit 7402 may be set to a character input mode mainly for inputting characters, and the characters displayed on the screen may be input. In this case, it is preferable to display the keyboard or the number button on most of the screen of the display unit 7402.
  • the orientation (vertical or horizontal) of the mobile terminal is determined, and the screen display of the display unit 7402 is automatically displayed. Can be switched.
  • the screen mode can be switched by touching the display unit 7402 or by operating the operation button 7403 of the housing 7401. It is also possible to switch depending on the type of the image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is moving image data, the display mode is switched, and if the image signal is text data, the input mode is switched.
  • the input mode the signal detected by the optical sensor of the display unit 7402 is detected, and if there is no input by the touch operation of the display unit 7402 for a certain period of time, the screen mode is switched from the input mode to the display mode. You may control it.
  • the display unit 7402 can also function as an image sensor.
  • the person can be authenticated by touching the display unit 7402 with a palm or a finger and taking an image of a palm print, a fingerprint, or the like.
  • a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display unit, it is possible to image finger veins, palmar veins, and the like.
  • FIG. 8A is a schematic diagram showing an example of a cleaning robot.
  • the cleaning robot 5100 has a display 5101 arranged on the upper surface, a plurality of cameras 5102 arranged on the side surface, a brush 5103, and an operation button 5104. Although not shown, the lower surface of the cleaning robot 5100 is provided with tires, suction ports, and the like.
  • the cleaning robot 5100 also includes various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, an optical sensor, and a gyro sensor. Further, the cleaning robot 5100 is provided with a wireless communication means.
  • the cleaning robot 5100 is self-propelled, can detect dust 5120, and can suck dust from a suction port provided on the lower surface.
  • the cleaning robot 5100 can analyze the image taken by the camera 5102 and determine the presence or absence of an obstacle such as a wall, furniture, or a step. Further, when an object that is likely to be entangled with the brush 5103 such as wiring is detected by image analysis, the rotation of the brush 5103 can be stopped.
  • the display 5101 can display the remaining battery level, the amount of sucked dust, and the like.
  • the route traveled by the cleaning robot 5100 may be displayed on the display 5101. Further, the display 5101 may be a touch panel, and the operation buttons 5104 may be provided on the display 5101.
  • the cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone.
  • the image taken by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when he / she is out. Further, the display of the display 5101 can be confirmed by a portable electronic device such as a smartphone.
  • the light emitting device of one aspect of the present invention can be used for the display 5101.
  • the robot 2100 shown in FIG. 8B includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.
  • the microphone 2102 has a function of detecting a user's voice, environmental sound, and the like. Further, the speaker 2104 has a function of emitting sound.
  • the robot 2100 can communicate with the user by using the microphone 2102 and the speaker 2104.
  • the display 2105 has a function of displaying various information.
  • the robot 2100 can display the information desired by the user on the display 2105.
  • the display 2105 may be equipped with a touch panel. Further, the display 2105 may be a removable information terminal, and by installing the display 2105 at a fixed position of the robot 2100, charging and data transfer are possible.
  • the upper camera 2103 and the lower camera 2106 have a function of photographing the surroundings of the robot 2100. Further, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the traveling direction when the robot 2100 moves forward by using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely by using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107.
  • the light emitting device of one aspect of the present invention can be used for the display 2105.
  • FIG. 8C is a diagram showing an example of a goggle type display.
  • the goggle type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, a connection terminal 5006, and a sensor 5007 (force, displacement, position, speed, acceleration, angular speed, rotation speed, distance, light, liquid, etc. Includes functions to measure magnetism, temperature, chemicals, voice, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), microphone 5008, display 5002 , Support portion 5012, earphone 5013, etc.
  • the light emitting device of one aspect of the present invention can be used for the display unit 5001 and the display unit 5002.
  • FIG. 9 is an example in which the light emitting device according to the second embodiment is used for a desk lamp which is a lighting device.
  • the desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002, and the lighting device according to the third embodiment may be used as the light source 2002.
  • FIG. 10 is an example in which the light emitting device according to the second embodiment is used as an indoor lighting device 3001. Since the light emitting device according to the second embodiment is a light emitting device having high luminous efficiency, it can be a lighting device having low power consumption. Further, since the light emitting device according to the second embodiment can have a large area, it can be used as a lighting device having a large area. Further, since the light emitting device according to the second embodiment is thin, it can be used as a thin lighting device.
  • the light emitting device according to the second embodiment can also be mounted on the windshield and dashboard of an automobile.
  • FIG. 11 shows an aspect in which the light emitting device according to the second embodiment is used for a windshield and a dashboard of an automobile.
  • the display area 5200 to the display area 5203 are displays provided by using the light emitting device according to the second embodiment.
  • the display area 5200 and the display area 5201 are display devices equipped with the light emitting device according to the second embodiment provided on the windshield of the automobile.
  • the light emitting device according to the second embodiment can be a so-called see-through display device in which the opposite side can be seen through by manufacturing the first electrode and the second electrode with electrodes having translucency. .. If the display is in a see-through state, even if it is installed on the windshield of an automobile, it can be installed without obstructing the view.
  • a transistor for driving it is preferable to use a transistor having translucency, such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor.
  • the display area 5202 is a display device provided with the light emitting device according to the second embodiment provided in the pillar portion.
  • the display area 5203 provided in the dashboard portion compensates for blind spots and enhances safety by projecting an image from an imaging means provided on the outside of the automobile in a field of view blocked by the vehicle body. Can be done. By projecting the image so as to complement the invisible part, it is possible to confirm the safety more naturally and without discomfort.
  • the display area 5203 can provide various information such as navigation information, running speed, engine speed, mileage, and remaining amount of fuel.
  • the display items and layout can be changed as appropriate according to the user's preference. It should be noted that these information can also be provided in the display area 5200 to the display area 5202. Further, the display area 5200 to the display area 5203 can also be used as a lighting device.
  • FIGS. 12A and 12B show a foldable mobile information terminal 5150.
  • the foldable personal digital assistant 5150 includes a housing 5151, a display area 5152, and a bent portion 5153.
  • FIG. 12A shows a mobile information terminal 5150 in an expanded state.
  • FIG. 12B shows a mobile information terminal in a folded state.
  • the portable information terminal 5150 has a large display area 5152, it is compact and excellent in portability when folded.
  • the display area 5152 can be folded in half by the bent portion 5153.
  • the bent portion 5153 is composed of a stretchable member and a plurality of support members, and when folded, the stretchable member stretches.
  • the bent portion 5153 is folded with a radius of curvature of 2 mm or more, preferably 3 mm or more.
  • the display area 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device).
  • the light emitting device of one aspect of the present invention can be used for the display area 5152.
  • FIGS. 13A to 13C show a foldable mobile information terminal 9310.
  • FIG. 13A shows a mobile information terminal 9310 in an expanded state.
  • FIG. 13B shows a mobile information terminal 9310 in a state of being changed from one of the expanded state or the folded state to the other.
  • FIG. 13C shows a mobile information terminal 9310 in a folded state.
  • the mobile information terminal 9310 is excellent in portability in the folded state, and is excellent in the listability of the display due to the wide seamless display area in the unfolded state.
  • the display panel 9311 is supported by three housings 9315 connected by a hinge 9313.
  • the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Further, the display panel 9311 can be reversibly deformed from the unfolded state to the folded state of the portable information terminal 9310 by bending between the two housings 9315 via the hinge 9313.
  • the light emitting device of one aspect of the present invention can be used for the display panel 9311.
  • the configurations shown in the present embodiment can be used by appropriately combining the configurations shown in the first to fourth embodiments.
  • the range of application of the light emitting device provided with the light emitting device according to the second embodiment is extremely wide, and this light emitting device can be applied to electronic devices in all fields.
  • an electronic device having low power consumption can be obtained.
  • Step 1 Synthesis of 5-chloro-2- (3,5-dimethylphenyl) -3-methylpyrazine> 2-Bromo-5-chloro-3-methylpyrazine 4.6 g (22 mmol), 3,5-dimethylphenylboronic acid 3.3 g (22 mmol), tripotassium phosphate 9.3 g (44 mmol), acetonitrile 50 mL, water 5 mL was placed in a 100 mL round bottom flask, and the inside of the flask was replaced with argon.
  • step 1 The synthesis scheme of step 1 is shown in the following formula (a-1).
  • Step 2 Synthesis of 5- (4-cyano-2-methylphenyl) -2- (3,5-dimethylphenyl) -3-methylpyrazine (abbreviation: Hdmmppr-mCP)> 1.2 g (5.2 mmol) of 5-chloro-2- (3,5-dimethylphenyl) -3-methylpyrazine and 1.0 g (6.) of 4-cyano-2-methylphenylboronic acid synthesized in step 1.
  • step 3 The synthesis scheme of step 3 is shown in the following formula (a-3).
  • Step 4 Synthesis of [Ir (dmmppr-mCP) 2 (debm)]> 20 mL of 2-ethoxyethanol, [Ir (dmmppr-mCP) 2 Cl] 2 0.39 g (0.23 mmol), 3,7-diethylnonane-4,6-dione 0.15 g (0.69 mmol), and sodium carbonate 0.24 g (2.3 mmol) was placed in a 100 mL round bottom flask, and the inside of the flask was substituted with argon. The reaction vessel was irradiated with microwaves (2.45 GHz 120 W) for 2 hours to react.
  • the obtained red solid was recrystallized from dichloromethane / ethanol to obtain 0.19 g of the red solid and a yield of 40%. 0.17 g of the obtained red solid was sublimated and purified by the train sublimation method. It was heated at 270 ° C. for 22 hours under the conditions of a pressure of 2.6 Pa and an argon flow rate of 10.6 mL / min. After sublimation purification, 0.12 g of a red solid was obtained with a recovery rate of 68%.
  • the synthesis scheme of step 4 is shown in the following formula (a-4).
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the dichloromethane solution of [Ir (dmmppr-mCP) 2 (debm)] were measured.
  • the absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation), a dichloromethane solution (0.0115 mmol / L) was placed in a quartz cell, and the measurement was performed at room temperature.
  • An absolute PL quantum yield measuring device (C11347-01 manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum, and a glove box (LABstar M13 (1250/780) manufactured by Bright Co., Ltd.) was used to create a nitrogen atmosphere.
  • a dichloromethane deoxidizing solution (0.0115 mmol / L) was placed in a quartz cell, sealed tightly, and measured at room temperature. The measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • the thin solid line shows the absorption spectrum and the thick solid line shows the emission spectrum.
  • the absorption spectrum shown in FIG. 15 shows the result of subtracting the absorption spectrum measured by putting only dichloromethane in the quartz cell from the absorption spectrum measured by putting the dichloromethane solution (0.0115 mmol / L) in the quartz cell.
  • the organometallic complex [Ir (dmmppr-mCP) 2 (dbm)] had an emission peak at 639 nm, and red emission was observed from dichloromethane.
  • Step 1 Synthesis of 5-chloro-2- (3-t-butyl-5-methylphenyl) -3-methylpyrazine> 2-bromo-5-chloro-3-methylpyrazine 2.5 g (12 mmol), 3-t-butyl-5-methylphenylboronic acid 2.3 g (12 mmol), tripotassium phosphate 5.1 g (24 mmol), [ 1,1'-Bis (diphenylphosphino) ferrocene] Palladium (II) dichloride dichloromethane additive 0.90 g (1.1 mmol), 50 mL of acetonitrile and 5 mL of water were placed in a 100 mL round bottom flask, and the inside of the flask was replaced with argon.
  • step 1 The synthesis scheme of step 1 is shown in the following formula (b-1).
  • Step 2 Synthesis of 5- (4-cyano-2-methylphenyl) -2- (3-t-butyl-5-methylphenyl) -3-methylpyrazine> 5-Chloro-2- (3-t-butyl-5-methylphenyl) -3-methylpyrazine 1.5 g (5.5 mmol) synthesized in step 1, 4-cyano-2-methylphenylboronic acid 1.1 g (6.6 mmol), 3.5 g (16 mmol) of tripotassium phosphate, 49 mL of toluene, and 5 mL of water were placed in a 300 mL three-necked flask, the inside of the flask was replaced with nitrogen, and the inside of the flask was stirred while reducing the pressure to degas the mixture.
  • tris (dibenzylideneacetone) dipalladium (0) 0.051 g (0.056 mmol) and tris (2,6-dimethoxyphenyl) phosphine 0.096 g (0.22 mmol) were added, and under a nitrogen stream, 110 The mixture was stirred at ° C for 8 hours.
  • the white solid obtained by nuclear magnetic resonance (NMR) is 5- (4-cyano-2-methylphenyl) -2- (3-t-butyl-5-methylphenyl) -3-methylpyrazine. confirmed.
  • the synthesis scheme of step 2 is shown in the following formula (b-2).
  • Step 3 Bis ⁇ 4-t-butyl-6-methyl-2- [5- (4-cyano-2-methylphenyl) -3-methyl-2-pyrazinyl- ⁇ N] phenyl- ⁇ C ⁇ (3,7) -Diethyl-4,6-nonandionato- ⁇ 2O, O') Synthesis of iridium (III) (abbreviation: [Ir (tBummppr-mCP) 2 (dbm)])> 1.26 g (3.) 5- (4-cyano-2-methylphenyl) -2- (3-t-butyl-5-methylphenyl) -3-methylpyrazine (abbreviation: HtBummppr-mCP) synthesized in step 2.
  • step 3 The synthesis scheme of step 3 is shown in the following formula (b-3).
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the dichloromethane solution of [Ir (tBummppr-mCP) 2 (debm)] were measured.
  • the absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation), a dichloromethane solution (0.0110 mmol / L) was placed in a quartz cell, and the measurement was performed at room temperature.
  • An absolute PL quantum yield measuring device (C11347-01 manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum, and a glove box (LABstar M13 (1250/780) manufactured by Bright Co., Ltd.) was used to create a nitrogen atmosphere.
  • a dichloromethane deoxidizing solution (0.0110 mmol / L) was placed in a quartz cell, sealed tightly, and measured at room temperature.
  • the measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • the absorption spectrum shown in FIG. 17 shows the result of subtracting the absorption spectrum measured by putting only dichloromethane in the quartz cell from the absorption spectrum measured by putting the dichloromethane solution (0.0110 mmol / L) in the quartz cell. There is.
  • the iridium complex [Ir (tBummppr-mCP) 2 (debm)] had an emission peak at 632 nm, and red emission was observed from dichloromethane.
  • the light emitting device 1, the light emitting device 2, the light emitting device 3, and the organometallic complex according to one aspect of the present invention, [Ir (dmmppr-mCP) 2 (debm)] (structural formula (100)), are used.
  • the light emitting device 4 were produced respectively. The production of each light emitting device will be described with reference to FIG. The chemical formulas of the materials used in this example are shown below.
  • ITO indium tin oxide
  • silicon oxide was formed on a glass substrate 900 by a sputtering method to form a first electrode 901 that functions as an anode.
  • the film thickness was 70 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 1 ⁇ 10 -4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate 900 was placed at 30. Allowed to cool for about a minute.
  • the substrate 900 was fixed to a holder provided in the vacuum vapor deposition apparatus so that the surface on which the first electrode 901 was formed was facing downward.
  • the hole injection layer 911, the hole transport layer 912, the light emitting layer 913, the electron transport layer 914, and the electron injection layer 915 constituting the EL layer 902 are sequentially formed by the vacuum vapor deposition method will be described. ..
  • PCBBiF was deposited at 90 nm to form a hole transport layer 912.
  • a light emitting layer 913 was formed on the hole transport layer 912.
  • 9mDBTBPNfpr was vapor-deposited on the light emitting layer 913 at 30 nm, and then NBphen was deposited at 15 nm to form an electron transport layer 914.
  • Table 1 shows the element structures of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4 obtained as described above.
  • the produced light emitting device 1, light emitting device 2, light emitting device 3, and light emitting device 4 were sealed in a glove box having a nitrogen atmosphere so as not to be exposed to the atmosphere (a sealing material was applied around the element and sealed. UV treatment at stop and heat treatment at 80 ° C. for 1 hour).
  • the current density-luminance characteristics of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4 are shown in FIG. 19, the voltage-luminance characteristics are shown in FIG. 20, the brightness-current efficiency characteristics are shown in FIG. Is shown in FIG.
  • the main initial characteristic values of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4 in the vicinity of 1000 cd / m 2 are shown in Table 2 below.
  • FIG. 23 shows the emission spectra of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4 in the vicinity of 1000 cd / m 2 .
  • the emission spectra of the light emitting device 1, the light emitting device 2, the light emitting device 3, and the light emitting device 4 all have a peak near 642 nm.
  • the vertical axis shows the normalized luminance (%) when the initial luminance is 100%
  • the horizontal axis shows the driving time (h) of the element.
  • the reliability test was carried out with the current density fixed at 75 mA / cm 2 .
  • the light emitting device used showed high reliability as the concentration of [Ir (dmmppr-mCP) 2 (debm)] decreased. This is considered to be due to the relaxation of the carrier trapping property due to the dopant. In configurations where a small amount of dopant is added, the dopant has the ability to trap carriers. It is considered that by reducing the concentration of this dopant, the trapping property was relaxed, the drive voltage was reduced, the localization inside the light emitting layer of the carrier was relaxed, the light emitting region was expanded accordingly, and the life was extended. Be done.
  • a light emitting device 5 using the organometallic complex [Ir (tBummppr-mCP) 2 (debm)] (structural formula (101)), which is one aspect of the present invention, is produced, and various light emitting devices 5 are manufactured.
  • the evaluation result of the characteristic will be described.
  • the production of the light emitting device 5 is substantially the same as that in the third embodiment. Therefore, in this embodiment, the points different from those in the third embodiment will be mainly described.
  • the chemical formulas of the materials used in this example, which are not shown in Example 3, are shown below.
  • the light emitting device 5 differs from the light emitting devices 1 to 4 shown in Example 3 in the configurations of the hole injection layer 911, the light emitting layer 913, and the electron transport layer 914.
  • the film thickness was 10 nm, which was the same as in Example 3.
  • Table 3 shows the element structure of the light emitting device 5 obtained as described above.
  • the produced light emitting device 5 was sealed in a glove box having a nitrogen atmosphere so as not to be exposed to the atmosphere (a sealing material was applied around the element, UV treatment was performed at the time of sealing, and heat treatment was performed at 80 ° C. for 1 hour. did.).
  • the current density-luminance characteristic of the light emitting device 5 is shown in FIG. 25, the voltage-luminance characteristic is shown in FIG. 26, the brightness-current efficiency characteristic is shown in FIG. 27, and the voltage-current characteristic is shown in FIG. 28.
  • FIG. 29 shows the emission spectrum of the light emitting device 5 in the vicinity of 1000 cd / m 2 . As shown in FIG. 29, it can be seen that the emission spectrum of the emission device 5 has a peak near 638 nm.
  • the reliability test was carried out with the current density fixed at 75 mA / cm 2 .
  • the light emitting device 5 has higher reliability than the light emitting devices 1 to 4.

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JP2010120931A (ja) * 2008-10-23 2010-06-03 Semiconductor Energy Lab Co Ltd 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器
JP2017066135A (ja) * 2015-09-30 2017-04-06 株式会社半導体エネルギー研究所 有機金属錯体、発光素子、発光装置、電子機器、および照明装置
JP2017114853A (ja) * 2015-12-18 2017-06-29 株式会社半導体エネルギー研究所 有機金属錯体、発光素子、発光装置、電子機器、および照明装置

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JP2007284432A (ja) * 2006-03-21 2007-11-01 Semiconductor Energy Lab Co Ltd 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器
JP2010120931A (ja) * 2008-10-23 2010-06-03 Semiconductor Energy Lab Co Ltd 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器
JP2017066135A (ja) * 2015-09-30 2017-04-06 株式会社半導体エネルギー研究所 有機金属錯体、発光素子、発光装置、電子機器、および照明装置
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