WO2018178818A1 - Organic compound, light emitting element, light emitting device, electronic equipment, and lighting device - Google Patents

Organic compound, light emitting element, light emitting device, electronic equipment, and lighting device Download PDF

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WO2018178818A1
WO2018178818A1 PCT/IB2018/051913 IB2018051913W WO2018178818A1 WO 2018178818 A1 WO2018178818 A1 WO 2018178818A1 IB 2018051913 W IB2018051913 W IB 2018051913W WO 2018178818 A1 WO2018178818 A1 WO 2018178818A1
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light
carbon atoms
substituted
unsubstituted
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PCT/IB2018/051913
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French (fr)
Japanese (ja)
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鈴木宏記
瀬尾哲史
鈴木恒徳
門間裕史
橋本直明
滝田悠介
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株式会社半導体エネルギー研究所
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Publication of WO2018178818A1 publication Critical patent/WO2018178818A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

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  • One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device.
  • one embodiment of the present invention is not limited to the above technical field. That is, one embodiment of the present invention relates to an object, a method, a manufacturing method, or a driving method. Alternatively, one embodiment of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter).
  • a semiconductor device, a display device, a liquid crystal display device, and the like can be given as examples.
  • a light-emitting element (also referred to as an organic EL element) in which an EL layer is sandwiched between a pair of electrodes has characteristics such as thin and light weight, high-speed response to input signals, and low power consumption. It is attracting attention as a next-generation flat panel display.
  • the light-emitting element by applying a voltage between a pair of electrodes, electrons and holes injected from each electrode are recombined in the EL layer, and a light-emitting substance (organic compound) contained in the EL layer is in an excited state. Light is emitted when the excited state returns to the ground state.
  • the types of excited states include a singlet excited state (S * ) and a triplet excited state (T * ). Light emitted from the singlet excited state is fluorescent, and light emitted from the triplet excited state is phosphorescent. being called.
  • An emission spectrum obtained from the light-emitting substance is peculiar to the light-emitting substance, and light-emitting elements having various emission colors can be obtained by using different kinds of organic compounds as the light-emitting substance.
  • a novel organic compound used for the light emitting element is very important for enhancing its characteristics.
  • a novel organic compound is provided. That is, a novel organic compound that is effective in improving device characteristics and reliability is provided.
  • a novel organic compound that can be used for a light-emitting element is provided.
  • a novel organic compound that can be used for an EL layer of a light-emitting element is provided.
  • a novel light-emitting element with high efficiency and high reliability using the novel organic compound which is one embodiment of the present invention is provided.
  • One embodiment of the present invention is an organic compound having a condensed ring structure in a carbazole skeleton and represented by the following general formula (G1).
  • Ar 1 represents a substituted or unsubstituted phenylene group.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • 6 alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ⁇ 13 aryl groups.
  • Another embodiment of the present invention is an organic compound represented by General Formula (G2) below.
  • Ar 2 represents an unsubstituted phenylene group.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • Another embodiment of the present invention is an organic compound represented by General Formula (G3) below.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • Another embodiment of the present invention is an organic compound represented by General Formula (G4) below.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • at least one of R 9 and R 10 , and R 11 and R 12 is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent.
  • Alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms having 6 to 6 carbon atoms Any of the 13 aryl groups.
  • the organic compound which is one embodiment of the present invention described above has a condensed ring structure in the carbazole skeleton.
  • one benzene ring forming the carbazole skeleton has a structure condensed at two or more positions.
  • a guest material dopant
  • it when it uses in combination with a guest material (dopant), it has the characteristic that the energy transfer to a dopant can be performed efficiently by having such a structure.
  • the arylene group bonded to nitrogen of the carbazole skeleton is an unsubstituted phenylene group, steric hindrance in the molecule can be prevented, and thus it can be easily synthesized.
  • Another embodiment of the present invention is an organic compound represented by Structural Formula (100), Structural Formula (101), Structural Formula (102), or Structural Formula (103).
  • Another embodiment of the present invention is a light-emitting element using an organic compound having a condensed ring structure in a carbazole skeleton. Note that a light-emitting element including a guest material in addition to the above organic compound is also included in the present invention.
  • Another embodiment of the present invention is a light-emitting element using the organic compound which is one embodiment of the present invention.
  • a light-emitting element formed using the organic compound which is one embodiment of the present invention for an EL layer between a pair of electrodes or a light-emitting layer included in the EL layer is also included in the present invention.
  • a light-emitting device including a transistor, a substrate, and the like is also included in the scope of the invention.
  • an electronic device or lighting device including a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support base, a speaker, or the like is also included in the scope of the invention.
  • One embodiment of the present invention includes a light-emitting device including a light-emitting element, and further includes a lighting device including the light-emitting device. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device).
  • a module in which a connector such as FPC (Flexible printed circuit) or TCP (Tape Carrier Package) is attached to a light emitting device a module in which a printed wiring board is provided at the end of TCP, or a COG (Chip On All modules in which IC (integrated circuit) is directly mounted by the (Glass) method are also included in the light emitting device.
  • One embodiment of the present invention can provide a novel organic compound. That is, it is possible to provide a novel organic compound effective for enhancing device characteristics.
  • a novel organic compound that can be used for a light-emitting element can be provided.
  • a novel organic compound that can be used for an EL layer of a light-emitting element can be provided.
  • a novel light-emitting element with high efficiency and high reliability using the novel organic compound which is one embodiment of the present invention can be provided.
  • a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. Note that the description of these effects does not disturb the existence of other effects.
  • FIG. 4A and 4B illustrate a structure of a light-emitting element.
  • FIG. 6 illustrates a light-emitting device.
  • FIG. 6 illustrates a light-emitting device.
  • 6A and 6B illustrate electronic devices.
  • 6A and 6B illustrate electronic devices.
  • FIG. 11 shows current density-luminance characteristics of Light-Emitting Element 1 and Light-Emitting Element 2.
  • FIG. 11 shows voltage-luminance characteristics of Light-Emitting Element 1 and Light-Emitting Element 2.
  • FIG. 6 shows luminance-current efficiency characteristics of the light-emitting element 1 and the light-emitting element 2;
  • FIG. 10 shows voltage-current characteristics of the light-emitting element 1 and the light-emitting element 2;
  • FIG. 6 shows emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3.
  • FIG. 9 shows reliability of the light-emitting element 1 and the comparative light-emitting element 3.
  • FIG. 6 shows current density-luminance characteristics of the light-emitting element 4;
  • FIG. 11 shows voltage-luminance characteristics of the light-emitting element 4;
  • FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 4;
  • FIG. 11 shows voltage-current characteristics of the light-emitting element 4;
  • FIG. 6 shows an emission spectrum of the light-emitting element 4.
  • FIG. 6 shows reliability of the light-emitting element 4.
  • the organic compound described in this embodiment has a structure represented by the following general formula (G1), which has a condensed ring structure in a carbazole skeleton.
  • Ar 1 represents a substituted or unsubstituted phenylene group.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • 6 alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ⁇ 13 aryl groups.
  • the organic compound shown in this embodiment is represented by the following general formula (G2).
  • Ar 2 represents an unsubstituted phenylene group.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • the organic compound shown in this embodiment is represented by the following general formula (G3).
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • the organic compound shown in this embodiment is represented by the following general formula (G4).
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • at least one of R 9 and R 10 , and R 11 and R 12 is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent.
  • Alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms having 6 to 6 carbon atoms Any of the 13 aryl groups.
  • a substituted or unsubstituted phenylene group a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon number 7
  • the substituent is a methyl group, an ethyl group, a propyl group, isopropyl Group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, alkyl group having 1 to 6 carbon atoms, cyclopentyl group, cyclohexyl group, cycloheptyl group, 8,9,
  • Examples thereof include cycloalkyl groups having 5 to 7 carbon atoms such as 10-trin
  • alkyl group having 1 to 6 carbon atoms in the general formulas (G1) to (G4) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2 -A dimethylbutyl group, a 2, 3- dimethylbutyl group, etc. are mentioned.
  • Specific examples of the monocyclic saturated hydrocarbon having 5 to 7 carbon atoms in the general formulas (G1) to (G4) include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 2-methylcyclohexyl group, and the like. It is done.
  • polycyclic saturated hydrocarbon having 7 to 10 carbon atoms in the general formulas (G1) to (G4) include an 8,9,10-trinorbornanyl group, a decahydronaphthyl group, and an adamantyl group. Etc.
  • aryl group having 6 to 13 carbon atoms in the general formulas (G1) to (G4) include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o- Biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group and the like can be mentioned.
  • the organic compound which is one embodiment of the present invention represented by the above general formulas (G1) to (G4) has a condensed ring structure in the carbazole skeleton.
  • one benzene ring forming the carbazole skeleton has a structure condensed at two or more positions.
  • a guest material dopant
  • it when it uses in combination with a guest material (dopant), it has the characteristic that the energy transfer to a dopant can be performed efficiently by having such a structure.
  • the arylene group bonded to nitrogen of the carbazole skeleton is an unsubstituted phenylene group, it has a feature that steric hindrance in the molecule can be prevented and that it can be easily synthesized.
  • organic compound represented by the structural formulas (100) to (144) is an example of the organic compound represented by the general formula (G1), and the organic compound which is one embodiment of the present invention includes Not limited.
  • Ar 1 represents a substituted or unsubstituted phenylene group.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • 6 alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ⁇ 13 aryl groups.
  • the organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (A-1) shown below. That is, the heterocyclic compound derivative (a1) and the halide (a2) of the anthracene derivative are coupled with a metal catalyst, a metal, or a metal compound in the presence of a base, thereby being represented by the above general formula (G1). An organic compound can be obtained.
  • Ar 1 represents a substituted or unsubstituted phenylene group.
  • X represents halogen.
  • R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms.
  • 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent.
  • 6 alkyl groups substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ⁇ 13 aryl groups.
  • X represents a halogen or a triflate group.
  • halogen iodine, bromine or chlorine is preferable.
  • palladium complexes or palladium compounds such as bis (dibenzylideneacetone) palladium (0) and palladium (II) acetate, and tri (tert-butyl) phosphine coordinated thereto, tri (n-hexyl) phosphine,
  • a palladium catalyst using a ligand such as tricyclohexylphosphine is used.
  • the base examples include organic bases such as sodium tert-butoxide, inorganic bases such as potassium carbonate, and the like. Moreover, when using a solvent, toluene, xylene, benzene, tetrahydrofuran, etc. can be used.
  • X represents a halogen.
  • halogen iodine, bromine or chlorine is preferable.
  • the catalyst copper or a copper compound is used.
  • R 22 and R 23 in the formula (A-1) each represent a halogen, an acetyl group or the like, and examples of the halogen include chlorine, bromine and iodine.
  • copper iodide (I) which is iodine as R 22 or copper acetate (II) where R 23 is an acetyl group.
  • the base to be used include inorganic bases such as potassium carbonate.
  • DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone
  • the said solvent is not restricted to these.
  • DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone
  • the target product can be obtained in a shorter time and with a higher yield when the reaction temperature is 100 ° C. or higher, it is preferable to use DMPU or xylene having a high boiling point.
  • DMPU is used more preferably.
  • the above-described organic compound which is one embodiment of the present invention has an electron transporting property and a hole transporting property, and thus can be used as a host material for the light-emitting layer, or for an electron transporting layer and a hole transporting layer. Further, it is preferably used as a host material in combination with a substance that emits fluorescence (fluorescent material). Further, since it exhibits fluorescence, it can be used as a light-emitting substance of the light-emitting element itself. Therefore, a light-emitting element including any of these organic compounds is also one embodiment of the present invention.
  • a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency can be realized.
  • a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be realized.
  • Embodiment 2 In this embodiment, a light-emitting element using the organic compound described in Embodiment 1 will be described with reference to FIGS.
  • FIG. 1A illustrates a light-emitting element having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, the EL layer 103 is sandwiched between the first electrode 101 and the second electrode 102.
  • FIG. 1B a plurality of (two layers in FIG. 1B) EL layers (103a and 103b) are provided between a pair of electrodes, and the charge generation layer 104 is provided between the EL layers.
  • 1 illustrates a light-emitting element having a stacked structure (tandem structure).
  • a light-emitting element having a tandem structure can realize a light-emitting device that can be driven at a low voltage and has low power consumption.
  • the charge generation layer 104 injects electrons into one EL layer (103a or 103b) and the other EL layer (103b or 103a). It has a function of injecting holes. Therefore, in FIG. 1B, when a voltage is applied to the first electrode 101 so that the potential is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a, and the EL layer 103b. Holes are injected into this.
  • the charge generation layer 104 has a property of transmitting visible light in terms of light extraction efficiency (specifically, the visible light transmittance of the charge generation layer 104 is 40% or more). preferable. In addition, the charge generation layer 104 functions even when it has lower conductivity than the first electrode 101 or the second electrode 102.
  • FIG. 1C illustrates a stacked structure of the EL layer 103 of the light-emitting element which is one embodiment of the present invention.
  • the first electrode 101 functions as an anode.
  • the EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked over the first electrode 101.
  • a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked over the first electrode 101.
  • each EL layer is sequentially stacked from the anode side as described above.
  • the stacking order is reversed.
  • Each of the light-emitting layers 113 included in the EL layers (103, 103a, and 103b) includes a light-emitting substance and a plurality of substances as appropriate in combination, so that fluorescent light emission or phosphorescence light emission having a desired light emission color can be obtained. be able to.
  • the light-emitting layer 113 may have a stacked structure with different emission colors. Note that in this case, different materials may be used for the light-emitting substance and other substances used for the stacked light-emitting layers. Alternatively, different light emission colors may be obtained from the plurality of EL layers (103a and 103b) illustrated in FIG. In this case as well, the light-emitting substance and other substances used for each light-emitting layer may be different materials.
  • the first electrode 101 illustrated in FIG. 1C is used as a reflective electrode
  • the second electrode 102 is used as a semi-transmissive / semi-reflective electrode
  • a micro optical resonator is used.
  • the (microcavity) structure light emission obtained from the light-emitting layer 113 included in the EL layer 103 can resonate between both electrodes, and light emission obtained from the second electrode 102 can be strengthened.
  • the first electrode 101 of the light-emitting element is a reflective electrode having a stacked structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film)
  • a film of the transparent conductive film Optical adjustment can be performed by controlling the thickness.
  • the distance between the first electrode 101 and the second electrode 102 is near m ⁇ / 2 (where m is a natural number) with respect to the wavelength ⁇ of light obtained from the light-emitting layer 113. It is preferable to adjust as follows.
  • an optical distance from the first electrode 101 to a region (light emitting region) where desired light of the light emitting layer is obtained, and a second The optical distance from the electrode 102 of the light emitting layer 113 to the region (light emitting region) from which desired light can be obtained is adjusted to be in the vicinity of (2m ′ + 1) ⁇ / 4 (where m ′ is a natural number). Is preferred.
  • the light emitting region herein refers to a recombination region between holes and electrons in the light emitting layer 113.
  • the spectrum of specific monochromatic light obtained from the light emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.
  • the optical distance between the first electrode 101 and the second electrode 102 is strictly the total thickness from the reflective region of the first electrode 101 to the reflective region of the second electrode 102. it can. However, since it is difficult to precisely determine the reflection region in the first electrode 101 or the second electrode 102, it is assumed that any position of the first electrode 101 and the second electrode 102 is the reflection region. The above-mentioned effect can be sufficiently obtained. Strictly speaking, the optical distance between the first electrode 101 and the light emitting layer from which desired light can be obtained is the optical distance between the reflective region in the first electrode 101 and the light emitting region in the light emitting layer from which desired light can be obtained. It can be said that it is a distance.
  • any position of the first electrode 101 can be set as the reflection region, the desired region. It is assumed that the above-described effect can be sufficiently obtained by assuming an arbitrary position of the light emitting layer from which light is obtained as a light emitting region.
  • the light-emitting element illustrated in FIG. 1C has a microcavity structure, light having different wavelengths (monochromatic light) can be extracted even when the light-emitting element has the same EL layer. Accordingly, there is no need for separate coloring (for example, RGB) for obtaining different emission colors. Therefore, it is easy to realize high definition. A combination with a colored layer (color filter) is also possible. Furthermore, since it is possible to increase the emission intensity of the specific wavelength in the front direction, it is possible to reduce power consumption.
  • the light-emitting element illustrated in FIG. 1E is an example of the light-emitting element having the tandem structure illustrated in FIG. 1B.
  • three EL layers (103a, 103b, and 103c) are charge generation layers. (104a, 104b). Note that the three EL layers (103a, 103b, and 103c) each have a light emitting layer (113a, 113b, and 113c), and the light emission colors of the light emitting layers can be freely combined.
  • the light-emitting layer 113a can be blue, the light-emitting layer 113b can be red, green, or yellow, and the light-emitting layer 113c can be blue, but the light-emitting layer 113a can be red and the light-emitting layer 113b can be blue, green, or yellow. In any case, the light emitting layer 113c may be red.
  • At least one of the first electrode 101 and the second electrode 102 includes a light-transmitting electrode (a transparent electrode, a semi-transmissive / semi-reflective electrode, or the like).
  • a light-transmitting electrode a transparent electrode
  • the transparent electrode has a visible light transmittance of 40% or more.
  • the visible light reflectance of the semi-transmissive / semi-reflective electrode is 20% to 80%, preferably 40% to 70%.
  • These electrodes preferably have a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less.
  • the reflective electrode when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode is visible.
  • the light reflectance is 40% to 100%, preferably 70% to 100%.
  • the electrode preferably has a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less.
  • the first electrode 101 is formed as a reflective electrode
  • the second electrode 102 is formed as a semi-transmissive / semi-reflective electrode. Therefore, a desired electrode material can be formed by using a single layer or a plurality of layers and forming a single layer or a stack. Note that the second electrode 102 is formed by selecting a material in the same manner as described above after the EL layer 103b is formed. In addition, a sputtering method or a vacuum evaporation method can be used for manufacturing these electrodes.
  • First electrode and second electrode> As materials for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the functions of both electrodes described above can be satisfied.
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, and the like can be used as appropriate.
  • an In—Sn oxide also referred to as ITO
  • an In—Si—Sn oxide also referred to as ITSO
  • an In—Zn oxide an In—W—Zn oxide
  • elements belonging to Group 1 or Group 2 of the periodic table of elements not exemplified above for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium Rare earth metals such as (Yb), alloys containing these in appropriate combinations, other graphene, and the like can be used.
  • the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially formed over the first electrode 101 by a vacuum evaporation method. Stacked. After the EL layer 103a and the charge generation layer 104 are formed, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 104 in the same manner.
  • the hole injection layer (111, 111a, 111b) is a layer for injecting holes from the first electrode 101, which is an anode, or the intermediate layer (104) into the EL layer (103, 103a, 103b). It is a layer containing a material having a high hole injection property.
  • Examples of the material having a high hole injection property include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide.
  • phthalocyanine compounds such as phthalocyanine (abbreviation: H 2 Pc) and copper phthalocyanine (abbreviation: 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 ( An aromatic amine compound such as abbreviation (DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (abbreviation: PEDOT / PS
  • a composite material including a hole-transporting material and an acceptor material can also be used.
  • electrons are extracted from the hole transporting material by the acceptor material, and holes are generated in the hole injection layer (111, 111a, 111b), via the hole transporting layer (112, 112a, 112b). Holes are injected into the light emitting layer (113, 113a, 113b).
  • the hole injection layer (111, 111a, 111b) may be formed as a single layer made of a composite material including a hole transporting material and an acceptor material (electron accepting material).
  • the material and the acceptor material (electron-accepting material) may be stacked in separate layers.
  • the hole transport layer (112, 112a, 112b) transports holes injected from the first electrode 101 to the light emitting layer (113, 113a, 113b) by the hole injection layer (111, 111a, 111b). Is a layer.
  • the hole transport layers (112, 112a, 112b) are layers containing a hole transport material.
  • a material having a HOMO level that is the same as or close to the HOMO level of the hole injection layer (111, 111a, 111b) should be used. Is preferred.
  • an oxide of a metal belonging to Groups 4 to 8 in the periodic table can be used.
  • Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide.
  • molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.
  • organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used.
  • F 4 -TCNQ 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane
  • chloranil 2,3,6,7,10,11 -Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) or the like
  • HAT-CN 2,3,6,7,10,11 -Hexacyano-1,4,5,8,9,12-hexaazatriphenylene
  • a hole transporting material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b) a substance having a hole mobility of 10 ⁇ 6 cm 2 / Vs or more is used. preferable. Note that other than these substances, any substance that has a property of transporting more holes than electrons can be used.
  • a ⁇ -electron rich heteroaromatic compound for example, a carbazole derivative or an indole derivative
  • an aromatic amine compound is preferable.
  • 4,4′-bis [N- (1-naphthyl) is preferable.
  • NPB or ⁇ -NPD N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4,4 '-Diamine (abbreviation: TPD), 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP) ), 4-phenyl-4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP),
  • poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide] (abbreviation: PTPDMA) poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Poly High molecular compounds such as -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)
  • the hole transporting material is not limited to the above, and a hole injection layer (111, 111a, 111b) and a hole transporting layer may be used as a hole transporting material by combining one or more known various materials. (112, 112a, 112b). Note that each of the hole transport layers (112, 112a, 112b) may be formed of a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer may be laminated.
  • the light-emitting layer 113a is formed over the hole-transport layer 112a of the EL layer 103a by a vacuum evaporation method.
  • the light emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by a vacuum evaporation method.
  • the light emitting layers (113, 113a, 113b, 113c) are layers containing a light emitting substance.
  • a substance exhibiting a luminescent color such as blue, purple, blue-violet, green, yellow-green, yellow, orange, or red is appropriately used.
  • a structure exhibiting different light emission colors for example, white light emission obtained by combining light emission colors having complementary colors
  • a stacked structure in which one light emitting layer includes different light emitting substances may be used.
  • the light emitting layer may include one or more organic compounds (host material, assist material) in addition to the light emitting substance (guest material).
  • organic compounds host material, assist material
  • guest material the one or more kinds of organic compounds, one or both of a hole transporting material and an electron transporting material described in this embodiment can be used.
  • a light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b, and 113c) a light-emitting substance that changes singlet excitation energy into light emission in the visible light region, or light emission that changes triplet excitation energy into light emission in the visible light region. Substances can be used.
  • Examples of other luminescent substances include the following.
  • Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials).
  • fluorescent materials include fluorescence (fluorescent materials).
  • Examples include quinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives.
  • a pyrene derivative is preferable because of its high emission quantum yield.
  • pyrene derivative examples include N, N′-bis (3-methylphenyl) -N, N′-bis [3- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6. -Diamine (1,6mMemFLPAPrn), (N, N'-diphenyl-N, N'-bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6-diamine) (1 , 6FLPAPrn), N, N′-bis (dibenzofuran-2-yl) -N, N′-diphenylpyrene-1,6-diamine (1,6FrAPrn), N, N′-bis (dibenzothiophen-2-yl) ) -N, N′-diphenylpyrene-1,6-diamine (1,6ThAPrn), N, N ′-(pyrene-1,6-di
  • Examples of the light-emitting substance that changes triplet excitation energy into light emission include phosphorescent substances (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence. .
  • phosphorescent substances phosphorescent materials
  • TADF thermally activated delayed fluorescence
  • phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as necessary.
  • Examples of phosphorescent materials that exhibit blue or green color and whose emission spectrum peak wavelength is 450 nm or more and 570 nm or less include the following substances.
  • Examples of the phosphorescent material which exhibits green or yellow and has an emission spectrum peak wavelength of 495 nm or more and 590 nm or less include the following substances.
  • tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) 3 ]
  • tris (4-t-butyl-6-phenylpyrimidinato) iridium (III) (Abbreviation: [Ir (tBupppm) 3 ])
  • (acetylacetonato) bis (6-methyl-4-phenylpyrimidinato) iridium (III) abbreviation: [Ir (mppm) 2 (acac)]
  • Acetylacetonato bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (tBupppm) 2 (acac)]
  • Acetylacetonato) bis [6- (2- Norbornyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (nbpppm
  • Examples of the phosphorescent material which exhibits yellow or red and has an emission spectrum peak wavelength of 570 nm or more and 750 nm or less include the following substances.
  • the organic compound (host material, assist material) used for the light emitting layer (113, 113a, 113b, 113c) one or more kinds of substances having an energy gap larger than that of the light emitting substance (guest material) are selected. Use it.
  • the light-emitting substance is a fluorescent material
  • an anthracene derivative or a tetracene derivative it is preferable to use an anthracene derivative or a tetracene derivative.
  • an organic compound having a triplet excitation energy larger than the triplet excitation energy (energy difference between the ground state and the triplet excited state) of the light-emitting substance may be selected as the host material.
  • oxadiazole derivatives triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives
  • aromatic amines and carbazole derivatives can be used.
  • the following hole transporting materials and electron transporting materials can be used as the host material.
  • Examples of these host materials having a high hole transporting property include N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 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), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B)
  • An aromatic amine compound such as
  • PCzDPA1 3- [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole
  • PCzDPA2 3,6-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] -9-phenylcarbazole
  • PCzTPN2 3,6-bis [N- (4-diphenylaminophenyl) -N- (1-naphthyl) amino] -9-phenylcarbazole
  • PCzTPN2 3 -[N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole
  • PCzPCA1 3,6-bis [N- (9-phenylcarbazol-3-yl)- N-phenylamino] -9-phenylcarbazole
  • CBP 4,4′-di (N-carbazolyl) biphenyl
  • TCPB 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene
  • NPB or ⁇ -NPD 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • NPB or ⁇ -NPD 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • NPB or ⁇ -NPD N, N ′ -Bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine
  • TPD 4,4 ', 4 "-tris (carbazole- 9-yl) triphenylamine
  • TCTA 4,4 ′, 4 ′′ -tris [N- (1-naphthyl) -N-phenylamino] triphenylamine
  • 1′-TNATA 4 , 4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine
  • PCPN 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole
  • PCPPn 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole
  • PCCP 3,3′-bis (9-phenyl-9H-carbazole)
  • mCP 1,3-bis (N-carbazolyl) benzene
  • CzTP 3,6-bis ( 3,5-diphenylphenyl) -9-phenylcarbazole
  • CzTP 3,6-bis ( 3,5-diphenylphenyl) -9-phenylcarbazole
  • Examples of the host material having a high electron transporting property include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), and bis. (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis ( Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as 8-quinolinolato) zinc (II) (abbreviation: Znq).
  • bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), etc.
  • ZnPBO bis [2- (2-benzoxazolyl) phenolato] zinc
  • ZnBTZ bis [2- (2-benzothiazolyl) phenolato] zinc
  • a metal complex having an oxazole-based or thiazole-based ligand can also be used.
  • 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [4- (5-phenyl-1,3,4-oxa) Oxadiazole derivatives such as diazol-2-7yl) phenyl] -9H-carbazole (abbreviation: CO11) and 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) Triazole derivatives such as -1,2,4-triazole (abbreviation: TAZ) and 2,2 ′, 2 ′′-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole)
  • poly (2,5-pyridinediyl) (abbreviation: PPy)
  • poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py)
  • poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy)
  • PPy poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)]
  • PF-BPy Molecular compounds
  • Examples of the host material include condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives.
  • first compound and second compound are mixed with an organometallic complex. May be used.
  • various organic compounds can be used in appropriate combination.
  • a compound that easily receives holes (hole transporting material) and a compound that easily receives electrons (electrons) A combination with a transportable material) is particularly preferred.
  • the materials described in this embodiment can be used. With this configuration, high efficiency, low voltage, and long life can be realized simultaneously.
  • TADF material is a material that can up-convert triplet excited state to singlet excited state with a little thermal energy (interverse crossing) and efficiently emits light (fluorescence) from singlet excited state. is there.
  • the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less.
  • delayed fluorescence in the TADF material refers to light emission having a remarkably long lifetime while having a spectrum similar to that of normal fluorescence. The lifetime is 10 ⁇ 6 seconds or longer, preferably 10 ⁇ 3 seconds or longer.
  • TADF material examples include fullerene and derivatives thereof, acridine derivatives such as proflavine, and eosin.
  • metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like can be given.
  • metal-containing porphyrin examples include a protoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Proto IX)), a mesoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Meso IX)), and hematoporphyrin-tin fluoride.
  • SnF 2 Proto IX
  • SnF 2 mesoporphyrin-tin fluoride complex
  • hematoporphyrin-tin fluoride examples include hematoporphyrin-tin fluoride.
  • SnF 2 Hemato IX
  • SnF 2 coproporphyrin tetramethyl ester-tin fluoride complex
  • SnF 2 Copro III-4Me
  • SnF 2 octaethylporphyrin-tin fluoride complex
  • SnF 2 (OEP) Etioporphyrin-tin fluoride complex
  • PtCl 2 OEP octaethylporphyrin-platinum chloride complex
  • a substance in which a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring are directly bonded increases both the donor property of the ⁇ -electron rich heteroaromatic ring and the acceptor property of the ⁇ -electron deficient heteroaromatic ring. This is particularly preferable because the energy difference between the singlet excited state and the triplet excited state becomes small.
  • TADF material when using TADF material, it can also be used in combination with another organic compound.
  • the electron-transport layer 114a is formed over the light-emitting layer 113a of the EL layer 103a by a vacuum evaporation method.
  • the electron transport layer 114b is formed on the light emitting layer 113b of the EL layer 103b by a vacuum evaporation method.
  • the electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 to the light emitting layer (113, 113a, 113b) by the electron injection layer (115, 115a, 115b).
  • the electron transport layers (114, 114a, 114b) are layers containing an electron transport material.
  • the electron transporting material used for the electron transporting layer (114, 114a, 114b) is preferably a substance having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher. Note that other than these substances, any substance that has a property of transporting more electrons than holes can be used.
  • electron transporting materials include metal complexes having quinoline ligand, benzoquinoline ligand, oxazole ligand, or thiazole ligand, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. Is mentioned.
  • a ⁇ -electron deficient heteroaromatic compound such as a nitrogen-containing heteroaromatic compound can also be used.
  • Alq 3 tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ) , BAlq, bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (II) (abbreviation: Zn (BOX) 2 ), bis [2- (2-hydroxyphenyl) benzothiazolate] zinc (II) (abbreviation) : Metal complex such as Zn (BTZ) 2 ), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), OXD-7, 3- (4′-tert-butylphenyl) -4-phenyl-5- (4 ′′ -biphenyl) -1,2,4- (riazole (abbreviation:
  • poly (2,5-pyridinediyl) (abbreviation: PPy)
  • poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py)
  • poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy)
  • PPy poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)]
  • PF-BPy Molecular compounds
  • the electron-transport layer (114, 114a, 114b) is not limited to a single layer, and may have a structure in which two or more layers made of the above substances are stacked.
  • an electron injection layer 115a is formed over the electron transport layer 114a of the EL layer 103a by a vacuum evaporation method. Thereafter, the EL layer 103a and the charge generation layer 104 are formed, and the electron transport layer 114b of the EL layer 103b is formed, and then the electron injection layer 115b is formed thereon by a vacuum deposition method.
  • the electron injection layers (115, 115a, 115b) are layers containing a substance having a high electron injection property.
  • the electron injection layer (115, 115a, 115b) includes an alkali metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x ), or the like. Earth metals or their compounds can be used. Alternatively, a rare earth metal compound such as erbium fluoride (ErF 3 ) can be used.
  • electride may be used for the electron injection layer (115, 115a, 115b). Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum. In addition, the substance which comprises the electron carrying layer (114, 114a, 114b) mentioned above can also be used.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b).
  • a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material excellent in transporting the generated electrons.
  • an electron transport material metal complex used for the electron transport layer (114, 114a, 114b) described above, for example.
  • a heteroaromatic compound may be any substance that exhibits an electron donating property to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • the optical distance between the second electrode 102 and the light-emitting layer 113b is less than ⁇ / 4 with respect to the wavelength of light exhibited by the light-emitting layer 113b. It is preferable to form such that In this case, adjustment can be performed by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.
  • the charge generation layer 104 injects electrons into the EL layer 103a and applies holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. Has the function of injecting.
  • the charge generation layer 104 may have a structure in which an electron acceptor is added to a hole transporting material or a structure in which an electron donor (donor) is added to an electron transporting material. Good. Or both of these structures may be laminated. Note that by forming the charge generation layer 104 using the above-described material, an increase in driving voltage in the case where an EL layer is stacked can be suppressed.
  • the materials described in this embodiment can be used as the hole-transporting material.
  • the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, and the like.
  • oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.
  • the materials described in this embodiment can be used as the electron transporting material.
  • the electron donor an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Groups 2 and 13 of the periodic table, or an oxide or carbonate thereof can be used.
  • lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like is preferably used.
  • An organic compound such as tetrathianaphthacene may be used as an electron donor.
  • the EL layer 103c in FIG. 1E may have a structure similar to that of the above-described EL layers (103, 103a, and 103b).
  • the charge generation layers 104a and 104b may have the same structure as the charge generation layer 104 described above.
  • the light-emitting element described in this embodiment can be formed over various substrates.
  • substrate is not limited to a specific thing.
  • a semiconductor substrate for example, a single crystal substrate or a silicon substrate
  • an SOI substrate for example, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having stainless steel foil, a tungsten substrate
  • Examples include a substrate having a tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film.
  • examples of the material of the glass substrate include barium borosilicate glass, alumino borosilicate glass, and soda lime glass.
  • Examples of flexible substrates, bonded films, base films, etc. are synthetic materials such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyether sulfone (PES), acrylic, etc. Examples thereof include resin, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid, epoxy, an inorganic vapor deposition film, and papers.
  • a vacuum process such as an evaporation method or a solution process such as a spin coating method or an inkjet method can be used.
  • vapor deposition physical vapor deposition (PVD) such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, or vacuum vapor deposition, or chemical vapor deposition (CVD) is used. be able to.
  • PVD physical vapor deposition
  • CVD chemical vapor deposition
  • functional layers hole injection layer (111, 111a, 111b), hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport included in the EL layer of the light-emitting element.
  • a vapor deposition method vacuum vapor deposition method, etc.
  • a coating method dip coating method
  • Die coating method bar coating method
  • spin coating method spin coating method
  • spray coating method etc.
  • printing method inkjet method, screen (stencil printing) method, offset (lithographic printing) method, flexographic (letter printing) method, gravure method, microcontact And the like.
  • each functional layer (a hole injection layer (111, 111a, 111b), a hole transport layer (112, 112a, 112b) included in the EL layer (103, 103a, 103b) of the light-emitting element described in this embodiment mode.
  • the light emitting layer (113, 113a, 113b, 113c), the electron transport layer (114, 114a, 114b), the electron injection layer (115, 115a, 115b)) and the charge generation layer (104, 104a, 104b) are described above.
  • the material is not limited, and other materials can be used in combination as long as they can satisfy the function of each layer.
  • high molecular compounds oligomers, dendrimers, polymers, etc.
  • medium molecular compounds compounds in the middle region between low molecules and polymers: molecular weight 400 to 4000
  • inorganic compounds quantum dot materials, etc.
  • quantum dot material a colloidal quantum dot material, an alloy type quantum dot material, a core / shell type quantum dot material, a core type quantum dot material, or the like can be used.
  • 2A is an active matrix light-emitting device in which a transistor (FET) 202 over a first substrate 201 and light-emitting elements (203R, 203G, 203B, and 203W) are electrically connected to each other.
  • the plurality of light emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and the optical distance between the electrodes of each light emitting element depends on the emission color of each light emitting element. It has a tuned microcavity structure.
  • the light-emitting device is a top-emission light-emitting device in which light emission obtained from the EL layer 204 is emitted through color filters (206R, 206G, and 206B) formed over the second substrate 205.
  • the first electrode 207 is formed so as to function as a reflective electrode.
  • the second electrode 208 is formed so as to function as a semi-transmissive / semi-reflective electrode. Note that an electrode material for forming the first electrode 207 and the second electrode 208 may be used as appropriate with reference to the description of the other embodiments.
  • the light emitting element 203R is a red light emitting element
  • the light emitting element 203G is a green light emitting element
  • the light emitting element 203B is a blue light emitting element
  • the light emitting element 203W is a white light emitting element, FIG.
  • the light emitting element 203R is adjusted so that the optical distance 200R is between the first electrode 207 and the second electrode 208
  • the light emitting element 203G includes the first electrode 207 and the second electrode.
  • the light emitting element 203B is adjusted so that the optical distance 200B is between the first electrode 207 and the second electrode 208.
  • the conductive layer 207R is stacked over the first electrode 207 in the light-emitting element 203R
  • the conductive adjustment layer 207G is stacked over the first electrode 207 in the light-emitting element 203G. It can be performed.
  • color filters (206R, 206G, 206B) are formed on the second substrate 205.
  • the color filter is a filter that passes a specific wavelength range of visible light and blocks the specific wavelength range. Therefore, as shown in FIG. 2A, red light emission can be obtained from the light emitting element 203R by providing the color filter 206R that allows only the red wavelength region to pass through the position overlapping the light emitting element 203R.
  • green light emission can be obtained from the light emitting element 203G.
  • the color filter 206B that allows only the blue wavelength region to pass at a position overlapping the light emitting element 203B, blue light emission can be obtained from the light emitting element 203B.
  • the light emitting element 203W can obtain white light emission without providing a color filter.
  • a black layer (black matrix) 209 may be provided at an end of one type of color filter.
  • the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer using a transparent material.
  • FIG. 2A a light emitting device having a structure for extracting light emission to the second substrate 205 side (top emission type) is shown, but the first substrate on which the FET 202 is formed as shown in FIG.
  • a light emitting device having a structure for extracting light to the 201 side (bottom emission type) may be used.
  • the first electrode 207 is formed to function as a semi-transmissive / semi-reflective electrode
  • the second electrode 208 is formed to function as a reflective electrode.
  • the first substrate 201 is at least a light-transmitting substrate.
  • the color filters (206R ′, 206G ′, and 206B ′) may be provided on the first substrate 201 side with respect to the light emitting elements (203R, 203G, and 203B) as shown in FIG.
  • the light-emitting element is a red light-emitting element, a green light-emitting element, a blue light-emitting element, or a white light-emitting element
  • the light-emitting element which is one embodiment of the present invention is limited to the structure.
  • a structure having a yellow light emitting element or an orange light emitting element may be used.
  • a material used for EL layers (a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc.) for manufacturing these light emitting elements, other embodiments are used. May be used as appropriate with reference to the description. In this case, it is necessary to select a color filter as appropriate in accordance with the emission color of the light emitting element.
  • a light-emitting device including a light-emitting element that exhibits a plurality of emission colors can be obtained.
  • an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured.
  • an active matrix light-emitting device has a structure in which a light-emitting element and a transistor (FET) are combined. Therefore, both the passive matrix light-emitting device and the active matrix light-emitting device are embodiments of the present invention.
  • the light-emitting element described in any of the other embodiments can be applied to the light-emitting device described in this embodiment.
  • an active matrix light-emitting device is described with reference to FIGS.
  • FIG. 3A is a top view illustrating the light-emitting device
  • FIG. 3B is a cross-sectional view taken along the chain line A-A ′ in FIG. 3A.
  • the active matrix light-emitting device includes a pixel portion 302, a driver circuit portion (source line driver circuit) 303, and driver circuit portions (gate line driver circuits) (304a and 304b) provided over the first substrate 301. .
  • the pixel portion 302 and the driver circuit portions 303, 304 a, and 304 b) are sealed between the first substrate 301 and the second substrate 306 by a sealant 305.
  • a lead wiring 307 is provided over the first substrate 301.
  • the lead wiring 307 is connected to the FPC 308 which is an external input terminal.
  • the FPC 308 transmits signals (eg, a video signal, a clock signal, a start signal, a reset signal, and the like) and a potential from the outside to the driving circuit units (303, 304a, and 304b).
  • a printed wiring board (PWB) may be attached to the FPC 308. Note that the state in which the FPC or PWB is attached is included in the light emitting device.
  • the pixel portion 302 is formed by a plurality of pixels including a FET (switching FET) 311, a FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312.
  • a FET switching FET
  • FET current control FET
  • first electrode 313 electrically connected to the FET 312. Note that the number of FETs included in each pixel is not particularly limited, and can be appropriately provided as necessary.
  • crystallinity of the semiconductor there is no particular limitation on the crystallinity of the semiconductor that can be used for these FETs 309, 310, 311, and 312; an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, Alternatively, a semiconductor having a crystal region in part) may be used. Note that it is preferable to use a crystalline semiconductor because deterioration of transistor characteristics can be suppressed.
  • Group 14 elements for example, Group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, and the like can be used.
  • a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, or the like can be used.
  • the drive circuit unit 303 includes an FET 309 and an FET 310.
  • the FET 309 and the FET 310 may be formed of a circuit including a unipolar transistor (N-type or P-type only) or a CMOS circuit including an N-type transistor and a P-type transistor. May be.
  • a configuration in which a drive circuit is provided outside may be employed.
  • an end portion of the first electrode 313 is covered with an insulator 314.
  • the insulator 314 can be formed using an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride. . It is preferable that an upper end portion or a lower end portion of the insulator 314 have a curved surface having a curvature. Thereby, the coverage of the film formed in the upper layer of the insulating portion 314 can be improved.
  • the EL layer 315 and a second electrode 316 are stacked over the first electrode 313.
  • the EL layer 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like.
  • the structures and materials described in the other embodiments can be applied to the structure of the light-emitting element 317 described in this embodiment.
  • the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.
  • 3B illustrates only one light-emitting element 317, it is assumed that a plurality of light-emitting elements are arranged in a matrix in the pixel portion 302.
  • light emitting elements capable of emitting three types (R, G, and B) of light emission can be selectively formed, so that a light emitting device capable of full color display can be formed.
  • the light emitting element that can obtain three types of light emission (R, G, B) for example, light emission that can emit light such as white (W), yellow (Y), magenta (M), and cyan (C).
  • An element may be formed.
  • a light emitting device capable of full color display may be obtained by combining with a color filter.
  • types of color filters red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), and the like can be used.
  • the FETs (309, 310, 311 and 312) and the light emitting element 317 over the first substrate 301 are bonded to each other by attaching the second substrate 306 and the first substrate 301 with the sealant 305. 301, the second substrate 306, and a structure provided in a space 318 surrounded by the sealant 305.
  • the space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealant 305).
  • an epoxy resin or glass frit can be used as the sealant 305. Note that it is preferable to use a material that does not transmit moisture and oxygen as much as possible for the sealant 305.
  • a substrate that can be used for the first substrate 301 can be used as well. Therefore, various substrates described in other embodiments can be used as appropriate.
  • a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as the substrate.
  • the first substrate 301 and the second substrate 306 are preferably glass substrates from the viewpoint of adhesiveness.
  • an active matrix light-emitting device can be obtained.
  • the FET and the light-emitting element may be directly formed over the flexible substrate, but the FET and the light-emitting element are formed over another substrate having a release layer.
  • the FET and the light-emitting element may be peeled off by a peeling layer by applying heat, force, laser irradiation, and transferred to a flexible substrate.
  • the peeling layer for example, a laminated inorganic film of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used.
  • flexible substrates include paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, fabric substrates (natural fibers (silk, cotton, hemp), synthetic fibers ( Nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrates, rubber substrates, and the like.
  • paper substrates cellophane substrates
  • aramid film substrates polyimide film substrates
  • fabric substrates natural fibers (silk, cotton, hemp), synthetic fibers ( Nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrates, rubber substrates, and the like.
  • 4A to 4E includes a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), a connection terminal 7006, Sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity , Including a function of measuring inclination, vibration, odor, or infrared light), a microphone 7008, and the like.
  • FIG. 4A illustrates a mobile computer, which can include a switch 7009, an infrared port 7010, and the like in addition to the above objects.
  • FIG. 4B illustrates a portable image reproducing device (eg, a DVD reproducing device) provided with a recording medium, which includes a second display portion 7002, a recording medium reading portion 7011, and the like in addition to those described above. it can.
  • a portable image reproducing device eg, a DVD reproducing device
  • a recording medium which includes a second display portion 7002, a recording medium reading portion 7011, and the like in addition to those described above. it can.
  • FIG. 4C illustrates a goggle type display which can include a second display portion 7002, a support portion 7012, an earphone 7013, and the like in addition to the above components.
  • FIG. 4D illustrates a digital camera with a television receiving function, which can include an antenna 7014, a shutter button 7015, an image receiving portion 7016, and the like in addition to the above objects.
  • FIG. 4E illustrates a mobile phone (including a smartphone), which can include a display portion 7001, a microphone 7008, a speaker 7003, a camera 7020, an external connection portion 7021, an operation button 7022, and the like in a housing 7000. .
  • FIG. 4F illustrates a large television device (also referred to as a television or a television receiver) which can include a housing 7000, a display portion 7001, speakers 7003, and the like.
  • a configuration in which the casing 7000 is supported by a stand 7018 is shown.
  • the electronic devices illustrated in FIGS. 4A to 4F can have a variety of functions. For example, a function for displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function for displaying a calendar, date or time, etc., a function for controlling processing by various software (programs) , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded in recording medium
  • a function of displaying on the display portion can be provided. Further, in an electronic device having a plurality of display units, one display unit mainly displays image information and another one display unit mainly displays character information, or the plurality of display units consider parallax.
  • a function of displaying a three-dimensional image, etc. by displaying the obtained image. Furthermore, in an electronic device having an image receiving unit, a function for capturing a still image, a function for capturing a moving image, a function for correcting a captured image automatically or manually, and a captured image on a recording medium (externally or incorporated in a camera) A function of saving, a function of displaying a photographed image on a display portion, and the like can be provided. Note that the functions of the electronic devices illustrated in FIGS. 4A to 4F are not limited to these, and the electronic devices can have various functions.
  • FIG. 4G illustrates a smart watch, which includes a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a clasp 7026, and the like.
  • a display portion 7001 mounted on a housing 7000 that also serves as a bezel portion has a non-rectangular display region.
  • the display portion 7001 can display an icon 7027 representing time, other icons 7028, and the like.
  • the display unit 7001 may be a touch panel (input / output device) equipped with a touch sensor (input device).
  • the smart watch illustrated in FIG. 4G can have a variety of functions. For example, a function for displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function for displaying a calendar, date or time, etc., a function for controlling processing by various software (programs) , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded in recording medium A function of displaying on the display portion can be provided.
  • a speaker In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, number of rotations, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current are included in the housing 7000. , Voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared measurement function), microphone, and the like.
  • the light-emitting device which is one embodiment of the present invention and the display device including the light-emitting element which is one embodiment of the present invention can be used for each display portion of the electronic device described in this embodiment and display with high color purity. Is possible.
  • FIGS. 5A to 5C a foldable portable information terminal as illustrated in FIGS. 5A to 5C can be given.
  • FIG. 5A illustrates the portable information terminal 9310 in a developed state.
  • FIG. 5B illustrates the portable information terminal 9310 in a state of changing from one of the expanded state and the folded state to the other.
  • FIG. 5C illustrates the portable information terminal 9310 in a folded state.
  • the portable information terminal 9310 is excellent in portability in the folded state and excellent in display listability due to a seamless wide display area in the expanded state.
  • the display portion 9311 is supported by three housings 9315 connected by a hinge 9313.
  • the display unit 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device).
  • the display portion 9311 can be reversibly deformed from the expanded state to the folded state by bending the two housings 9315 via the hinge 9313.
  • the light-emitting device of one embodiment of the present invention can be used for the display portion 9311.
  • display with good color purity is possible.
  • a display region 9312 in the display portion 9311 is a display region located on a side surface of the portable information terminal 9310 in a folded state. In the display area 9312, information icons, frequently used applications, program shortcuts, and the like can be displayed, so that information can be confirmed and applications can be activated smoothly.
  • FIGS. 6A and 6B illustrate an automobile to which the light-emitting device is applied. That is, the light emitting device can be provided integrally with the automobile.
  • the present invention can be applied to a light 5101 (including a rear part of a vehicle body), a wheel 5102 of a tire, a part of or the whole of a door 5103 shown in FIG.
  • the present invention can be applied to a display portion 5104, a handle 5105, a shift lever 5106, a seat seat 5107, an inner rear view mirror 5108, and the like inside the automobile shown in FIG.
  • an electronic device or a vehicle using the light-emitting device or the display device which is one embodiment of the present invention can be obtained.
  • display with good color purity is possible.
  • applicable electronic devices and automobiles are not limited to those described in this embodiment, and can be applied in any field.
  • FIGS. 7A, 7B, 7C, and 7D each show an example of a cross-sectional view of a lighting device.
  • 7A and 7B are bottom emission type lighting devices that extract light to the substrate side
  • FIGS. 7C and 7D are top emission type lighting devices that extract light to the sealing substrate side. It is a lighting device.
  • a lighting device 4000 illustrated in FIG. 7A includes a light-emitting element 4002 over a substrate 4001.
  • a substrate 4003 having unevenness is provided outside the substrate 4001.
  • the light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.
  • the first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. Further, an auxiliary wiring 4009 that is electrically connected to the first electrode 4004 may be provided. Note that an insulating layer 4010 is formed over the auxiliary wiring 4009.
  • the substrate 4001 and the sealing substrate 4011 are bonded with a sealant 4012.
  • a desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. Note that since the substrate 4003 has unevenness as illustrated in FIG. 7A, the light extraction efficiency of the light-emitting element 4002 can be improved.
  • a diffusion plate 4015 may be provided outside the substrate 4001 as in the lighting device 4100 in FIG.
  • a lighting device 4200 in FIG. 7C includes a light-emitting element 4202 over a substrate 4201.
  • the light-emitting element 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.
  • the first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. Further, an auxiliary wiring 4209 that is electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided below the auxiliary wiring 4209.
  • the substrate 4201 and the uneven sealing substrate 4211 are bonded with a sealant 4212. Further, a barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light-emitting element 4202. Note that the sealing substrate 4211 has unevenness as illustrated in FIG. 7C, so that extraction efficiency of light generated in the light-emitting element 4202 can be improved.
  • a diffusion plate 4215 may be provided over the light-emitting element 4202 as in the lighting device 4300 in FIG.
  • a lighting device having desired chromaticity can be provided by using a light-emitting device which is one embodiment of the present invention or a light-emitting element which is a part thereof.
  • the ceiling light 8001 includes a direct ceiling type and a ceiling embedded type. Note that such an illumination device is configured by combining a light emitting device with a housing or a cover. In addition, it can be applied to a cord pendant type (a cord hanging type from the ceiling).
  • the foot lamp 8002 can illuminate the floor surface and enhance the safety of the foot. For example, it is effective to use it for a bedroom, a staircase or a passage. In that case, the size and shape can be appropriately changed according to the size and structure of the room.
  • a stationary illumination device configured by combining a light emitting device and a support base can be provided.
  • the sheet-like illumination 8003 is a thin sheet-like illumination device. Since it is attached to the wall surface, it can be used for a wide range of purposes without taking up space. It is easy to increase the area. In addition, it can also be used for the wall surface and housing
  • an illumination device 8004 in which light from a light source is controlled only in a desired direction can be used.
  • a lighting device having a function as furniture can be obtained by applying the light-emitting device which is one embodiment of the present invention to a part of the furniture provided in the room or the light-emitting element which is a part of the light-emitting device. can do.
  • Sublimation purification of 3.1 g of the obtained pale yellow solid was performed by a train sublimation method.
  • the sublimation purification was performed by heating a pale yellow solid at 300 ° C. under conditions of a pressure of 3.7 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 2.9 g of a pale yellow solid was obtained with a recovery rate of 93%.
  • FIG. 9B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 9A is enlarged. From this result, it was found that in this example, an organic compound, acDBCzPA, which is one embodiment of the present invention represented by the above structural formula (100), was obtained.
  • an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of acDBCzPA and a solid thin film were measured.
  • the solid thin film was produced on a quartz substrate by a vacuum deposition method.
  • an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used.
  • the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10) determined from the transmittance and reflectance of the thin film including the substrate. [% T / (100-% R)] where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). ) was used.
  • FIG. 10A shows the measurement results of the absorption spectrum and emission spectrum of acDBCzPA in toluene.
  • the horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
  • FIG. 10B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
  • acDBCzPA emitted blue light.
  • the organic compound acDBCzPA which is one embodiment of the present invention can also be used as a host for a light-emitting substance or a visible-light fluorescent substance. Moreover, it was found that the thin film of acDBCzPA has a good film quality that hardly aggregates even in the atmosphere.
  • the HOMO level and LUMO level of acDBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
  • an electrochemical analyzer manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C
  • DMF dehydrated dimethylformamide
  • tetra-n-butylammonium perchlorate supporting electrolyte
  • n-Bu 4 NClO 4 tetra-n-butylammonium perchlorate
  • T0836 tetra-n-butylammonium perchlorate
  • a platinum electrode manufactured by BAS Co., Ltd., PTE platinum electrode
  • a platinum electrode manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)
  • Ag / Ag + electrode manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode
  • the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured.
  • Ea was an intermediate potential of the oxidation-reduction wave
  • Ec was an intermediate potential of the reduction-oxidation wave.
  • the HOMO level [eV] ⁇ 4.94 ⁇ Ea
  • CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
  • Sublimation purification of 1.0 g of the obtained pale yellow solid was performed by a train sublimation method. Sublimation purification was performed by heating a pale yellow solid at 290 ° C. under conditions of a pressure of 3.2 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.92 g of a pale yellow solid was obtained with a recovery rate of 93%.
  • FIG. 11B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, acgTBCzPA, which is one embodiment of the present invention represented by the above structural formula (101), was obtained in this example.
  • an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and emission spectrum of acgTBCzPA in a toluene solution and a solid thin film were measured.
  • the solid thin film was produced on a quartz substrate by a vacuum deposition method.
  • an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used.
  • the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
  • FIG. 12B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • acgTBCzPA emitted blue light.
  • the organic compound acgTBCzPA which is one embodiment of the present invention can also be used as a host of a light-emitting substance or a visible-light fluorescent substance.
  • the acgTBCzPA thin film has a good film quality that hardly aggregates in the air.
  • the HOMO level and LUMO level of acgTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
  • an electrochemical analyzer manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C
  • DMF dehydrated dimethylformamide
  • tetra-n-butylammonium perchlorate supporting electrolyte
  • n-Bu 4 NClO 4 tetra-n-butylammonium perchlorate
  • T0836 tetra-n-butylammonium perchlorate
  • a platinum electrode manufactured by BAS Co., Ltd., PTE platinum electrode
  • a platinum electrode manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)
  • Ag / Ag + electrode manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode
  • the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured.
  • Ea was an intermediate potential of the oxidation-reduction wave
  • Ec was an intermediate potential of the reduction-oxidation wave.
  • the HOMO level [eV] ⁇ 4.94 ⁇ Ea
  • CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
  • the light-emitting element 1 using acDBCzPA (structural formula (100)) described in Example 1 for the light-emitting layer and the acgTBCzPA (described in Example 2) are used.
  • the light-emitting element 2 using the structural formula (101) for the light-emitting layer, the comparative organic compound, and the comparative light-emitting element 3 using cgDBCzPA (structural formula (201)) for the light-emitting layer these element structures, manufacturing methods, and The characteristics will be described.
  • FIG. 13 shows an element structure of a light-emitting element used in this example, and Table 1 shows a specific structure.
  • chemical formulas of materials used in this example are shown below.
  • the light-emitting element described in this example includes a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and a first electrode 901 formed over a substrate 900.
  • the electron injection layer 915 is sequentially stacked, and the second electrode 903 is stacked on the electron injection layer 915.
  • the first electrode 901 was formed over the substrate 900.
  • the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
  • a glass substrate was used as the substrate 900.
  • the first electrode 901 was formed by depositing indium tin oxide containing silicon oxide (ITSO) with a thickness of 70 nm by a sputtering method.
  • ITSO indium tin oxide containing silicon oxide
  • the surface of the substrate was washed with water and baked at 200 ° C. for 1 hour, followed by UV ozone treatment for 370 seconds. Thereafter, the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 60 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
  • a hole injection layer 911 was formed over the first electrode 901.
  • the hole injection layer 911 is formed by reducing the pressure in the vacuum evaporation apparatus to 10 ⁇ 4 Pa, and then 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum oxide.
  • a hole transport layer 912 was formed over the hole injection layer 911.
  • the hole transport layer 912 was formed by vapor deposition using PCPPn so as to have a film thickness of 30 nm.
  • a light-emitting layer 913 was formed over the hole transport layer 912.
  • the light emitting layer 913 uses acDBCzPA as a host material and N, N′-bis (3-methylphenyl) -N, N′-bis [3- (9-phenyl-9H) as a guest material.
  • the film thickness was 25 nm.
  • the film thickness was 25 nm.
  • the film thickness was 25 nm.
  • an electron transport layer 914 was formed over the light emitting layer 913.
  • the electron-transport layer 914 was formed by sequentially vapor-depositing so that the thickness of acDBCzPA was 15 nm and the thickness of bathophenanthroline (abbreviation: Bphen) was 10 nm.
  • the acg TBCzPA was formed by vapor deposition so that the film thickness was 15 nm and the film thickness of Bphen was 10 nm.
  • the cgDBCzPA was formed by sequentially vapor-depositing so that the film thickness of cgDBCzPA was 15 nm and the film thickness of Bphen was 10 nm.
  • the electron injection layer 915 was formed over the electron transport layer 914.
  • the electron injection layer 915 was formed by vapor deposition using lithium fluoride (LiF) so as to have a film thickness of 1 nm.
  • a second electrode 903 was formed over the electron injection layer 915.
  • the second electrode 903 was formed by vapor deposition of aluminum so that the film thickness becomes 200 nm. Note that in this embodiment, the second electrode 903 functions as a cathode.
  • a light-emitting element in which an EL layer was sandwiched between a pair of electrodes was formed over the substrate 900.
  • 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 described in the above steps are functional layers that constitute the EL layer in one embodiment of the present invention.
  • a vapor deposition method using a resistance heating method was used.
  • the light-emitting element manufactured as described above is sealed by another substrate (not shown).
  • another substrate (not shown) is fixed on the substrate 900 using a sealing material in a glove box in a nitrogen atmosphere and sealed. The material was applied to the periphery of the light emitting element formed on the substrate 900, and irradiated with 6 J / cm 2 of 365 nm ultraviolet light at the time of sealing, and heat-treated at 80 ° C. for 1 hour.
  • Table 2 shows main initial characteristic values of the light-emitting element 1 and the light-emitting element 2 around 1000 cd / m 2 .
  • each light-emitting element manufactured in this example exhibits good current efficiency and high external quantum efficiency.
  • FIG. 18 shows emission spectra obtained when a current was passed through the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 at a current density of 12.5 mA / cm 2 .
  • the emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 all have a peak near 468 nm, and are derived from light emission of 1,6 mM emFLPAPrn contained in the light-emitting layer 913. It is suggested that
  • the reliability test was a constant current drive test at 2 mA.
  • the light-emitting element 1 which is one embodiment of the present invention exhibited characteristics superior in reliability to the comparative light-emitting element 3. Therefore, even when the same luminescent material (1,6 mM emFLPAPrn) is used, it is useful for extending the lifetime to use acDBCzPA (structural formula (100)) described in Example 1 as the luminescent layer host. It can be said that.
  • 1.2 g of the obtained white solid was purified by sublimation by a train sublimation method.
  • the sublimation purification was performed by heating a pale yellow solid at 305 ° C. under conditions of a pressure of 4.0 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 1.0 g of a pale yellow solid was obtained with a recovery rate of 85%.
  • FIG. 20B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, aciTBCzPA, which is one embodiment of the present invention represented by the above structural formula (102) was obtained in this example.
  • an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of aciTBCzPA and a solid thin film were measured.
  • the solid thin film was produced on a quartz substrate by a vacuum deposition method.
  • an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used.
  • the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
  • FIG. 21A shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution.
  • the horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
  • FIG. 21B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
  • aciTBCzPA emits blue light.
  • the organic compound, aciTBCzPA, which is one embodiment of the present invention can also be used as a host of a light-emitting substance or a visible-light fluorescent substance. It was also found that the thin film of aciTBCzPA has a good film quality that hardly aggregates even in the atmosphere.
  • the HOMO level and LUMO level of aciTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
  • an electrochemical analyzer manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C
  • DMF dehydrated dimethylformamide
  • tetra-n-butylammonium perchlorate as a supporting electrolyte ( n-Bu 4 NClO 4 ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 2 mmol / L. did.
  • a platinum electrode manufactured by BAS Co., Ltd., PTE platinum electrode
  • a platinum electrode manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)
  • Ag / Ag + electrode manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode
  • the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured.
  • Ea was an intermediate potential of the oxidation-reduction wave
  • Ec was an intermediate potential of the reduction-oxidation wave.
  • the HOMO level [eV] ⁇ 4.94 ⁇ Ea
  • CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
  • FIG. 22B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, TeBCzPA, which is one embodiment of the present invention represented by the above structural formula (103), was obtained in this example.
  • an ultraviolet-visible absorption spectrum and an emission spectrum of a toluene solution of TeBCzPA were measured.
  • An ultraviolet-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation) was used for the measurement of the absorption spectrum.
  • the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell.
  • a fluorometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum.
  • the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • TeBCzPA was confirmed to emit blue light.
  • the organic compound, TeBCzPA, which is one embodiment of the present invention can also be used as a host for a light-emitting substance or a visible-light fluorescent substance.
  • a light-emitting element 4 using aciTBCzPA (structural formula (102)) described in Example 4 as a light-emitting layer as a light-emitting element which is one embodiment of the present invention was manufactured, and the characteristics thereof were measured. Indicates.
  • the element structure of the light-emitting element used in this example is the same as that in FIG. 13 shown in Example 3, but the specific structure of each layer constituting the element structure is as shown in Table 3. .
  • chemical formulas of materials used in this example are shown below.
  • Table 4 shows main initial characteristic values of the light-emitting element around 1000 cd / m 2 .
  • the light-emitting element 4 manufactured in this example is driven at a very low voltage and exhibits good efficiency.
  • the emission spectrum of the light-emitting element has a peak in the vicinity of 469 nm, which is suggested to be derived from light emission of the light-emitting substance contained in the light-emitting layer 913.
  • the reliability test was a constant current drive test at 2 mA.
  • the light-emitting element 4 which is one embodiment of the present invention exhibits excellent characteristics in reliability.
  • the use of the organic compound, aciTBCzPA (structural formula (102)), which is one embodiment of the present invention, as a light-emitting layer host is useful for extending the lifetime.
  • First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b Hole injection layer 112, 112a, 112b Hole transport layer 113, 113a, 113b Light emitting layer 114, 114a , 114b Electron transport layer 115, 115a, 115b Electron injection layer 201 First substrate 202 Transistor (FET) 203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second substrate 206R, 206G, 206B Color filter 206R ′, 206G ′, 206B ′ Color filter 207 First electrode 208 Second electrode 209 Black layer (black matrix ) 210R, 210G Conductive layer 301 First substrate 302 Pixel portion 303 Drive circuit portion (source line drive circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second substrate 307 Route wiring 308 FPC 309 FET 310

Abstract

Provided is a novel organic compound. That is, provided is a novel organic compound which is effective for enhancing device properties and reliability. The organic compound comprises a fused ring structure in a carbazole skeleton and is represented by general formula (G1), provided that the organic compound contains a substance in which a substituent of a dibenzocarbazole group forms a ring by annelating to the carbazole skeleton.

Description

有機化合物、発光素子、発光装置、電子機器、および照明装置Organic compound, light emitting element, light emitting device, electronic device, and lighting device
本発明の一態様は、有機化合物、発光素子、発光装置、電子機器、および照明装置に関する。但し、本発明の一態様は、上記の技術分野に限定されない。すなわち、本発明の一態様は、物、方法、製造方法、または駆動方法に関する。または、本発明の一態様は、プロセス、マシン、マニュファクチャ、または、組成物（コンポジション・オブ・マター）に関する。また、具体的には、半導体装置、表示装置、液晶表示装置などを一例として挙げることができる。 One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. Note that one embodiment of the present invention is not limited to the above technical field. That is, one embodiment of the present invention relates to an object, a method, a manufacturing method, or a driving method. Alternatively, one embodiment of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter). Specifically, a semiconductor device, a display device, a liquid crystal display device, and the like can be given as examples.
一対の電極間にＥＬ層を挟んでなる発光素子（有機ＥＬ素子ともいう）は、薄型軽量、入力信号に対する高速な応答性、低消費電力などの特性を有することから、これらを適用したディスプレイは、次世代のフラットパネルディスプレイとして注目されている。 A light-emitting element (also referred to as an organic EL element) in which an EL layer is sandwiched between a pair of electrodes has characteristics such as thin and light weight, high-speed response to input signals, and low power consumption. It is attracting attention as a next-generation flat panel display.
発光素子は、一対の電極間に電圧を印加することにより、各電極から注入された電子およびホールがＥＬ層において再結合し、ＥＬ層に含まれる発光物質（有機化合物）が励起状態となり、その励起状態が基底状態に戻る際に発光する。なお、励起状態の種類としては、一重項励起状態（Ｓ＊）と三重項励起状態（Ｔ＊）とがあり、一重項励起状態からの発光が蛍光、三重項励起状態からの発光が燐光と呼ばれている。また、発光素子におけるそれらの統計的な生成比率は、Ｓ＊：Ｔ＊＝１：３であると考えられている。発光物質から得られる発光スペクトルはその発光物質特有のものであり、異なる種類の有機化合物を発光物質として用いることによって、様々な発光色の発光素子を得ることができる。 In the light-emitting element, by applying a voltage between a pair of electrodes, electrons and holes injected from each electrode are recombined in the EL layer, and a light-emitting substance (organic compound) contained in the EL layer is in an excited state. Light is emitted when the excited state returns to the ground state. The types of excited states include a singlet excited state (S * ) and a triplet excited state (T * ). Light emitted from the singlet excited state is fluorescent, and light emitted from the triplet excited state is phosphorescent. being called. In addition, the statistical generation ratio of the light emitting elements is considered to be S * : T * = 1: 3. An emission spectrum obtained from the light-emitting substance is peculiar to the light-emitting substance, and light-emitting elements having various emission colors can be obtained by using different kinds of organic compounds as the light-emitting substance.
この様な発光素子に関しては、その素子特性を向上させる為に、素子構造の改良や材料開発等が盛んに行われている（例えば、特許文献１参照。）。 With respect to such a light emitting element, improvement of the element structure, material development, and the like have been actively performed in order to improve the element characteristics (for example, see Patent Document 1).
特開２０１０−１８２６９９号公報JP 2010-182699 A
発光素子の開発において、発光素子に用いる有機化合物は、その特性を高める上で非常に重要である。そこで、本発明の一態様では、新規な有機化合物を提供する。すなわち、素子特性や信頼性を高める上で有効な新規の有機化合物を提供する。また、本発明の一態様では、発光素子に用いることができる新規な有機化合物を提供する。また、本発明の一態様では、発光素子のＥＬ層に用いることができる、新規な有機化合物を提供する。また、本発明の一態様である新規な有機化合物を用いた高効率で信頼性の高い新規な発光素子を提供する。また、新規な発光装置、新規な電子機器、または新規な照明装置を提供する。なお、これらの課題の記載は、他の課題の存在を妨げるものではない。なお、本発明の一態様は、必ずしも、これらの課題の全てを解決する必要はない。なお、これら以外の課題は、明細書、図面、請求項などの記載から、自ずと明らかとなるものであり、明細書、図面、請求項などの記載から、これら以外の課題を抽出することが可能である。 In the development of a light emitting element, an organic compound used for the light emitting element is very important for enhancing its characteristics. Thus, in one embodiment of the present invention, a novel organic compound is provided. That is, a novel organic compound that is effective in improving device characteristics and reliability is provided. In one embodiment of the present invention, a novel organic compound that can be used for a light-emitting element is provided. In one embodiment of the present invention, a novel organic compound that can be used for an EL layer of a light-emitting element is provided. In addition, a novel light-emitting element with high efficiency and high reliability using the novel organic compound which is one embodiment of the present invention is provided. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. Note that the description of these problems does not disturb the existence of other problems. Note that one embodiment of the present invention does not necessarily have to solve all of these problems. Issues other than these will be apparent from the description of the specification, drawings, claims, etc., and other issues can be extracted from the descriptions of the specification, drawings, claims, etc. It is.
本発明の一態様は、カルバゾール骨格に縮環構造を有し、下記一般式（Ｇ１）で表される有機化合物である。 One embodiment of the present invention is an organic compound having a condensed ring structure in a carbazole skeleton and represented by the following general formula (G1).
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
なお、一般式（Ｇ１）において、Ａｒ１は置換もしくは無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G1), Ar 1 represents a substituted or unsubstituted phenylene group. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本発明の別の一態様は、下記一般式（Ｇ２）で表される有機化合物である。 Another embodiment of the present invention is an organic compound represented by General Formula (G2) below.
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
なお、一般式（Ｇ２）において、Ａｒ２は無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 In General Formula (G2), Ar 2 represents an unsubstituted phenylene group. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本発明の別の一態様は、下記一般式（Ｇ３）で表される有機化合物である。 Another embodiment of the present invention is an organic compound represented by General Formula (G3) below.
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
なお、一般式（Ｇ３）において、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G3), R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本発明の別の一態様は、下記一般式（Ｇ４）で表される有機化合物である。 Another embodiment of the present invention is an organic compound represented by General Formula (G4) below.
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
なお、一般式（Ｇ４）において、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０、およびＲ１１とＲ１２、の少なくとも一方は、縮環してベンゼン環を形成し、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G4), R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, at least one of R 9 and R 10 , and R 11 and R 12 is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent. Alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms having 6 to 6 carbon atoms Any of the 13 aryl groups.
上述した本発明の一態様である有機化合物は、カルバゾール骨格に縮環構造を有する。具体的には、カルバゾール骨格を形成する一方のベンゼン環が２か所以上で縮環された構造を有することを特徴とする。なお、このような構造を有することで、ゲスト材料（ドーパント）と組み合わせて用いる場合には、ドーパントへのエネルギー移動を効率よく行えるという特徴を有する。また、カルバゾール骨格の窒素と結合するアリーレン基が無置換のフェニレン基の場合は、分子内における立体障害を防ぐことができるため、容易に合成できるという特徴を有する。 The organic compound which is one embodiment of the present invention described above has a condensed ring structure in the carbazole skeleton. Specifically, one benzene ring forming the carbazole skeleton has a structure condensed at two or more positions. In addition, when it uses in combination with a guest material (dopant), it has the characteristic that the energy transfer to a dopant can be performed efficiently by having such a structure. In addition, when the arylene group bonded to nitrogen of the carbazole skeleton is an unsubstituted phenylene group, steric hindrance in the molecule can be prevented, and thus it can be easily synthesized.
本発明の別の一態様は、構造式（１００）、構造式（１０１）、構造式（１０２）、または構造式（１０３）で表される有機化合物である。 Another embodiment of the present invention is an organic compound represented by Structural Formula (100), Structural Formula (101), Structural Formula (102), or Structural Formula (103).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
本発明の別の一態様は、カルバゾール骨格に縮環構造を有する有機化合物を用いた発光素子である。なお、上記有機化合物に加えてゲスト材料を有する発光素子も本発明に含める。 Another embodiment of the present invention is a light-emitting element using an organic compound having a condensed ring structure in a carbazole skeleton. Note that a light-emitting element including a guest material in addition to the above organic compound is also included in the present invention.
本発明の別の一態様は、上述した本発明の一態様である有機化合物を用いた発光素子である。なお、一対の電極間に有するＥＬ層や、ＥＬ層に含まれる発光層に本発明の一態様である有機化合物を用いて形成された発光素子も本発明に含まれることとする。また、発光素子に加えて、トランジスタ、基板などを有する発光装置も発明の範疇に含める。さらに、これらの発光装置に加えて、マイク、カメラ、操作用ボタン、外部接続部、筐体、カバー、支持台または、スピーカ等を有する電子機器や照明装置も発明の範疇に含める。 Another embodiment of the present invention is a light-emitting element using the organic compound which is one embodiment of the present invention. Note that a light-emitting element formed using the organic compound which is one embodiment of the present invention for an EL layer between a pair of electrodes or a light-emitting layer included in the EL layer is also included in the present invention. In addition to a light-emitting element, a light-emitting device including a transistor, a substrate, and the like is also included in the scope of the invention. Furthermore, in addition to these light-emitting devices, an electronic device or lighting device including a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support base, a speaker, or the like is also included in the scope of the invention.
また、本発明の一態様は、発光素子を有する発光装置を含み、さらに発光装置を有する照明装置も範疇に含めるものである。従って、本明細書中における発光装置とは、画像表示デバイス、または光源（照明装置含む）を指す。また、発光装置に、例えばＦＰＣ（Ｆｌｅｘｉｂｌｅ　ｐｒｉｎｔｅｄ　ｃｉｒｃｕｉｔ）もしくはＴＣＰ（Ｔａｐｅ　Ｃａｒｒｉｅｒ　Ｐａｃｋａｇｅ）等のコネクターが取り付けられたモジュール、ＴＣＰの先にプリント配線板が設けられたモジュール、または発光素子にＣＯＧ（Ｃｈｉｐ　Ｏｎ　Ｇｌａｓｓ）方式によりＩＣ（集積回路）が直接実装されたモジュールも全て発光装置に含むものとする。 One embodiment of the present invention includes a light-emitting device including a light-emitting element, and further includes a lighting device including the light-emitting device. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). In addition, a module in which a connector such as FPC (Flexible printed circuit) or TCP (Tape Carrier Package) is attached to a light emitting device, a module in which a printed wiring board is provided at the end of TCP, or a COG (Chip On All modules in which IC (integrated circuit) is directly mounted by the (Glass) method are also included in the light emitting device.
本発明の一態様は、新規な有機化合物を提供することができる。すなわち、素子特性を高める上で有効な新規の有機化合物を提供することができる。また、本発明の一態様では、発光素子に用いることができる新規な有機化合物を提供することができる。また、本発明の一態様では、発光素子のＥＬ層に用いることができる、新規な有機化合物を提供することができる。また、本発明の一態様である新規な有機化合物を用いた高効率で信頼性の高い新規な発光素子を提供することができる。また、新規な発光装置、新規な電子機器、または新規な照明装置を提供することができる。なお、これらの効果の記載は、他の効果の存在を妨げるものではない。なお、本発明の一態様は、必ずしも、これらの効果の全てを有する必要はない。なお、これら以外の効果は、明細書、図面、請求項なとの記載から、自ずと明らかとなるものであり、明細書、図面、請求項などの記載から、これら以外の効果を抽出することが可能である。 One embodiment of the present invention can provide a novel organic compound. That is, it is possible to provide a novel organic compound effective for enhancing device characteristics. In one embodiment of the present invention, a novel organic compound that can be used for a light-emitting element can be provided. In one embodiment of the present invention, a novel organic compound that can be used for an EL layer of a light-emitting element can be provided. In addition, a novel light-emitting element with high efficiency and high reliability using the novel organic compound which is one embodiment of the present invention can be provided. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. Note that the description of these effects does not disturb the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. It should be noted that the effects other than these are naturally obvious from the description of the specification, drawings, and claims, and the effects other than these can be extracted from the descriptions of the specification, drawings, claims, and the like. Is possible.
発光素子の構造について説明する図。4A and 4B illustrate a structure of a light-emitting element. 発光装置について説明する図。FIG. 6 illustrates a light-emitting device. 発光装置について説明する図。FIG. 6 illustrates a light-emitting device. 電子機器について説明する図。6A and 6B illustrate electronic devices. 電子機器について説明する図。6A and 6B illustrate electronic devices. 自動車について説明する図。The figure explaining a motor vehicle. 照明装置について説明する図。The figure explaining an illuminating device. 照明装置について説明する図。The figure explaining an illuminating device. 構造式（１００）に示す有機化合物の１Ｈ−ＮＭＲチャート。 1 H-NMR chart of an organic compound represented by Structural Formula (100). 構造式（１００）に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトル。An ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by Structural Formula (100). 構造式（１０１）に示す有機化合物の１Ｈ−ＮＭＲチャート。 1 H-NMR chart of an organic compound represented by Structural Formula (101). 構造式（１０１）に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトル。The ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by Structural Formula (101). 発光素子について説明する図。3A and 3B illustrate a light-emitting element. 発光素子１および発光素子２の電流密度−輝度特性を示す図。FIG. 11 shows current density-luminance characteristics of Light-Emitting Element 1 and Light-Emitting Element 2. 発光素子１および発光素子２の電圧−輝度特性を示す図。FIG. 11 shows voltage-luminance characteristics of Light-Emitting Element 1 and Light-Emitting Element 2. 発光素子１および発光素子２の輝度−電流効率特性を示す図。FIG. 6 shows luminance-current efficiency characteristics of the light-emitting element 1 and the light-emitting element 2; 発光素子１および発光素子２の電圧−電流特性を示す図。FIG. 10 shows voltage-current characteristics of the light-emitting element 1 and the light-emitting element 2; 発光素子１、発光素子２、および比較発光素子３の発光スペクトルを示す図。FIG. 6 shows emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. 発光素子１および比較発光素子３の信頼性を示す図。FIG. 9 shows reliability of the light-emitting element 1 and the comparative light-emitting element 3. 構造式（１０２）に示す有機化合物の１Ｈ−ＮＭＲチャート。 1 H-NMR chart of an organic compound represented by Structural Formula (102). 構造式（１０２）に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトル。An ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (102). 構造式（１０３）に示す有機化合物の１Ｈ−ＮＭＲチャート。 1 H-NMR chart of an organic compound represented by Structural Formula (103). 構造式（１０３）に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトル。An ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (103). 発光素子４の電流密度−輝度特性を示す図。FIG. 6 shows current density-luminance characteristics of the light-emitting element 4; 発光素子４の電圧−輝度特性を示す図。FIG. 11 shows voltage-luminance characteristics of the light-emitting element 4; 発光素子４の輝度−電流効率特性を示す図。FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 4; 発光素子４の電圧−電流特性を示す図。FIG. 11 shows voltage-current characteristics of the light-emitting element 4; 発光素子４の発光スペクトルを示す図。FIG. 6 shows an emission spectrum of the light-emitting element 4. 発光素子４の信頼性を示す図。FIG. 6 shows reliability of the light-emitting element 4.
以下、本発明の実施の態様について図面を用いて詳細に説明する。但し、本発明は以下の説明に限定されず、本発明の趣旨及びその範囲から逸脱することなくその形態及び詳細を様々に変更し得ることが可能である。従って、本発明は以下に示す実施の形態の記載内容に限定して解釈されるものではない。 Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and various changes can be made in form and details without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments below.
なお、図面等において示す各構成の、位置、大きさ、範囲などは、理解の簡単のため、実際の位置、大きさ、範囲などを表していない場合がある。このため、開示する発明は、必ずしも、図面等に開示された位置、大きさ、範囲などに限定されない。 Note that the position, size, range, and the like of each component illustrated in the drawings and the like may not represent the actual position, size, range, or the like for easy understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, range, or the like disclosed in the drawings and the like.
また、本明細書等において、図面を用いて発明の構成を説明するにあたり、同じものを指す符号は異なる図面間でも共通して用いる。 Further, in this specification and the like, in describing the structure of the invention with reference to the drawings, the same reference numerals are used in different drawings.
（実施の形態１）
本実施の形態では、本発明の一態様である有機化合物について説明する。 (Embodiment 1)
In this embodiment, an organic compound which is one embodiment of the present invention will be described.
なお、本実施の形態で示す有機化合物は、カルバゾール骨格に縮環構造を有する、下記一般式（Ｇ１）で表される構造を有する。 Note that the organic compound described in this embodiment has a structure represented by the following general formula (G1), which has a condensed ring structure in a carbazole skeleton.
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
なお、一般式（Ｇ１）において、Ａｒ１は置換もしくは無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G1), Ar 1 represents a substituted or unsubstituted phenylene group. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本実施の形態で示す有機化合物は、下記一般式（Ｇ２）で表される。 The organic compound shown in this embodiment is represented by the following general formula (G2).
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
なお、一般式（Ｇ２）において、Ａｒ２は無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 In General Formula (G2), Ar 2 represents an unsubstituted phenylene group. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本実施の形態で示す有機化合物は、下記一般式（Ｇ３）で表される。 The organic compound shown in this embodiment is represented by the following general formula (G3).
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
なお、一般式（Ｇ３）において、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G3), R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
また、本実施の形態で示す有機化合物は、下記一般式（Ｇ４）で表される。 The organic compound shown in this embodiment is represented by the following general formula (G4).
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
なお、一般式（Ｇ４）において、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０、およびＲ１１とＲ１２、の少なくとも一方は、縮環してベンゼン環を形成し、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in General Formula (G4), R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, at least one of R 9 and R 10 , and R 11 and R 12 is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent. Alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms having 6 to 6 carbon atoms Any of the 13 aryl groups.
なお、上記一般式（Ｇ１）~一般式（Ｇ４）において、置換もしくは無置換のフェニレン基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれか、が置換基を有する場合、該置換基としてはメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基のような炭素数１~６のアルキル基や、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、８，９，１０−トリノルボルナニル基、のような炭素数５~７のシクロアルキル基や、フェニル基、ナフチル基、ビフェニル基のような炭素数６~１２のアリール基、等が挙げられる。 In the above general formulas (G1) to (G4), a substituted or unsubstituted phenylene group, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon number 7 When any one of a polycyclic saturated hydrocarbon having 10 to 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms has a substituent, the substituent is a methyl group, an ethyl group, a propyl group, isopropyl Group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, alkyl group having 1 to 6 carbon atoms, cyclopentyl group, cyclohexyl group, cycloheptyl group, 8,9, Examples thereof include cycloalkyl groups having 5 to 7 carbon atoms such as 10-trinorbornanyl group, aryl groups having 6 to 12 carbon atoms such as phenyl group, naphthyl group, and biphenyl group. It is.
また、上記一般式（Ｇ１）~（Ｇ４）における炭素数１~６のアルキル基の具体例としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、ｓｅｃ−ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ペンチル基、イソペンチル基、ｓｅｃ−ペンチル基、ｔｅｒｔ−ペンチル基、ネオペンチル基、ヘキシル基、イソヘキシル基、３−メチルペンチル基、２−メチルペンチル基、２−エチルブチル基、１，２−ジメチルブチル基、２，３−ジメチルブチル基等が挙げられる。 Specific examples of the alkyl group having 1 to 6 carbon atoms in the general formulas (G1) to (G4) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2 -A dimethylbutyl group, a 2, 3- dimethylbutyl group, etc. are mentioned.
また、上記一般式（Ｇ１）~（Ｇ４）における炭素数５~７の単環式飽和炭化水素の具体例としては、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、２−メチルシクロヘキシル基、等が挙げられる。 Specific examples of the monocyclic saturated hydrocarbon having 5 to 7 carbon atoms in the general formulas (G1) to (G4) include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 2-methylcyclohexyl group, and the like. It is done.
また、上記一般式（Ｇ１）~（Ｇ４）における炭素数７~１０の多環式飽和炭化水素の具体例としては、８，９，１０−トリノルボルナニル基、デカヒドロナフチル基、アダマンチル基等が挙げられる。 Specific examples of the polycyclic saturated hydrocarbon having 7 to 10 carbon atoms in the general formulas (G1) to (G4) include an 8,9,10-trinorbornanyl group, a decahydronaphthyl group, and an adamantyl group. Etc.
また、上記一般式（Ｇ１）~（Ｇ４）における炭素数６~１３のアリール基の具体例としては、フェニル基、ｏ−トリル基、ｍ−トリル基、ｐ−トリル基、メシチル基、ｏ−ビフェニル基、ｍ−ビフェニル基、ｐ−ビフェニル基、１−ナフチル基、２−ナフチル基、フルオレニル基、等が挙げられる。 Specific examples of the aryl group having 6 to 13 carbon atoms in the general formulas (G1) to (G4) include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o- Biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group and the like can be mentioned.
上述した一般式（Ｇ１）~（Ｇ４）で示される本発明の一態様である有機化合物は、カルバゾール骨格に縮環構造を有する。具体的には、カルバゾール骨格を形成する一方のベンゼン環が２か所以上で縮環された構造を有することを特徴とする。なお、このような構造を有することで、ゲスト材料（ドーパント）と組み合わせて用いる場合には、ドーパントへのエネルギー移動を効率よく行えるという特徴を有する。また、カルバゾール骨格の窒素と結合するアリーレン基が無置換のフェニレン基の場合は、特に分子内における立体障害を防ぐことができ、容易に合成することができるという特徴を有する。 The organic compound which is one embodiment of the present invention represented by the above general formulas (G1) to (G4) has a condensed ring structure in the carbazole skeleton. Specifically, one benzene ring forming the carbazole skeleton has a structure condensed at two or more positions. In addition, when it uses in combination with a guest material (dopant), it has the characteristic that the energy transfer to a dopant can be performed efficiently by having such a structure. Further, when the arylene group bonded to nitrogen of the carbazole skeleton is an unsubstituted phenylene group, it has a feature that steric hindrance in the molecule can be prevented and that it can be easily synthesized.
次に、上述した本発明の一態様である有機化合物の具体的な構造式を下記に示す。ただし、本発明はこれらに限定されることはない。 Next, specific structural formulas of the organic compound which is one embodiment of the present invention described above are shown below. However, the present invention is not limited to these.
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
なお、上記構造式（１００）~（１４４）で表される有機化合物は、上記一般式（Ｇ１）で表される有機化合物の一例であり、本発明の一態様である有機化合物は、これに限られない。 Note that the organic compound represented by the structural formulas (100) to (144) is an example of the organic compound represented by the general formula (G1), and the organic compound which is one embodiment of the present invention includes Not limited.
次に、一般式（Ｇ１）で表される有機化合物の合成方法の一例について説明する。 Next, an example of a method for synthesizing the organic compound represented by General Formula (G1) will be described.
≪一般式（Ｇ１）で表される有機化合物の合成方法≫
まず、下記一般式（Ｇ１）で表される有機化合物の合成方法の一例について説明する。 << Method for Synthesizing Organic Compound Represented by General Formula (G1) >>
First, an example of a method for synthesizing an organic compound represented by the following general formula (G1) will be described.
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
一般式（Ｇ１）において、Ａｒ１は置換もしくは無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 In General Formula (G1), Ar 1 represents a substituted or unsubstituted phenylene group. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
上記一般式（Ｇ１）で表される有機化合物は、下記に示す合成スキーム（Ａ−１）により合成することができる。すなわち、複素環化合物誘導体（ａ１）とアントラセン誘導体のハロゲン化物（ａ２）と、を、塩基存在下で金属触媒、金属、または金属化合物によりカップリングさせることにより、上記一般式（Ｇ１）で表される有機化合物を得ることができる。 The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (A-1) shown below. That is, the heterocyclic compound derivative (a1) and the halide (a2) of the anthracene derivative are coupled with a metal catalyst, a metal, or a metal compound in the presence of a base, thereby being represented by the above general formula (G1). An organic compound can be obtained.
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
なお、上記合成スキーム（Ａ−１）において、Ａｒ１は置換もしくは無置換のフェニレン基を表す。また、Ｘは、ハロゲンを表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。 Note that in the above synthesis scheme (A-1), Ar 1 represents a substituted or unsubstituted phenylene group. X represents halogen. R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 7 carbon atoms. 10 represents a polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted carbon atoms of 6 Any of ˜13 aryl groups.
上記合成スキーム（Ａ−１）において、ハートウィック・ブッフバルト反応を行う場合、Ｘはハロゲン又はトリフラート基を表す。ハロゲンとしては、ヨウ素、臭素又は塩素が好ましい。当該反応では、ビス（ジベンジリデンアセトン）パラジウム（０）、酢酸パラジウム（ＩＩ）等のパラジウム錯体又はパラジウム化合物と、それに配位するトリ（ｔｅｒｔ−ブチル）ホスフィンや、トリ（ｎ−ヘキシル）ホスフィンや、トリシクロヘキシルホスフィン等の配位子を用いるパラジウム触媒を利用する。塩基としては、ナトリウム　ｔｅｒｔ−ブトキシド等の有機塩基や、炭酸カリウム等の無機塩基等が挙げられる。また、溶媒を使用する場合、トルエン、キシレン、ベンゼン、テトラヒドロフラン等を用いることができる。 In the synthesis scheme (A-1), when the Hartwick-Buchwald reaction is performed, X represents a halogen or a triflate group. As halogen, iodine, bromine or chlorine is preferable. In the reaction, palladium complexes or palladium compounds such as bis (dibenzylideneacetone) palladium (0) and palladium (II) acetate, and tri (tert-butyl) phosphine coordinated thereto, tri (n-hexyl) phosphine, A palladium catalyst using a ligand such as tricyclohexylphosphine is used. Examples of the base include organic bases such as sodium tert-butoxide, inorganic bases such as potassium carbonate, and the like. Moreover, when using a solvent, toluene, xylene, benzene, tetrahydrofuran, etc. can be used.
また、合成スキーム（Ａ−１）において、ウルマン反応を行う場合、Ｘはハロゲンを表す。ハロゲンとしては、ヨウ素、臭素又は塩素が好ましい。触媒としては、銅もしくは銅化合物を用いる。銅化合物を触媒として用いる場合、式（Ａ−１）中における、Ｒ２２、Ｒ２３は、それぞれ、ハロゲンやアセチル基等を表し、ハロゲンとしては塩素、臭素、ヨウ素が挙げられる。なお、Ｒ２２としてヨウ素であるヨウ化銅（Ｉ）、又はＲ２３がアセチル基である酢酸銅（ＩＩ）を用いることが好ましい。用いる塩基としては、炭酸カリウム等の無機塩基が挙げられる。また、溶媒は、１，３−ジメチル−３，４，５，６−テトラヒドロ−２（１Ｈ）ピリミジノン（ＤＭＰＵ）、トルエン、キシレン、ベンゼン等を用いる。但し、上記溶媒はこれらに限られるものでは無い。ウルマン反応では、反応温度が１００℃以上の方がより短時間かつ高収率で目的物が得られるため、沸点の高いＤＭＰＵ、キシレンを用いることが好ましい。また、反応温度は１５０℃以上のより高い温度が更に好ましいため、より好ましくはＤＭＰＵを用いることとする。 In the synthesis scheme (A-1), when an Ullmann reaction is performed, X represents a halogen. As halogen, iodine, bromine or chlorine is preferable. As the catalyst, copper or a copper compound is used. In the case of using a copper compound as a catalyst, R 22 and R 23 in the formula (A-1) each represent a halogen, an acetyl group or the like, and examples of the halogen include chlorine, bromine and iodine. In addition, it is preferable to use copper iodide (I) which is iodine as R 22 or copper acetate (II) where R 23 is an acetyl group. Examples of the base to be used include inorganic bases such as potassium carbonate. As the solvent, 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone (DMPU), toluene, xylene, benzene, or the like is used. However, the said solvent is not restricted to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and with a higher yield when the reaction temperature is 100 ° C. or higher, it is preferable to use DMPU or xylene having a high boiling point. Moreover, since the higher reaction temperature of 150 degreeC or more is still more preferable, DMPU is used more preferably.
以上、一般式（Ｇ１）で表される有機化合物の合成方法について説明したが、本発明はこれに限定されることはなく、他の合成方法によって合成してもよい。 Although the method for synthesizing the organic compound represented by the general formula (G1) has been described above, the present invention is not limited to this and may be synthesized by other synthesis methods.
なお、上述した本発明の一態様である有機化合物は、電子輸送性及び正孔輸送性を有するため、発光層のホスト材料として、あるいは電子輸送層、正孔輸送層にも用いることができる。また、蛍光を発光する物質（蛍光材料）と組み合わせて、ホスト材料として用いることが好ましい。また、蛍光発光を示すため、それ自体、発光素子の発光物質として使うことも可能である。従って、これらの有機化合物を含む発光素子も本発明の一態様である。 Note that the above-described organic compound which is one embodiment of the present invention has an electron transporting property and a hole transporting property, and thus can be used as a host material for the light-emitting layer, or for an electron transporting layer and a hole transporting layer. Further, it is preferably used as a host material in combination with a substance that emits fluorescence (fluorescent material). Further, since it exhibits fluorescence, it can be used as a light-emitting substance of the light-emitting element itself. Therefore, a light-emitting element including any of these organic compounds is also one embodiment of the present invention.
また、本発明の一態様である有機化合物を用いることで、発光効率の高い発光素子、発光装置、電子機器、または照明装置を実現することができる。また、消費電力が低い発光素子、発光装置、電子機器、または照明装置を実現することができる。 In addition, by using the organic compound which is one embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency can be realized. In addition, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be realized.
なお、本実施の形態において、本発明の一態様について述べた。また、他の実施の形態において、本発明の別の一態様について述べる。ただし、本発明の一態様は、これらに限定されない。つまり、本実施の形態および他の実施の形態では、様々な発明の態様が記載されているため、本発明の一態様は、特定の態様に限定されない。 Note that one embodiment of the present invention is described in this embodiment. In another embodiment, another embodiment of the present invention will be described. Note that one embodiment of the present invention is not limited thereto. That is, in this embodiment and other embodiments, various aspects of the invention are described; therefore, one embodiment of the present invention is not limited to a particular aspect.
本実施の形態に示す構成は、他の実施の形態に示した構成と適宜組み合わせて用いることができる。 The structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
（実施の形態２）
本実施の形態では、実施の形態１で示した有機化合物を用いた発光素子について図１を用いて説明する。 (Embodiment 2)
In this embodiment, a light-emitting element using the organic compound described in Embodiment 1 will be described with reference to FIGS.
≪発光素子の基本的な構造≫
まず、発光素子の基本的な構造について説明する。図１（Ａ）には、一対の電極間に発光層を含むＥＬ層を有する発光素子を示す。具体的には、第１の電極１０１と第２の電極１０２との間にＥＬ層１０３が挟まれた構造を有する。 ≪Basic structure of light emitting element≫
First, the basic structure of the light emitting element will be described. FIG. 1A illustrates a light-emitting element having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, the EL layer 103 is sandwiched between the first electrode 101 and the second electrode 102.
また、図１（Ｂ）には、一対の電極間に複数（図１（Ｂ）では、２層）のＥＬ層（１０３ａ、１０３ｂ）を有し、ＥＬ層の間に電荷発生層１０４を有する積層構造（タンデム構造）の発光素子を示す。タンデム構造の発光素子は、低電圧駆動が可能で消費電力が低い発光装置を実現することができる。 In FIG. 1B, a plurality of (two layers in FIG. 1B) EL layers (103a and 103b) are provided between a pair of electrodes, and the charge generation layer 104 is provided between the EL layers. 1 illustrates a light-emitting element having a stacked structure (tandem structure). A light-emitting element having a tandem structure can realize a light-emitting device that can be driven at a low voltage and has low power consumption.
電荷発生層１０４は、第１の電極１０１と第２の電極１０２に電圧を印加したときに、一方のＥＬ層（１０３ａまたは１０３ｂ）に電子を注入し、他方のＥＬ層（１０３ｂまたは１０３ａ）に正孔を注入する機能を有する。従って、図１（Ｂ）において、第１の電極１０１に第２の電極１０２よりも電位が高くなるように電圧を印加すると、電荷発生層１０４からＥＬ層１０３ａに電子が注入され、ＥＬ層１０３ｂに正孔が注入されることとなる。 When a voltage is applied to the first electrode 101 and the second electrode 102, the charge generation layer 104 injects electrons into one EL layer (103a or 103b) and the other EL layer (103b or 103a). It has a function of injecting holes. Therefore, in FIG. 1B, when a voltage is applied to the first electrode 101 so that the potential is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a, and the EL layer 103b. Holes are injected into this.
なお、電荷発生層１０４は、光の取り出し効率の点から、可視光に対して透光性を有する（具体的には、電荷発生層１０４に対する可視光の透過率が、４０％以上）ことが好ましい。また、電荷発生層１０４は、第１の電極１０１や第２の電極１０２よりも低い導電率であっても機能する。 Note that the charge generation layer 104 has a property of transmitting visible light in terms of light extraction efficiency (specifically, the visible light transmittance of the charge generation layer 104 is 40% or more). preferable. In addition, the charge generation layer 104 functions even when it has lower conductivity than the first electrode 101 or the second electrode 102.
また、図１（Ｃ）には、本発明の一態様である発光素子のＥＬ層１０３の積層構造を示す。但し、この場合、第１の電極１０１は陽極として機能するものとする。ＥＬ層１０３は、第１の電極１０１上に、正孔（ホール）注入層１１１、正孔（ホール）輸送層１１２、発光層１１３、電子輸送層１１４、電子注入層１１５が順次積層された構造を有する。なお、図１（Ｂ）に示すタンデム構造のように複数のＥＬ層を有する場合であっても、各ＥＬ層が、陽極側から上記のように順次積層される構造とする。また、第１の電極１０１が陰極で、第２の電極１０２が陽極の場合は、積層順は逆になる。 FIG. 1C illustrates a stacked structure of the EL layer 103 of the light-emitting element which is one embodiment of the present invention. However, in this case, the first electrode 101 functions as an anode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked over the first electrode 101. Have Note that even in the case where a plurality of EL layers are provided as in the tandem structure illustrated in FIG. 1B, each EL layer is sequentially stacked from the anode side as described above. Further, when the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.
ＥＬ層（１０３、１０３ａ、１０３ｂ）に含まれる発光層１１３は、それぞれ発光物質や複数の物質を適宜組み合わせて有しており、所望の発光色を呈する蛍光発光や燐光発光が得られる構成とすることができる。また、発光層１１３を発光色の異なる積層構造としてもよい。なお、この場合、積層された各発光層に用いる発光物質やその他の物質は、それぞれ異なる材料を用いればよい。また、図１（Ｂ）に示す複数のＥＬ層（１０３ａ、１０３ｂ）から、それぞれ異なる発光色が得られる構成としても良い。この場合も各発光層に用いる発光物質やその他の物質を異なる材料とすればよい。 Each of the light-emitting layers 113 included in the EL layers (103, 103a, and 103b) includes a light-emitting substance and a plurality of substances as appropriate in combination, so that fluorescent light emission or phosphorescence light emission having a desired light emission color can be obtained. be able to. Alternatively, the light-emitting layer 113 may have a stacked structure with different emission colors. Note that in this case, different materials may be used for the light-emitting substance and other substances used for the stacked light-emitting layers. Alternatively, different light emission colors may be obtained from the plurality of EL layers (103a and 103b) illustrated in FIG. In this case as well, the light-emitting substance and other substances used for each light-emitting layer may be different materials.
また、本発明の一態様である発光素子において、例えば、図１（Ｃ）に示す第１の電極１０１を反射電極とし、第２の電極１０２を半透過・半反射電極とし、微小光共振器（マイクロキャビティ）構造とすることにより、ＥＬ層１０３に含まれる発光層１１３から得られる発光を両電極間で共振させ、第２の電極１０２から得られる発光を強めることができる。 In the light-emitting element of one embodiment of the present invention, for example, the first electrode 101 illustrated in FIG. 1C is used as a reflective electrode, the second electrode 102 is used as a semi-transmissive / semi-reflective electrode, and a micro optical resonator is used. With the (microcavity) structure, light emission obtained from the light-emitting layer 113 included in the EL layer 103 can resonate between both electrodes, and light emission obtained from the second electrode 102 can be strengthened.
なお、発光素子の第１の電極１０１が、反射性を有する導電性材料と透光性を有する導電性材料（透明導電膜）との積層構造からなる反射電極である場合、透明導電膜の膜厚を制御することにより光学調整を行うことができる。具体的には、発光層１１３から得られる光の波長λに対して、第１の電極１０１と、第２の電極１０２との電極間距離がｍλ／２（ただし、ｍは自然数）近傍となるように調整するのが好ましい。 Note that in the case where the first electrode 101 of the light-emitting element is a reflective electrode having a stacked structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), a film of the transparent conductive film Optical adjustment can be performed by controlling the thickness. Specifically, the distance between the first electrode 101 and the second electrode 102 is near mλ / 2 (where m is a natural number) with respect to the wavelength λ of light obtained from the light-emitting layer 113. It is preferable to adjust as follows.
また、発光層１１３から得られる所望の光（波長：λ）を増幅させるために、第１の電極１０１から発光層の所望の光が得られる領域（発光領域）までの光学距離と、第２の電極１０２から発光層１１３の所望の光が得られる領域（発光領域）までの光学距離と、をそれぞれ（２ｍ’＋１）λ／４（ただし、ｍ’は自然数）近傍となるように調節するのが好ましい。なお、ここでいう発光領域とは、発光層１１３における正孔（ホール）と電子との再結合領域を示す。 Further, in order to amplify desired light (wavelength: λ) obtained from the light emitting layer 113, an optical distance from the first electrode 101 to a region (light emitting region) where desired light of the light emitting layer is obtained, and a second The optical distance from the electrode 102 of the light emitting layer 113 to the region (light emitting region) from which desired light can be obtained is adjusted to be in the vicinity of (2m ′ + 1) λ / 4 (where m ′ is a natural number). Is preferred. Note that the light emitting region herein refers to a recombination region between holes and electrons in the light emitting layer 113.
このような光学調整を行うことにより、発光層１１３から得られる特定の単色光のスペクトルを狭線化させ、色純度の良い発光を得ることができる。 By performing such optical adjustment, the spectrum of specific monochromatic light obtained from the light emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.
但し、上記の場合、第１の電極１０１と第２の電極１０２との光学距離は、厳密には第１の電極１０１における反射領域から第２の電極１０２における反射領域までの総厚ということができる。しかし、第１の電極１０１や第２の電極１０２における反射領域を厳密に決定することは困難であるため、第１の電極１０１と第２の電極１０２の任意の位置を反射領域と仮定することで充分に上述の効果を得ることができるものとする。また、第１の電極１０１と、所望の光が得られる発光層との光学距離は、厳密には第１の電極１０１における反射領域と、所望の光が得られる発光層における発光領域との光学距離であるということができる。しかし、第１の電極１０１における反射領域や、所望の光が得られる発光層における発光領域を厳密に決定することは困難であるため、第１の電極１０１の任意の位置を反射領域、所望の光が得られる発光層の任意の位置を発光領域と仮定することで充分に上述の効果を得ることができるものとする。 However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly the total thickness from the reflective region of the first electrode 101 to the reflective region of the second electrode 102. it can. However, since it is difficult to precisely determine the reflection region in the first electrode 101 or the second electrode 102, it is assumed that any position of the first electrode 101 and the second electrode 102 is the reflection region. The above-mentioned effect can be sufficiently obtained. Strictly speaking, the optical distance between the first electrode 101 and the light emitting layer from which desired light can be obtained is the optical distance between the reflective region in the first electrode 101 and the light emitting region in the light emitting layer from which desired light can be obtained. It can be said that it is a distance. However, since it is difficult to strictly determine the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light can be obtained, any position of the first electrode 101 can be set as the reflection region, the desired region. It is assumed that the above-described effect can be sufficiently obtained by assuming an arbitrary position of the light emitting layer from which light is obtained as a light emitting region.
図１（Ｃ）に示す発光素子は、マイクロキャビティ構造を有するため、同じＥＬ層を有していても異なる波長の光（単色光）を取り出すことができる。従って、異なる発光色を得るための塗り分け（例えば、ＲＧＢ）が不要となる。従って、高精細化を実現することが容易である。また、着色層（カラーフィルタ）との組み合わせも可能である。さらに、特定波長の正面方向の発光強度を強めることが可能となるため、低消費電力化を図ることができる。 Since the light-emitting element illustrated in FIG. 1C has a microcavity structure, light having different wavelengths (monochromatic light) can be extracted even when the light-emitting element has the same EL layer. Accordingly, there is no need for separate coloring (for example, RGB) for obtaining different emission colors. Therefore, it is easy to realize high definition. A combination with a colored layer (color filter) is also possible. Furthermore, since it is possible to increase the emission intensity of the specific wavelength in the front direction, it is possible to reduce power consumption.
図１（Ｅ）に示す発光素子は、図１（Ｂ）に示したタンデム構造の発光素子の一例であり、図に示すように、３つのＥＬ層（１０３ａ、１０３ｂ、１０３ｃ）が電荷発生層（１０４ａ、１０４ｂ）を挟んで積層される構造を有する。なお、３つのＥＬ層（１０３ａ、１０３ｂ、１０３ｃ）は、それぞれに発光層（１１３ａ、１１３ｂ、１１３ｃ）を有しており、各発光層の発光色は、自由に組み合わせることができる。例えば、発光層１１３ａを青色、発光層１１３ｂを赤色、緑色、または黄色のいずれか、発光層１１３ｃを青色とすることができるが、発光層１１３ａを赤色、発光層１１３ｂを青色、緑色、または黄色のいずれか、発光層１１３ｃを赤色とすることもできる。 The light-emitting element illustrated in FIG. 1E is an example of the light-emitting element having the tandem structure illustrated in FIG. 1B. As illustrated, three EL layers (103a, 103b, and 103c) are charge generation layers. (104a, 104b). Note that the three EL layers (103a, 103b, and 103c) each have a light emitting layer (113a, 113b, and 113c), and the light emission colors of the light emitting layers can be freely combined. For example, the light-emitting layer 113a can be blue, the light-emitting layer 113b can be red, green, or yellow, and the light-emitting layer 113c can be blue, but the light-emitting layer 113a can be red and the light-emitting layer 113b can be blue, green, or yellow. In any case, the light emitting layer 113c may be red.
なお、上述した本発明の一態様である発光素子において、第１の電極１０１と第２の電極１０２の少なくとも一方は、透光性を有する電極（透明電極、半透過・半反射電極など）とする。透光性を有する電極が透明電極の場合、透明電極の可視光の透過率は、４０％以上とする。また、半透過・半反射電極の場合、半透過・半反射電極の可視光の反射率は、２０％以上８０％以下、好ましくは４０％以上７０％以下とする。また、これらの電極は、抵抗率が１×１０−２Ωｃｍ以下とするのが好ましい。 Note that in the above light-emitting element which is one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 includes a light-transmitting electrode (a transparent electrode, a semi-transmissive / semi-reflective electrode, or the like). To do. When the light-transmitting electrode is a transparent electrode, the transparent electrode has a visible light transmittance of 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the visible light reflectance of the semi-transmissive / semi-reflective electrode is 20% to 80%, preferably 40% to 70%. These electrodes preferably have a resistivity of 1 × 10 −2 Ωcm or less.
また、上述した本発明の一態様である発光素子において、第１の電極１０１と第２の電極１０２の一方が、反射性を有する電極（反射電極）である場合、反射性を有する電極の可視光の反射率は、４０％以上１００％以下、好ましくは７０％以上１００％以下とする。また、この電極は、抵抗率が１×１０−２Ωｃｍ以下とするのが好ましい。 In the light-emitting element which is one embodiment of the present invention described above, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode is visible. The light reflectance is 40% to 100%, preferably 70% to 100%. The electrode preferably has a resistivity of 1 × 10 −2 Ωcm or less.
≪発光素子の具体的な構造および作製方法≫
次に、本発明の一態様である発光素子の具体的な構造および作製方法について、図１を用いて説明する。また、ここでは、図１（Ｂ）に示すタンデム構造を有し、マイクロキャビティ構造を備えた発光素子についても図１（Ｄ）を用いて説明する。図１（Ｄ）に示す発光素子がマイクロキャビティ構造を有する場合は、第１の電極１０１を反射電極として形成し、第２の電極１０２を半透過・半反射電極として形成する。従って、所望の電極材料を単数または複数用い、単層または積層して形成することができる。なお、第２の電極１０２は、ＥＬ層１０３ｂを形成した後、上記と同様に材料を選択して形成する。また、これらの電極の作製には、スパッタ法や真空蒸着法を用いることができる。 << Specific structure and manufacturing method of light-emitting element >>
Next, a specific structure and a manufacturing method of the light-emitting element which is one embodiment of the present invention will be described with reference to FIGS. Here, a light-emitting element having the tandem structure illustrated in FIG. 1B and including a microcavity structure is also described with reference to FIG. In the case where the light-emitting element illustrated in FIG. 1D has a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive / semi-reflective electrode. Therefore, a desired electrode material can be formed by using a single layer or a plurality of layers and forming a single layer or a stack. Note that the second electrode 102 is formed by selecting a material in the same manner as described above after the EL layer 103b is formed. In addition, a sputtering method or a vacuum evaporation method can be used for manufacturing these electrodes.
＜第１の電極および第２の電極＞
第１の電極１０１および第２の電極１０２を形成する材料としては、上述した両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、Ｉｎ−Ｓｎ酸化物（ＩＴＯともいう）、Ｉｎ−Ｓｉ−Ｓｎ酸化物（ＩＴＳＯともいう）、Ｉｎ−Ｚｎ酸化物、Ｉｎ−Ｗ−Ｚｎ酸化物が挙げられる。その他、アルミニウム（Ａｌ）、チタン（Ｔｉ）、クロム（Ｃｒ）、マンガン（Ｍｎ）、鉄（Ｆｅ）、コバルト（Ｃｏ）、ニッケル（Ｎｉ）、銅（Ｃｕ）、ガリウム（Ｇａ）、亜鉛（Ｚｎ）、インジウム（Ｉｎ）、スズ（Ｓｎ）、モリブデン（Ｍｏ）、タンタル（Ｔａ）、タングステン（Ｗ）、パラジウム（Ｐｄ）、金（Ａｕ）、白金（Ｐｔ）、銀（Ａｇ）、イットリウム（Ｙ）、ネオジム（Ｎｄ）などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第１族または第２族に属する元素（例えば、リチウム（Ｌｉ）、セシウム（Ｃｓ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ））、ユウロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。 <First electrode and second electrode>
As materials for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the functions of both electrodes described above can be satisfied. For example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and the like can be used as appropriate. Specifically, an In—Sn oxide (also referred to as ITO), an In—Si—Sn oxide (also referred to as ITSO), an In—Zn oxide, and an In—W—Zn oxide can be given. In addition, aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn ), Indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y ), A metal such as neodymium (Nd), and an alloy containing an appropriate combination thereof. In addition, elements belonging to Group 1 or Group 2 of the periodic table of elements not exemplified above (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium Rare earth metals such as (Yb), alloys containing these in appropriate combinations, other graphene, and the like can be used.
図１（Ｄ）に示す発光素子において、第１の電極１０１が陽極である場合、第１の電極１０１上にＥＬ層１０３ａの正孔注入層１１１ａおよび正孔輸送層１１２ａが真空蒸着法により順次積層形成される。ＥＬ層１０３ａおよび電荷発生層１０４が形成された後、電荷発生層１０４上にＥＬ層１０３ｂの正孔注入層１１１ｂおよび正孔輸送層１１２ｂが同様に順次積層形成される。 In the light-emitting element illustrated in FIG. 1D, when the first electrode 101 is an anode, the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially formed over the first electrode 101 by a vacuum evaporation method. Stacked. After the EL layer 103a and the charge generation layer 104 are formed, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 104 in the same manner.
＜正孔注入層および正孔輸送層＞
正孔注入層（１１１、１１１ａ、１１１ｂ）は、陽極である第１の電極１０１や中間層（１０４）からＥＬ層（１０３、１０３ａ、１０３ｂ）に正孔（ホール）を注入する層であり、正孔注入性の高い材料を含む層である。 <Hole injection layer and hole transport layer>
The hole injection layer (111, 111a, 111b) is a layer for injecting holes from the first electrode 101, which is an anode, or the intermediate layer (104) into the EL layer (103, 103a, 103b). It is a layer containing a material having a high hole injection property.
正孔注入性の高い材料としては、モリブデン酸化物やバナジウム酸化物、ルテニウム酸化物、タングステン酸化物、マンガン酸化物等の遷移金属酸化物が挙げられる。この他、フタロシアニン（略称：Ｈ２Ｐｃ）や銅フタロシアニン（略称：ＣｕＰＣ）等のフタロシアニン系の化合物、４，４’−ビス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＤＰＡＢ）、Ｎ，Ｎ’−ビス｛４−［ビス（３−メチルフェニル）アミノ］フェニル｝−Ｎ，Ｎ’−ジフェニル−（１，１’−ビフェニル）−４，４’−ジアミン（略称：ＤＮＴＰＤ）等の芳香族アミン化合物、またはポリ（３，４−エチレンジオキシチオフェン）／ポリ（スチレンスルホン酸）（略称：ＰＥＤＯＴ／ＰＳＳ）等の高分子等を用いることができる。 Examples of the material having a high hole injection property include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. In addition, phthalocyanine compounds such as phthalocyanine (abbreviation: H 2 Pc) and copper phthalocyanine (abbreviation: 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 ( An aromatic amine compound such as abbreviation (DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (abbreviation: PEDOT / PSS) can be used.
また、正孔注入性の高い材料としては、正孔輸送性材料とアクセプター性材料（電子受容性材料）を含む複合材料を用いることもできる。この場合、アクセプター性材料により正孔輸送性材料から電子が引き抜かれて正孔注入層（１１１、１１１ａ、１１１ｂ）で正孔が発生し、正孔輸送層（１１２、１１２ａ、１１２ｂ）を介して発光層（１１３、１１３ａ、１１３ｂ）に正孔が注入される。なお、正孔注入層（１１１、１１１ａ、１１１ｂ）は、正孔輸送性材料とアクセプター性材料（電子受容性材料）を含む複合材料からなる単層で形成しても良いが、正孔輸送性材料とアクセプター性材料（電子受容性材料）とをそれぞれ別の層で積層して形成しても良い。 As a material having a high hole-injecting property, a composite material including a hole-transporting material and an acceptor material (electron-accepting material) can also be used. In this case, electrons are extracted from the hole transporting material by the acceptor material, and holes are generated in the hole injection layer (111, 111a, 111b), via the hole transporting layer (112, 112a, 112b). Holes are injected into the light emitting layer (113, 113a, 113b). Note that the hole injection layer (111, 111a, 111b) may be formed as a single layer made of a composite material including a hole transporting material and an acceptor material (electron accepting material). The material and the acceptor material (electron-accepting material) may be stacked in separate layers.
正孔輸送層（１１２、１１２ａ、１１２ｂ）は、正孔注入層（１１１、１１１ａ、１１１ｂ）によって、第１の電極１０１から注入された正孔を発光層（１１３、１１３ａ、１１３ｂ）に輸送する層である。なお、正孔輸送層（１１２、１１２ａ、１１２ｂ）は、正孔輸送性材料を含む層である。正孔輸送層（１１２、１１２ａ、１１２ｂ）に用いる正孔輸送性材料は、特に正孔注入層（１１１、１１１ａ、１１１ｂ）のＨＯＭＯ準位と同じ、あるいは近いＨＯＭＯ準位を有するものを用いることが好ましい。 The hole transport layer (112, 112a, 112b) transports holes injected from the first electrode 101 to the light emitting layer (113, 113a, 113b) by the hole injection layer (111, 111a, 111b). Is a layer. Note that the hole transport layers (112, 112a, 112b) are layers containing a hole transport material. As the hole transporting material used for the hole transport layer (112, 112a, 112b), a material having a HOMO level that is the same as or close to the HOMO level of the hole injection layer (111, 111a, 111b) should be used. Is preferred.
正孔注入層（１１１、１１１ａ、１１１ｂ）に用いるアクセプター性材料としては、元素周期表における第４族乃至第８族に属する金属の酸化物を用いることができる。具体的には、酸化モリブデン、酸化バナジウム、酸化ニオブ、酸化タンタル、酸化クロム、酸化タングステン、酸化マンガン、酸化レニウムが挙げられる。中でも特に、酸化モリブデンは大気中でも安定であり、吸湿性が低く、扱いやすいため好ましい。その他、キノジメタン誘導体やクロラニル誘導体、ヘキサアザトリフェニレン誘導体などの有機アクセプターを用いることができる。具体的には、７，７，８，８−テトラシアノ−２，３，５，６−テトラフルオロキノジメタン（略称：Ｆ４−ＴＣＮＱ）、クロラニル、２，３，６，７，１０，１１−ヘキサシアノ−１，４，５，８，９，１２−ヘキサアザトリフェニレン（略称：ＨＡＴ−ＣＮ）等を用いることができる。 As an acceptor material used for the hole-injection layer (111, 111a, 111b), an oxide of a metal belonging to Groups 4 to 8 in the periodic table can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among these, molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, 2,3,6,7,10,11 -Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) or the like can be used.
正孔注入層（１１１、１１１ａ、１１１ｂ）および正孔輸送層（１１２、１１２ａ、１１２ｂ）に用いる正孔輸送性材料としては、１０−６ｃｍ２／Ｖｓ以上の正孔移動度を有する物質が好ましい。なお、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いることができる。 As a hole transporting material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b), a substance having a hole mobility of 10 −6 cm 2 / Vs or more is used. preferable. Note that other than these substances, any substance that has a property of transporting more holes than electrons can be used.
正孔輸送性材料としては、π電子過剰型複素芳香族化合物（例えばカルバゾール誘導体やインドール誘導体）や芳香族アミン化合物が好ましく、具体例としては、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＮＰＢまたはα−ＮＰＤ）、Ｎ，Ｎ’−ビス（３−メチルフェニル）−Ｎ，Ｎ’−ジフェニル−［１，１’−ビフェニル］−４，４’−ジアミン（略称：ＴＰＤ）、４，４’−ビス［Ｎ−（スピロ−９，９’−ビフルオレン−２−イル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＢＳＰＢ）、４−フェニル−４’−（９−フェニルフルオレン−９−イル）トリフェニルアミン（略称：ＢＰＡＦＬＰ）、４−フェニル−３’−（９−フェニルフルオレン−９−イル）トリフェニルアミン（略称：ｍＢＰＡＦＬＰ）、４−フェニル−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡ１ＢＰ）、３−［４−（９−フェナントリル）−フェニル］−９−フェニル−９Ｈ−カルバゾール（略称：ＰＣＰＰｎ）、
Ｎ−（４−ビフェニル）−Ｎ−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）−９−フェニル−９Ｈ−カルバゾール−３−アミン（略称：ＰＣＢｉＦ）、Ｎ−（１，１’−ビフェニル−４−イル）−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（略称：ＰＣＢＢｉＦ）４，４’−ジフェニル−４’’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＢｉ１ＢＰ）、４−（１−ナフチル）−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡＮＢ）、４，４’−ジ（１−ナフチル）−４’’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＮＢＢ）、９，９−ジメチル−Ｎ−フェニル−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］フルオレン−２−アミン（略称：ＰＣＢＡＦ）、Ｎ−フェニル−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］スピロ−９，９’−ビフルオレン−２−アミン（略称：ＰＣＢＡＳＦ）、４，４’，４’’−トリス（カルバゾール−９−イル）トリフェニルアミン（略称：ＴＣＴＡ）、４，４’，４’’−トリス（Ｎ，Ｎ−ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４’’−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミン（略称：ＭＴＤＡＴＡ）などの芳香族アミン骨格を有する化合物、１，３−ビス（Ｎ−カルバゾリル）ベンゼン（略称：ｍＣＰ）、４，４’−ジ（Ｎ−カルバゾリル）ビフェニル（略称：ＣＢＰ）、３，６−ビス（３，５−ジフェニルフェニル）−９−フェニルカルバゾール（略称：ＣｚＴＰ）、３，３’−ビス（９−フェニル−９Ｈ−カルバゾール）（略称：ＰＣＣＰ）、３−［Ｎ−（９−フェニルカルバゾール−３−イル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＡ１）、３，６−ビス［Ｎ−（９−フェニルカルバゾール−３−イル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＡ２）、３−［Ｎ−（１−ナフチル）−Ｎ−（９−フェニルカルバゾール−３−イル）アミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＮ１）、１，３，５−トリス［４−（Ｎ−カルバゾリル）フェニル］ベンゼン（略称：ＴＣＰＢ）、９−［４−（１０−フェニル−９−アントラセニル）フェニル］−９Ｈ−カルバゾール（略称：ＣｚＰＡ）などのカルバゾール骨格を有する化合物、４，４’，４’’−（ベンゼン−１，３，５−トリイル）トリ（ジベンゾチオフェン）（略称：ＤＢＴ３Ｐ−ＩＩ）、２，８−ジフェニル−４−［４−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］ジベンゾチオフェン（略称：ＤＢＴＦＬＰ−ＩＩＩ）、４−［４−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］−６−フェニルジベンゾチオフェン（略称：ＤＢＴＦＬＰ−ＩＶ）などのチオフェン骨格を有する化合物、４，４’，４’’−（ベンゼン−１，３，５−トリイル）トリ（ジベンゾフラン）（略称：ＤＢＦ３Ｐ−ＩＩ）、４−｛３−［３−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］フェニル｝ジベンゾフラン（略称：ｍｍＤＢＦＦＬＢｉ−ＩＩ）などのフラン骨格を有する化合物が挙げられる。 As the hole transporting material, a π-electron rich heteroaromatic compound (for example, a carbazole derivative or an indole derivative) or an aromatic amine compound is preferable. As a specific example, 4,4′-bis [N- (1-naphthyl) is preferable. ) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4,4 '-Diamine (abbreviation: TPD), 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP) ), 4-phenyl-4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP), 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H -Carbazole (abbreviation: PCPPn),
N- (4-biphenyl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1 ′ -Biphenyl-4-yl) -N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) 4,4 '-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4'-(9-phenyl-9H-carbazole- 3-yl) triphenylamine (abbreviation: PCBANB), 4,4′-di (1-naphthyl) -4 ″-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBN) B), 9,9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF), 4,4 ′, 4 ″ -tris (carbazole-9 -Yl) triphenylamine (abbreviation: TCTA), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [ N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA) and other compounds having an aromatic amine skeleton, 1,3-bis (N-carbazolyl) benzene (abbreviation: mC) ), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 3,6-bis (3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6 -Bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9-phenylcarbazole) -3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene ( Name: TCPB), 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA) and other compounds having a carbazole skeleton, 4,4 ′, 4 ″-(benzene- 1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] dibenzothiophene ( Abbreviations: DBTFLP-III), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and the like, 4, 4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 4- {3- [3- (9 Phenyl -9H- fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) compound having a furan skeleton such like.
さらに、ポリ（Ｎ−ビニルカルバゾール）（略称：ＰＶＫ）、ポリ（４−ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）、ポリ［Ｎ−（４−｛Ｎ’−［４−（４−ジフェニルアミノ）フェニル］フェニル−Ｎ’−フェニルアミノ｝フェニル）メタクリルアミド］（略称：ＰＴＰＤＭＡ）ポリ［Ｎ，Ｎ’−ビス（４−ブチルフェニル）−Ｎ，Ｎ’−ビス（フェニル）ベンジジン］（略称：Ｐｏｌｙ−ＴＰＤ）などの高分子化合物を用いることもできる。 Further, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA) poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Poly High molecular compounds such as -TPD) can also be used.
但し、正孔輸送性材料は、上記に限られることなく公知の様々な材料を１種または複数種組み合わせて正孔輸送性材料として正孔注入層（１１１、１１１ａ、１１１ｂ）および正孔輸送層（１１２、１１２ａ、１１２ｂ）に用いることができる。なお、正孔輸送層（１１２、１１２ａ、１１２ｂ）は、各々複数の層から形成されていても良い。すなわち、例えば第１の正孔輸送層と第２の正孔輸送層とが積層されていても良い。 However, the hole transporting material is not limited to the above, and a hole injection layer (111, 111a, 111b) and a hole transporting layer may be used as a hole transporting material by combining one or more known various materials. (112, 112a, 112b). Note that each of the hole transport layers (112, 112a, 112b) may be formed of a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer may be laminated.
図１（Ｄ）に示す発光素子においては、ＥＬ層１０３ａの正孔輸送層１１２ａ上に発光層１１３ａが真空蒸着法により形成される。また、ＥＬ層１０３ａおよび電荷発生層１０４が形成された後、ＥＬ層１０３ｂの正孔輸送層１１２ｂ上に発光層１１３ｂが真空蒸着法により形成される。 In the light-emitting element illustrated in FIG. 1D, the light-emitting layer 113a is formed over the hole-transport layer 112a of the EL layer 103a by a vacuum evaporation method. In addition, after the EL layer 103a and the charge generation layer 104 are formed, the light emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by a vacuum evaporation method.
＜発光層＞
発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）は、発光物質を含む層である。なお、発光物質としては、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いる。また、複数の発光層（１１３ａ、１１３ｂ、１１３ｃ）に異なる発光物質を用いることにより異なる発光色を呈する構成（例えば、補色の関係にある発光色を組み合わせて得られる白色発光）とすることができる。さらに、一つの発光層が異なる発光物質を有する積層構造であっても良い。 <Light emitting layer>
The light emitting layers (113, 113a, 113b, 113c) are layers containing a light emitting substance. Note that as the light-emitting substance, a substance exhibiting a luminescent color such as blue, purple, blue-violet, green, yellow-green, yellow, orange, or red is appropriately used. In addition, by using different light emitting substances for the plurality of light emitting layers (113a, 113b, 113c), a structure exhibiting different light emission colors (for example, white light emission obtained by combining light emission colors having complementary colors) can be obtained. . Furthermore, a stacked structure in which one light emitting layer includes different light emitting substances may be used.
また、発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）は、発光物質（ゲスト材料）に加えて、１種または複数種の有機化合物（ホスト材料、アシスト材料）を有していても良い。また、１種または複数種の有機化合物としては、本実施の形態で説明する正孔輸送性材料や電子輸送性材料の一方または両方を用いることができる。 Further, the light emitting layer (113, 113a, 113b, 113c) may include one or more organic compounds (host material, assist material) in addition to the light emitting substance (guest material). As the one or more kinds of organic compounds, one or both of a hole transporting material and an electron transporting material described in this embodiment can be used.
発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）に用いることができる発光物質としては、一重項励起エネルギーを可視光領域の発光に変える発光物質、または三重項励起エネルギーを可視光領域の発光に変える発光物質を用いることができる。 As a light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b, and 113c), a light-emitting substance that changes singlet excitation energy into light emission in the visible light region, or light emission that changes triplet excitation energy into light emission in the visible light region. Substances can be used.
なお、他の発光物質としては、例えば、以下のようなものが挙げられる。 Examples of other luminescent substances include the following.
一重項励起エネルギーを発光に変える発光物質としては、蛍光を発する物質（蛍光材料）が挙げられ、例えば、ピレン誘導体、アントラセン誘導体、トリフェニレン誘導体、フルオレン誘導体、カルバゾール誘導体、ジベンゾチオフェン誘導体、ジベンゾフラン誘導体、ジベンゾキノキサリン誘導体、キノキサリン誘導体、ピリジン誘導体、ピリミジン誘導体、フェナントレン誘導体、ナフタレン誘導体などが挙げられる。特にピレン誘導体は発光量子収率が高いので好ましい。ピレン誘導体の具体例としては、Ｎ，Ｎ’−ビス（３−メチルフェニル）−Ｎ，Ｎ’−ビス［３−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル〕ピレン−１，６−ジアミン（１，６ｍＭｅｍＦＬＰＡＰｒｎ）、（Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ビス［４−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］ピレン−１，６−ジアミン）（１，６ＦＬＰＡＰｒｎ）、Ｎ，Ｎ’−ビス（ジベンゾフラン−２−イル）−Ｎ，Ｎ’−ジフェニルピレン−１，６−ジアミン（１，６ＦｒＡＰｒｎ）、Ｎ，Ｎ’−ビス（ジベンゾチオフェン−２−イル）−Ｎ，Ｎ’−ジフェニルピレン−１，６−ジアミン（１，６ＴｈＡＰｒｎ）、Ｎ，Ｎ’−（ピレン−１，６−ジイル）ビス［（Ｎ−フェニルベンゾ［ｂ］ナフト［１，２−ｄ］フラン）−６−アミン］（略称：１，６ＢｎｆＡＰｒｎ）、Ｎ，Ｎ’−（ピレン−１，６−ジイル）ビス［（Ｎ−フェニルベンゾ［ｂ］ナフト［１，２−ｄ］フラン）−８−アミン］（略称：１，６ＢｎｆＡＰｒｎ−０２）、Ｎ，Ｎ’−（ピレン−１，６−ジイル）ビス［（６，Ｎ−ジフェニルベンゾ［ｂ］ナフト［１，２−ｄ］フラン）−８−アミン］（略称：１，６ＢｎｆＡＰｒｎ−０３）などが挙げられる。 Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials). For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzos Examples include quinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives. In particular, a pyrene derivative is preferable because of its high emission quantum yield. Specific examples of the pyrene derivative include N, N′-bis (3-methylphenyl) -N, N′-bis [3- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6. -Diamine (1,6mMemFLPAPrn), (N, N'-diphenyl-N, N'-bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6-diamine) (1 , 6FLPAPrn), N, N′-bis (dibenzofuran-2-yl) -N, N′-diphenylpyrene-1,6-diamine (1,6FrAPrn), N, N′-bis (dibenzothiophen-2-yl) ) -N, N′-diphenylpyrene-1,6-diamine (1,6ThAPrn), N, N ′-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] naphtho [1,2 -D] Lan) -6-amine] (abbreviation: 1,6BnfAPrn), N, N '-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] naphtho [1,2-d] furan)- 8-amine] (abbreviation: 1,6BnfAPrn-02), N, N ′-(pyrene-1,6-diyl) bis [(6, N-diphenylbenzo [b] naphtho [1,2-d] furan) -8-amine] (abbreviation: 1,6BnfAPrn-03).
その他にも、５，６−ビス［４−（１０−フェニル−９−アントリル）フェニル］−２，２’−ビピリジン（略称：ＰＡＰ２ＢＰｙ）、５，６−ビス［４’−（１０−フェニル−９−アントリル）ビフェニル−４−イル］−２，２’−ビピリジン（略称：ＰＡＰＰ２ＢＰｙ）、Ｎ，Ｎ’−ビス［４−（９Ｈ−カルバゾール−９−イル）フェニル］−Ｎ，Ｎ’−ジフェニルスチルベン−４，４’−ジアミン（略称：ＹＧＡ２Ｓ）、４−（９Ｈ−カルバゾール−９−イル）−４’−（１０−フェニル−９−アントリル）トリフェニルアミン（略称：ＹＧＡＰＡ）、４−（９Ｈ−カルバゾール−９−イル）−４’−（９，１０−ジフェニル−２−アントリル）トリフェニルアミン（略称：２ＹＧＡＰＰＡ）、Ｎ，９−ジフェニル−Ｎ−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−カルバゾール−３−アミン（略称：ＰＣＡＰＡ）、４−（１０−フェニル−９−アントリル）−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡＰＡ）、４−［４−（１０−フェニル−９−アントリル）フェニル］−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡＰＢＡ）、ペリレン、２，５，８，１１−テトラ（ｔｅｒｔ−ブチル）ペリレン（略称：ＴＢＰ）、Ｎ，Ｎ’’−（２−ｔｅｒｔ−ブチルアントラセン−９，１０−ジイルジ−４，１−フェニレン）ビス［Ｎ，Ｎ’，Ｎ’−トリフェニル−１，４−フェニレンジアミン］（略称：ＤＰＡＢＰＡ）、Ｎ，９−ジフェニル−Ｎ−［４−（９，１０−ジフェニル−２−アントリル）フェニル］−９Ｈ−カルバゾール−３−アミン（略称：２ＰＣＡＰＰＡ）、Ｎ−［４−（９，１０−ジフェニル−２−アントリル）フェニル］−Ｎ，Ｎ’，Ｎ’−トリフェニル−１，４−フェニレンジアミン（略称：２ＤＰＡＰＰＡ）等を用いることができる。 In addition, 5,6-bis [4- (10-phenyl-9-anthryl) phenyl] -2,2′-bipyridine (abbreviation: PAP2BPy), 5,6-bis [4 ′-(10-phenyl-) 9-anthryl) biphenyl-4-yl] -2,2′-bipyridine (abbreviation: PAPP2BPy), N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenyl Stilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H-carbazol-9-yl) -4 ′-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- ( 9H-carbazol-9-yl) -4 ′-(9,10-diphenyl-2-anthryl) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N- [4- (10 Phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), 4- (10-phenyl-9-anthryl) -4 ′-(9-phenyl-9H-carbazol-3-yl) Triphenylamine (abbreviation: PCBAPA), 4- [4- (10-phenyl-9-anthryl) phenyl] -4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBAPBA) Perylene, 2,5,8,11-tetra (tert-butyl) perylene (abbreviation: TBP), N, N ″-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene) Bis [N, N ′, N′-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N, 9-diphenyl-N- [4- ( , 10-diphenyl-2-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4- (9,10-diphenyl-2-anthryl) phenyl] -N, N ′, N '-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like can be used.
また、三重項励起エネルギーを発光に変える発光物質としては、例えば、燐光を発する物質（燐光材料）や熱活性化遅延蛍光を示す熱活性化遅延蛍光（Ｔｈｅｒｍａｌｌｙ　ａｃｔｉｖａｔｅｄ　ｄｅｌａｙｅｄ　ｆｌｕｏｒｅｓｃｅｎｃｅ：ＴＡＤＦ）材料が挙げられる。 Examples of the light-emitting substance that changes triplet excitation energy into light emission include phosphorescent substances (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence. .
燐光材料としては、有機金属錯体、金属錯体（白金錯体）、希土類金属錯体等が挙げられる。これらは、物質ごとに異なる発光色（発光ピーク）を示すため、必要に応じて適宜選択して用いる。 Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as necessary.
青色または緑色を呈し、発光スペクトルのピーク波長が４５０ｎｍ以上５７０ｎｍ以下である燐光材料としては、以下のような物質が挙げられる。 Examples of phosphorescent materials that exhibit blue or green color and whose emission spectrum peak wavelength is 450 nm or more and 570 nm or less include the following substances.
例えば、トリス｛２−［５−（２−メチルフェニル）−４−（２，６−ジメチルフェニル）−４Ｈ−１，２，４−トリアゾール−３−イル−κＮ２］フェニル−κＣ｝イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｐｔｚ−ｄｍｐ）３］）、トリス（５−メチル−３，４−ジフェニル−４Ｈ−１，２，４−トリアゾラト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（Ｍｐｔｚ）３］）、トリス［４−（３−ビフェニル）−５−イソプロピル−３−フェニル−４Ｈ−１，２，４−トリアゾラト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｉＰｒｐｔｚ−３ｂ）３］）トリス［３−（５−ビフェニル）−５−イソプロピル−４−フェニル−４Ｈ−１，２，４−トリアゾラト］イリジウム（ＩＩＩ）（略称：Ｉｒ（ｉＰｒ５ｂｔｚ）３］）、のような４Ｈ−トリアゾール骨格を有する有機金属錯体、トリス［３−メチル−１−（２−メチルフェニル）−５−フェニル−１Ｈ−１，２，４−トリアゾラト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（Ｍｐｔｚ１−ｍｐ）３］）、トリス（１−メチル−５−フェニル−３−プロピル−１Ｈ−１，２，４−トリアゾラト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（Ｐｒｐｔｚ１−Ｍｅ）３］）のような１Ｈ−トリアゾール骨格を有する有機金属錯体、ｆａｃ−トリス［（２，６−ジイソプロピルフェニル）−２−フェニル−１Ｈ−イミダゾール］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｉＰｒｐｍｉ）３］）、トリス［３−（２，６−ジメチルフェニル）−７−メチルイミダゾ［１，２−ｆ］フェナントリジナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｍｐｉｍｐｔ−Ｍｅ）３］）のようなイミダゾール骨格を有する有機金属錯体、ビス［２−（４’，６’−ジフルオロフェニル）ピリジナト−Ｎ，Ｃ２’］イリジウム（ＩＩＩ）テトラキス（１−ピラゾリル）ボラート（略称：ＦＩｒ６）、ビス［２−（４’，６’−ジフルオロフェニル）ピリジナト−Ｎ，Ｃ２’］イリジウム（ＩＩＩ）ピコリナート（略称：ＦＩｒｐｉｃ）、ビス｛２−［３’，５’−ビス（トリフルオロメチル）フェニル］ピリジナト−Ｎ，Ｃ２’］イリジウム（ＩＩＩ）ピコリナート（略称：［Ｉｒ（ＣＦ３ｐｐｙ）２（ｐｉｃ）］）、ビス［２−（４’，６’−ジフルオロフェニル）ピリジナト−Ｎ，Ｃ２’］イリジウム（ＩＩＩ）アセチルアセトナート（略称：ＦＩｒ（ａｃａｃ））のように電子吸引基を有するフェニルピリジン誘導体を配位子とする有機金属錯体等が挙げられる。 For example, tris {2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III ) (Abbreviation: [Ir (mpppz-dmp) 3 ]), tris (5-methyl-3,4-diphenyl-4H-1,2,4-triazolato) 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 ]) Tris [ 3- (5-biphenyl) -5-isopropyl-4-phenyl-4H-1,2,4-triazolato] iridium (III) (abbreviation: Ir (iPr5btz) 3]) , 4 such as An organometallic complex having a triazole skeleton, tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolato] iridium (III) (abbreviation: [Ir (Mptz1- mp) 3 ]), tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolate) iridium (III) (abbreviation: [Ir (Prptz1-Me) 3 ]) Organometallic complex having 1H-triazole skeleton, fac-tris [(2,6-diisopropylphenyl) -2-phenyl-1H-imidazole] iridium (III) (abbreviation: [Ir (iPrpmi) 3 ]), tris [3 -(2,6-Dimethylphenyl) -7-methylimidazo [1,2-f] phenanthridinato] iridium (III) (abbreviation: [I (Dmpimpt-Me) 3] an organometallic complex having an imidazole skeleton, such as), bis [2- (4 ', 6'-difluorophenyl) pyridinato -N, C 2'] iridium (III) tetrakis (1-pyrazolyl ) Borate (abbreviation: FIr6), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C 2 ′ ] iridium (III) picolinate (abbreviation: FIrpic), bis {2- [3 ′, 5 '-Bis (trifluoromethyl) phenyl] pyridinato-N, C 2' ] iridium (III) picolinate (abbreviation: [Ir (CF 3 ppy) 2 (pic)]), bis [2- (4 ', 6' - difluorophenyl) pyridinato -N, C 2 '] iridium (III) acetylacetonate (abbreviation: FIr (acac) off with an electron withdrawing group such as) The Nirupirijin derivatives and organic metal complexes having a ligand.
緑色または黄色を呈し、発光スペクトルのピーク波長が４９５ｎｍ以上５９０ｎｍ以下である燐光材料としては、以下のような物質が挙げられる。 Examples of the phosphorescent material which exhibits green or yellow and has an emission spectrum peak wavelength of 495 nm or more and 590 nm or less include the following substances.
例えば、トリス（４−メチル−６−フェニルピリミジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｐｍ）３］）、トリス（４−ｔ−ブチル−６−フェニルピリミジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｔＢｕｐｐｍ）３］）、（アセチルアセトナト）ビス（６−メチル−４−フェニルピリミジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｐｍ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス（６−ｔｅｒｔ−ブチル−４−フェニルピリミジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｔＢｕｐｐｍ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス［６−（２−ノルボルニル）−４−フェニルピリミジナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｎｂｐｐｍ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス［５−メチル−６−（２−メチルフェニル）−４−フェニルピリミジナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｍｐｐｍ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス｛４，６−ジメチル−２−［６−（２，６−ジメチルフェニル）−４−ピリミジニル−κＮ３］フェニル−κＣ｝イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｍｐｐｍ−ｄｍｐ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス（４，６−ジフェニルピリミジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｐｐｍ）２（ａｃａｃ）］）のようなピリミジン骨格を有する有機金属イリジウム錯体、（アセチルアセトナト）ビス（３，５−ジメチル−２−フェニルピラジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｐｒ−Ｍｅ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス（５−イソプロピル−３−メチル−２−フェニルピラジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｐｒ−ｉＰｒ）２（ａｃａｃ）］）のようなピラジン骨格を有する有機金属イリジウム錯体、トリス（２−フェニルピリジナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｐｐｙ）３］）、ビス（２−フェニルピリジナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｐｐｙ）２（ａｃａｃ）］）、ビス（ベンゾ［ｈ］キノリナト）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｂｚｑ）２（ａｃａｃ）］）、トリス（ベンゾ［ｈ］キノリナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｂｚｑ）３］）、トリス（２−フェニルキノリナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｐｑ）３］）、ビス（２−フェニルキノリナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｐｑ）２（ａｃａｃ）］）のようなピリジン骨格を有する有機金属イリジウム錯体、ビス（２，４−ジフェニル−１，３−オキサゾラト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｄｐｏ）２（ａｃａｃ）］）、ビス｛２−［４’−（パーフルオロフェニル）フェニル］ピリジナト−Ｎ，Ｃ２’｝イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｐ−ＰＦ−ｐｈ）２（ａｃａｃ）］）、ビス（２−フェニルベンゾチアゾラト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｂｔ）２（ａｃａｃ）］）などの有機金属錯体の他、トリス（アセチルアセトナト）（モノフェナントロリン）テルビウム（ＩＩＩ）（略称：［Ｔｂ（ａｃａｃ）３（Ｐｈｅｎ）］）のような希土類金属錯体が挙げられる。 For example, tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) 3 ]), tris (4-t-butyl-6-phenylpyrimidinato) iridium (III) (Abbreviation: [Ir (tBupppm) 3 ]), (acetylacetonato) bis (6-methyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) 2 (acac)]), ( Acetylacetonato) bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (tBupppm) 2 (acac)]), (acetylacetonato) bis [6- (2- Norbornyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (nbppm) 2 (acac)]), (acetylacetona G) Bis [5-methyl-6- (2-methylphenyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpmppm) 2 (acac)]), (acetylacetonato) bis { 4,6-dimethyl-2- [6- (2,6-dimethylphenyl) -4-pyrimidinyl-κN3] phenyl-κC} iridium (III) (abbreviation: [Ir (dmppm-dmp) 2 (acac)]) , (Acetylacetonato) bis (4,6-diphenylpyrimidinato) iridium (III) (abbreviation: [Ir (dppm) 2 (acac)]), an organometallic iridium complex having a pyrimidine skeleton, isocyanatomethyl) bis (3,5-dimethyl-2-phenylpyrazinato) iridium (III) (abbreviation: [Ir (mppr-Me) 2 (acac ]), (Acetylacetonato) bis (5-isopropyl-3-methyl-2-phenylpyrazinato) iridium (III) (abbreviation: [Ir (mppr-iPr) pyrazine skeleton, such as 2 (acac)]) , Tris (2-phenylpyridinato-N, C 2 ′ ) iridium (III) (abbreviation: [Ir (ppy) 3 ]), bis (2-phenylpyridinato-N, C 2 ′ ) iridium (III) acetylacetonate (abbreviation: [Ir (ppy) 2 (acac)]), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: [Ir (bzq) 2 ( acac)]), tris (benzo [h] quinolinato) iridium (III) (abbreviation: [Ir (bzq) 3] ), tris (2-Fenirukinori DOO -N, C 2 ') iridium (III) (abbreviation: [Ir (pq) 3] ), bis (2-phenylquinolinato--N, C 2') iridium (III) acetylacetonate (abbreviation: [Ir (Pq) 2 (acac)]), an organometallic iridium complex having a pyridine skeleton, bis (2,4-diphenyl-1,3-oxazolate-N, C 2 ′ ) iridium (III) acetylacetonate (abbreviation) : [Ir (dpo) 2 (acac)]), bis {2- [4 ′-(perfluorophenyl) phenyl] pyridinato-N, C 2 ′ } iridium (III) acetylacetonate (abbreviation: [Ir (p -PF-ph) 2 (acac) ]), bis (2-phenyl-benzothiazyl Zola DOO -N, C 2 ') iridium (III) acetylacetonate (abbreviation: [Ir (bt 2 (acac)]) other organometallic complexes such as tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: [Tb (acac) 3 ( Phen)]) include rare earth metal complex such as It is done.
黄色または赤色を呈し、発光スペクトルのピーク波長が５７０ｎｍ以上７５０ｎｍ以下である燐光材料としては、以下のような物質が挙げられる。 Examples of the phosphorescent material which exhibits yellow or red and has an emission spectrum peak wavelength of 570 nm or more and 750 nm or less include the following substances.
例えば、（ジイソブチリルメタナト）ビス［４，６−ビス（３−メチルフェニル）ピリミジナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（５ｍｄｐｐｍ）２（ｄｉｂｍ）］）、ビス［４，６−ビス（３−メチルフェニル）ピリミジナト］（ジピバロイルメタナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（５ｍｄｐｐｍ）２（ｄｐｍ）］）、（ジピバロイルメタナト）ビス［４，６−ジ（ナフタレン−１−イル）ピリミジナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄ１ｎｐｍ）２（ｄｐｍ）］）のようなピリミジン骨格を有する有機金属錯体、（アセチルアセトナト）ビス（２，３，５−トリフェニルピラジナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｔｐｐｒ）２（ａｃａｃ）］）、ビス（２，３，５−トリフェニルピラジナト）（ジピバロイルメタナト）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｔｐｐｒ）２（ｄｐｍ）］）、ビス｛４，６−ジメチル−２−［３−（３，５−ジメチルフェニル）−５−フェニル−２−ピラジニル−κＮ］フェニル−κＣ｝（２，６−ジメチル−３，５−ヘプタンジオナト−κ２Ｏ，Ｏ’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｍｄｐｐｒ−Ｐ）２（ｄｉｂｍ）］）、ビス｛４，６−ジメチル−２−［５−（４−シアノ−２，６−ジメチルフェニル）−３−（３，５−ジメチルフェニル）−２−ピラジニル−κＮ］フェニル−κＣ｝（２，２，６，６−テトラメチル−３，５−ヘプタンジオナト−κ２Ｏ，Ｏ’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｍｄｐｐｒ−ｄｍＣＰ）２（ｄｐｍ）］）、（アセチルアセトナト）ビス［２−メチル−３−フェニルキノキサリナト−Ｎ，Ｃ２’］イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｍｐｑ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス（２，３−ジフェニルキノキサリナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｄｐｑ）２（ａｃａｃ）］）、（アセチルアセトナト）ビス［２，３−ビス（４−フルオロフェニル）キノキサリナト］イリジウム（ＩＩＩ）（略称：［Ｉｒ（Ｆｄｐｑ）２（ａｃａｃ）］）のようなピラジン骨格を有する有機金属錯体や、トリス（１−フェニルイソキノリナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）（略称：［Ｉｒ（ｐｉｑ）３］）、ビス（１−フェニルイソキノリナト−Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：［Ｉｒ（ｐｉｑ）２（ａｃａｃ）］）のようなピリジン骨格を有する有機金属錯体、２，３，７，８，１２，１３，１７，１８−オクタエチル−２１Ｈ，２３Ｈ−ポルフィリン白金（ＩＩ）（略称：［ＰｔＯＥＰ］）のような白金錯体、トリス（１，３−ジフェニル−１，３−プロパンジオナト）（モノフェナントロリン）ユーロピウム（ＩＩＩ）（略称：［Ｅｕ（ＤＢＭ）３（Ｐｈｅｎ）］）、トリス［１−（２−テノイル）−３，３，３−トリフルオロアセトナト］（モノフェナントロリン）ユーロピウム（ＩＩＩ）（略称：［Ｅｕ（ＴＴＡ）３（Ｐｈｅｎ）］）のような希土類金属錯体が挙げられる。 For example, (diisobutyrylmethanato) bis [4,6-bis (3-methylphenyl) pyrimidinato] iridium (III) (abbreviation: [Ir (5 mdppm) 2 (divm)]), bis [4,6-bis ( 3-methylphenyl) pyrimidinato] (dipivaloylmethanato) iridium (III) (abbreviation: [Ir (5 mdppm) 2 (dpm)]), (dipivaloylmethanato) bis [4,6-di (naphthalene- Organometallic complexes having a pyrimidine skeleton such as 1-yl) pyrimidinato] iridium (III) (abbreviation: [Ir (d1npm) 2 (dpm)]), (acetylacetonato) bis (2,3,5-triphenyl) Pirajinato) iridium (III) (abbreviation: [Ir (tppr) 2 ( acac)]), bis (2,3,5-triphenylpyrazinato (Dipivaloylmethanato) iridium (III) (abbreviation: [Ir (tppr) 2 ( dpm)]), bis {4,6-dimethyl-2- [3- (3,5-dimethylphenyl) -5- Phenyl-2-pyrazinyl-κN] phenyl-κC} (2,6-dimethyl-3,5-heptanedionato-κ 2 O, O ′) iridium (III) (abbreviation: [Ir (dmdppr-P) 2 (divm) ], Bis {4,6-dimethyl-2- [5- (4-cyano-2,6-dimethylphenyl) -3- (3,5-dimethylphenyl) -2-pyrazinyl-κN] phenyl-κC} (2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O, O ′) iridium (III) (abbreviation: [Ir (dmdppr-dmCP) 2 (dpm)]), (acetylacetonato ) Screw [2 -Methyl-3-phenylquinoxalinato-N, C 2 ′ ] iridium (III) (abbreviation: [Ir (mpq) 2 (acac)]), (acetylacetonato) bis (2,3-diphenylquinoxalinato -N, C2 ' ) iridium (III) (abbreviation: [Ir (dpq) 2 (acac)]), (acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (Abbreviation: [Ir (Fdpq) 2 (acac)]) or an organometallic complex having a pyrazine skeleton, or tris (1-phenylisoquinolinato-N, C 2 ′ ) iridium (III) (abbreviation: [Ir (Piq) 3 ]), bis (1-phenylisoquinolinato-N, C 2 ′ ) iridium (III) acetylacetonate (abbreviation: [Ir (piq) 2 (aca c)])) of an organometallic complex having a pyridine skeleton, 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation: [PtOEP]) Platinum complexes such as tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: [Eu (DBM) 3 (Phen)]), tris [1- (2 -Thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu (TTA) 3 (Phen)]).
発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）に用いる有機化合物（ホスト材料、アシスト材料）としては、発光物質（ゲスト材料）のエネルギーギャップより大きなエネルギーギャップを有する物質を、一種もしくは複数種選択して用いればよい。 As the organic compound (host material, assist material) used for the light emitting layer (113, 113a, 113b, 113c), one or more kinds of substances having an energy gap larger than that of the light emitting substance (guest material) are selected. Use it.
発光物質が蛍光材料である場合、ホスト材料としては一重項励起状態のエネルギー準位が大きく、三重項励起状態のエネルギー準位が小さい有機化合物を用いるのが好ましい。例えば、アントラセン誘導体やテトラセン誘導体を用いるのが好ましい。具体的には、９−フェニル−３−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−カルバゾール（略称：ＰＣｚＰＡ）、３−［４−（１−ナフチル）−フェニル］−９−フェニル−９Ｈ−カルバゾール（略称：ＰＣＰＮ）、９−［４−（１０−フェニル−９−アントラセニル）フェニル］−９Ｈ−カルバゾール（略称：ＣｚＰＡ）、７−［４−（１０−フェニル−９−アントリル）フェニル］−７Ｈ−ジベンゾ［ｃ，ｇ］カルバゾール（略称：ｃｇＤＢＣｚＰＡ）、６−［３−（９，１０−ジフェニル−２−アントリル）フェニル］−ベンゾ［ｂ］ナフト［１，２−ｄ］フラン（略称：２ｍＢｎｆＰＰＡ）、９−フェニル−１０−｛４−（９−フェニル−９Ｈ−フルオレン−９−イル）−ビフェニル−４’−イル｝アントラセン（略称：ＦＬＰＰＡ）、５，１２−ジフェニルテトラセン、５，１２−ビス（ビフェニル−２−イル）テトラセンなどが挙げられる。 When the light-emitting substance is a fluorescent material, it is preferable to use an organic compound having a large singlet excited state energy level and a small triplet excited state energy level as the host material. For example, it is preferable to use an anthracene derivative or a tetracene derivative. Specifically, 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-anthracenyl) 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 ] Furan (abbreviation: 2 mBnfPPA), 9-phenyl-10- {4- (9-phenyl-9H-fluoren-9-yl) -biphenyl-4'-yl} anthrace (Abbreviation: FLPPA), 5,12 diphenyltetracene, 5,12-bis (biphenyl-2-yl) tetracene, and the like.
発光物質が燐光材料である場合、ホスト材料としては、発光物質の三重項励起エネルギー（基底状態と三重項励起状態とのエネルギー差）よりも三重項励起エネルギーの大きい有機化合物を選択すれば良い。なお、この場合には、亜鉛やアルミニウム系金属錯体の他、オキサジアゾール誘導体、トリアゾール誘導体、ベンゾイミダゾール誘導体、キノキサリン誘導体、ジベンゾキノキサリン誘導体、ジベンゾチオフェン誘導体、ジベンゾフラン誘導体、ピリミジン誘導体、トリアジン誘導体、ピリジン誘導体、ビピリジン誘導体、フェナントロリン誘導体等の他、芳香族アミンやカルバゾール誘導体等を用いることができる。 When the light-emitting substance is a phosphorescent material, an organic compound having a triplet excitation energy larger than the triplet excitation energy (energy difference between the ground state and the triplet excited state) of the light-emitting substance may be selected as the host material. In this case, in addition to zinc and aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives In addition to bipyridine derivatives and phenanthroline derivatives, aromatic amines and carbazole derivatives can be used.
ホスト材料として、より具体的には、例えば以下の正孔輸送性材料および電子輸送性材料を用いることができる。 More specifically, for example, the following hole transporting materials and electron transporting materials can be used as the host material.
これら正孔輸送性の高いホスト材料としては、例えば、Ｎ，Ｎ’−ジ（ｐ−トリル）−Ｎ，Ｎ’−ジフェニル−ｐ−フェニレンジアミン（略称：ＤＴＤＰＰＡ）、４，４’−ビス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＤＰＡＢ）、Ｎ，Ｎ’−ビス｛４−［ビス（３−メチルフェニル）アミノ］フェニル｝−Ｎ，Ｎ’−ジフェニル−（１，１’−ビフェニル）−４，４’−ジアミン（略称：ＤＮＴＰＤ）、１，３，５−トリス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］ベンゼン（略称：ＤＰＡ３Ｂ）等の芳香族アミン化合物を挙げることができる。 Examples of these host materials having a high hole transporting property include N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 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), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B) An aromatic amine compound such as
また、３−［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＤＰＡ１）、３，６−ビス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＤＰＡ２）、３，６−ビス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−（１−ナフチル）アミノ］−９−フェニルカルバゾール（略称：ＰＣｚＴＰＮ２）、３−［Ｎ−（９−フェニルカルバゾール−３−イル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＡ１）、３，６−ビス［Ｎ−（９−フェニルカルバゾール−３−イル）−Ｎ−フェニルアミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＡ２）、３−［Ｎ−（１−ナフチル）−Ｎ−（９−フェニルカルバゾール−３−イル）アミノ］−９−フェニルカルバゾール（略称：ＰＣｚＰＣＮ１）等のカルバゾール誘導体を挙げることができる。また、カルバゾール誘導体としては、他に、４，４’−ジ（Ｎ−カルバゾリル）ビフェニル（略称：ＣＢＰ）、１，３，５−トリス［４−（Ｎ−カルバゾリル）フェニル］ベンゼン（略称：ＴＣＰＢ）、１，４−ビス［４−（Ｎ−カルバゾリル）フェニル］−２，３，５，６−テトラフェニルベンゼン等を用いることもできる。 In addition, 3- [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] -9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis [N- (4-diphenylaminophenyl) -N- (1-naphthyl) amino] -9-phenylcarbazole (abbreviation: PCzTPN2), 3 -[N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl)- N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9 Phenyl-3-yl) amino] phenyl carbazole (abbreviation: PCzPCNl) can be mentioned carbazole derivatives such. As other carbazole derivatives, 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation: TCPB) ), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5,6-tetraphenylbenzene and the like can also be used.
また、正孔輸送性の高いホスト材料としては、例えば、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＮＰＢまたはα−ＮＰＤ）やＮ，Ｎ’−ビス（３−メチルフェニル）−Ｎ，Ｎ’−ジフェニル−［１，１’−ビフェニル］−４，４’−ジアミン（略称：ＴＰＤ）、４，４’，４’’−トリス（カルバゾール−９−イル）トリフェニルアミン（略称：ＴＣＴＡ）、４，４’，４’’−トリス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］トリフェニルアミン（略称：１’−ＴＮＡＴＡ）、４，４’，４’’−トリス（Ｎ，Ｎ−ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４’’−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミン（略称：ｍ−ＭＴＤＡＴＡ）、４，４’−ビス［Ｎ−（スピロ−９，９’−ビフルオレン−２−イル）−Ｎ−フェニルアミノ］ビフェニル（略称：ＢＳＰＢ）、４−フェニル−４’−（９−フェニルフルオレン−９−イル）トリフェニルアミン（略称：ＢＰＡＦＬＰ）、４−フェニル−３’−（９−フェニルフルオレン−９−イル）トリフェニルアミン（略称：ｍＢＰＡＦＬＰ）、Ｎ−（９，９ｆ−ジメチル−９Ｈ−フルオレン−２−イル）−Ｎ−｛９，９−ジメチル−２−［Ｎ’−フェニル−Ｎ’−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）アミノ］−９Ｈ−フルオレン−７−イル｝フェニルアミン（略称：ＤＦＬＡＤＦＬ）、Ｎ−（９，９−ジメチル−２−ジフェニルアミノ−９Ｈ−フルオレン−７−イル）ジフェニルアミン（略称：ＤＰＮＦ）、２−［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］スピロ−９，９’−ビフルオレン（略称：ＤＰＡＳＦ）、４−フェニル−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡ１ＢＰ）、４，４’−ジフェニル−４’’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＢｉ１ＢＰ）、４−（１−ナフチル）−４’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＡＮＢ）、４，４’−ジ（１−ナフチル）−４’’−（９−フェニル−９Ｈ−カルバゾール−３−イル）トリフェニルアミン（略称：ＰＣＢＮＢＢ）、４−フェニルジフェニル−（９−フェニル−９Ｈ−カルバゾール−３−イル）アミン（略称：ＰＣＡ１ＢＰ）、Ｎ，Ｎ’−ビス（９−フェニルカルバゾール−３−イル）−Ｎ，Ｎ’−ジフェニルベンゼン−１，３−ジアミン（略称：ＰＣＡ２Ｂ）、Ｎ，Ｎ’，Ｎ’’−トリフェニル−Ｎ，Ｎ’，Ｎ’’−トリス（９−フェニルカルバゾール−３−イル）ベンゼン−１，３，５−トリアミン（略称：ＰＣＡ３Ｂ）、Ｎ−（４−ビフェニル）−Ｎ−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）−９−フェニル−９Ｈ−カルバゾール−３−アミン（略称：ＰＣＢｉＦ）、Ｎ−（１，１’−ビフェニル−４−イル）−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（略称：ＰＣＢＢｉＦ）、９，９−ジメチル−Ｎ−フェニル−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］フルオレン−２−アミン（略称：ＰＣＢＡＦ）、Ｎ−フェニル−Ｎ−［４−（９−フェニル−９Ｈ−カルバゾール−３−イル）フェニル］スピロ−９，９’−ビフルオレン−２−アミン（略称：ＰＣＢＡＳＦ）、２−［Ｎ−（９−フェニルカルバゾール−３−イル）−Ｎ−フェニルアミノ］スピロ−９，９’−ビフルオレン（略称：ＰＣＡＳＦ）、２，７−ビス［Ｎ−（４−ジフェニルアミノフェニル）−Ｎ−フェニルアミノ］−スピロ−９，９’−ビフルオレン（略称：ＤＰＡ２ＳＦ）、Ｎ−［４−（９Ｈ−カルバゾール−９−イル）フェニル］−Ｎ−（４−フェニル）フェニルアニリン（略称：ＹＧＡ１ＢＰ）、Ｎ，Ｎ’−ビス［４−（カルバゾール−９−イル）フェニル］−Ｎ，Ｎ’−ジフェニル−９，９−ジメチルフルオレン−２，７−ジアミン（略称：ＹＧＡ２Ｆ）などの芳香族アミン化合物等を用いることができる。また、３−［４−（１−ナフチル）−フェニル］−９−フェニル−９Ｈ−カルバゾール（略称：ＰＣＰＮ）、３−［４−（９−フェナントリル）−フェニル］−９−フェニル−９Ｈ−カルバゾール（略称：ＰＣＰＰｎ）、３，３’−ビス（９−フェニル−９Ｈ−カルバゾール）（略称：ＰＣＣＰ）、１，３−ビス（Ｎ−カルバゾリル）ベンゼン（略称：ｍＣＰ）、３，６−ビス（３，５−ジフェニルフェニル）−９−フェニルカルバゾール（略称：ＣｚＴＰ）、４−｛３−［３−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］フェニル｝ジベンゾフラン（略称：ｍｍＤＢＦＦＬＢｉ−ＩＩ）、４，４’，４’’−（ベンゼン−１，３，５−トリイル）トリ（ジベンゾフラン）（略称：ＤＢＦ３Ｐ−ＩＩ）、１，３，５−トリ（ジベンゾチオフェン−４−イル）−ベンゼン（略称：ＤＢＴ３Ｐ−ＩＩ）、２，８−ジフェニル−４−［４−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］ジベンゾチオフェン（略称：ＤＢＴＦＬＰ−ＩＩＩ）、４−［４−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］−６−フェニルジベンゾチオフェン（略称：ＤＢＴＦＬＰ−ＩＶ）、４−［３−（トリフェニレン−２−イル）フェニル］ジベンゾチオフェン（略称：ｍＤＢＴＰＴｐ−ＩＩ）等のカルバゾール化合物、チオフェン化合物、フラン化合物、フルオレン化合物、トリフェニレン化合物、フェナントレン化合物等を用いることができる。 As a host material having a high hole-transport property, for example, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD), N, N ′ -Bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (abbreviation: TPD), 4,4 ', 4 "-tris (carbazole- 9-yl) triphenylamine (abbreviation: TCTA), 4,4 ′, 4 ″ -tris [N- (1-naphthyl) -N-phenylamino] triphenylamine (abbreviation: 1′-TNATA), 4 , 4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino ] Triphenylamine (abbreviation m-MTDATA), 4,4′-bis [N- (spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 ′-(9 -Phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3 '-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP), N- (9,9f- Dimethyl-9H-fluoren-2-yl) -N- {9,9-dimethyl-2- [N′-phenyl-N ′-(9,9-dimethyl-9H-fluoren-2-yl) amino] -9H -Fluoren-7-yl} phenylamine (abbreviation: DFLADFL), N- (9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl) diphenylamine (abbreviation: DPNF), 2- [N- (4-diphenylaminophenyl) -N-phenylamino] spiro-9,9′-bifluorene (abbreviation: DPASF), 4-phenyl-4 ′-(9-phenyl-9H-carbazole) -3-yl) triphenylamine (abbreviation: PCBA1BP), 4,4′-diphenyl-4 ″-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- ( 1-naphthyl) -4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBANB), 4,4′-di (1-naphthyl) -4 ″-(9-phenyl) -9H-carbazol-3-yl) triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl- (9-phenyl-9H-carbazole-3- ) Amine (abbreviation: PCA1BP), N, N′-bis (9-phenylcarbazol-3-yl) -N, N′-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N, N ′, N ″ -triphenyl-N, N ′, N ″ -tris (9-phenylcarbazol-3-yl) benzene-1,3,5-triamine (abbreviation: PCA3B), N- (4-biphenyl)- N- (9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1′-biphenyl-4-yl)- N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 9,9-dimethyl-N-phenyl- N- [ -(9-phenyl-9H-carbazol-3-yl) phenyl] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] Spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF), 2- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] spiro-9,9′-bifluorene (abbreviation) : PCASF), 2,7-bis [N- (4-diphenylaminophenyl) -N-phenylamino] -spiro-9,9'-bifluorene (abbreviation: DPA2SF), N- [4- (9H-carbazole- 9-yl) phenyl] -N- (4-phenyl) phenylaniline (abbreviation: YGA1BP), N, N′-bis [4- (carbazol-9-yl) phenyl An aromatic amine compound such as —N, N′-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) can be used. 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (Abbreviation: PCPPn), 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis (N-carbazolyl) benzene (abbreviation: mCP), 3,6-bis ( 3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 4- {3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) ), 4,4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri (di) Nzothiophen-4-yl) -benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] dibenzothiophene (abbreviation: DBTFLP-III) ), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4- [3- (triphenylene-2-yl) phenyl] A carbazole compound such as dibenzothiophene (abbreviation: mDBTPTp-II), a thiophene compound, a furan compound, a fluorene compound, a triphenylene compound, a phenanthrene compound, or the like can be used.
　電子輸送性の高いホスト材料としては、例えば、トリス（８−キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｑ）、トリス（４−メチル−８−キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｍｑ３）、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（ＩＩ）（略称：ＢｅＢｑ２）、ビス（２−メチル−８−キノリノラト）（４−フェニルフェノラト）アルミニウム（ＩＩＩ）（略称：ＢＡｌｑ）、ビス（８−キノリノラト）亜鉛（ＩＩ）（略称：Ｚｎｑ）など、キノリン骨格またはベンゾキノリン骨格を有する金属錯体等である。また、この他ビス［２−（２−ベンゾオキサゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＰＢＯ）、ビス［２−（２−ベンゾチアゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＢＴＺ）などのオキサゾール系、チアゾール系配位子を有する金属錯体なども用いることができる。さらに、金属錯体以外にも、２−（４−ビフェニリル）−５−（４−ｔｅｒｔ−ブチルフェニル）−１，３，４−オキサジアゾール（略称：ＰＢＤ）や、１，３−ビス［５−（ｐ−ｔｅｒｔ−ブチルフェニル）−１，３，４−オキサジアゾール−２−イル］ベンゼン（略称：ＯＸＤ−７）、９−［４−（５−フェニル−１，３，４−オキサジアゾール−２−７イル）フェニル］−９Ｈ−カルバゾール（略称：ＣＯ１１）のようなオキサジアゾール誘導体や、３−（４−ビフェニリル）−４−フェニル−５−（４−ｔｅｒｔ−ブチルフェニル）−１，２，４−トリアゾール（略称：ＴＡＺ）のようなトリアゾール誘導体や、２，２’，２’’−（１，３，５−ベンゼントリイル）トリス（１−フェニル−１Ｈ−ベンゾイミダゾール）（略称：ＴＰＢＩ）、２−［３−（ジベンゾチオフェン−４−イル）フェニル］−１−フェニル−１Ｈ−ベンゾイミダゾール（略称：ｍＤＢＴＢＩｍ−ＩＩ）のようなイミダゾール骨格を有する化合物（特にベンゾイミダゾール誘導体）や、４，４’−ビス（５−メチルベンゾオキサゾール−２−イル）スチルベン（略称：ＢｚＯＳ）などのオキサゾール骨格を有する化合物（特にベンゾオキサゾール誘導体）や、バソフェナントロリン（略称：ＢＰｈｅｎ）、バソキュプロイン（略称：ＢＣＰ）、２，９−ビス（ナフタレン−２−イル）−４，７−ジフェニル−１，１０−フェナントロリン（略称：ＮＢｐｈｅｎ）などのフェナントロリン誘導体や、２−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ｍＤＢＴＰＤＢｑ−ＩＩ）、２−［３’−（ジベンゾチオフェン−４−イル）ビフェニル−３−イル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ｍＤＢＴＢＰＤＢｑ−ＩＩ）、２−［３’−（９Ｈ−カルバゾール−９−イル）ビフェニル−３−イル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ｍＣｚＢＰＤＢｑ）、２−［４−（３，６−ジフェニル−９Ｈ−カルバゾール−９−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ＣｚＰＤＢｑ−ＩＩＩ）、７−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：７ｍＤＢＴＦＰＤＢｑ−ＩＩ）、及び６−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：６ｍＤＢＴＰＤＢｑ−ＩＩ）、４，６−ビス［３−（フェナントレン−９−イル）フェニル］ピリミジン（略称：４，６ｍＰｎＰ２Ｐｍ）、４，６−ビス［３−（４−ジベンゾチエニル）フェニル］ピリミジン（略称：４，６ｍＤＢＴＰ２Ｐｍ−ＩＩ）、４，６−ビス［３−（９Ｈ−カルバゾール−９−イル）フェニル］ピリミジン（略称：４，６ｍＣｚＰ２Ｐｍ）などのジアジン骨格を有する複素環化合物や、２−｛４−［３−（Ｎ−フェニル−９Ｈ−カルバゾール−３−イル）−９Ｈ−カルバゾール−９−イル］フェニル｝−４，６−ジフェニル−１，３，５−トリアジン（略称：ＰＣＣｚＰＴｚｎ）などのトリアジン骨格を有する複素環化合物や、３，５−ビス［３−（９Ｈ−カルバゾール−９−イル）フェニル］ピリジン（略称：３５ＤＣｚＰＰｙ）、１，３，５−トリ［３−（３−ピリジル）フェニル］ベンゼン（略称：ＴｍＰｙＰＢ）などのピリジン骨格を有する複素環化合物も用いることができる。また、ポリ（２，５−ピリジンジイル）（略称：ＰＰｙ）、ポリ［（９，９−ジヘキシルフルオレン−２，７−ジイル）−ｃｏ−（ピリジン−３，５−ジイル）］（略称：ＰＦ−Ｐｙ）、ポリ［（９，９−ジオクチルフルオレン−２，７−ジイル）−ｃｏ−（２，２’−ビピリジン−６，６’−ジイル）］（略称：ＰＦ−ＢＰｙ）のような高分子化合物を用いることもできる。 Examples of the host material having a high electron transporting property include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), and bis. (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis ( Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as 8-quinolinolato) zinc (II) (abbreviation: Znq). In addition, bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), etc. A metal complex having an oxazole-based or thiazole-based ligand can also be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [4- (5-phenyl-1,3,4-oxa) Oxadiazole derivatives such as diazol-2-7yl) phenyl] -9H-carbazole (abbreviation: CO11) and 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) Triazole derivatives such as -1,2,4-triazole (abbreviation: TAZ) and 2,2 ′, 2 ″-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) ) (Abbreviation: TPB ), 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) (particularly benzimidazole derivatives), 4 , 4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: BzOS) and other compounds having an oxazole skeleton (particularly benzoxazole derivatives), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP) ), 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), and 2- [3- (dibenzothiophen-4-yl) Phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2 mD TPDBq-II), 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3 ′-(9H-carbazole) -9-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mCzBPDBq), 2- [4- (3,6-diphenyl-9H-carbazol-9-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2CzPDBq-III), 7- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 7mDBTFPDBq-II), and 6- [3- (dibenzothiophene) -4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bi Su [3- (phenanthrene-9-yl) phenyl] pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [3- (4-dibenzothienyl) phenyl] pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4 , 6-bis [3- (9H-carbazol-9-yl) phenyl] pyrimidine (abbreviation: 4,6mCzP2Pm) and other heterocyclic compounds having a diazine skeleton, 2- {4- [3- (N-phenyl- 9H-carbazol-3-yl) -9H-carbazol-9-yl] phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) and other heterocyclic compounds having 3 , 5-bis [3- (9H-carbazol-9-yl) phenyl] pyridine (abbreviation: 35DCzPPy), 1,3,5-tri [3 (3-pyridyl) phenyl] benzene (abbreviation: TmPyPB) can also be used a heterocyclic compound having a pyridine skeleton such. In addition, poly (2,5-pyridinediyl) (abbreviation: PPy), poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py), poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) Molecular compounds can also be used.
また、ホスト材料として、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、クリセン誘導体、ジベンゾ［ｇ，ｐ］クリセン誘導体等の縮合多環芳香族化合物が挙げられ、具体的には、９，１０−ジフェニルアントラセン（略称：ＤＰＡｎｔｈ）、Ｎ，Ｎ−ジフェニル−９−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−カルバゾール−３−アミン（略称：ＣｚＡ１ＰＡ）、４−（１０−フェニル−９−アントリル）トリフェニルアミン（略称：ＤＰｈＰＡ）、ＹＧＡＰＡ、ＰＣＡＰＡ、Ｎ，９−ジフェニル−Ｎ−｛４−［４−（１０−フェニル−９−アントリル）フェニル］フェニル｝−９Ｈ−カルバゾール−３−アミン（略称：ＰＣＡＰＢＡ）２ＰＣＡＰＡ、６，１２−ジメトキシ−５，１１−ジフェニルクリセン、ＤＢＣ１、９−［４−（１０−フェニル−９−アントラセニル）フェニル］−９Ｈ−カルバゾール（略称：ＣｚＰＡ）、３，６−ジフェニル−９−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−カルバゾール（略称：ＤＰＣｚＰＡ）、９，１０−ビス（３，５−ジフェニルフェニル）アントラセン（略称：ＤＰＰＡ）、９，１０−ジ（２−ナフチル）アントラセン（略称：ＤＮＡ）、２−ｔｅｒｔ−ブチル−９，１０−ジ（２−ナフチル）アントラセン（略称：ｔ−ＢｕＤＮＡ）、９，９’−ビアントリル（略称：ＢＡＮＴ）、９，９’−（スチルベン−３，３’−ジイル）ジフェナントレン（略称：ＤＰＮＳ）、９，９’−（スチルベン−４，４’−ジイル）ジフェナントレン（略称：ＤＰＮＳ２）、１，３，５−トリ（１−ピレニル）ベンゼン（略称：ＴＰＢ３）などを用いることができる。 Examples of the host material include condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives. Specifically, 9,10-diphenylanthracene ( Abbreviations: DPAnth), N, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10-phenyl-9- Anthryl) triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl] phenyl} -9H-carbazol-3-amine (Abbreviation: PCAPBA) 2PCAPA, 6,12-dimethoxy-5,11-diphenyl Sen, DBC1, 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) Phenyl] -9H-carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2 -Tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene-3,3'-diyl ) Diphenanthrene (abbreviation: DPNS), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2), 1, 3, 5 Tri (1-pyrenyl) benzene (abbreviation: TPB3), or the like can be used.
また、発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）に有機化合物を複数用いる場合、励起錯体を形成する２種類の化合物（第１の化合物および第２の化合物）と、有機金属錯体とを混合して用いてもよい。この場合、様々な有機化合物を適宜組み合わせて用いることができるが、効率よく励起錯体を形成するためには、正孔を受け取りやすい化合物（正孔輸送性材料）と、電子を受け取りやすい化合物（電子輸送性材料）とを組み合わせることが特に好ましい。なお、正孔輸送性材料および電子輸送性材料の具体例については、本実施の形態で示す材料を用いることができる。この構成により、高効率、低電圧、長寿命を同時に実現できる。 In the case where a plurality of organic compounds are used for the light-emitting layer (113, 113a, 113b, 113c), two types of compounds (first compound and second compound) that form an exciplex are mixed with an organometallic complex. May be used. In this case, various organic compounds can be used in appropriate combination. However, in order to efficiently form an exciplex, a compound that easily receives holes (hole transporting material) and a compound that easily receives electrons (electrons) A combination with a transportable material) is particularly preferred. Note that as specific examples of the hole-transport material and the electron-transport material, the materials described in this embodiment can be used. With this configuration, high efficiency, low voltage, and long life can be realized simultaneously.
ＴＡＤＦ材料とは、三重項励起状態をわずかな熱エネルギーによって一重項励起状態にアップコンバート（逆項間交差）が可能で、一重項励起状態からの発光（蛍光）を効率よく呈する材料のことである。また、熱活性化遅延蛍光が効率良く得られる条件としては、三重項励起準位と一重項励起準位のエネルギー差が０ｅＶ以上０．２ｅＶ以下、好ましくは０ｅＶ以上０．１ｅＶ以下であることが挙げられる。また、ＴＡＤＦ材料における遅延蛍光とは、通常の蛍光と同様のスペクトルを持ちながら、寿命が著しく長い発光をいう。その寿命は、１０−６秒以上、好ましくは１０−３秒以上である。 TADF material is a material that can up-convert triplet excited state to singlet excited state with a little thermal energy (interverse crossing) and efficiently emits light (fluorescence) from singlet excited state. is there. As a condition for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Can be mentioned. In addition, delayed fluorescence in the TADF material refers to light emission having a remarkably long lifetime while having a spectrum similar to that of normal fluorescence. The lifetime is 10 −6 seconds or longer, preferably 10 −3 seconds or longer.
ＴＡＤＦ材料としては、例えば、フラーレンやその誘導体、プロフラビン等のアクリジン誘導体、エオシン等が挙げられる。また、マグネシウム（Ｍｇ）、亜鉛（Ｚｎ）、カドミウム（Ｃｄ）、スズ（Ｓｎ）、白金（Ｐｔ）、インジウム（Ｉｎ）、もしくはパラジウム（Ｐｄ）等を含む金属含有ポルフィリンが挙げられる。金属含有ポルフィリンとしては、例えば、プロトポルフィリン−フッ化スズ錯体（略称：ＳｎＦ２（Ｐｒｏｔｏ　ＩＸ））、メソポルフィリン−フッ化スズ錯体（略称：ＳｎＦ２（Ｍｅｓｏ　ＩＸ））、ヘマトポルフィリン−フッ化スズ錯体（略称：ＳｎＦ２（Ｈｅｍａｔｏ　ＩＸ））、コプロポルフィリンテトラメチルエステル−フッ化スズ錯体（略称：ＳｎＦ２（Ｃｏｐｒｏ　ＩＩＩ−４Ｍｅ））、オクタエチルポルフィリン−フッ化スズ錯体（略称：ＳｎＦ２（ＯＥＰ））、エチオポルフィリン−フッ化スズ錯体（略称：ＳｎＦ２（Ｅｔｉｏ　Ｉ））、オクタエチルポルフィリン−塩化白金錯体（略称：ＰｔＣｌ２ＯＥＰ）等が挙げられる。 Examples of the TADF material include fullerene and derivatives thereof, acridine derivatives such as proflavine, and eosin. In addition, metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like can be given. Examples of the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Proto IX)), a mesoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Meso IX)), and hematoporphyrin-tin fluoride. Complex (abbreviation: SnF 2 (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF 2 (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF 2 (OEP) )), Etioporphyrin-tin fluoride complex (abbreviation: SnF 2 (Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl 2 OEP), and the like.
その他にも、２−（ビフェニル−４−イル）−４，６−ビス（１２−フェニルインドロ［２，３−ａ］カルバゾール−１１−イル）−１，３，５−トリアジン（略称：ＰＩＣ−ＴＲＺ）、２−｛４−［３−（Ｎ−フェニル−９Ｈ−カルバゾール−３−イル）−９Ｈ−カルバゾール−９−イル］フェニル｝−４，６−ジフェニル−１，３，５−トリアジン（略称：ＰＣＣｚＰＴｚｎ）、２−［４−（１０Ｈ−フェノキサジン−１０−イル）フェニル］−４，６−ジフェニル−１，３，５−トリアジン（略称：ＰＸＺ−ＴＲＺ）、３−［４−（５−フェニル−５，１０−ジヒドロフェナジン−１０−イル）フェニル］−４，５−ジフェニル−１，２，４−トリアゾール（略称：ＰＰＺ−３ＴＰＴ）、３−（９，９−ジメチル−９Ｈ−アクリジン−１０−イル）−９Ｈ−キサンテン−９−オン（略称：ＡＣＲＸＴＮ）、ビス［４−（９，９−ジメチル−９，１０−ジヒドロアクリジン）フェニル］スルホン（略称：ＤＭＡＣ−ＤＰＳ）、１０−フェニル−１０Ｈ，１０’Ｈ−スピロ［アクリジン−９，９’−アントラセン］−１０’−オン（略称：ＡＣＲＳＡ）、等のπ電子過剰型複素芳香環及びπ電子不足型複素芳香環を有する複素環化合物を用いることができる。なお、π電子過剰型複素芳香環とπ電子不足型複素芳香環とが直接結合した物質は、π電子過剰型複素芳香環のドナー性とπ電子不足型複素芳香環のアクセプター性が共に強くなり、一重項励起状態と三重項励起状態のエネルギー差が小さくなるため、特に好ましい。 In addition, 2- (biphenyl-4-yl) -4,6-bis (12-phenylindolo [2,3-a] carbazol-11-yl) -1,3,5-triazine (abbreviation: PIC) -TRZ), 2- {4- [3- (N-phenyl-9H-carbazol-3-yl) -9H-carbazol-9-yl] phenyl} -4,6-diphenyl-1,3,5-triazine (Abbreviation: PCCzPTzn), 2- [4- (10H-phenoxazin-10-yl) phenyl] -4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3- [4- (5-phenyl-5,10-dihydrophenazin-10-yl) phenyl] -4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3- (9,9-dimethyl-9H -Acridine- 0-yl) -9H-xanthen-9-one (abbreviation: ACRXTN), bis [4- (9,9-dimethyl-9,10-dihydroacridine) phenyl] sulfone (abbreviation: DMAC-DPS), 10-phenyl -10H, 10'H-spiro [acridine-9,9'-anthracene] -10'-one (abbreviation: ACRSA), etc., a heterocyclic ring having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring Compounds can be used. In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded increases both the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π-electron deficient heteroaromatic ring. This is particularly preferable because the energy difference between the singlet excited state and the triplet excited state becomes small.
なお、ＴＡＤＦ材料を用いる場合、他の有機化合物と組み合わせて用いることもできる。 In addition, when using TADF material, it can also be used in combination with another organic compound.
図１（Ｄ）に示す発光素子においては、ＥＬ層１０３ａの発光層１１３ａ上に電子輸送層１１４ａが真空蒸着法により形成される。また、ＥＬ層１０３ａおよび電荷発生層１０４が形成された後、ＥＬ層１０３ｂの発光層１１３ｂ上に電子輸送層１１４ｂが真空蒸着法により形成される。 In the light-emitting element illustrated in FIG. 1D, the electron-transport layer 114a is formed over the light-emitting layer 113a of the EL layer 103a by a vacuum evaporation method. In addition, after the EL layer 103a and the charge generation layer 104 are formed, the electron transport layer 114b is formed on the light emitting layer 113b of the EL layer 103b by a vacuum evaporation method.
＜電子輸送層＞
電子輸送層（１１４、１１４ａ、１１４ｂ）は、電子注入層（１１５、１１５ａ、１１５ｂ）によって、第２の電極１０２から注入された電子を発光層（１１３、１１３ａ、１１３ｂ）に輸送する層である。なお、電子輸送層（１１４、１１４ａ、１１４ｂ）は、電子輸送性材料を含む層である。電子輸送層（１１４、１１４ａ、１１４ｂ）に用いる電子輸送性材料は、１×１０−６ｃｍ２／Ｖｓ以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。 <Electron transport layer>
The electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 to the light emitting layer (113, 113a, 113b) by the electron injection layer (115, 115a, 115b). . Note that the electron transport layers (114, 114a, 114b) are layers containing an electron transport material. The electron transporting material used for the electron transporting layer (114, 114a, 114b) is preferably a substance having an electron mobility of 1 × 10 −6 cm 2 / Vs or higher. Note that other than these substances, any substance that has a property of transporting more electrons than holes can be used.
電子輸送性材料としては、キノリン配位子、ベンゾキノリン配位子、オキサゾール配位子、あるいはチアゾール配位子を有する金属錯体、オキサジアゾール誘導体、トリアゾール誘導体、フェナントロリン誘導体、ピリジン誘導体、ビピリジン誘導体などが挙げられる。その他、含窒素複素芳香族化合物のようなπ電子不足型複素芳香族化合物を用いることもできる。 Examples of electron transporting materials include metal complexes having quinoline ligand, benzoquinoline ligand, oxazole ligand, or thiazole ligand, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. Is mentioned. In addition, a π-electron deficient heteroaromatic compound such as a nitrogen-containing heteroaromatic compound can also be used.
具体的には、Ａｌｑ３、トリス（４−メチル−８−キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｍｑ３）、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（ＩＩ）（略称：ＢｅＢｑ２）、ＢＡｌｑ、ビス［２−（２−ヒドロキシフェニル）ベンゾオキサゾラト］亜鉛（ＩＩ）（略称：Ｚｎ（ＢＯＸ）２）、ビス［２−（２−ヒドロキシフェニル）ベンゾチアゾラト］亜鉛（ＩＩ）（略称：Ｚｎ（ＢＴＺ）２）などの金属錯体、２−（４−ビフェニリル）−５−（４−ｔｅｒｔ−ブチルフェニル）−１，３，４−オキサジアゾール（略称：ＰＢＤ）、ＯＸＤ−７、３−（４’−ｔｅｒｔ−ブチルフェニル）−４−フェニル−５−（４’’−ビフェニル）−１，２，４−（リアゾール（略称：ＴＡＺ）、３−（４−ｔｅｒｔ−ブチルフェニル）−４−（４−エチルフェニル）−５−（４−ビフェニリル）−１，２，４−トリアゾール（略称：ｐ−ＥｔＴＡＺ）、バソフェナントロリン（略称：ＢＰｈｅｎ）、バソキュプロイン（略称：ＢＣＰ）、４，４’−ビス（５−メチルベンゾオキサゾール−２−イル）スチルベン（略称：ＢｚＯＳ）などの複素芳香族化合物、２−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ｍＤＢＴＰＤＢｑ−ＩＩ）、２−［３’−（ジベンゾチオフェン−４−イル）ビフェニル−３−イル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ｍＤＢＴＢＰＤＢｑ−ＩＩ）、２−［４−（３，６−ジフェニル−９Ｈ−カルバゾール−９−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：２ＣｚＰＤＢｑ−ＩＩＩ）、７−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：７ｍＤＢＴＰＤＢｑ−ＩＩ）、６−［３−（ジベンゾチオフェン−４−イル）フェニル］ジベンゾ［ｆ，ｈ］キノキサリン（略称：６ｍＤＢＴＰＤＢｑ−ＩＩ）等のキノキサリンないしはジベンゾキノキサリン誘導体を用いることができる。 Specifically, Alq 3 , tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ) , BAlq, bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (II) (abbreviation: Zn (BOX) 2 ), bis [2- (2-hydroxyphenyl) benzothiazolate] zinc (II) (abbreviation) : Metal complex such as Zn (BTZ) 2 ), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), OXD-7, 3- (4′-tert-butylphenyl) -4-phenyl-5- (4 ″ -biphenyl) -1,2,4- (riazole (abbreviation: TAZ), 3- (4-te rt-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), heteroaromatic compounds such as 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: BzOS), 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [ f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPBPDBq-II), 2- [4- (3,6-diphenyl-9H-carbazol-9-yl) phenyl] dibenzo [f, h] quinoxaline ( Name: 2CzPDBq-III), 7- [3- (Dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 7mDBTPDBq-II), 6- [3- (Dibenzothiophen-4-yl) A quinoxaline or dibenzoquinoxaline derivative such as phenyl] dibenzo [f, h] quinoxaline (abbreviation: 6mDBTPDBq-II) can be used.
また、ポリ（２，５−ピリジンジイル）（略称：ＰＰｙ）、ポリ［（９，９−ジヘキシルフルオレン−２，７−ジイル）−ｃｏ−（ピリジン−３，５−ジイル）］（略称：ＰＦ−Ｐｙ）、ポリ［（９，９−ジオクチルフルオレン−２，７−ジイル）−ｃｏ−（２，２’−ビピリジン−６，６’−ジイル）］（略称：ＰＦ−ＢＰｙ）のような高分子化合物を用いることもできる。 In addition, poly (2,5-pyridinediyl) (abbreviation: PPy), poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py), poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) Molecular compounds can also be used.
また、電子輸送層（１１４、１１４ａ、１１４ｂ）は、単層のものだけでなく、上記物質からなる層が２層以上積層した構造であってもよい。 Further, the electron-transport layer (114, 114a, 114b) is not limited to a single layer, and may have a structure in which two or more layers made of the above substances are stacked.
図１（Ｄ）に示す発光素子においては、ＥＬ層１０３ａの電子輸送層１１４ａ上に電子注入層１１５ａが真空蒸着法により形成される。その後、ＥＬ層１０３ａおよび電荷発生層１０４が形成され、ＥＬ層１０３ｂの電子輸送層１１４ｂまで形成された後、上に電子注入層１１５ｂが真空蒸着法により形成される。 In the light-emitting element illustrated in FIG. 1D, an electron injection layer 115a is formed over the electron transport layer 114a of the EL layer 103a by a vacuum evaporation method. Thereafter, the EL layer 103a and the charge generation layer 104 are formed, and the electron transport layer 114b of the EL layer 103b is formed, and then the electron injection layer 115b is formed thereon by a vacuum deposition method.
＜電子注入層＞
電子注入層（１１５、１１５ａ、１１５ｂ）は、電子注入性の高い物質を含む層である。電子注入層（１１５、１１５ａ、１１５ｂ）には、フッ化リチウム（ＬｉＦ）、フッ化セシウム（ＣｓＦ）、フッ化カルシウム（ＣａＦ２）、リチウム酸化物（ＬｉＯｘ）等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム（ＥｒＦ３）のような希土類金属化合物を用いることができる。また、電子注入層（１１５、１１５ａ、１１５ｂ）にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層（１１４、１１４ａ、１１４ｂ）を構成する物質を用いることもできる。 <Electron injection layer>
The electron injection layers (115, 115a, 115b) are layers containing a substance having a high electron injection property. The electron injection layer (115, 115a, 115b) includes an alkali metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x ), or the like. Earth metals or their compounds can be used. Alternatively, a rare earth metal compound such as erbium fluoride (ErF 3 ) can be used. Further, electride may be used for the electron injection layer (115, 115a, 115b). Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum. In addition, the substance which comprises the electron carrying layer (114, 114a, 114b) mentioned above can also be used.
また、電子注入層（１１５、１１５ａ、１１５ｂ）に、有機化合物と電子供与体（ドナー）とを混合してなる複合材料を用いてもよい。このような複合材料は、電子供与体によって有機化合物に電子が発生するため、電子注入性および電子輸送性に優れている。この場合、有機化合物としては、発生した電子の輸送に優れた材料であることが好ましく、具体的には、例えば上述した電子輸送層（１１４、１１４ａ、１１４ｂ）に用いる電子輸送性材料（金属錯体や複素芳香族化合物等）を用いることができる。電子供与体としては、有機化合物に対し電子供与性を示す物質であればよい。具体的には、アルカリ金属やアルカリ土類金属や希土類金属が好ましく、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン（略称：ＴＴＦ）等の有機化合物を用いることもできる。 Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b). Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, an electron transport material (metal complex) used for the electron transport layer (114, 114a, 114b) described above, for example. Or a heteroaromatic compound). The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
なお、例えば、発光層１１３ｂから得られる光を増幅させる場合には、第２の電極１０２と、発光層１１３ｂとの光学距離が、発光層１１３ｂが呈する光の波長に対してλ／４未満となるように形成するのが好ましい。この場合、電子輸送層１１４ｂまたは電子注入層１１５ｂの膜厚を変えることにより、調整することができる。 For example, in the case of amplifying light obtained from the light-emitting layer 113b, the optical distance between the second electrode 102 and the light-emitting layer 113b is less than λ / 4 with respect to the wavelength of light exhibited by the light-emitting layer 113b. It is preferable to form such that In this case, adjustment can be performed by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.
＜電荷発生層＞
電荷発生層１０４は、第１の電極（陽極）１０１と第２の電極（陰極）１０２との間に電圧を印加したときに、ＥＬ層１０３ａに電子を注入し、ＥＬ層１０３ｂに正孔を注入する機能を有する。なお、電荷発生層１０４は、正孔輸送性材料に電子受容体（アクセプター）が添加された構成であっても、電子輸送性材料に電子供与体（ドナー）が添加された構成であってもよい。または、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層１０４を形成することにより、ＥＬ層が積層された場合における駆動電圧の上昇を抑制することができる。 <Charge generation layer>
The charge generation layer 104 injects electrons into the EL layer 103a and applies holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. Has the function of injecting. Note that the charge generation layer 104 may have a structure in which an electron acceptor is added to a hole transporting material or a structure in which an electron donor (donor) is added to an electron transporting material. Good. Or both of these structures may be laminated. Note that by forming the charge generation layer 104 using the above-described material, an increase in driving voltage in the case where an EL layer is stacked can be suppressed.
電荷発生層１０４において、正孔輸送性材料に電子受容体が添加された構成とする場合、正孔輸送性材料としては、本実施の形態で示した材料を用いることができる。また、電子受容体としては、７，７，８，８−テトラシアノ−２，３，５，６−テトラフルオロキノジメタン（略称：Ｆ４−ＴＣＮＱ）、クロラニル等を挙げることができる。また元素周期表における第４族乃至第８族に属する金属の酸化物を挙げることができる。具体的には、酸化バナジウム、酸化ニオブ、酸化タンタル、酸化クロム、酸化モリブデン、酸化タングステン、酸化マンガン、酸化レニウムなどが挙げられる。 In the case where the charge generation layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, the materials described in this embodiment can be used as the hole-transporting material. Examples of the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, and the like. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.
電荷発生層１０４において、電子輸送性材料に電子供与体が添加された構成とする場合、電子輸送性材料としては、本実施の形態で示した材料を用いることができる。また、電子供与体としては、アルカリ金属またはアルカリ土類金属または希土類金属または元素周期表における第２、第１３族に属する金属およびその酸化物、炭酸塩を用いることができる。具体的には、リチウム（Ｌｉ）、セシウム（Ｃｓ）、マグネシウム（Ｍｇ）、カルシウム（Ｃａ）、イッテルビウム（Ｙｂ）、インジウム（Ｉｎ）、酸化リチウム、炭酸セシウムなどを用いることが好ましい。また、テトラチアナフタセンのような有機化合物を電子供与体として用いてもよい。 In the case where the charge generation layer 104 has a structure in which an electron donor is added to an electron transporting material, the materials described in this embodiment can be used as the electron transporting material. As the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Groups 2 and 13 of the periodic table, or an oxide or carbonate thereof can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like is preferably used. An organic compound such as tetrathianaphthacene may be used as an electron donor.
なお、図１（Ｅ）のＥＬ層１０３ｃは、上述したＥＬ層（１０３、１０３ａ、１０３ｂ）と同様の構成とすればよい。また、電荷発生層１０４ａ、１０４ｂについても、上述した電荷発生層１０４と同様の構成とすればよい。 Note that the EL layer 103c in FIG. 1E may have a structure similar to that of the above-described EL layers (103, 103a, and 103b). The charge generation layers 104a and 104b may have the same structure as the charge generation layer 104 described above.
＜基板＞
本実施の形態で示した発光素子は、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板（例えば単結晶基板又はシリコン基板）、ＳＯＩ基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。 <Board>
The light-emitting element described in this embodiment can be formed over various substrates. In addition, the kind of board | substrate is not limited to a specific thing. As an example of the substrate, a semiconductor substrate (for example, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having stainless steel foil, a tungsten substrate, Examples include a substrate having a tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film.
なお、ガラス基板の材料の一例としては、バリウムホウケイ酸ガラス、アルミノホウケイ酸ガラス、又はソーダライムガラスなどが挙げられる。また、可撓性基板、貼り合わせフィルム、基材フィルムなどの一例としては、ポリエチレンテレフタレート（ＰＥＴ）、ポリエチレンナフタレート（ＰＥＮ）、ポリエーテルサルフォン（ＰＥＳ）に代表されるプラスチック、アクリル等の合成樹脂、ポリプロピレン、ポリエステル、ポリフッ化ビニル、又はポリ塩化ビニル、ポリアミド、ポリイミド、アラミド、エポキシ、無機蒸着フィルム、又は紙類などが挙げられる。 Note that examples of the material of the glass substrate include barium borosilicate glass, alumino borosilicate glass, and soda lime glass. Examples of flexible substrates, bonded films, base films, etc. are synthetic materials such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyether sulfone (PES), acrylic, etc. Examples thereof include resin, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid, epoxy, an inorganic vapor deposition film, and papers.
なお、本実施の形態で示す発光素子の作製には、蒸着法などの真空プロセスや、スピンコート法やインクジェット法などの溶液プロセスを用いることができる。蒸着法を用いる場合には、スパッタ法、イオンプレーティング法、イオンビーム蒸着法、分子線蒸着法、真空蒸着法などの物理蒸着法（ＰＶＤ法）や、化学蒸着法（ＣＶＤ法）等を用いることができる。特に発光素子のＥＬ層に含まれる機能層（正孔注入層（１１１、１１１ａ、１１１ｂ）、正孔輸送層（１１２、１１２ａ、１１２ｂ）、発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）、電子輸送層（１１４、１１４ａ、１１４ｂ）、電子注入層（１１５、１１５ａ、１１５ｂ）、および電荷発生層（１０４、１０４ａ、１０４ｂ））については、蒸着法（真空蒸着法等）、塗布法（ディップコート法、ダイコート法、バーコート法、スピンコート法、スプレーコート法等）、印刷法（インクジェット法、スクリーン（孔版印刷）法、オフセット（平版印刷）法、フレキソ（凸版印刷）法、グラビア法、マイクロコンタクト法等）などの方法により形成することができる。 Note that for manufacturing the light-emitting element described in this embodiment, a vacuum process such as an evaporation method or a solution process such as a spin coating method or an inkjet method can be used. When vapor deposition is used, physical vapor deposition (PVD) such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, or vacuum vapor deposition, or chemical vapor deposition (CVD) is used. be able to. In particular, functional layers (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport included in the EL layer of the light-emitting element. For the layers (114, 114a, 114b), the electron injection layer (115, 115a, 115b), and the charge generation layer (104, 104a, 104b)), a vapor deposition method (vacuum vapor deposition method, etc.), a coating method (dip coating method) , Die coating method, bar coating method, spin coating method, spray coating method, etc.), printing method (inkjet method, screen (stencil printing) method, offset (lithographic printing) method, flexographic (letter printing) method, gravure method, microcontact And the like.
なお、本実施の形態で示す発光素子のＥＬ層（１０３、１０３ａ、１０３ｂ）を構成する各機能層（正孔注入層（１１１、１１１ａ、１１１ｂ）、正孔輸送層（１１２、１１２ａ、１１２ｂ）、発光層（１１３、１１３ａ、１１３ｂ、１１３ｃ）、電子輸送層（１１４、１１４ａ、１１４ｂ）、電子注入層（１１５、１１５ａ、１１５ｂ））や電荷発生層（１０４、１０４ａ、１０４ｂ）は、上述した材料に限られることはなく、それ以外の材料であっても各層の機能を満たせるものであれば組み合わせて用いることができる。一例としては、高分子化合物（オリゴマー、デンドリマー、ポリマー等）、中分子化合物（低分子と高分子の中間領域の化合物：分子量４００~４０００）、無機化合物（量子ドット材料等）等を用いることができる。なお、量子ドット材料としては、コロイド状量子ドット材料、合金型量子ドット材料、コア・シェル型量子ドット材料、コア型量子ドット材料などを用いることができる。 Note that each functional layer (a hole injection layer (111, 111a, 111b), a hole transport layer (112, 112a, 112b) included in the EL layer (103, 103a, 103b) of the light-emitting element described in this embodiment mode. The light emitting layer (113, 113a, 113b, 113c), the electron transport layer (114, 114a, 114b), the electron injection layer (115, 115a, 115b)) and the charge generation layer (104, 104a, 104b) are described above. The material is not limited, and other materials can be used in combination as long as they can satisfy the function of each layer. For example, high molecular compounds (oligomers, dendrimers, polymers, etc.), medium molecular compounds (compounds in the middle region between low molecules and polymers: molecular weight 400 to 4000), inorganic compounds (quantum dot materials, etc.), etc. may be used. it can. As the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core / shell type quantum dot material, a core type quantum dot material, or the like can be used.
本実施の形態に示す構成は、他の実施の形態に示す構成と適宜組み合わせて用いることができるものとする。 The structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
（実施の形態３）
本実施の形態では、本発明の一態様である発光装置について説明する。なお、図２（Ａ）に示す発光装置は、第１の基板２０１上のトランジスタ（ＦＥＴ）２０２と発光素子（２０３Ｒ、２０３Ｇ、２０３Ｂ、２０３Ｗ）が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光素子（２０３Ｒ、２０３Ｇ、２０３Ｂ、２０３Ｗ）は、共通のＥＬ層２０４を有し、また、各発光素子の発光色に応じて、各発光素子の電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、ＥＬ層２０４から得られた発光が第２の基板２０５に形成されたカラーフィルタ（２０６Ｒ、２０６Ｇ、２０６Ｂ）を介して射出されるトップエミッション型の発光装置である。 (Embodiment 3)
In this embodiment, a light-emitting device which is one embodiment of the present invention will be described. 2A is an active matrix light-emitting device in which a transistor (FET) 202 over a first substrate 201 and light-emitting elements (203R, 203G, 203B, and 203W) are electrically connected to each other. The plurality of light emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and the optical distance between the electrodes of each light emitting element depends on the emission color of each light emitting element. It has a tuned microcavity structure. In addition, the light-emitting device is a top-emission light-emitting device in which light emission obtained from the EL layer 204 is emitted through color filters (206R, 206G, and 206B) formed over the second substrate 205.
図２（Ａ）に示す発光装置は、第１の電極２０７を反射電極として機能するように形成する。また、第２の電極２０８を半透過・半反射電極として機能するように形成する。なお、第１の電極２０７および第２の電極２０８を形成する電極材料としては、他の実施形態の記載を参照し、適宜用いればよい。 In the light-emitting device illustrated in FIG. 2A, the first electrode 207 is formed so as to function as a reflective electrode. Further, the second electrode 208 is formed so as to function as a semi-transmissive / semi-reflective electrode. Note that an electrode material for forming the first electrode 207 and the second electrode 208 may be used as appropriate with reference to the description of the other embodiments.
また、図２（Ａ）において、例えば、発光素子２０３Ｒを赤色発光素子、発光素子２０３Ｇを緑色発光素子、発光素子２０３Ｂを青色発光素子、発光素子２０３Ｗを白色発光素子とする場合、図２（Ｂ）に示すように発光素子２０３Ｒは、第１の電極２０７と第２の電極２０８との間が光学距離２００Ｒとなるように調整し、発光素子２０３Ｇは、第１の電極２０７と第２の電極２０８との間が光学距離２００Ｇとなるように調整し、発光素子２０３Ｂは、第１の電極２０７と第２の電極２０８との間が光学距離２００Ｂとなるように調整する。なお、図２（Ｂ）に示すように、発光素子２０３Ｒにおいて導電層２０７Ｒを第１の電極２０７に積層し、発光素子２０３Ｇにおいて導電層２０７Ｇを第１の電極２０７に積層することにより、光学調整を行うことができる。 In FIG. 2A, for example, when the light emitting element 203R is a red light emitting element, the light emitting element 203G is a green light emitting element, the light emitting element 203B is a blue light emitting element, and the light emitting element 203W is a white light emitting element, FIG. ), The light emitting element 203R is adjusted so that the optical distance 200R is between the first electrode 207 and the second electrode 208, and the light emitting element 203G includes the first electrode 207 and the second electrode. The light emitting element 203B is adjusted so that the optical distance 200B is between the first electrode 207 and the second electrode 208. 2B, the conductive layer 207R is stacked over the first electrode 207 in the light-emitting element 203R, and the conductive adjustment layer 207G is stacked over the first electrode 207 in the light-emitting element 203G. It can be performed.
第２の基板２０５には、カラーフィルタ（２０６Ｒ、２０６Ｇ、２０６Ｂ）が形成されている。なお、カラーフィルタは、可視光のうち特定の波長域を通過させ、特定の波長域を阻止するフィルタである。従って、図２（Ａ）に示すように、発光素子２０３Ｒと重なる位置に赤の波長域のみを通過させるカラーフィルタ２０６Ｒを設けることにより、発光素子２０３Ｒから赤色発光を得ることができる。また、発光素子２０３Ｇと重なる位置に緑の波長域のみを通過させるカラーフィルタ２０６Ｇを設けることにより、発光素子２０３Ｇから緑色発光を得ることができる。また、発光素子２０３Ｂと重なる位置に青の波長域のみを通過させるカラーフィルタ２０６Ｂを設けることにより、発光素子２０３Ｂから青色発光を得ることができる。但し、発光素子２０３Ｗは、カラーフィルタを設けることなく白色発光を得ることができる。なお、１種のカラーフィルタの端部には、黒色層（ブラックマトリックス）２０９が設けられていてもよい。さらに、カラーフィルタ（２０６Ｒ、２０６Ｇ、２０６Ｂ）や黒色層２０９は、透明な材料を用いたオーバーコート層で覆われていても良い。 On the second substrate 205, color filters (206R, 206G, 206B) are formed. The color filter is a filter that passes a specific wavelength range of visible light and blocks the specific wavelength range. Therefore, as shown in FIG. 2A, red light emission can be obtained from the light emitting element 203R by providing the color filter 206R that allows only the red wavelength region to pass through the position overlapping the light emitting element 203R. In addition, by providing the color filter 206G that allows only the green wavelength region to pass at a position overlapping the light emitting element 203G, green light emission can be obtained from the light emitting element 203G. Further, by providing the color filter 206B that allows only the blue wavelength region to pass at a position overlapping the light emitting element 203B, blue light emission can be obtained from the light emitting element 203B. However, the light emitting element 203W can obtain white light emission without providing a color filter. Note that a black layer (black matrix) 209 may be provided at an end of one type of color filter. Further, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer using a transparent material.
図２（Ａ）では、第２の基板２０５側に発光を取り出す構造（トップエミッション型）の発光装置を示したが、図２（Ｃ）に示すようにＦＥＴ２０２が形成されている第１の基板２０１側に光を取り出す構造（ボトムエミッション型）の発光装置としても良い。なお、ボトムエミッション型の発光装置の場合には、第１の電極２０７を半透過・半反射電極として機能するように形成し、第２の電極２０８を反射電極として機能するように形成する。また、第１の基板２０１は、少なくとも透光性の基板を用いる。また、カラーフィルタ（２０６Ｒ’、２０６Ｇ’、２０６Ｂ’）は、図２（Ｃ）に示すように発光素子（２０３Ｒ、２０３Ｇ、２０３Ｂ）よりも第１の基板２０１側に設ければよい。 In FIG. 2A, a light emitting device having a structure for extracting light emission to the second substrate 205 side (top emission type) is shown, but the first substrate on which the FET 202 is formed as shown in FIG. A light emitting device having a structure for extracting light to the 201 side (bottom emission type) may be used. Note that in the case of a bottom emission type light-emitting device, the first electrode 207 is formed to function as a semi-transmissive / semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. The first substrate 201 is at least a light-transmitting substrate. Further, the color filters (206R ′, 206G ′, and 206B ′) may be provided on the first substrate 201 side with respect to the light emitting elements (203R, 203G, and 203B) as shown in FIG.
また、図２（Ａ）において、発光素子が、赤色発光素子、緑色発光素子、青色発光素子、白色発光素子の場合について示したが、本発明の一態様である発光素子はその構成に限られることはなく、黄色の発光素子や橙色の発光素子を有する構成であっても良い。なお、これらの発光素子を作製するためにＥＬ層（発光層、正孔注入層、正孔輸送層、電子輸送層、電子注入層、電荷発生層など）に用いる材料としては、他の実施形態の記載を参照し、適宜用いればよい。なお、その場合には、また、発光素子の発光色に応じてカラーフィルタを適宜選択する必要がある。 2A illustrates the case where the light-emitting element is a red light-emitting element, a green light-emitting element, a blue light-emitting element, or a white light-emitting element, the light-emitting element which is one embodiment of the present invention is limited to the structure. In other words, a structure having a yellow light emitting element or an orange light emitting element may be used. In addition, as a material used for EL layers (a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc.) for manufacturing these light emitting elements, other embodiments are used. May be used as appropriate with reference to the description. In this case, it is necessary to select a color filter as appropriate in accordance with the emission color of the light emitting element.
以上のような構成とすることにより、複数の発光色を呈する発光素子を備えた発光装置を得ることができる。 With the above structure, a light-emitting device including a light-emitting element that exhibits a plurality of emission colors can be obtained.
なお、本実施の形態に示す構成は、他の実施の形態に示す構成と適宜組み合わせて用いることができるものとする。 Note that the structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
（実施の形態４）
本実施の形態では、本発明の一態様である発光装置について説明する。 (Embodiment 4)
In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.
本発明の一態様である発光素子の素子構成を適用することで、アクティブマトリクス型の発光装置やパッシブマトリクス型の発光装置を作製することができる。なお、アクティブマトリクス型の発光装置は、発光素子とトランジスタ（ＦＥＴ）とを組み合わせた構成を有する。従って、パッシブマトリクス型の発光装置、アクティブマトリクス型の発光装置は、いずれも本発明の一態様である。なお、本実施の形態に示す発光装置には、他の実施形態で説明した発光素子を適用することが可能である。 By applying the element structure of the light-emitting element which is one embodiment of the present invention, an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured. Note that an active matrix light-emitting device has a structure in which a light-emitting element and a transistor (FET) are combined. Therefore, both the passive matrix light-emitting device and the active matrix light-emitting device are embodiments of the present invention. Note that the light-emitting element described in any of the other embodiments can be applied to the light-emitting device described in this embodiment.
本実施の形態では、アクティブマトリクス型の発光装置について図３を用いて説明する。 In this embodiment, an active matrix light-emitting device is described with reference to FIGS.
なお、図３（Ａ）は発光装置を示す上面図であり、図３（Ｂ）は図３（Ａ）を鎖線Ａ−Ａ’で切断した断面図である。アクティブマトリクス型の発光装置は、第１の基板３０１上に設けられた画素部３０２、駆動回路部（ソース線駆動回路）３０３と、駆動回路部（ゲート線駆動回路）（３０４ａ、３０４ｂ）を有する。画素部３０２および駆動回路部３０３、３０４ａ、３０４ｂ）は、シール材３０５によって、第１の基板３０１と第２の基板３０６との間に封止される。 3A is a top view illustrating the light-emitting device, and FIG. 3B is a cross-sectional view taken along the chain line A-A ′ in FIG. 3A. The active matrix light-emitting device includes a pixel portion 302, a driver circuit portion (source line driver circuit) 303, and driver circuit portions (gate line driver circuits) (304a and 304b) provided over the first substrate 301. . The pixel portion 302 and the driver circuit portions 303, 304 a, and 304 b) are sealed between the first substrate 301 and the second substrate 306 by a sealant 305.
また、第１の基板３０１上には、引き回し配線３０７が設けられる。引き回し配線３０７は、外部入力端子であるＦＰＣ３０８と接続される。なお、ＦＰＣ３０８は、駆動回路部（３０３、３０４ａ、３０４ｂ）に外部からの信号（例えば、ビデオ信号、クロック信号、スタート信号、リセット信号等）や電位を伝達する。また、ＦＰＣ３０８にはプリント配線基板（ＰＷＢ）が取り付けられていても良い。なお、これらＦＰＣやのＰＷＢが取り付けられた状態は、発光装置に含まれる。 A lead wiring 307 is provided over the first substrate 301. The lead wiring 307 is connected to the FPC 308 which is an external input terminal. Note that the FPC 308 transmits signals (eg, a video signal, a clock signal, a start signal, a reset signal, and the like) and a potential from the outside to the driving circuit units (303, 304a, and 304b). Further, a printed wiring board (PWB) may be attached to the FPC 308. Note that the state in which the FPC or PWB is attached is included in the light emitting device.
次に、図３（Ｂ）に断面構造を示す。 Next, a cross-sectional structure is shown in FIG.
画素部３０２は、ＦＥＴ（スイッチング用ＦＥＴ）３１１、ＦＥＴ（電流制御用ＦＥＴ）３１２、およびＦＥＴ３１２と電気的に接続された第１の電極３１３を有する複数の画素により形成される。なお、各画素が有するＦＥＴの数は、特に限定されることはなく、必要に応じて適宜設けることができる。 The pixel portion 302 is formed by a plurality of pixels including a FET (switching FET) 311, a FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. Note that the number of FETs included in each pixel is not particularly limited, and can be appropriately provided as necessary.
ＦＥＴ３０９、３１０、３１１、３１２は、特に限定されることはなく、例えば、スタガ型や逆スタガ型などのトランジスタを適用することができる。また、トップゲート型やボトムゲート型などのトランジスタ構造であってもよい。 The FETs 309, 310, 311, and 312 are not particularly limited, and for example, a staggered type transistor or an inverted staggered type transistor can be applied. Further, a transistor structure such as a top gate type or a bottom gate type may be used.
なお、これらのＦＥＴ３０９、３１０、３１１、３１２に用いることのできる半導体の結晶性については特に限定されず、非晶質半導体、結晶性を有する半導体（微結晶半導体、多結晶半導体、単結晶半導体、又は一部に結晶領域を有する半導体）のいずれを用いてもよい。なお、結晶性を有する半導体を用いることで、トランジスタ特性の劣化を抑制できるため好ましい。 Note that there is no particular limitation on the crystallinity of the semiconductor that can be used for these FETs 309, 310, 311, and 312; an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, Alternatively, a semiconductor having a crystal region in part) may be used. Note that it is preferable to use a crystalline semiconductor because deterioration of transistor characteristics can be suppressed.
また、これらの半導体としては、例えば、第１４族の元素、化合物半導体、酸化物半導体、有機半導体などを用いることができる。代表的には、シリコンを含む半導体、ガリウムヒ素を含む半導体、インジウムを含む酸化物半導体などを適用することができる。 As these semiconductors, for example, Group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, and the like can be used. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, or the like can be used.
駆動回路部３０３は、ＦＥＴ３０９とＦＥＴ３１０とを有する。なお、ＦＥＴ３０９とＦＥＴ３１０は、単極性（Ｎ型またはＰ型のいずれか一方のみ）のトランジスタを含む回路で形成されても良いし、Ｎ型のトランジスタとＰ型のトランジスタを含むＣＭＯＳ回路で形成されても良い。また、外部に駆動回路を有する構成としても良い。 The drive circuit unit 303 includes an FET 309 and an FET 310. Note that the FET 309 and the FET 310 may be formed of a circuit including a unipolar transistor (N-type or P-type only) or a CMOS circuit including an N-type transistor and a P-type transistor. May be. In addition, a configuration in which a drive circuit is provided outside may be employed.
第１の電極３１３の端部は、絶縁物３１４により覆われている。なお、絶縁物３１４には、ネガ型の感光性樹脂や、ポジ型の感光性樹脂（アクリル樹脂）などの有機化合物や、酸化シリコン、酸化窒化シリコン、窒化シリコン等の無機化合物を用いることができる。絶縁物３１４の上端部または下端部には、曲率を有する曲面を有するのが好ましい。これにより、絶縁部３１４の上層に形成される膜の被覆性を良好なものとすることができる。 An end portion of the first electrode 313 is covered with an insulator 314. Note that the insulator 314 can be formed using an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride. . It is preferable that an upper end portion or a lower end portion of the insulator 314 have a curved surface having a curvature. Thereby, the coverage of the film formed in the upper layer of the insulating portion 314 can be improved.
第１の電極３１３上には、ＥＬ層３１５及び第２の電極３１６が積層形成される。ＥＬ層３１５は、発光層、正孔注入層、正孔輸送層、電子輸送層、電子注入層、電荷発生層等を有する。 An EL layer 315 and a second electrode 316 are stacked over the first electrode 313. The EL layer 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like.
なお、本実施の形態で示す発光素子３１７の構成は、他の実施の形態で説明した構成や材料を適用することができる。なお、ここでは図示しないが、第２の電極３１６は外部入力端子であるＦＰＣ３０８に電気的に接続されている。 Note that the structures and materials described in the other embodiments can be applied to the structure of the light-emitting element 317 described in this embodiment. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.
また、図３（Ｂ）に示す断面図では発光素子３１７を１つのみ図示しているが、画素部３０２において、複数の発光素子がマトリクス状に配置されているものとする。画素部３０２には、３種類（Ｒ、Ｇ、Ｂ）の発光が得られる発光素子をそれぞれ選択的に形成し、フルカラー表示可能な発光装置を形成することができる。また、３種類（Ｒ、Ｇ、Ｂ）の発光が得られる発光素子の他に、例えば、ホワイト（Ｗ）、イエロー（Ｙ）、マゼンタ（Ｍ）、シアン（Ｃ）等の発光が得られる発光素子を形成してもよい。例えば、３種類（Ｒ、Ｇ、Ｂ）の発光が得られる発光素子に上述の数種類の発光が得られる発光素子を追加することにより、色純度の向上、消費電力の低減等の効果が得ることができる。また、カラーフィルタと組み合わせることによってフルカラー表示可能な発光装置としてもよい。なお、カラーフィルタの種類としては、赤（Ｒ）、緑（Ｇ）、青（Ｂ）、シアン（Ｃ）、マゼンタ（Ｍ）、イエロー（Ｙ）等を用いることができる。 3B illustrates only one light-emitting element 317, it is assumed that a plurality of light-emitting elements are arranged in a matrix in the pixel portion 302. In the pixel portion 302, light emitting elements capable of emitting three types (R, G, and B) of light emission can be selectively formed, so that a light emitting device capable of full color display can be formed. In addition to the light emitting element that can obtain three types of light emission (R, G, B), for example, light emission that can emit light such as white (W), yellow (Y), magenta (M), and cyan (C). An element may be formed. For example, by adding the above-described light emitting elements capable of obtaining several types of light emission (R, G, B) to the light emitting elements capable of obtaining three types of light emission (R, G, B), effects such as improvement in color purity and reduction in power consumption can be obtained. Can do. Alternatively, a light emitting device capable of full color display may be obtained by combining with a color filter. Note that as types of color filters, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), and the like can be used.
第１の基板３０１上のＦＥＴ（３０９、３１０、３１１、３１２）や、発光素子３１７は、第２の基板３０６と第１の基板３０１とをシール材３０５により貼り合わせることにより、第１の基板３０１、第２の基板３０６、およびシール材３０５で囲まれた空間３１８に備えられた構造を有する。なお、空間３１８には、不活性気体（窒素やアルゴン等）や有機物（シール材３０５を含む）で充填されていてもよい。 The FETs (309, 310, 311 and 312) and the light emitting element 317 over the first substrate 301 are bonded to each other by attaching the second substrate 306 and the first substrate 301 with the sealant 305. 301, the second substrate 306, and a structure provided in a space 318 surrounded by the sealant 305. Note that the space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealant 305).
シール材３０５には、エポキシ系樹脂やガラスフリットを用いることができる。なお、シール材３０５には、できるだけ水分や酸素を透過しない材料を用いることが好ましい。また、第２の基板３０６は、第１の基板３０１に用いることができるものを同様に用いることができる。従って、他の実施形態で説明した様々な基板を適宜用いることができるものとする。基板としてガラス基板や石英基板の他、ＦＲＰ（Ｆｉｂｅｒ−Ｒｅｉｎｆｏｒｃｅｄ　Ｐｌａｓｔｉｃｓ）、ＰＶＦ（ポリビニルフロライド）、ポリエステルまたはアクリル等からなるプラスチック基板を用いることができる。シール材としてガラスフリットを用いる場合には、接着性の観点から第１の基板３０１及び第２の基板３０６はガラス基板であることが好ましい。 As the sealant 305, an epoxy resin or glass frit can be used. Note that it is preferable to use a material that does not transmit moisture and oxygen as much as possible for the sealant 305. In addition, as the second substrate 306, a substrate that can be used for the first substrate 301 can be used as well. Therefore, various substrates described in other embodiments can be used as appropriate. In addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as the substrate. In the case where glass frit is used as the sealing material, the first substrate 301 and the second substrate 306 are preferably glass substrates from the viewpoint of adhesiveness.
以上のようにして、アクティブマトリクス型の発光装置を得ることができる。 As described above, an active matrix light-emitting device can be obtained.
また、アクティブマトリクス型の発光装置を可撓性基板に形成する場合、可撓性基板上にＦＥＴと発光素子とを直接形成しても良いが、剥離層を有する別の基板にＦＥＴと発光素子を形成した後、熱、力、レーザ照射などを与えることによりＦＥＴと発光素子を剥離層で剥離し、さらに可撓性基板に転載して作製しても良い。なお、剥離層としては、例えば、タングステン膜と酸化シリコン膜との無機膜の積層や、ポリイミド等の有機樹脂膜等を用いることができる。また可撓性基板としては、トランジスタを形成することが可能な基板に加え、紙基板、セロファン基板、アラミドフィルム基板、ポリイミドフィルム基板、布基板（天然繊維（絹、綿、麻）、合成繊維（ナイロン、ポリウレタン、ポリエステル）若しくは再生繊維（アセテート、キュプラ、レーヨン、再生ポリエステル）などを含む）、皮革基板、又はゴム基板などが挙げられる。これらの基板を用いることにより、耐久性や耐熱性に優れ、軽量化および薄型化を図ることができる。 In the case where an active matrix light-emitting device is formed over a flexible substrate, the FET and the light-emitting element may be directly formed over the flexible substrate, but the FET and the light-emitting element are formed over another substrate having a release layer. After forming, the FET and the light-emitting element may be peeled off by a peeling layer by applying heat, force, laser irradiation, and transferred to a flexible substrate. Note that as the peeling layer, for example, a laminated inorganic film of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. In addition to substrates that can form transistors, flexible substrates include paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, fabric substrates (natural fibers (silk, cotton, hemp), synthetic fibers ( Nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrates, rubber substrates, and the like. By using these substrates, it is excellent in durability and heat resistance, and can be reduced in weight and thickness.
なお、本実施の形態に示す構成は、他の実施の形態に示した構成を適宜組み合わせて用いることができる。 Note that the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.
（実施の形態５）
本実施の形態では、本発明の一態様である発光装置、本発明の一態様である発光素子を有する表示装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。 (Embodiment 5)
In this embodiment, examples of various electronic devices and automobiles completed by applying the light-emitting device which is one embodiment of the present invention and the display device including the light-emitting element which is one embodiment of the present invention will be described.
図４（Ａ）~図４（Ｅ）に示す電子機器は、筐体７０００、表示部７００１、スピーカ７００３、ＬＥＤランプ７００４、操作キー７００５（電源スイッチ、又は操作スイッチを含む）、接続端子７００６、センサ７００７（力、変位、位置、速度、加速度、角速度、回転数、距離、光、液、磁気、温度、化学物質、音声、時間、硬度、電場、電流、電圧、電力、放射線、流量、湿度、傾度、振動、におい、又は赤外線を測定する機能を含むもの）、マイクロフォン７００８、等を有することができる。 4A to 4E includes a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), a connection terminal 7006, Sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity , Including a function of measuring inclination, vibration, odor, or infrared light), a microphone 7008, and the like.
図４（Ａ）はモバイルコンピュータであり、上述したものの他に、スイッチ７００９、赤外線ポート７０１０、等を有することができる。 FIG. 4A illustrates a mobile computer, which can include a switch 7009, an infrared port 7010, and the like in addition to the above objects.
図４（Ｂ）は記録媒体を備えた携帯型の画像再生装置（たとえば、ＤＶＤ再生装置）であり、上述したものの他に、第２表示部７００２、記録媒体読込部７０１１、等を有することができる。 FIG. 4B illustrates a portable image reproducing device (eg, a DVD reproducing device) provided with a recording medium, which includes a second display portion 7002, a recording medium reading portion 7011, and the like in addition to those described above. it can.
図４（Ｃ）はゴーグル型ディスプレイであり、上述したものの他に、第２表示部７００２、支持部７０１２、イヤホン７０１３、等を有することができる。 FIG. 4C illustrates a goggle type display which can include a second display portion 7002, a support portion 7012, an earphone 7013, and the like in addition to the above components.
図４（Ｄ）はテレビ受像機能付きデジタルカメラであり、上述したものの他に、アンテナ７０１４、シャッターボタン７０１５、受像部７０１６、等を有することができる。 FIG. 4D illustrates a digital camera with a television receiving function, which can include an antenna 7014, a shutter button 7015, an image receiving portion 7016, and the like in addition to the above objects.
図４（Ｅ）は携帯電話機（スマートフォンを含む）であり、筐体７０００に、表示部７００１、マイクロフォン７００８、スピーカ７００３、カメラ７０２０、外部接続部７０２１、操作用ボタン７０２２、等を有することができる。 FIG. 4E illustrates a mobile phone (including a smartphone), which can include a display portion 7001, a microphone 7008, a speaker 7003, a camera 7020, an external connection portion 7021, an operation button 7022, and the like in a housing 7000. .
図４（Ｆ）は、大型のテレビジョン装置（テレビ、又はテレビジョン受信機ともいう）であり、筐体７０００、表示部７００１、スピーカ７００３、等を有することができる。また、ここでは、スタンド７０１８により筐体７０００を支持した構成を示している。 FIG. 4F illustrates a large television device (also referred to as a television or a television receiver) which can include a housing 7000, a display portion 7001, speakers 7003, and the like. Here, a configuration in which the casing 7000 is supported by a stand 7018 is shown.
図４（Ａ）~図４（Ｆ）に示す電子機器は、様々な機能を有することができる。例えば、様々な情報（静止画、動画、テキスト画像など）を表示部に表示する機能、タッチパネル機能、カレンダー、日付又は時刻などを表示する機能、様々なソフトウエア（プログラム）によって処理を制御する機能、無線通信機能、無線通信機能を用いて様々なコンピュータネットワークに接続する機能、無線通信機能を用いて様々なデータの送信又は受信を行う機能、記録媒体に記録されているプログラム又はデータを読み出して表示部に表示する機能、等を有することができる。さらに、複数の表示部を有する電子機器においては、一つの表示部を主として画像情報を表示し、別の一つの表示部を主として文字情報を表示する機能、または、複数の表示部に視差を考慮した画像を表示することで立体的な画像を表示する機能、等を有することができる。さらに、受像部を有する電子機器においては、静止画を撮影する機能、動画を撮影する機能、撮影した画像を自動または手動で補正する機能、撮影した画像を記録媒体（外部又はカメラに内蔵）に保存する機能、撮影した画像を表示部に表示する機能、等を有することができる。なお、図４（Ａ）乃至図４（Ｆ）に示す電子機器が有することのできる機能はこれらに限定されず、様々な機能を有することができる。 The electronic devices illustrated in FIGS. 4A to 4F can have a variety of functions. For example, a function for displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function for displaying a calendar, date or time, etc., a function for controlling processing by various software (programs) , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded in recording medium A function of displaying on the display portion can be provided. Further, in an electronic device having a plurality of display units, one display unit mainly displays image information and another one display unit mainly displays character information, or the plurality of display units consider parallax. It is possible to have a function of displaying a three-dimensional image, etc. by displaying the obtained image. Furthermore, in an electronic device having an image receiving unit, a function for capturing a still image, a function for capturing a moving image, a function for correcting a captured image automatically or manually, and a captured image on a recording medium (externally or incorporated in a camera) A function of saving, a function of displaying a photographed image on a display portion, and the like can be provided. Note that the functions of the electronic devices illustrated in FIGS. 4A to 4F are not limited to these, and the electronic devices can have various functions.
図４（Ｇ）は、スマートウオッチであり、筐体７０００、表示部７００１、操作用ボタン７０２２、７０２３、接続端子７０２４、バンド７０２５、留め金７０２６、等を有する。 FIG. 4G illustrates a smart watch, which includes a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a clasp 7026, and the like.
ベゼル部分を兼ねる筐体７０００に搭載された表示部７００１は、非矩形状の表示領域を有している。表示部７００１は、時刻を表すアイコン７０２７、その他のアイコン７０２８等を表示することができる。また、表示部７００１は、タッチセンサ（入力装置）を搭載したタッチパネル（入出力装置）であってもよい。 A display portion 7001 mounted on a housing 7000 that also serves as a bezel portion has a non-rectangular display region. The display portion 7001 can display an icon 7027 representing time, other icons 7028, and the like. The display unit 7001 may be a touch panel (input / output device) equipped with a touch sensor (input device).
なお、図４（Ｇ）に示すスマートウオッチは、様々な機能を有することができる。例えば、様々な情報（静止画、動画、テキスト画像など）を表示部に表示する機能、タッチパネル機能、カレンダー、日付又は時刻などを表示する機能、様々なソフトウエア（プログラム）によって処理を制御する機能、無線通信機能、無線通信機能を用いて様々なコンピュータネットワークに接続する機能、無線通信機能を用いて様々なデータの送信又は受信を行う機能、記録媒体に記録されているプログラム又はデータを読み出して表示部に表示する機能、等を有することができる。 Note that the smart watch illustrated in FIG. 4G can have a variety of functions. For example, a function for displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function for displaying a calendar, date or time, etc., a function for controlling processing by various software (programs) , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded in recording medium A function of displaying on the display portion can be provided.
また、筐体７０００の内部に、スピーカ、センサ（力、変位、位置、速度、加速度、角速度、回転数、距離、光、液、磁気、温度、化学物質、音声、時間、硬度、電場、電流、電圧、電力、放射線、流量、湿度、傾度、振動、におい又は赤外線を測定する機能を含むもの）、マイクロフォン等を有することができる。 In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, number of rotations, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current are included in the housing 7000. , Voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared measurement function), microphone, and the like.
なお、本発明の一態様である発光装置および本発明の一態様である発光素子を有する表示装置は、本実施の形態に示す電子機器の各表示部に用いることができ、色純度の良い表示が可能となる。 Note that the light-emitting device which is one embodiment of the present invention and the display device including the light-emitting element which is one embodiment of the present invention can be used for each display portion of the electronic device described in this embodiment and display with high color purity. Is possible.
また、発光装置を適用した電子機器として、図５（Ａ）~（Ｃ）に示すような折りたたみ可能な携帯情報端末が挙げられる。図５（Ａ）には、展開した状態の携帯情報端末９３１０を示す。また、図５（Ｂ）には、展開した状態又は折りたたんだ状態の一方から他方に変化する途中の状態の携帯情報端末９３１０を示す。さらに、図５（Ｃ）には、折りたたんだ状態の携帯情報端末９３１０を示す。携帯情報端末９３１０は、折りたたんだ状態では可搬性に優れ、展開した状態では、継ぎ目のない広い表示領域により表示の一覧性に優れる。 In addition, as an electronic device to which the light-emitting device is applied, a foldable portable information terminal as illustrated in FIGS. 5A to 5C can be given. FIG. 5A illustrates the portable information terminal 9310 in a developed state. FIG. 5B illustrates the portable information terminal 9310 in a state of changing from one of the expanded state and the folded state to the other. Further, FIG. 5C illustrates the portable information terminal 9310 in a folded state. The portable information terminal 9310 is excellent in portability in the folded state and excellent in display listability due to a seamless wide display area in the expanded state.
表示部９３１１はヒンジ９３１３によって連結された３つの筐体９３１５に支持されている。なお、表示部９３１１は、タッチセンサ（入力装置）を搭載したタッチパネル（入出力装置）であってもよい。また、表示部９３１１は、ヒンジ９３１３を介して２つの筐体９３１５間を屈曲させることにより、携帯情報端末９３１０を展開した状態から折りたたんだ状態に可逆的に変形させることができる。本発明の一態様の発光装置を表示部９３１１に用いることができる。また、色純度の良い表示が可能となる。表示部９３１１における表示領域９３１２は折りたたんだ状態の携帯情報端末９３１０の側面に位置する表示領域である。表示領域９３１２には、情報アイコンや使用頻度の高いアプリやプログラムのショートカットなどを表示させることができ、情報の確認やアプリなどの起動をスムーズに行うことができる。 The display portion 9311 is supported by three housings 9315 connected by a hinge 9313. Note that the display unit 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). In addition, the display portion 9311 can be reversibly deformed from the expanded state to the folded state by bending the two housings 9315 via the hinge 9313. The light-emitting device of one embodiment of the present invention can be used for the display portion 9311. In addition, display with good color purity is possible. A display region 9312 in the display portion 9311 is a display region located on a side surface of the portable information terminal 9310 in a folded state. In the display area 9312, information icons, frequently used applications, program shortcuts, and the like can be displayed, so that information can be confirmed and applications can be activated smoothly.
また、発光装置を適用した自動車について、図６（Ａ）（Ｂ）に示す。すなわち、発光装置を、自動車と一体にして設けることができる。具体的には、図６（Ａ）に示す自動車の外側のライト５１０１（車体後部も含む）、タイヤのホイール５１０２、ドア５１０３の一部または全体などに適用することができる。また、図６（Ｂ）に示す自動車の内側の表示部５１０４、ハンドル５１０５、シフトレバー５１０６、座席シート５１０７、インナーリアビューミラー５１０８等に適用することができる。その他、ガラス窓の一部に適用してもよい。 FIGS. 6A and 6B illustrate an automobile to which the light-emitting device is applied. That is, the light emitting device can be provided integrally with the automobile. Specifically, the present invention can be applied to a light 5101 (including a rear part of a vehicle body), a wheel 5102 of a tire, a part of or the whole of a door 5103 shown in FIG. Further, the present invention can be applied to a display portion 5104, a handle 5105, a shift lever 5106, a seat seat 5107, an inner rear view mirror 5108, and the like inside the automobile shown in FIG. In addition, you may apply to some glass windows.
以上のようにして、本発明の一態様である発光装置や表示装置を適用した電子機器や自動車を得ることができる。なお、その場合には、色純度の良い表示が可能となる。なお、適用できる電子機器や自動車は、本実施の形態に示したものに限らず、あらゆる分野において適用することが可能である。 As described above, an electronic device or a vehicle using the light-emitting device or the display device which is one embodiment of the present invention can be obtained. In this case, display with good color purity is possible. Note that applicable electronic devices and automobiles are not limited to those described in this embodiment, and can be applied in any field.
なお、本実施の形態に示す構成は、他の実施の形態に示した構成と適宜組み合わせて用いることができる。 Note that the structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
（実施の形態６）
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の構成について図７を用いて説明する。 (Embodiment 6)
In this embodiment, a structure of a light-emitting device which is one embodiment of the present invention or a lighting device manufactured using a light-emitting element which is a part thereof will be described with reference to FIGS.
図７（Ａ）、（Ｂ）、（Ｃ）、（Ｄ）には、照明装置の断面図の一例を示す。なお、図７（Ａ）、（Ｂ）は基板側に光を取り出すボトムエミッション型の照明装置であり、図７（Ｃ）、（Ｄ）は、封止基板側に光を取り出すトップエミッション型の照明装置である。 FIGS. 7A, 7B, 7C, and 7D each show an example of a cross-sectional view of a lighting device. 7A and 7B are bottom emission type lighting devices that extract light to the substrate side, and FIGS. 7C and 7D are top emission type lighting devices that extract light to the sealing substrate side. It is a lighting device.
図７（Ａ）に示す照明装置４０００は、基板４００１上に発光素子４００２を有する。また、基板４００１の外側に凹凸を有する基板４００３を有する。発光素子４００２は、第１の電極４００４と、ＥＬ層４００５と、第２の電極４００６を有する。 A lighting device 4000 illustrated in FIG. 7A includes a light-emitting element 4002 over a substrate 4001. In addition, a substrate 4003 having unevenness is provided outside the substrate 4001. The light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.
第１の電極４００４は、電極４００７と電気的に接続され、第２の電極４００６は電極４００８と電気的に接続される。また、第１の電極４００４と電気的に接続される補助配線４００９を設けてもよい。なお、補助配線４００９上には、絶縁層４０１０が形成されている。 The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. Further, an auxiliary wiring 4009 that is electrically connected to the first electrode 4004 may be provided. Note that an insulating layer 4010 is formed over the auxiliary wiring 4009.
また、基板４００１と封止基板４０１１は、シール材４０１２で接着されている。また、封止基板４０１１と発光素子４００２の間には、乾燥剤４０１３が設けられていることが好ましい。なお、基板４００３は、図７（Ａ）のような凹凸を有するため、発光素子４００２で生じた光の取り出し効率を向上させることができる。 In addition, the substrate 4001 and the sealing substrate 4011 are bonded with a sealant 4012. In addition, a desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. Note that since the substrate 4003 has unevenness as illustrated in FIG. 7A, the light extraction efficiency of the light-emitting element 4002 can be improved.
また、基板４００３に代えて、図７（Ｂ）の照明装置４１００のように、基板４００１の外側に拡散板４０１５を設けてもよい。 Further, instead of the substrate 4003, a diffusion plate 4015 may be provided outside the substrate 4001 as in the lighting device 4100 in FIG.
図７（Ｃ）の照明装置４２００は、基板４２０１上に発光素子４２０２を有する。発光素子４２０２は第１の電極４２０４と、ＥＬ層４２０５と、第２の電極４２０６とを有する。 A lighting device 4200 in FIG. 7C includes a light-emitting element 4202 over a substrate 4201. The light-emitting element 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.
第１の電極４２０４は、電極４２０７と電気的に接続され、第２の電極４２０６は電極４２０８と電気的に接続される。また第２の電極４２０６と電気的に接続される補助配線４２０９を設けてもよい。また、補助配線４２０９の下部に、絶縁層４２１０を設けてもよい。 The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. Further, an auxiliary wiring 4209 that is electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided below the auxiliary wiring 4209.
基板４２０１と凹凸のある封止基板４２１１は、シール材４２１２で接着されている。また、封止基板４２１１と発光素子４２０２の間にバリア膜４２１３および平坦化膜４２１４を設けてもよい。なお、封止基板４２１１は、図７（Ｃ）のような凹凸を有するため、発光素子４２０２で生じた光の取り出し効率を向上させることができる。 The substrate 4201 and the uneven sealing substrate 4211 are bonded with a sealant 4212. Further, a barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light-emitting element 4202. Note that the sealing substrate 4211 has unevenness as illustrated in FIG. 7C, so that extraction efficiency of light generated in the light-emitting element 4202 can be improved.
また、封止基板４２１１に代えて、図７（Ｄ）の照明装置４３００のように、発光素子４２０２の上に拡散板４２１５を設けてもよい。 Further, instead of the sealing substrate 4211, a diffusion plate 4215 may be provided over the light-emitting element 4202 as in the lighting device 4300 in FIG.
なお、本実施の形態で示すように、本発明の一態様である発光装置、またはその一部である発光素子を適用することで、所望の色度を有する照明装置を提供することができる。 Note that as described in this embodiment, a lighting device having desired chromaticity can be provided by using a light-emitting device which is one embodiment of the present invention or a light-emitting element which is a part thereof.
なお、本実施の形態に示す構成は、他の実施の形態に示した構成と適宜組み合わせて用いることができる。 Note that the structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
（実施の形態７）
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の応用例について、図８を用いて説明する。 (Embodiment 7)
In this embodiment, application examples of a lighting device manufactured using a light-emitting device which is one embodiment of the present invention or a light-emitting element which is a part thereof will be described with reference to FIGS.
室内の照明装置としては、シーリングライト８００１として応用できる。シーリングライト８００１には、天井直付型や天井埋め込み型がある。なお、このような照明装置は、発光装置を筐体やカバーと組み合わせることにより構成される。その他にもコードペンダント型（天井からのコード吊り下げ式）への応用も可能である。 As an indoor lighting device, it can be applied as a ceiling light 8001. The ceiling light 8001 includes a direct ceiling type and a ceiling embedded type. Note that such an illumination device is configured by combining a light emitting device with a housing or a cover. In addition, it can be applied to a cord pendant type (a cord hanging type from the ceiling).
また、足元灯８００２は、床面に灯りを照射し、足元の安全性を高めることができる。例えば、寝室や階段や通路などに使用するのが有効である。その場合、部屋の広さや構造に応じて適宜サイズや形状を変えることができる。また、発光装置と支持台とを組み合わせて構成される据え置き型の照明装置とすることも可能である。 Also, the foot lamp 8002 can illuminate the floor surface and enhance the safety of the foot. For example, it is effective to use it for a bedroom, a staircase or a passage. In that case, the size and shape can be appropriately changed according to the size and structure of the room. In addition, a stationary illumination device configured by combining a light emitting device and a support base can be provided.
また、シート状照明８００３は、薄型のシート状の照明装置である。壁面に張り付けて使用するため、場所を取らず幅広い用途に用いることができる。なお、大面積化も容易である。なお、曲面を有する壁面や筐体に用いることもできる。 Further, the sheet-like illumination 8003 is a thin sheet-like illumination device. Since it is attached to the wall surface, it can be used for a wide range of purposes without taking up space. It is easy to increase the area. In addition, it can also be used for the wall surface and housing | casing which have a curved surface.
また、光源からの光が所望の方向のみに制御された照明装置８００４を用いることもできる。 Alternatively, an illumination device 8004 in which light from a light source is controlled only in a desired direction can be used.
なお、上記以外にも室内に備えられた家具の一部に本発明の一態様である発光装置、またはその一部である発光素子を適用することにより、家具としての機能を備えた照明装置とすることができる。 In addition to the above, a lighting device having a function as furniture can be obtained by applying the light-emitting device which is one embodiment of the present invention to a part of the furniture provided in the room or the light-emitting element which is a part of the light-emitting device. can do.
以上のように、発光装置を適用した様々な照明装置が得られる。なお、これらの照明装置は本発明の一態様であるものとする。 As described above, various lighting devices to which the light-emitting device is applied can be obtained. Note that these lighting devices are one embodiment of the present invention.
また、本実施の形態に示す構成は、他の実施の形態に示した構成と適宜組み合わせて用いることができる。 The structure described in this embodiment can be combined as appropriate with any of the structures described in the other embodiments.
≪合成例１≫
本実施例では、実施の形態１の構造式（１００）で表される本発明の一態様である有機化合物、９−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−ジベンゾ［ａ，ｃ］カルバゾール（略称：ａｃＤＢＣｚＰＡ）の合成方法について説明する。なお、ａｃＤＢＣｚＰＡの構造を以下に示す。 << Synthesis Example 1 >>
In this example, an organic compound which is one embodiment of the present invention represented by Structural Formula (100) of Embodiment 1, 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-dibenzo [ A synthesis method of a, c] carbazole (abbreviation: acDBCzPA) will be described. The structure of acDBCzPA is shown below.
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
２００ｍＬ３口フラスコに９−（４−ブロモフェニル）−１０−フェニルアントラセン３．１ｇ（７．５ｍｍｏｌ）、９Ｈ−ジベンゾ［ａ，ｃ］カルバゾール２．０ｇ（７．５ｍｍｏｌ）、ナトリウム　ｔｅｒｔ−ブトキシド１．４ｇ（１５ｍｍｏｌ）を加え、フラスコ内を窒素置換した。この混合物にキシレン３８ｍＬを加え、減圧下で攪拌する事で脱気した。この混合物に、トリ（ｔｅｒｔ−ブチル）ホスフィン０．３ｍＬ、ビス（ジベンジリデンアセトン）パラジウム（０）４３ｍｇ（７５μｍｏｌ）を加え、窒素気流下、１６０℃で３時間還流した。 In a 200 mL three-necked flask, 3.1 g (7.5 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 2.0 g (7.5 mmol) of 9H-dibenzo [a, c] carbazole, sodium tert-butoxide 1. 4 g (15 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. The mixture was deaerated by adding 38 mL of xylene and stirring under reduced pressure. To this mixture, 0.3 mL of tri (tert-butyl) phosphine and 43 mg (75 μmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was refluxed at 160 ° C. for 3 hours under a nitrogen stream.
この混合物を濾過し、固体を水で洗浄した。この固体をトルエンに溶解し、この溶液をセライト、アルミナ、フロリジールを通して吸引濾過した。得られたろ液を濃縮して得た固体をトルエンで再結晶したところ、目的物の淡黄色固体を収量３．１ｇ、収率７０％で得た。上記合成方法の合成スキームを下記式（ａ）に示す。 The mixture was filtered and the solid was washed with water. This solid was dissolved in toluene, and this solution was subjected to suction filtration through celite, alumina and Florisil. The solid obtained by concentrating the obtained filtrate was recrystallized with toluene. As a result, 3.1 g (70% yield) of the target pale yellow solid was obtained. A synthesis scheme of the above synthesis method is shown in the following formula (a).
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
得られた淡黄色固体３．１ｇをトレインサブリメーション法により昇華精製した。昇華精製は、圧力３．７Ｐａ、アルゴン流量５．０ｍＬ／ｍｉｎの条件で、淡黄色固体を３００℃で加熱して行った。昇華精製後、淡黄色固体を２．９ｇ、回収率９３％で得た。 Sublimation purification of 3.1 g of the obtained pale yellow solid was performed by a train sublimation method. The sublimation purification was performed by heating a pale yellow solid at 300 ° C. under conditions of a pressure of 3.7 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 2.9 g of a pale yellow solid was obtained with a recovery rate of 93%.
得られた黄色固体の核磁気共鳴分光法（１Ｈ−ＮＭＲ）による分析結果を下記に示す。また、１Ｈ−ＮＭＲチャートを図９（Ａ）（Ｂ）に示す。なお、図９（Ｂ）は、図９（Ａ）における７．０ｐｐｍ~９．５ｐｐｍの範囲を拡大して表したチャートである。この結果から、本実施例において、上述の構造式（１００）で表される本発明の一態様である有機化合物、ａｃＤＢＣｚＰＡが得られたことがわかった。 The analysis result of the obtained yellow solid by nuclear magnetic resonance spectroscopy ( 1 H-NMR) is shown below. Further, 1 H-NMR charts are shown in FIGS. Note that FIG. 9B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 9A is enlarged. From this result, it was found that in this example, an organic compound, acDBCzPA, which is one embodiment of the present invention represented by the above structural formula (100), was obtained.
１Ｈ　ＮＭＲ（ＣＤＣｌ３，３００ＭＨｚ）：δ＝７．４２−７．６９（ｍ、１５Ｈ）、７．７６−７．９６（ｍ、１０Ｈ）、８．７１−８．７５（ｍ、１Ｈ）、８．８７（ｔ、Ｊ＝９．０Ｈｚ、２Ｈ）、９．００（ｄｄ、Ｊ１＝８．４Ｈｚ、Ｊ２＝１．２Ｈｚ、１Ｈ）。 1 H NMR (CDCl 3 , 300 MHz): δ = 7.42-7.69 (m, 15H), 7.76-7.96 (m, 10H), 8.71-8.75 (m, 1H) 8.87 (t, J = 9.0 Hz, 2H), 9.00 (dd, J 1 = 8.4 Hz, J 2 = 1.2 Hz, 1H).
次に、ａｃＤＢＣｚＰＡのトルエン溶液および固体薄膜の紫外可視吸収スペクトル（以下、単に「吸収スペクトル」という）及び発光スペクトルを測定した。固体薄膜は石英基板上に真空蒸着法にて作製した。吸収スペクトルの測定には、紫外可視分光光度計（溶液：日本分光株式会社製、Ｖ−５５０、薄膜：（株）日立ハイテクノロジーズ製、Ｕ−４１００）を用いた。なお溶液の吸収スペクトルは、石英セルにトルエンのみを入れて測定した吸収スペクトルを差し引いて算出し、薄膜の吸収スペクトルは、基板を含めた薄膜の透過率と反射率から求めた吸光度（−ｌｏｇ１０［％Ｔ／（１００−％Ｒ）］より算出した。なお％Ｔは透過率、％Ｒは反射率を表す。また、発光スペクトルの測定には、蛍光光度計（（株）浜松ホトニクス製　ＦＳ９２０）を用いた。 Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of acDBCzPA and a solid thin film were measured. The solid thin film was produced on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance (−log 10) determined from the transmittance and reflectance of the thin film including the substrate. [% T / (100-% R)] where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). ) Was used.
ａｃＤＢＣｚＰＡのトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図１０（Ａ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、固体薄膜の吸収スペクトルおよび発光スペクトルの測定結果を図１０（Ｂ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。 FIG. 10A shows the measurement results of the absorption spectrum and emission spectrum of acDBCzPA in toluene. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In addition, FIG. 10B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
図１０（Ａ）の結果より、ａｃＤＢＣｚＰＡのトルエン溶液では、３９６ｎｍ、３７５ｎｍ、３５７ｎｍ、３２５ｎｍ付近に吸収ピークが見られ、４３２ｎｍ、４１７ｎｍ（励起波長３７６ｎｍ）付近に発光波長のピークが見られた。また、図１０（Ｂ）の結果より、ａｃＤＢＣｚＰＡの固体薄膜では、４００ｎｍ、３７８ｎｍ、３５９ｎｍ、３２８ｎｍ、２６６ｎｍ付近に吸収ピークが見られ、４８４ｎｍ、４４９ｎｍ、４２７ｎｍ付近（励起波長３８０ｎｍ）に発光波長のピークが見られた。 From the results of FIG. 10A, in the acDBCzPA toluene solution, absorption peaks were observed in the vicinity of 396 nm, 375 nm, 357 nm, and 325 nm, and emission wavelength peaks were observed in the vicinity of 432 nm and 417 nm (excitation wavelength: 376 nm). Further, from the results of FIG. 10B, in the solid thin film of acDBCzPA, absorption peaks are observed in the vicinity of 400 nm, 378 nm, 359 nm, 328 nm, and 266 nm, and the emission wavelength peaks in the vicinity of 484 nm, 449 nm, and 427 nm (excitation wavelength: 380 nm). It was observed.
なお、ａｃＤＢＣｚＰＡは青色に発光することを確認した。本発明の一態様である有機化合物、ａｃＤＢＣｚＰＡは、発光物質や可視域の蛍光発光物質のホストとしても利用可能である。また、ａｃＤＢＣｚＰＡの薄膜は、大気下においても凝集しにくい良好な膜質であることがわかった。 It was confirmed that acDBCzPA emitted blue light. The organic compound acDBCzPA which is one embodiment of the present invention can also be used as a host for a light-emitting substance or a visible-light fluorescent substance. Moreover, it was found that the thin film of acDBCzPA has a good film quality that hardly aggregates even in the atmosphere.
ａｃＤＢＣｚＰＡのＨＯＭＯ準位およびＬＵＭＯ準位をサイクリックボルタンメトリ（ＣＶ）測定を元に算出した。算出方法を以下に示す。 The HOMO level and LUMO level of acDBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
測定装置としては電気化学アナライザー（ビー・エー・エス（株）製、型番：ＡＬＳモデル６００Ａまたは６００Ｃ）を用いた。ＣＶ測定における溶液は、溶媒として脱水ジメチルホルムアミド（ＤＭＦ）（（株）アルドリッチ製、９９．８％、カタログ番号；２２７０５−６）を用い、支持電解質である過塩素酸テトラ−ｎ−ブチルアンモニウム（ｎ−Ｂｕ４ＮＣｌＯ４）（（株）東京化成製、カタログ番号；Ｔ０８３６）を１００ｍｍｏｌ／Ｌの濃度となるように溶解させ、さらに測定対象を２ｍｍｏｌ／Ｌの濃度となるように溶解させて調製した。 As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) ( n-Bu 4 NClO 4 ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 2 mmol / L. did.
また、作用電極としては白金電極（ビー・エー・エス（株）製、ＰＴＥ白金電極）を、補助電極としては白金電極（ビー・エー・エス（株）製、ＶＣ−３用Ｐｔカウンター電極（５ｃｍ））を、参照電極としてはＡｇ／Ａｇ＋電極（ビー・エー・エス（株）製、ＲＥ７非水溶媒系参照電極）をそれぞれ用いた。なお、測定は室温（２０以上２５℃以下）で行った。 In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag + electrode (manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).
また、ＣＶ測定時のスキャン速度は、０．１Ｖ／ｓｅｃに統一し、参照電極に対する酸化電位Ｅａ［Ｖ］および還元電位Ｅｃ［Ｖ］を測定した。Ｅａは酸化−還元波の中間電位とし、Ｅｃは還元−酸化波の中間電位とした。ここで、本実施例で用いる参照電極の真空準位に対するポテンシャルエネルギーは、−４．９４［ｅＶ］であることが分かっているため、ＨＯＭＯ準位［ｅＶ］＝−４．９４−Ｅａ、ＬＵＭＯ準位［ｅＶ］＝−４．９４−Ｅｃという式から、ＨＯＭＯ準位およびＬＵＭＯ準位をそれぞれ求めることができる。 Further, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was an intermediate potential of the oxidation-reduction wave, and Ec was an intermediate potential of the reduction-oxidation wave. Here, since it is known that the potential energy with respect to the vacuum level of the reference electrode used in this example is −4.94 [eV], the HOMO level [eV] = − 4.94−Ea, LUMO. From the equation of level [eV] = − 4.94−Ec, the HOMO level and the LUMO level can be obtained respectively.
また、ＣＶ測定を１００回繰り返し行い、１００サイクル目の測定での酸化−還元波と、１サイクル目の酸化−還元波を比較して、化合物の電気的安定性を調べた。 In addition, CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
この結果、ａｃＤＢＣｚＰＡの酸化電位Ｅａ［Ｖ］の測定において、ＨＯＭＯ準位は−５．７５ｅＶであることがわかった。一方、還元電位Ｅｃ［Ｖ］の測定において、ＬＵＭＯ準位は−２．７４ｅＶであることがわかった。また、酸化−還元波の繰り返し測定において１サイクル目と１００サイクル後の波形と比較したところ、Ｅａ測定においては８０％、のピーク強度を保っていたことから、ａｃＤＢＣｚＰＡは酸化に対する耐性が非常に良好であることが確認された。 As a result, in the measurement of the oxidation potential Ea [V] of acDBCzPA, it was found that the HOMO level was −5.75 eV. On the other hand, in the measurement of the reduction potential Ec [V], it was found that the LUMO level was −2.74 eV. In addition, when compared with the waveform after the first cycle and after 100 cycles in the repeated measurement of the oxidation-reduction wave, the peak intensity of 80% was maintained in the Ea measurement. Therefore, acDBCzPA has very good resistance to oxidation. It was confirmed that.
≪合成例２≫
本実施例では、実施の形態１の構造式（１０１）で表される本発明の一態様である有機化合物、７−［４−（１０−フェニル−９−アントリル）フェニル］−７Ｈ−トリベンゾ［ａ，ｃ，ｇ］カルバゾール（略称：ａｃｇＴＢＣｚＰＡ）の合成方法について説明する。なお、ａｃｇＴＢＣｚＰＡの構造を以下に示す。 << Synthesis Example 2 >>
In this example, an organic compound which is one embodiment of the present invention represented by Structural Formula (101) in Embodiment 1, 7- [4- (10-phenyl-9-anthryl) phenyl] -7H-tribenzo [ a, c, g] carbazole (abbreviation: acgTBCzPA) will be described. The structure of acgTBCzPA is shown below.
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
２００ｍＬ３口フラスコに９−（４−ブロモフェニル）−１０−フェニルアントラセン１．３ｇ（３．２ｍｍｏｌ）、７Ｈ−トリベンゾ［ａ，ｃ，ｇ］カルバゾール１．０ｇ（３．２ｍｍｏｌ）、ナトリウム　ｔｅｒｔ−ブトキシド０．６１ｇ（６．４ｍｍｏｌ）を加え、フラスコ内を窒素置換した。この混合物にキシレン１６ｍＬを加え、減圧下で攪拌する事で脱気した。この混合物に、トリ（ｔｅｒｔ−ブチル）ホスフィン０．６ｍＬ、ビス（ジベンジリデンアセトン）パラジウム（０）８６ｍｇ（０．１５ｍｍｏｌ）を加え、窒素気流下、１６０℃で２０時間還流した。 In a 200 mL three-necked flask, 1.3 g (3.2 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.0 g (3.2 mmol) of 7H-tribenzo [a, c, g] carbazole, sodium tert-butoxide 0.61 g (6.4 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. The mixture was deaerated by adding 16 mL of xylene and stirring under reduced pressure. To this mixture, 0.6 mL of tri (tert-butyl) phosphine and 86 mg (0.15 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was refluxed at 160 ° C. for 20 hours under a nitrogen stream.
この混合物を濾過し、固体を水で洗浄した。この固体をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：３）で精製し、更にトルエンで再結晶したところ、目的物の淡黄色固体を収量１．０ｇ、収率４８％で得た。上記合成方法の合成スキームを下記式（ｂ）に示す。 The mixture was filtered and the solid was washed with water. This solid was purified by silica gel column chromatography (toluene: hexane = 1: 3), and further recrystallized from toluene to obtain 1.0 g of a target pale yellow solid in a yield of 48%. A synthesis scheme of the above synthesis method is shown in the following formula (b).
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
得られた淡黄色固体１．０ｇをトレインサブリメーション法により昇華精製した。昇華精製は、圧力３．２Ｐａ、アルゴン流量５．０ｍＬ／ｍｉｎの条件で、淡黄色固体を２９０℃で加熱して行った。昇華精製後、淡黄色固体を０．９２ｇ、回収率９３％で得た。 Sublimation purification of 1.0 g of the obtained pale yellow solid was performed by a train sublimation method. Sublimation purification was performed by heating a pale yellow solid at 290 ° C. under conditions of a pressure of 3.2 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.92 g of a pale yellow solid was obtained with a recovery rate of 93%.
得られた淡黄色固体の核磁気共鳴分光法（１Ｈ−ＮＭＲ）による分析結果を下記に示す。また、１Ｈ−ＮＭＲチャートを図１１（Ａ）（Ｂ）に示す。なお、図１１（Ｂ）は、図１１（Ａ）における７．０ｐｐｍ~９．５ｐｐｍの範囲を拡大して表したチャートである。この結果から、本実施例において、上述の構造式（１０１）で表される本発明の一態様である有機化合物、ａｃｇＴＢＣｚＰＡが得られたことがわかった。 The analysis result by nuclear magnetic resonance spectroscopy ( 1 H-NMR) of the obtained pale yellow solid is shown below. 1 H-NMR charts are shown in FIGS. Note that FIG. 11B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, acgTBCzPA, which is one embodiment of the present invention represented by the above structural formula (101), was obtained in this example.
１Ｈ　ＮＭＲ（ＣＤＣｌ３，３００ＭＨｚ）：δ＝７．４０−７．８２（ｍ、２３Ｈ）、７．９１−７．９４（ｍ、３Ｈ）、８．０９（ｄ、Ｊ＝７．２Ｈｚ、１Ｈ）、８．８２−８．８７（ｍ、２Ｈ）、９．１８（ｄ、Ｊ＝８．４Ｈｚ、１Ｈ）、９．２４（ｄ、Ｊ＝７．８Ｈｚ、１Ｈ）。 1 H NMR (CDCl 3 , 300 MHz): δ = 7.40-7.82 (m, 23H), 7.91-7.94 (m, 3H), 8.09 (d, J = 7.2 Hz, 1H), 8.82-8.87 (m, 2H), 9.18 (d, J = 8.4 Hz, 1H), 9.24 (d, J = 7.8 Hz, 1H).
次に、ａｃｇＴＢＣｚＰＡのトルエン溶液および固体薄膜の紫外可視吸収スペクトル（以下、単に「吸収スペクトル」という）及び発光スペクトルを測定した。固体薄膜は石英基板上に真空蒸着法にて作製した。吸収スペクトルの測定には、紫外可視分光光度計（溶液：日本分光株式会社製、Ｖ−５５０、薄膜：（株）日立ハイテクノロジーズ製、Ｕ−４１００）を用いた。なお溶液の吸収スペクトルは、石英セルにトルエンのみを入れて測定した吸収スペクトルを差し引いて算出し、薄膜の吸収スペクトルは、基板を含めた透過率と反射率から求めた吸光度（−ｌｏｇ１０　［％Ｔ／（１００−％Ｒ）］より算出した。なお％Ｔは透過率、％Ｒは反射率を表す。また、発光スペクトルの測定には、蛍光光度計（（株）浜松ホトニクス製　ＦＳ９２０）を用いた。 Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and emission spectrum of acgTBCzPA in a toluene solution and a solid thin film were measured. The solid thin film was produced on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance (−log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
得られたトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図１２（Ａ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、固体薄膜の吸収スペクトルおよび発光スペクトルの測定結果を図１２（Ｂ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。 The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In addition, FIG. 12B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
図１２（Ａ）の結果より、ａｃｇＴＢＣｚＰＡのトルエン溶液では、３９６ｎｍ、３７６ｎｍ、３６１ｎｍ、３４６ｎｍ付近に吸収ピークが見られ、４３４ｎｍ、４１７ｎｍ付近（励起波長３７６ｎｍ）に発光波長のピークが見られた。また、図１２（Ｂ）の結果より、ａｃｇＴＢＣｚＰＡの固体薄膜では、４０２ｎｍ、３８０ｎｍ、３６５ｎｍ、３４５ｎｍ、３０５ｎｍ、２６６ｎｍ付近に吸収ピークが見られ、４４３ｎｍ付近（励起波長３８０ｎｍ）に発光波長のピークが見られた。 From the result of FIG. 12A, in the toluene solution of acgTBCzPA, absorption peaks were observed in the vicinity of 396 nm, 376 nm, 361 nm, and 346 nm, and the emission wavelength peak was observed in the vicinity of 434 nm and 417 nm (excitation wavelength: 376 nm). From the results shown in FIG. 12B, in the solid thin film of acgTBCzPA, an absorption peak is observed in the vicinity of 402 nm, 380 nm, 365 nm, 345 nm, 305 nm, and 266 nm, and an emission wavelength peak is observed in the vicinity of 443 nm (excitation wavelength: 380 nm). It was.
なお、ａｃｇＴＢＣｚＰＡは青色に発光することを確認した。本発明の一態様である有機化合物、ａｃｇＴＢＣｚＰＡは、発光物質や可視域の蛍光発光物質のホストとしても利用可能である。また、ａｃｇＴＢＣｚＰＡの薄膜は、大気下においても凝集しにくい良好な膜質であることがわかった。 It was confirmed that acgTBCzPA emitted blue light. The organic compound acgTBCzPA which is one embodiment of the present invention can also be used as a host of a light-emitting substance or a visible-light fluorescent substance. In addition, it was found that the acgTBCzPA thin film has a good film quality that hardly aggregates in the air.
ａｃｇＴＢＣｚＰＡのＨＯＭＯ準位およびＬＵＭＯ準位をサイクリックボルタンメトリ（ＣＶ）測定を元に算出した。算出方法を以下に示す。 The HOMO level and LUMO level of acgTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
測定装置としては電気化学アナライザー（ビー・エー・エス（株）製、型番：ＡＬＳモデル６００Ａまたは６００Ｃ）を用いた。ＣＶ測定における溶液は、溶媒として脱水ジメチルホルムアミド（ＤＭＦ）（（株）アルドリッチ製、９９．８％、カタログ番号；２２７０５−６）を用い、支持電解質である過塩素酸テトラ−ｎ−ブチルアンモニウム（ｎ−Ｂｕ４ＮＣｌＯ４）（（株）東京化成製、カタログ番号；Ｔ０８３６）を１００ｍｍｏｌ／Ｌの濃度となるように溶解させ、さらに測定対象を２ｍｍｏｌ／Ｌの濃度となるように溶解させて調製した。 As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) ( n-Bu 4 NClO 4 ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 2 mmol / L. did.
また、作用電極としては白金電極（ビー・エー・エス（株）製、ＰＴＥ白金電極）を、補助電極としては白金電極（ビー・エー・エス（株）製、ＶＣ−３用Ｐｔカウンター電極（５ｃｍ））を、参照電極としてはＡｇ／Ａｇ＋電極（ビー・エー・エス（株）製、ＲＥ７非水溶媒系参照電極）をそれぞれ用いた。なお、測定は室温（２０以上２５℃以下）で行った。 In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag + electrode (manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).
また、ＣＶ測定時のスキャン速度は、０．１Ｖ／ｓｅｃに統一し、参照電極に対する酸化電位Ｅａ［Ｖ］および還元電位Ｅｃ［Ｖ］を測定した。Ｅａは酸化−還元波の中間電位とし、Ｅｃは還元−酸化波の中間電位とした。ここで、本実施例で用いる参照電極の真空準位に対するポテンシャルエネルギーは、−４．９４［ｅＶ］であることが分かっているため、ＨＯＭＯ準位［ｅＶ］＝−４．９４−Ｅａ、ＬＵＭＯ準位［ｅＶ］＝−４．９４−Ｅｃという式から、ＨＯＭＯ準位およびＬＵＭＯ準位をそれぞれ求めることができる。 Further, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was an intermediate potential of the oxidation-reduction wave, and Ec was an intermediate potential of the reduction-oxidation wave. Here, since it is known that the potential energy with respect to the vacuum level of the reference electrode used in this example is −4.94 [eV], the HOMO level [eV] = − 4.94−Ea, LUMO. From the equation of level [eV] = − 4.94−Ec, the HOMO level and the LUMO level can be obtained respectively.
また、ＣＶ測定を１００回繰り返し行い、１００サイクル目の測定での酸化−還元波と、１サイクル目の酸化−還元波を比較して、化合物の電気的安定性を調べた。 In addition, CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
この結果、ａｃｇＴＢＣｚＰＡの酸化電位Ｅａ［Ｖ］の測定において、ＨＯＭＯ準位は−５．６４ｅＶであることがわかった。一方、還元電位Ｅｃ［Ｖ］の測定において、ＬＵＭＯ準位は−２．７５ｅＶであることがわかった。 As a result, it was found that the HOMO level was −5.64 eV in the measurement of the oxidation potential Ea [V] of acgTBCzPA. On the other hand, in the measurement of the reduction potential Ec [V], it was found that the LUMO level was -2.75 eV.
本実施例では、本発明の一態様である発光素子として、実施例１で説明した、ａｃＤＢＣｚＰＡ（構造式（１００））を発光層に用いた発光素子１、実施例２で説明した、ａｃｇＴＢＣｚＰＡ（構造式（１０１））を発光層に用いた発光素子２、比較とする有機化合物、ｃｇＤＢＣｚＰＡ（構造式（２０１））を発光層に用いた比較発光素子３、についてこれらの素子構造、作製方法およびその特性について説明する。なお、本実施例で用いる発光素子の素子構造を図１３に示し、具体的な構成について表１に示す。また、本実施例で用いる材料の化学式を以下に示す。 In this example, as a light-emitting element which is one embodiment of the present invention, the light-emitting element 1 using acDBCzPA (structural formula (100)) described in Example 1 for the light-emitting layer and the acgTBCzPA (described in Example 2) are used. Regarding the light-emitting element 2 using the structural formula (101) for the light-emitting layer, the comparative organic compound, and the comparative light-emitting element 3 using cgDBCzPA (structural formula (201)) for the light-emitting layer, these element structures, manufacturing methods, and The characteristics will be described. Note that FIG. 13 shows an element structure of a light-emitting element used in this example, and Table 1 shows a specific structure. In addition, chemical formulas of materials used in this example are shown below.
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
≪発光素子の作製≫
本実施例で示す発光素子は、図１３に示すように基板９００上に形成された第１の電極９０１上に正孔注入層９１１、正孔輸送層９１２、発光層９１３、電子輸送層９１４、電子注入層９１５が順次積層され、電子注入層９１５上に第２の電極９０３が積層された構造を有する。 ≪Production of light emitting element≫
As shown in FIG. 13, the light-emitting element described in this example includes a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and a first electrode 901 formed over a substrate 900. The electron injection layer 915 is sequentially stacked, and the second electrode 903 is stacked on the electron injection layer 915.
まず、基板９００上に第１の電極９０１を形成した。電極面積は、４ｍｍ２（２ｍｍ×２ｍｍ）とした。また、基板９００には、ガラス基板を用いた。また、第１の電極９０１は、酸化珪素を含むインジウム錫酸化物（ＩＴＳＯ）をスパッタリング法により、７０ｎｍの膜厚で成膜して形成した。 First, the first electrode 901 was formed over the substrate 900. The electrode area was 4 mm 2 (2 mm × 2 mm). As the substrate 900, a glass substrate was used. The first electrode 901 was formed by depositing indium tin oxide containing silicon oxide (ITSO) with a thickness of 70 nm by a sputtering method.
ここで、前処理として、基板の表面を水で洗浄し、２００℃で１時間焼成した後、ＵＶオゾン処理を３７０秒行った。その後、１０−４Ｐａ程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において、１７０℃で６０分間の真空焼成を行った後、基板を３０分程度放冷した。 Here, as a pretreatment, the surface of the substrate was washed with water and baked at 200 ° C. for 1 hour, followed by UV ozone treatment for 370 seconds. Thereafter, the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 −4 Pa, vacuum baking is performed at 170 ° C. for 60 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
次に、第１の電極９０１上に正孔注入層９１１を形成した。正孔注入層９１１は、真空蒸着装置内を１０−４Ｐａに減圧した後、３−［４−（９−フェナントリル）−フェニル］−９−フェニル−９Ｈ−カルバゾール（略称：ＰＣＰＰｎ）と酸化モリブデンとを、ＰＣＰＰｎ：酸化モリブデン＝４：２（質量比）とし、膜厚が１０ｎｍとなるように共蒸着して形成した。 Next, a hole injection layer 911 was formed over the first electrode 901. The hole injection layer 911 is formed by reducing the pressure in the vacuum evaporation apparatus to 10 −4 Pa, and then 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum oxide. And PCPPn: molybdenum oxide = 4: 2 (mass ratio), and co-evaporated to a thickness of 10 nm.
次に、正孔注入層９１１上に正孔輸送層９１２を形成した。正孔輸送層９１２は、ＰＣＰＰｎを用い、膜厚が３０ｎｍになるように蒸着して形成した。 Next, a hole transport layer 912 was formed over the hole injection layer 911. The hole transport layer 912 was formed by vapor deposition using PCPPn so as to have a film thickness of 30 nm.
次に、正孔輸送層９１２上に発光層９１３を形成した。 Next, a light-emitting layer 913 was formed over the hole transport layer 912.
発光層９１３は、発光素子１の場合は、ホスト材料としてａｃＤＢＣｚＰＡを用い、ゲスト材料としてＮ，Ｎ’−ビス（３−メチルフェニル）−Ｎ，Ｎ’−ビス［３−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル］−ピレン−１，６−ジアミン（略称：１，６ｍＭｅｍＦＬＰＡＰｒｎ）を用い、重量比がａｃＤＢＣｚＰＡ：１，６ｍＭｅｍＦＬＰＡＰｒｎ＝１：０．０３となるように共蒸着した。なお、膜厚は、２５ｎｍとした。 In the case of the light emitting element 1, the light emitting layer 913 uses acDBCzPA as a host material and N, N′-bis (3-methylphenyl) -N, N′-bis [3- (9-phenyl-9H) as a guest material. -Fluorene-9-yl) phenyl] -pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) was co-deposited so that the weight ratio was acDBCzPA: 1,6mMemFLPAPrn = 1: 0.03. The film thickness was 25 nm.
発光層９１３は、発光素子２の場合は、ホスト材料としてａｃｇＴＢＣｚＰＡを用い、ゲスト材料として１，６ｍＭｅｍＦＬＰＡＰｒｎを用い、重量比がａｃｇＴＢＣｚＰＡ：１，６ｍＭｅｍＦＬＰＡＰｒｎ＝１：０．０３となるように共蒸着した。なお、膜厚は、２５ｎｍとした。 In the case of the light emitting element 2, the light emitting layer 913 was co-deposited using acgTBCzPA as a host material, 1,6mMemFLPAPrn as a guest material, and having a weight ratio of acgTBCzPA: 1,6mMemFLPAPrn = 1: 0.03. The film thickness was 25 nm.
発光層９１３は、比較発光素子３の場合は、ホスト材料としてｃｇＤＢＣｚＰＡを用い、ゲスト材料として１，６ｍＭｅｍＦＬＰＡＰｒｎを用い、重量比がｃｇＤＢＣｚＰＡ：１，６ｍＭｅｍＦＬＰＡＰｒｎ＝１：０．０３となるように共蒸着した。なお、膜厚は、２５ｎｍとした。 In the case of the comparative light-emitting element 3, the light-emitting layer 913 was co-deposited using cgDBCzPA as a host material, 1,6mMemFLPAPrn as a guest material, and having a weight ratio of cgDBCzPA: 1,6mMemFLPAPrn = 1: 0.03. . The film thickness was 25 nm.
次に、発光層９１３上に電子輸送層９１４を形成した。電子輸送層９１４は、発光素子１の場合は、ａｃＤＢＣｚＰＡの膜厚が１５ｎｍ、バソフェナントロリン（略称：Ｂｐｈｅｎ）の膜厚が１０ｎｍとなるように順次蒸着して形成した。また、発光素子２の場合は、ａｃｇＴＢＣｚＰＡの膜厚が１５ｎｍ、Ｂｐｈｅｎの膜厚が１０ｎｍとなるように順次蒸着して形成した。また、比較発光素子３の場合は、ｃｇＤＢＣｚＰＡの膜厚が１５ｎｍ、Ｂｐｈｅｎの膜厚が１０ｎｍとなるように順次蒸着して形成した。 Next, an electron transport layer 914 was formed over the light emitting layer 913. In the case of the light-emitting element 1, the electron-transport layer 914 was formed by sequentially vapor-depositing so that the thickness of acDBCzPA was 15 nm and the thickness of bathophenanthroline (abbreviation: Bphen) was 10 nm. In the case of the light-emitting element 2, the acg TBCzPA was formed by vapor deposition so that the film thickness was 15 nm and the film thickness of Bphen was 10 nm. In the case of the comparative light-emitting element 3, the cgDBCzPA was formed by sequentially vapor-depositing so that the film thickness of cgDBCzPA was 15 nm and the film thickness of Bphen was 10 nm.
次に、電子輸送層９１４上に電子注入層９１５を形成した。電子注入層９１５は、フッ化リチウム（ＬｉＦ）を用い、膜厚が１ｎｍになるように蒸着して形成した。 Next, an electron injection layer 915 was formed over the electron transport layer 914. The electron injection layer 915 was formed by vapor deposition using lithium fluoride (LiF) so as to have a film thickness of 1 nm.
次に、電子注入層９１５上に第２の電極９０３を形成した。第２の電極９０３は、アルミニウムを蒸着法により、膜厚が２００ｎｍとなるように形成した。なお、本実施例において、第２の電極９０３は、陰極として機能する。 Next, a second electrode 903 was formed over the electron injection layer 915. The second electrode 903 was formed by vapor deposition of aluminum so that the film thickness becomes 200 nm. Note that in this embodiment, the second electrode 903 functions as a cathode.
以上の工程により、基板９００上に一対の電極間にＥＬ層を挟んでなる発光素子を形成した。なお、上記工程で説明した正孔注入層９１１、正孔輸送層９１２、発光層９１３、電子輸送層９１４、電子注入層９１５は、本発明の一態様におけるＥＬ層を構成する機能層である。また、上述した作製方法における蒸着工程では、全て抵抗加熱法による蒸着法を用いた。 Through the above process, a light-emitting element in which an EL layer was sandwiched between a pair of electrodes was formed over the substrate 900. Note that 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 described in the above steps are functional layers that constitute the EL layer in one embodiment of the present invention. In addition, in the vapor deposition process in the manufacturing method described above, a vapor deposition method using a resistance heating method was used.
また、上記に示すように作製した発光素子は、別の基板（図示せず）により封止される。なお、別の基板（図示せず）を用いた封止の際は、窒素雰囲気のグローブボックス内において、封止材を用いて別の基板（図示せず）を基板９００上に固定し、シール材を基板９００上に形成された発光素子の周囲に塗布し、封止時に３６５ｎｍの紫外光を６Ｊ／ｃｍ２照射し、８０℃にて１時間熱処理することにより行った。 In addition, the light-emitting element manufactured as described above is sealed by another substrate (not shown). When sealing using another substrate (not shown), another substrate (not shown) is fixed on the substrate 900 using a sealing material in a glove box in a nitrogen atmosphere and sealed. The material was applied to the periphery of the light emitting element formed on the substrate 900, and irradiated with 6 J / cm 2 of 365 nm ultraviolet light at the time of sealing, and heat-treated at 80 ° C. for 1 hour.
≪発光素子の動作特性≫
作製した発光素子１および発光素子２の動作特性について測定した。なお、測定は室温で行った。また、発光素子１および発光素子２の動作特性の結果を図１４~図１７に示す。 ≪Operating characteristics of light emitting element≫
The operating characteristics of the manufactured light-emitting element 1 and light-emitting element 2 were measured. The measurement was performed at room temperature. In addition, results of operating characteristics of the light-emitting element 1 and the light-emitting element 2 are shown in FIGS.
また、１０００ｃｄ／ｍ２付近における発光素子１および発光素子２の主な初期特性値を以下の表２に示す。 In addition, Table 2 below shows main initial characteristic values of the light-emitting element 1 and the light-emitting element 2 around 1000 cd / m 2 .
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
上記結果から、本実施例で作製した各発光素子は、良好な電流効率と高い外部量子効率を示していることが分かる。 From the above results, it can be seen that each light-emitting element manufactured in this example exhibits good current efficiency and high external quantum efficiency.
また、発光素子１、発光素子２および比較発光素子３に１２．５ｍＡ／ｃｍ２の電流密度で電流を流した際の発光スペクトルを、図１８に示す。図１８に示す通り、発光素子１、発光素子２、および比較発光素子３の発光スペクトルは、いずれも４６８ｎｍ付近にピークを有しており、発光層９１３に含まれる、１，６ｍＭｅｍＦＬＰＡＰｒｎの発光に由来していることが示唆される。 FIG. 18 shows emission spectra obtained when a current was passed through the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 at a current density of 12.5 mA / cm 2 . As shown in FIG. 18, the emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 all have a peak near 468 nm, and are derived from light emission of 1,6 mM emFLPAPrn contained in the light-emitting layer 913. It is suggested that
次に、発光素子１および比較発光素子３に対する信頼性試験を行った。信頼性試験の結果を図１９に示す。図１９において、縦軸は初期輝度を１００％とした時の規格化輝度（％）を示し、横軸は素子の駆動時間（ｈ）を示す。なお、信頼性試験は、２ｍＡにおける定電流駆動試験を行った。 Next, a reliability test on the light-emitting element 1 and the comparative light-emitting element 3 was performed. The result of the reliability test is shown in FIG. In FIG. 19, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the element drive time (h). The reliability test was a constant current drive test at 2 mA.
信頼性試験の結果より、本発明の一態様である発光素子１は、比較発光素子３よりも信頼性において優れた特性を示すことがわかった。このことから、同じ発光材料（１，６ｍＭｅｍＦＬＰＡＰｒｎ）を用いている場合であっても、実施例１で説明した、ａｃＤＢＣｚＰＡ（構造式（１００））を発光層ホストとして用いることは長寿命化に関して有用であると言える。 From the result of the reliability test, it was found that the light-emitting element 1 which is one embodiment of the present invention exhibited characteristics superior in reliability to the comparative light-emitting element 3. Therefore, even when the same luminescent material (1,6 mM emFLPAPrn) is used, it is useful for extending the lifetime to use acDBCzPA (structural formula (100)) described in Example 1 as the luminescent layer host. It can be said that.
≪合成例３≫
本実施例では、実施の形態１の構造式（１０２）で表される本発明の一態様である有機化合物、９−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−トリベンゾ［ａ，ｃ，ｉ］カルバゾール（略称：ａｃｉＴＢＣｚＰＡ）の合成方法について説明する。なお、ａｃｉＴＢＣｚＰＡの構造を以下に示す。 << Synthesis Example 3 >>
In this example, an organic compound which is one embodiment of the present invention represented by the structural formula (102) in Embodiment 1, 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-tribenzo [ a, c, i] A synthesis method of carbazole (abbreviation: aciTBCzPA) will be described. The structure of aciTBCzPA is shown below.
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
２００ｍＬ３口フラスコに９−（４−ブロモフェニル）−１０−フェニルアントラセン１．７ｇ（４．１ｍｍｏｌ）、９Ｈ−トリベンゾ［ａ，ｃ，ｉ］カルバゾール１．３ｇ（４．１ｍｍｏｌ）、ナトリウム　ｔｅｒｔ−ブトキシド０．３８ｇ（８．２ｍｍｏｌ）を加え、フラスコ内を窒素置換した。この混合物にキシレン２０ｍＬを加え、減圧下で攪拌する事で脱気した。この混合物に、トリ（ｔｅｒｔ−ブチル）ホスフィン０．８５ｍＬ、ビス（ジベンジリデンアセトン）パラジウム（０）０．１２ｇ（０．２１ｍｍｏｌ）を加え、窒素気流下、１５０℃で１２時間還流した。 In a 200 mL three-necked flask, 1.7 g (4.1 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.3 g (4.1 mmol) of 9H-tribenzo [a, c, i] carbazole, sodium tert-butoxide 0.38 g (8.2 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. The mixture was deaerated by adding 20 mL of xylene and stirring under reduced pressure. To this mixture, tri (tert-butyl) phosphine 0.85 mL and bis (dibenzylideneacetone) palladium (0) 0.12 g (0.21 mmol) were added, and the mixture was refluxed at 150 ° C. for 12 hours under a nitrogen stream.
この混合物を濾過し、固体を水で洗浄した。この固体をトルエンに溶解し、この溶液をセライト、アルミナ、フロリジールを通して吸引濾過した。得られた濾液を濃縮して得た固体をトルエンで再結晶した。得られた固体をＨＰＬＣにより精製し、得られた固体をトルエンで再結晶した所、目的物の白色固体を収量１．２ｇ、収率４６％で得た。上記合成方法の合成スキームを下記式（ｃ）に示す。 The mixture was filtered and the solid was washed with water. This solid was dissolved in toluene, and this solution was subjected to suction filtration through celite, alumina and Florisil. The solid obtained by concentrating the obtained filtrate was recrystallized with toluene. The obtained solid was purified by HPLC, and the obtained solid was recrystallized from toluene. As a result, 1.2 g of a target white solid was obtained in a yield of 46%. A synthesis scheme of the above synthesis method is shown in the following formula (c).
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
得られた白色固体１．２ｇをトレインサブリメーション法により昇華精製した。昇華精製は、圧力４．０Ｐａ、アルゴン流量５．０ｍＬ／ｍｉｎの条件で、淡黄色固体を３０５℃で加熱して行った。昇華精製後、淡黄色固体を１．０ｇ、回収率８５％で得た。 1.2 g of the obtained white solid was purified by sublimation by a train sublimation method. The sublimation purification was performed by heating a pale yellow solid at 305 ° C. under conditions of a pressure of 4.0 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 1.0 g of a pale yellow solid was obtained with a recovery rate of 85%.
得られた淡黄色固体の核磁気共鳴分光法（１Ｈ−ＮＭＲ）による分析結果を下記に示す。また、１Ｈ−ＮＭＲチャートを図２０（Ａ）（Ｂ）に示す。なお、図２０（Ｂ）は、図２０（Ａ）における７．０ｐｐｍ~９．５ｐｐｍの範囲を拡大して表したチャートである。この結果から、本実施例において、上述の構造式（１０２）で表される本発明の一態様である有機化合物、ａｃｉＴＢＣｚＰＡが得られたことがわかった。 The analysis result by nuclear magnetic resonance spectroscopy ( 1 H-NMR) of the obtained pale yellow solid is shown below. Further, 1 H-NMR charts are shown in FIGS. Note that FIG. 20B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, aciTBCzPA, which is one embodiment of the present invention represented by the above structural formula (102) was obtained in this example.
１Ｈ　ＮＭＲ（ＣＤＣｌ３，３００ＭＨｚ）：δ＝７．３９−７．７１（ｍ、１５Ｈ）、７．７９−７．９２（ｍ、７Ｈ）、７．９８−８．１０（ｍ、５Ｈ）、８．８６−８．９２（ｍ、３Ｈ）、９．１４（ｄｄ、Ｊ１＝８．４Ｈｚ、Ｊ２＝０．９Ｈｚ、１Ｈ）。 1 H NMR (CDCl 3 , 300 MHz): δ = 7.39-7.71 (m, 15H), 7.79-7.92 (m, 7H), 7.98-8.10 (m, 5H) , 8.86-8.92 (m, 3H), 9.14 (dd, J 1 = 8.4 Hz, J 2 = 0.9 Hz, 1H).
次に、ａｃｉＴＢＣｚＰＡのトルエン溶液および固体薄膜の紫外可視吸収スペクトル（以下、単に「吸収スペクトル」という）及び発光スペクトルを測定した。固体薄膜は石英基板上に真空蒸着法にて作製した。吸収スペクトルの測定には、紫外可視分光光度計（溶液：日本分光株式会社製、Ｖ−５５０、薄膜：（株）日立ハイテクノロジーズ製、Ｕ−４１００）を用いた。なお溶液の吸収スペクトルは、石英セルにトルエンのみを入れて測定した吸収スペクトルを差し引いて算出し、薄膜の吸収スペクトルは、基板を含めた透過率と反射率から求めた吸光度（−ｌｏｇ１０　［％Ｔ／（１００−％Ｒ）］より算出した。なお％Ｔは透過率、％Ｒは反射率を表す。また、発光スペクトルの測定には、蛍光光度計（（株）浜松ホトニクス製　ＦＳ９２０）を用いた。 Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of aciTBCzPA and a solid thin film were measured. The solid thin film was produced on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance (−log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
得られたトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図２１（Ａ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、固体薄膜の吸収スペクトルおよび発光スペクトルの測定結果を図２１（Ｂ）に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。 FIG. 21A shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In addition, FIG. 21B shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
図２１（Ａ）の結果より、ａｃｉＴＢＣｚＰＡのトルエン溶液では、３９６ｎｍ、３７４ｎｍ、３６２ｎｍ、３５４ｎｍ、３４６ｎｍ、３３７ｎｍ付近に吸収ピークが見られ、４３３ｎｍ、４１４ｎｍ付近（励起波長３７６ｎｍ）に発光波長のピークが見られた。また、図２１（Ｂ）の結果より、ａｃｉＴＢＣｚＰＡの固体薄膜では、４００ｎｍ、３７８ｎｍ、３６０ｎｍ、３００ｎｍ、２６４ｎｍ付近に吸収ピークが見られ、４４５ｎｍ、４３０ｎｍ付近（励起波長３６５ｎｍ）に発光波長のピークが見られた。 From the results shown in FIG. 21A, in the toluene solution of aciTBCzPA, an absorption peak is observed at around 396 nm, 374 nm, 362 nm, 354 nm, 346 nm, and 337 nm, and an emission wavelength peak is observed at around 433 nm and 414 nm (excitation wavelength: 376 nm). It was. Further, from the result of FIG. 21B, in the solid thin film of aciTBCzPA, absorption peaks are observed in the vicinity of 400 nm, 378 nm, 360 nm, 300 nm, and 264 nm, and the emission wavelength peak is observed in the vicinity of 445 nm and 430 nm (excitation wavelength 365 nm). It was.
なお、ａｃｉＴＢＣｚＰＡは青色に発光することを確認した。本発明の一態様である有機化合物、ａｃｉＴＢＣｚＰＡは、発光物質や可視域の蛍光発光物質のホストとしても利用可能である。また、ａｃｉＴＢＣｚＰＡの薄膜は、大気下においても凝集しにくい良好な膜質であることがわかった。 In addition, it was confirmed that aciTBCzPA emits blue light. The organic compound, aciTBCzPA, which is one embodiment of the present invention can also be used as a host of a light-emitting substance or a visible-light fluorescent substance. It was also found that the thin film of aciTBCzPA has a good film quality that hardly aggregates even in the atmosphere.
ａｃｉＴＢＣｚＰＡのＨＯＭＯ準位およびＬＵＭＯ準位をサイクリックボルタンメトリ（ＣＶ）測定を元に算出した。算出方法を以下に示す。 The HOMO level and LUMO level of aciTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
測定装置としては電気化学アナライザー（ビー・エー・エス（株）製、型番：ＡＬＳモデル６００Ａまたは６００Ｃ）を用いた。ＣＶ測定における溶液は、溶媒として脱水ジメチルホルムアミド（ＤＭＦ）（（株）アルドリッチ製、９９．８％、カタログ番号；２２７０５−６）を用い、支持電解質である過塩素酸テトラ−ｎ−ブチルアンモニウム（ｎ−Ｂｕ４ＮＣｌＯ４）（（株）東京化成製、カタログ番号；Ｔ０８３６）を１００ｍｍｏｌ／Ｌの濃度となるように溶解させ、さらに測定対象を２ｍｍｏｌ／Ｌの濃度となるように溶解させて調製した。 As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate as a supporting electrolyte ( n-Bu 4 NClO 4 ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 2 mmol / L. did.
また、作用電極としては白金電極（ビー・エー・エス（株）製、ＰＴＥ白金電極）を、補助電極としては白金電極（ビー・エー・エス（株）製、ＶＣ−３用Ｐｔカウンター電極（５ｃｍ））を、参照電極としてはＡｇ／Ａｇ＋電極（ビー・エー・エス（株）製、ＲＥ７非水溶媒系参照電極）をそれぞれ用いた。なお、測定は室温（２０以上２５℃以下）で行った。 In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag + electrode (manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).
また、ＣＶ測定時のスキャン速度は、０．１Ｖ／ｓｅｃに統一し、参照電極に対する酸化電位Ｅａ［Ｖ］および還元電位Ｅｃ［Ｖ］を測定した。Ｅａは酸化−還元波の中間電位とし、Ｅｃは還元−酸化波の中間電位とした。ここで、本実施例で用いる参照電極の真空準位に対するポテンシャルエネルギーは、−４．９４［ｅＶ］であることが分かっているため、ＨＯＭＯ準位［ｅＶ］＝−４．９４−Ｅａ、ＬＵＭＯ準位［ｅＶ］＝−４．９４−Ｅｃという式から、ＨＯＭＯ準位およびＬＵＭＯ準位をそれぞれ求めることができる。 Further, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was an intermediate potential of the oxidation-reduction wave, and Ec was an intermediate potential of the reduction-oxidation wave. Here, since it is known that the potential energy with respect to the vacuum level of the reference electrode used in this example is −4.94 [eV], the HOMO level [eV] = − 4.94−Ea, LUMO. From the equation of level [eV] = − 4.94−Ec, the HOMO level and the LUMO level can be obtained respectively.
また、ＣＶ測定を１００回繰り返し行い、１００サイクル目の測定での酸化−還元波と、１サイクル目の酸化−還元波を比較して、化合物の電気的安定性を調べた。 In addition, CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
この結果、ａｃｉＴＢＣｚＰＡの酸化電位Ｅａ［Ｖ］の測定において、ＨＯＭＯ準位は−５．７４ｅＶであることがわかった。一方、還元電位Ｅｃ［Ｖ］の測定において、ＬＵＭＯ準位は−２．７６ｅＶであることがわかった。また、酸化−還元波の繰り返し測定において１サイクル目と１００サイクル後の波形と比較したところ、Ｅａ測定においては８４％のピーク強度を保っていたことから、ａｃｉＴＢＣｚＰＡは酸化に対する耐性が非常に良好であることが確認された。 As a result, it was found that the HOMO level was −5.74 eV in the measurement of the oxidation potential Ea [V] of aciTBCzPA. On the other hand, in the measurement of the reduction potential Ec [V], it was found that the LUMO level was -2.76 eV. In comparison with the waveform after the first cycle and after 100 cycles in the repeated measurement of oxidation-reduction wave, the peak intensity of 84% was maintained in Ea measurement, so that aciTBCzPA has very good resistance to oxidation. It was confirmed that there was.
≪合成例４≫
本実施例では、実施の形態１の構造式（１０３）で表される本発明の一態様である有機化合物、９−［４−（１０−フェニル−９−アントリル）フェニル］−９Ｈ−テトラベンゾ［ａ，ｃ，ｇ，ｉ］カルバゾール（略称：ＴｅＢＣｚＰＡ）の合成方法について説明する。なお、ＴｅＢＣｚＰＡの構造を以下に示す。 << Synthesis Example 4 >>
In this example, an organic compound which is one embodiment of the present invention represented by the structural formula (103) of Embodiment 1, 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-tetrabenzo [ a, c, g, i] A synthesis method of carbazole (abbreviation: TeBCzPA) will be described. The structure of TeBCzPA is shown below.
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
２００ｍＬ３口フラスコに９−（４−ブロモフェニル）−１０−フェニルアントラセン１．２ｇ（３．０ｍｍｏｌ）、９Ｈ−テトラベンゾ［ａ，ｃ，ｇ，ｉ］カルバゾール１．１ｇ（３．０ｍｍｏｌ）、ナトリウム　ｔｅｒｔ−ブトキシド０．５８ｇ（６．０ｍｍｏｌ）を加え、フラスコ内を窒素置換した。この混合物にメシチレン１６ｍＬを加え、減圧下で攪拌する事で脱気した。この混合物に、トリ（ｔｅｒｔ−ブチル）ホスフィン０．６１ｍＬ、ビス（ジベンジリデンアセトン）パラジウム（０）８６ｍｇ（０．１５ｍｍｏｌ）を加え、窒素気流下、１４０℃で２０時間撹拌した。 In a 200 mL three-necked flask, 1.2 g (3.0 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.1 g (3.0 mmol) of 9H-tetrabenzo [a, c, g, i] carbazole, sodium tert -Butoxide (0.58 g, 6.0 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 16 mL of mesitylene was added to this mixture, and deaerated by stirring under reduced pressure. To this mixture, 0.61 mL of tri (tert-butyl) phosphine and 86 mg (0.15 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was stirred at 140 ° C. for 20 hours under a nitrogen stream.
この混合物を濾過し、固体を水で洗浄した。この固体をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：４）で精製し、トルエンで再結晶した。得られた固体をＨＰＬＣにより精製し、得られた固体をトルエンで再結晶した所、目的物の淡黄色固体を収量０．７６ｇ、収率３６％で得た。上記合成方法の合成スキームを下記式（ｄ）に示す。 The mixture was filtered and the solid was washed with water. This solid was purified by silica gel column chromatography (toluene: hexane = 1: 4) and recrystallized from toluene. The obtained solid was purified by HPLC, and the obtained solid was recrystallized from toluene. As a result, 0.76 g of a target light yellow solid was obtained in a yield of 36%. A synthesis scheme of the above synthesis method is shown in the following formula (d).
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
得られた淡黄色固体の核磁気共鳴分光法（１Ｈ−ＮＭＲ）による分析結果を下記に示す。また、１Ｈ−ＮＭＲチャートを図２２（Ａ）（Ｂ）に示す。なお、図２２（Ｂ）は、図２２（Ａ）における７．０ｐｐｍ~９．５ｐｐｍの範囲を拡大して表したチャートである。この結果から、本実施例において、上述の構造式（１０３）で表される本発明の一態様である有機化合物、ＴｅＢＣｚＰＡが得られたことがわかった。 The analysis result by nuclear magnetic resonance spectroscopy ( 1 H-NMR) of the obtained pale yellow solid is shown below. In addition, 1 H-NMR charts are shown in FIGS. Note that FIG. 22B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. From this result, it was found that an organic compound, TeBCzPA, which is one embodiment of the present invention represented by the above structural formula (103), was obtained in this example.
１Ｈ　ＮＭＲ（ＣＤＣｌ３，３００ＭＨｚ）：δ＝７．４２−７．４９（ｍ、４Ｈ）、７．５３−７．７１（ｍ、１５Ｈ）、７．８１（ｄ、Ｊ＝８．７Ｈｚ、２Ｈ）、７．８７−７．９０（ｍ、２Ｈ）、７．９８−８．０４（ｍ、４Ｈ）、８．７８−８．８１（ｍ、２Ｈ）、８．８６（ｄ、Ｊ＝７．８Ｈｚ、２Ｈ）、９．０６−９．１０（ｍ、２Ｈ）。 1 H NMR (CDCl 3 , 300 MHz): δ = 7.42-7.49 (m, 4H), 7.53-7.71 (m, 15H), 7.81 (d, J = 8.7 Hz, 2H), 7.87-7.90 (m, 2H), 7.98-8.04 (m, 4H), 8.78-8.81 (m, 2H), 8.86 (d, J = 7.8 Hz, 2H), 9.06-9.10 (m, 2H).
次に、ＴｅＢＣｚＰＡのトルエン溶液の紫外可視吸収スペクトル及び発光スペクトルを測定した。吸収スペクトルの測定には、紫外可視分光光度計（溶液：日本分光株式会社製、Ｖ−５５０）を用いた。なお溶液の吸収スペクトルは、石英セルにトルエンのみを入れて測定した吸収スペクトルを差し引いて算出した。また、発光スペクトルの測定には、蛍光光度計（（株）浜松ホトニクス製　ＦＳ９２０）を用いた。 Next, an ultraviolet-visible absorption spectrum and an emission spectrum of a toluene solution of TeBCzPA were measured. An ultraviolet-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation) was used for the measurement of the absorption spectrum. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell. In addition, a fluorometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum.
得られたトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図２３に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。 The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
図２３の結果より、ＴｅＢＣｚＰＡのトルエン溶液では、３９６ｎｍ、３７３ｎｍ、３５６ｎｍ、３４０ｎｍ、３０３ｎｍ付近に吸収ピークが見られ、４３３ｎｍ、４１５ｎｍ付近（励起波長３７４ｎｍ）に発光波長のピークが見られた。 From the results shown in FIG. 23, in the toluene solution of TeBCzPA, absorption peaks were observed in the vicinity of 396 nm, 373 nm, 356 nm, 340 nm, and 303 nm, and the emission wavelength peak was observed in the vicinity of 433 nm and 415 nm (excitation wavelength: 374 nm).
なお、ＴｅＢＣｚＰＡは青色に発光することを確認した。本発明の一態様である有機化合物、ＴｅＢＣｚＰＡは、発光物質や可視域の蛍光発光物質のホストとしても利用可能である。 TeBCzPA was confirmed to emit blue light. The organic compound, TeBCzPA, which is one embodiment of the present invention can also be used as a host for a light-emitting substance or a visible-light fluorescent substance.
本実施例では、本発明の一態様である発光素子として、実施例４で説明した、ａｃｉＴＢＣｚＰＡ（構造式（１０２））を発光層に用いた発光素子４を作製し、その特性について測定した結果を示す。 In this example, a light-emitting element 4 using aciTBCzPA (structural formula (102)) described in Example 4 as a light-emitting layer as a light-emitting element which is one embodiment of the present invention was manufactured, and the characteristics thereof were measured. Indicates.
なお、本実施例で用いる発光素子の素子構造は、実施例３で示した図１３と同様の構造であるが、素子構造を構成する各層の具体的な構成については表３に示す通りである。また、本実施例で用いる材料の化学式を以下に示す。 Note that the element structure of the light-emitting element used in this example is the same as that in FIG. 13 shown in Example 3, but the specific structure of each layer constituting the element structure is as shown in Table 3. . In addition, chemical formulas of materials used in this example are shown below.
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
≪発光素子の動作特性≫
作製した発光素子４の動作特性について測定した。なお、測定は室温で行った。また、結果を図２４~図２７に示す。 ≪Operating characteristics of light emitting element≫
The operating characteristics of the manufactured light-emitting element 4 were measured. The measurement was performed at room temperature. The results are shown in FIGS.
また、１０００ｃｄ／ｍ２付近における発光素子の主な初期特性値を以下の表４に示す。 In addition, Table 4 below shows main initial characteristic values of the light-emitting element around 1000 cd / m 2 .
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
上記結果から、本実施例で作製した発光素子４は非常に低電圧駆動であり、良好な効率を示すことが分かる。 From the above results, it can be seen that the light-emitting element 4 manufactured in this example is driven at a very low voltage and exhibits good efficiency.
また、発光素子４に１２．５ｍＡ／ｃｍ２の電流密度で電流を流した際の発光スペクトルを図２８に示す。図２８に示す通り、発光素子の発光スペクトルは、４６９ｎｍ付近にピークを有しており、発光層９１３に含まれる発光物質の発光に由来していることが示唆される。 28 shows a light emission spectrum when a current is passed through the light-emitting element 4 at a current density of 12.5 mA / cm 2 . As shown in FIG. 28, the emission spectrum of the light-emitting element has a peak in the vicinity of 469 nm, which is suggested to be derived from light emission of the light-emitting substance contained in the light-emitting layer 913.
次に、発光素子４に対する信頼性試験を行った。信頼性試験の結果を図２９に示す。図２９において、縦軸は初期輝度を１００％とした時の規格化輝度（％）を示し、横軸は素子の駆動時間（ｈ）を示す。なお、信頼性試験は、２ｍＡにおける定電流駆動試験を行った。 Next, a reliability test for the light-emitting element 4 was performed. The result of the reliability test is shown in FIG. In FIG. 29, the vertical axis represents normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents element driving time (h). The reliability test was a constant current drive test at 2 mA.
信頼性試験の結果より、本発明の一態様である発光素子４は、信頼性において優れた特性を示すことがわかった。このことから、本発明の一態様である有機化合物、ａｃｉＴＢＣｚＰＡ（構造式（１０２））を発光層ホストとして用いることは長寿命化に関して有用であると言える。 From the results of the reliability test, it was found that the light-emitting element 4 which is one embodiment of the present invention exhibits excellent characteristics in reliability. Thus, it can be said that the use of the organic compound, aciTBCzPA (structural formula (102)), which is one embodiment of the present invention, as a light-emitting layer host is useful for extending the lifetime.
１０１　　第１の電極
１０２　　第２の電極
１０３　　ＥＬ層
１０３ａ、１０３ｂ　　ＥＬ層
１０４　　電荷発生層
１１１、１１１ａ、１１１ｂ　　正孔注入層
１１２、１１２ａ、１１２ｂ　　正孔輸送層
１１３、１１３ａ、１１３ｂ　　発光層
１１４、１１４ａ、１１４ｂ　　電子輸送層
１１５、１１５ａ、１１５ｂ　　電子注入層
２０１　　第１の基板
２０２　　トランジスタ（ＦＥＴ）
２０３Ｒ、２０３Ｇ、２０３Ｂ、２０３Ｗ　　発光素子
２０４　　ＥＬ層
２０５　　第２の基板
２０６Ｒ、２０６Ｇ、２０６Ｂ　　カラーフィルタ
２０６Ｒ’、２０６Ｇ’、２０６Ｂ’　　カラーフィルタ
２０７　　第１の電極
２０８　　第２の電極
２０９　　黒色層（ブラックマトリックス）
２１０Ｒ、２１０Ｇ　　導電層
３０１　　第１の基板
３０２　　画素部
３０３　　駆動回路部（ソース線駆動回路）
３０４ａ、３０４ｂ　　駆動回路部（ゲート線駆動回路）
３０５　　シール材
３０６　　第２の基板
３０７　　引き回し配線
３０８　　ＦＰＣ
３０９　　ＦＥＴ
３１０　　ＦＥＴ
３１１　　ＦＥＴ
３１２　　ＦＥＴ
３１３　　第１の電極
３１４　　絶縁物
３１５　　ＥＬ層
３１６　　第２の電極
３１７　　発光素子
３１８　　空間
９００　　基板
９０１　　第１の電極
９０２　　ＥＬ層
９０３　　第２の電極
９１１　　正孔注入層
９１２　　正孔輸送層
９１３　　発光層
９１４　　電子輸送層
９１５　　電子注入層
４０００　　照明装置
４００１　　基板
４００２　　発光素子
４００３　　基板
４００４　　第１の電極
４００５　　ＥＬ層
４００６　　第２の電極
４００７　　電極
４００８　　電極
４００９　　補助配線
４０１０　　絶縁層
４０１１　　封止基板
４０１２　　シール材
４０１３　　乾燥剤
４０１５　　拡散板
４１００　　照明装置
４２００　　照明装置
４２０１　　基板
４２０２　　発光素子
４２０４　　第１の電極
４２０５　　ＥＬ層
４２０６　　第２の電極
４２０７　　電極
４２０８　　電極
４２０９　　補助配線
４２１０　　絶縁層
４２１１　　封止基板
４２１２　　シール材
４２１３　　バリア膜
４２１４　　平坦化膜
４２１５　　拡散板
４３００　　照明装置
５１０１　　ライト
５１０２　　ホイール
５１０３　　ドア
５１０４　　表示部
５１０５　　ハンドル
５１０６　　シフトレバー
５１０７　　座席シート
５１０８　　インナーリアビューミラー
７０００　　筐体
７００１　　表示部
７００２　　第２表示部
７００３　　スピーカ
７００４　　ＬＥＤランプ
７００５　　操作キー
７００６　　接続端子
７００７　　センサ
７００８　　マイクロフォン
７００９　　スイッチ
７０１０　　赤外線ポート
７０１１　　記録媒体読込部
７０１２　　支持部
７０１３　　イヤホン
７０１４　　アンテナ
７０１５　　シャッターボタン
７０１６　　受像部
７０１８　　スタンド
７０２０　　カメラ
７０２１　　外部接続部
７０２２、７０２３　　操作用ボタン
７０２４　　接続端子
７０２５　　バンド、
７０２６　　留め金
７０２７　　時刻を表すアイコン
７０２８　　その他のアイコン
８００１　　照明装置
８００２　　照明装置
８００３　　照明装置
８００４　　照明装置
９３１０　　携帯情報端末
９３１１　　表示部
９３１２　　表示領域
９３１３　　ヒンジ
９３１５　　筐体 101 First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b Hole injection layer 112, 112a, 112b Hole transport layer 113, 113a, 113b Light emitting layer 114, 114a , 114b Electron transport layer 115, 115a, 115b Electron injection layer 201 First substrate 202 Transistor (FET)
203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second substrate 206R, 206G, 206B Color filter 206R ′, 206G ′, 206B ′ Color filter 207 First electrode 208 Second electrode 209 Black layer (black matrix )
210R, 210G Conductive layer 301 First substrate 302 Pixel portion 303 Drive circuit portion (source line drive circuit)
304a, 304b Drive circuit section (gate line drive circuit)
305 Sealing material 306 Second substrate 307 Route wiring 308 FPC
309 FET
310 FET
311 FET
312 FET
313 First electrode 314 Insulator 315 EL layer 316 Second electrode 317 Light emitting element 318 Space 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Light emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting device 4001 Substrate 4002 Light emitting element 4003 Substrate 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulating layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4100 Lighting device 4200 Lighting device 4201 Substrate 4202 Light emitting element 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 212 Sealing material 4213 Barrier film 4214 Flattening film 4215 Diffuser 4300 Lighting device 5101 Light 5102 Wheel 5103 Door 5104 Display unit 5105 Handle 5106 Shift lever 5107 Seat seat 5108 Inner rear view mirror 7000 Housing 7001 Display unit 7002 Second display unit 7003 Speaker 7004 LED lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7012 Support unit 7013 Earphone 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7021 External connection unit 7022, 7023 Operation buttons 7024 Connection terminal 7025 Band
7026 Clasp 7027 Icon 7028 Other icons 8001 Lighting device 8002 Lighting device 8003 Lighting device 8004 Lighting device 9310 Portable information terminal 9311 Display unit 9312 Display area 9313 Hinge 9315 Case

Claims (11)

  1. 　一般式（Ｇ１）で表される有機化合物。
    Figure JPOXMLDOC01-appb-C000001
     （式中、Ａｒ１は置換もしくは無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。）     An organic compound represented by the general formula (G1).
    Figure JPOXMLDOC01-appb-C000001
     (In the formula, Ar 1 represents a substituted or unsubstituted phenylene group. R 1 to R 21 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted carbon group having 5 to 7 carbon atoms. A monocyclic saturated hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R 9. And R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or an alkyl group having 1 to 6 carbon atoms as a substituent. Substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or substituted or unsubstituted aryl having 6 to 13 carbon atoms Any of the groups.)
  2. 　一般式（Ｇ２）で表される有機化合物。
    Figure JPOXMLDOC01-appb-C000002
     （式中、Ａｒ２は無置換のフェニレン基を表す。また、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。）     An organic compound represented by the general formula (G2).
    Figure JPOXMLDOC01-appb-C000002
     (In the formula, Ar 2 represents an unsubstituted phenylene group. R 1 to R 21 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted single group having 5 to 7 carbon atoms. It represents either a cyclic saturated hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R 9 and R 10 and R 11 and R 12 may be independently condensed to form a benzene ring, and the benzene ring may be unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms as a substituent. Or an unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Have one.)
  3. 　一般式（Ｇ３）で表される有機化合物。
    Figure JPOXMLDOC01-appb-C000003
     　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　（式中、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０およびＲ１１とＲ１２は、それぞれ独立に縮環してベンゼン環を形成してもよく、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。）     An organic compound represented by the general formula (G3).
    Figure JPOXMLDOC01-appb-C000003
     (Wherein R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted carbon number. It represents either a 7-10 polycyclic saturated hydrocarbon, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R 9 and R 10 and R 11 and R 12 are each independently compressed. The benzene ring may be substituted to form a benzene ring, or the benzene ring may be unsubstituted, or a substituted or unsubstituted monocyclic group having 5 to 7 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. It has either a saturated hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)
  4. 　一般式（Ｇ４）で表される有機化合物。
    Figure JPOXMLDOC01-appb-C000004
     　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　（式中、Ｒ１~Ｒ２１はそれぞれ独立に、水素、炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、または置換もしくは無置換の炭素数６~１３のアリール基のいずれかを表す。また、Ｒ９とＲ１０、およびＲ１１とＲ１２、の少なくとも一方は、縮環してベンゼン環を形成し、前記ベンゼン環は無置換であるか、または、置換基として炭素数１~６のアルキル基、置換もしくは無置換の炭素数５~７の単環式飽和炭化水素、置換もしくは無置換の炭素数７~１０の多環式飽和炭化水素、又は置換もしくは無置換の炭素数６~１３のアリール基のいずれかを有する。）     An organic compound represented by the general formula (G4).
    Figure JPOXMLDOC01-appb-C000004
     (Wherein R 1 to R 21 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted carbon number. It represents either a 7-10 polycyclic saturated hydrocarbon or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and at least one of R 9 and R 10 , and R 11 and R 12 is , Condensed to form a benzene ring, the benzene ring being unsubstituted, or an alkyl group having 1 to 6 carbon atoms as a substituent, substituted or unsubstituted monocyclic saturated having 5 to 7 carbon atoms Any of hydrocarbons, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 13 carbon atoms)
  5. 　構造式（１００）、構造式（１０１）、構造式（１０２）、または構造式（１０３）で表される有機化合物。
    Figure JPOXMLDOC01-appb-C000005
         An organic compound represented by the structural formula (100), the structural formula (101), the structural formula (102), or the structural formula (103).
    Figure JPOXMLDOC01-appb-C000005
  6. 　請求項１乃至請求項５のいずれか一に記載の有機化合物を用いた発光素子。 A light emitting device using the organic compound according to any one of claims 1 to 5.
  7. 　一対の電極間にＥＬ層を有し、
    　前記ＥＬ層は、請求項１乃至請求項５のいずれか一に記載の有機化合物を有する発光素子。     An EL layer between the pair of electrodes;
    The EL layer is a light-emitting element including the organic compound according to any one of claims 1 to 5.
  8. 　一対の電極間にＥＬ層を有し、
    　前記ＥＬ層は、発光層を有し、
    　前記発光層は、請求項１乃至請求項５のいずれか一に記載の有機化合物を有する発光素子。     An EL layer between the pair of electrodes;
    The EL layer has a light emitting layer,
    The said light emitting layer is a light emitting element which has an organic compound as described in any one of Claims 1 thru | or 5.
  9. 　請求項６に記載の発光素子と、
    　トランジスタ、または基板の少なくとも一と、
    を有する発光装置。     A light emitting device according to claim 6;
    At least one of a transistor or a substrate;
    A light emitting device.
  10. 　請求項９に記載の発光装置と、
    　マイク、カメラ、操作用ボタン、外部接続部、または、スピーカの少なくとも一と、
    を有する電子機器。     A light emitting device according to claim 9;
    At least one of a microphone, a camera, an operation button, an external connection unit, or a speaker;
    Electronic equipment having
  11. 　請求項６に記載の発光素子と、
    　筐体、カバー、または、支持台の少なくとも一と、
    を有する照明装置。     A light emitting device according to claim 6;
    At least one of a housing, a cover, or a support base;
    A lighting device.
PCT/IB2018/051913 2017-03-31 2018-03-22 Organic compound, light emitting element, light emitting device, electronic equipment, and lighting device WO2018178818A1 (en)

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