WO2021059086A1 - 有機化合物、光デバイス、発光デバイス、発光装置、電子機器および照明装置 - Google Patents

有機化合物、光デバイス、発光デバイス、発光装置、電子機器および照明装置 Download PDF

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WO2021059086A1
WO2021059086A1 PCT/IB2020/058589 IB2020058589W WO2021059086A1 WO 2021059086 A1 WO2021059086 A1 WO 2021059086A1 IB 2020058589 W IB2020058589 W IB 2020058589W WO 2021059086 A1 WO2021059086 A1 WO 2021059086A1
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Prior art keywords
carbon atoms
light emitting
group
groups
emitting device
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English (en)
French (fr)
Japanese (ja)
Inventor
夛田杏奈
川上祥子
奥山拓夢
鈴木恒徳
瀬尾哲史
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Semiconductor Energy Laboratory Co Ltd
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Semiconductor Energy Laboratory Co Ltd
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Priority to US17/640,843 priority Critical patent/US12421201B2/en
Priority to JP2021547982A priority patent/JP7607571B2/ja
Priority to KR1020227013323A priority patent/KR20220070248A/ko
Priority to CN202080067230.3A priority patent/CN114514226A/zh
Publication of WO2021059086A1 publication Critical patent/WO2021059086A1/ja
Anticipated expiration legal-status Critical
Priority to JP2024220798A priority patent/JP2025060713A/ja
Priority to US19/297,099 priority patent/US20250368610A1/en
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Definitions

  • One aspect of the present invention relates to organic compounds, light emitting elements, light emitting devices, display modules, lighting modules, display devices, light emitting devices, electronic devices, lighting devices and electronic devices.
  • One aspect of the present invention is not limited to the above technical fields.
  • the technical field of one aspect of the invention disclosed in the present specification and the like relates to a product, a method, or a manufacturing method.
  • one aspect of the invention relates to a process, machine, manufacture, or composition of matter. Therefore, more specifically, the technical fields of one aspect of the present invention disclosed in the present specification include semiconductor devices, display devices, liquid crystal display devices, light emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and the like.
  • the driving method or the manufacturing method thereof can be given as an example.
  • organic EL devices that utilize electroluminescence (EL) using organic compounds
  • EL layer organic compound layer
  • EL layer organic compound layer
  • Such a light emitting device is a self-luminous type, when used as a pixel of a display, it has advantages such as higher visibility and no need for a backlight as compared with a liquid crystal, and is suitable as a flat panel display element.
  • a display using such a light emitting device has a great advantage that it can be manufactured in a thin and lightweight manner. Another feature is that the response speed is extremely fast.
  • these light emitting devices can form a light emitting layer continuously in two dimensions, light emission can be obtained in a planar manner. This is a feature that is difficult to obtain with a point light source represented by an incandescent lamp or an LED, or a line light source represented by a fluorescent lamp, and therefore has high utility value as a surface light source that can be applied to lighting or the like.
  • displays and lighting devices using light emitting devices are suitable for application to various electronic devices, but research and development are being carried out in search of light emitting devices having better characteristics.
  • One aspect of the present invention is to provide a novel organic compound. Alternatively, one aspect of the present invention is to provide a novel carrier transportable material. Alternatively, one aspect of the present invention is to provide a novel hole transporting material.
  • one aspect of the present invention is to provide a light emitting device having a low drive voltage.
  • one aspect of the present invention is to provide a light emitting device, a light emitting device, an electronic device, a display device, and an electronic device having low power consumption.
  • the present invention shall solve any one of the above-mentioned problems.
  • One aspect of the present invention is an organic compound represented by the following general formula (G1).
  • Q is an oxygen atom or a sulfur atom.
  • a and B is a group represented by the following general formula (g1), and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and carbon. It represents any of an alkoxy group of numbers 1 to 6, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 1 to R 8 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a carbon number of carbon atoms. Represents any of 1 to 6 haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.
  • R 11 to R 14 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a carbon number of carbons, respectively.
  • cyclic hydrocarbon groups 1 to 6 carbon alkoxy groups, cyano groups, halogens, 1 to 6 carbon haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups of 6 to 60 carbon atoms.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • another aspect of the present invention is an organic compound in which the general formula (G1) is represented by the following general formula (G1-1) in the above configuration.
  • Q is an oxygen atom or a sulfur atom.
  • A is a group represented by the following general formula (g1), R 20 is hydrogen, an alkyl group having 1 to 6 carbon atoms, cyclic hydrocarbon group having 3 to 6 carbon atoms, 1 to carbon atoms Represents any of 6 alkoxy groups, cyano groups, halogens, haloalkyl groups having 1 to 6 carbon atoms and substituted or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms.
  • R 1 to R 8 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a carbon number of carbon atoms. Represents either a haloalkyl group of 1 to 6 and an alkyl group of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.
  • R 11 to R 14 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a carbon number of carbons, respectively.
  • cyclic hydrocarbon groups 1 to 6 carbon alkoxy groups, cyano groups, halogens, 1 to 6 carbon haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups of 6 to 60 carbon atoms.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • another aspect of the present invention is an organic compound in which the general formula (G1) is represented by the following general formula (G1-2) in the above configuration.
  • Q is an oxygen atom or a sulfur atom.
  • B is a group represented by the general formula (g1), R 20 is hydrogen, an alkyl group having 1 to 6 carbon atoms, cyclic hydrocarbon group having 3 to 6 carbon atoms, 1 to carbon atoms Represents any of 6 alkoxy groups, cyano groups, halogens, haloalkyl groups having 1 to 6 carbon atoms and substituted or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms.
  • R 1 to R 8 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a carbon number of carbon atoms. Represents either a haloalkyl group of 1 to 6 and an alkyl group of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.
  • R 11 to R 14 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a carbon number of carbons, respectively.
  • cyclic hydrocarbon groups 1 to 6 carbon alkoxy groups, cyano groups, halogens, 1 to 6 carbon haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups of 6 to 60 carbon atoms.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • another aspect of the present invention is an organic compound in which the group represented by the general formula (g1) is a group represented by the following general formula (g1-1) in the above configuration.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and an alkoxy having 1 to 6 carbon atoms, respectively.
  • R11 to R14 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a carbon number of carbon atoms, respectively.
  • cyclic hydrocarbon groups 1 to 6 carbon alkoxy groups, cyano groups, halogens, 1 to 6 carbon haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups of 6 to 60 carbon atoms.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • another aspect of the present invention is an organic compound in which the group represented by the general formula (g1) is a group represented by the following general formula (g1-2) in the above configuration.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, and an alkoxy having 1 to 6 carbon atoms, respectively.
  • R 11 to R 14 are independently hydrogen and an alkyl group having 1 to 6 carbon atoms, respectively.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • the Ar is an organic compound represented by the following general formulas (Ar-1) to (Ar-3).
  • R A1 to R A9, R A11 to R A19 and R A21 to R A29 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, Cyclic hydrocarbon groups with 3 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, cyano groups, halogens, haloalkyl groups with 1 to 6 carbon atoms and substituted or unsubstituted aromatic hydrocarbons with 6 to 60 carbon atoms. Represents one of the groups.
  • R A1 to R A9, R A11 to R A19 and R A21 to R A29 is an organic compound is hydrogen.
  • another aspect of the present invention is an organic compound in which R 9 and R 10 are methyl groups in the above configuration.
  • another aspect of the present invention is an organic compound in which R 1 to R 8 are hydrogen in the above configuration.
  • another aspect of the present invention is an organic compound in which R 11 to R 14 are hydrogen in the above configuration.
  • another aspect of the present invention is an optical device containing the organic compound according to any of the above.
  • another aspect of the present invention is a light emitting device containing the organic compound according to any one of the above.
  • another aspect of the present invention is an electronic device having the above-mentioned optical device and a sensor, an operation button, a speaker, or a microphone.
  • another aspect of the present invention is a light emitting device having the above-mentioned optical device, a transistor, or a substrate.
  • another aspect of the present invention is a lighting device having the above-mentioned optical device and a housing.
  • the light emitting device in the present specification includes an image display device using the light emitting device. Further, a module in which a connector, for example, an anisotropic conductive film or TCP (Tape Carrier Package) is attached to the light emitting device, a module in which a printed wiring board is provided at the tip of TCP, or a COG (Chip On Glass) method in the light emitting device. A module in which an IC (integrated circuit) is directly mounted may have a light emitting device. Further, lighting equipment and the like may have a light emitting device.
  • a connector for example, an anisotropic conductive film or TCP (Tape Carrier Package) is attached to the light emitting device
  • a module in which a printed wiring board is provided at the tip of TCP or a COG (Chip On Glass) method in the light emitting device.
  • a module in which an IC (integrated circuit) is directly mounted may have a light emitting device. Further, lighting equipment and the like may have a light emit
  • a novel organic compound can be provided.
  • a material for a novel electron transport layer can be provided.
  • a novel host material for a phosphorescent device can be provided.
  • a light emitting device having high luminous efficiency can be provided.
  • a light emitting device, a light emitting device, an electronic device, a display device, and an electronic device having low power consumption can be provided.
  • FIG. 1A, 1B and 1C are schematic views of the light emitting device.
  • 2A and 2B are conceptual diagrams of an active matrix type light emitting device.
  • 3A and 3B are conceptual diagrams of an active matrix type light emitting device.
  • FIG. 4 is a conceptual diagram of an active matrix type light emitting device.
  • 5A and 5B are conceptual diagrams of a passive matrix type light emitting device.
  • 6A and 6B are diagrams showing a lighting device.
  • 7A, 7B1, 7B2 and 7C are diagrams representing electronic devices.
  • 8A, 8B and 8C are diagrams representing electronic devices.
  • FIG. 9 is a diagram showing a lighting device.
  • FIG. 10 is a diagram showing a lighting device.
  • FIG. 11 is a diagram showing an in-vehicle display device and a lighting device.
  • FIG. 12A and 12B are diagrams representing electronic devices.
  • 13A, 13B and 13C are diagrams representing electronic devices.
  • 14A and 14B are 1 1 H NMR charts of oFBiBnf (6).
  • FIG. 15 shows an absorption spectrum and an emission spectrum of oFBiBnf (6) in a toluene solution.
  • FIG. 16 shows an absorption spectrum and an emission spectrum of oFBiBnf (6) in a thin film state.
  • 17A and 17B are 1 1 H NMR charts of oFBi (4) Bnf (6).
  • FIG. 18 shows an absorption spectrum and an emission spectrum of oFBi (4) Bnf (6) in a toluene solution.
  • FIG. 19 shows an absorption spectrum and an emission spectrum of oFBi (4) Bnf (6) in a thin film state.
  • 20A and 20B are 1 1 H NMR charts of FBi (4) Bnf (6).
  • FIG. 21 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf (6) in a toluene solution.
  • FIG. 22 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf (6) in a thin film state.
  • 23A and 23B are 1 H NMR charts of FBiBnf (6).
  • FIG. 24 shows an absorption spectrum and an emission spectrum of FBiBnf (6) in a toluene solution.
  • FIG. 25 shows an absorption spectrum and an emission spectrum of FBiBnf (6) in a thin film state.
  • FIG. 26 shows the brightness-current density characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 27 shows the current efficiency-luminance characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 28 shows the luminance-voltage characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 29 shows the current-voltage characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 30 shows the external quantum efficiency-luminance characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 31 is an emission spectrum of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 32 shows the brightness-current density characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 33 shows the current efficiency-luminance characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 34 shows the luminance-voltage characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 35 shows the current-voltage characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 36 shows the external quantum efficiency-luminance characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 37 is an emission spectrum of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 38 shows the normalized luminance-time change characteristics of the light emitting device 1 and the comparative light emitting device 1.
  • FIG. 39 shows the normalized luminance-time change characteristics of the light emitting device 2 and the comparative light emitting device 2.
  • FIG. 40 shows the brightness-current density characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 41 shows the current efficiency-luminance characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 42 shows the luminance-voltage characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 43 shows the current-voltage characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 44 shows the external quantum efficiency-luminance characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 45 is an emission spectrum of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 46 shows the brightness-current density characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 47 shows the current efficiency-luminance characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 48 shows the luminance-voltage characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 49 shows the current-voltage characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 50 shows the external quantum efficiency-luminance characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 51 is an emission spectrum of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 52 shows the normalized luminance-time change characteristics of the light emitting device 3 and the comparative light emitting device 3.
  • FIG. 53 shows the normalized luminance-time change characteristics of the light emitting device 4 and the comparative light emitting device 4.
  • FIG. 54 shows the brightness-current density characteristics of the light emitting device 5 and the light emitting device 6.
  • FIG. 55 shows the current efficiency-luminance characteristics of the light emitting device 5 and the light emitting device 6.
  • FIG. 56 shows the luminance-voltage characteristics of the light emitting device 5 and the light emitting device 6.
  • FIG. 57 shows the current-voltage characteristics of the light emitting device 5 and the light emitting device 6.
  • FIG. 58 shows the external quantum efficiency-luminance characteristics of the light emitting device 5 and the light emitting device 6.
  • FIG. 59 is an emission spectrum of the light emitting device 5 and the light emitting device 6.
  • 60A and 60B are 1 H NMR charts of FBiBnf (8).
  • FIG. 61 shows an absorption spectrum and an emission spectrum of FBiBnf (8) in a toluene solution.
  • FIG. 62 shows an absorption spectrum and an emission spectrum of FBiBnf (8) in a thin film state.
  • 63A and 63B are 1 1 H NMR charts of oFBiBnf (8).
  • FIG. 64 shows an absorption spectrum and an emission spectrum of oFBiBnf (8) in a toluene solution.
  • FIG. 65 shows an absorption spectrum and an emission spectrum of oFBiBnf (8) in a thin film state.
  • FIG. 66A and 66B are 1 1 H NMR charts of FBi (4) Bnf (8).
  • FIG. 67 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf (8) in a toluene solution.
  • FIG. 68 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf (8) in a thin film state.
  • FIG. 69 shows an absorption spectrum and an emission spectrum of oFBi (4) Bnf (8) in a toluene solution.
  • FIG. 70 shows the absorption spectrum and the emission spectrum of oFBi (4) Bnf (8) in the thin film state.
  • FIG. 71 shows the brightness-current density characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 67 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf (8) in a toluene solution.
  • FIG. 68 shows an absorption spectrum and an emission spectrum of FBi (4) Bnf
  • FIG. 72 shows the current efficiency-luminance characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 73 shows the luminance-voltage characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 74 shows the current-voltage characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 75 shows the external quantum efficiency-luminance characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 76 is an emission spectrum of the light emitting device 7 and the light emitting device 8.
  • FIG. 77 shows the normalized luminance-time change characteristics of the light emitting device 7 and the light emitting device 8.
  • FIG. 78 shows the brightness-current density characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 79 shows the current efficiency-luminance characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 80 shows the luminance-voltage characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 81 shows the current-voltage characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 82 shows the external quantum efficiency-luminance characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 83 is an emission spectrum of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 84 shows the normalized luminance-time change characteristics of the light emitting device 9 and the comparative light emitting device 5.
  • FIG. 85 shows the brightness-current density characteristics of the light emitting device 10.
  • FIG. 86 shows the current efficiency-luminance characteristics of the light emitting device 10.
  • FIG. 87 shows the luminance-voltage characteristics of the light emitting device 10.
  • FIG. 88 shows the current-voltage characteristics of the light emitting device 10.
  • FIG. 89 shows the external quantum efficiency-luminance characteristic of the light emitting device 10.
  • FIG. 90 is an emission spectrum of the light emitting device 10.
  • the organic compound according to one aspect of the present invention is an organic compound represented by the following general formula (G1).
  • Q is an oxygen atom or a sulfur atom.
  • the refractive index is lower than that of a compound having a sulfur atom, and an element using a compound having a lower refractive index has an effect of increasing the light extraction efficiency, and emits light with high efficiency. It is preferable because the device can be provided.
  • a and B in the general formula (G1), A in the general formula (G1-1), and B in the general formula (G1-2) are groups represented by the following general formula (g1). Suppose that.
  • the position where the nitrogen of the amine is bonded to the fluorenyl group is preferably the 2-position or the 4-position. That is, when the group represented by the above general formula (g1) is a group represented by the following general formula (g1-1), the HOMO is relatively shallow because it is a compound having a fluorene-2-amine skeleton. Highly transportable compounds can be provided, resulting in low power consumption light emitting devices. Further, when the group is represented by the following general formula (g1-1), it is easy to synthesize and a merit in terms of cost can be obtained. Alternatively, it is preferable that the general formula (g1) is a group represented by the following general formula (g1-2) because a device having high luminous efficiency can be provided.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. It is preferable that Ar is a group represented by the following general formulas (Ar-1) to (Ar-3) in order to provide a highly efficient and highly reliable device. Further, when Ar of the general formula (g1-2) is a group represented by the following general formulas (Ar-1) to (Ar-3), it is easy to synthesize and there is a merit in terms of cost in providing a compound. can get.
  • R A1 to R A9, R A11 to R A19 and R A21 to R A29 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, Cyclic hydrocarbon groups with 3 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, cyano groups, halogens, haloalkyl groups with 1 to 6 carbon atoms and substituted or unsubstituted aromatic hydrocarbons with 6 to 60 carbon atoms. Represents one of the groups.
  • R A1 to R A9, R A11 to R A19 and R A21 to R A29 is a hydrogen, a phenyl group, a biphenyl group, be a fluorenyl group, the synthesis is simple, and is easy procurement of raw materials It is preferable because it can provide compounds and devices having high heat resistance, high reliability, and low power consumption.
  • R 9 and R 10 are independently hydrogen and an alkyl group having 1 to 6 carbon atoms, respectively. It represents either a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.
  • R 9 and R 10 are alkyl groups having 1 to 6 carbon atoms, R 9 and R 10 are bonded to each other and ring as shown in the following general formulas (g3-1) to (g3-4). May form a spiro structure.
  • R 1 to R 8 , R 11 to R 14 , and R 20 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cyclic hydrocarbon having 3 to 6 carbon atoms, respectively. It represents a group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted.
  • the substituent when the group described as "substituent or unsubstituted" has a substituent, the substituent includes an alkyl group having 1 to 6 carbon atoms, a phenyl group, and a biphenyl group (o-biphenyl group). , M-biphenyl group and p-biphenyl group), naphthyl group and the like.
  • hydrocarbon group having 1 to 6 carbon atoms examples include the following structural formulas (1-1) to (1-40).
  • aromatic hydrocarbon group having 6 to 60 carbon atoms include substituents represented by the following structural formulas (2-1) to (2-13).
  • the replacement positions of the following structural formulas (2-1) to (2-13) are not limited. Moreover, these may have a substituent.
  • R 1 to R 8 and R 11 to R 14 are aromatic hydrocarbon groups
  • the structural formula (2-1) of the following structural formulas (2-1) to (2-13) is described above.
  • To Structural formula (2-3) and structural formula (2-9) are preferable.
  • the substitution position of those aromatic hydrocarbon groups does not matter. Specific examples of such an aromatic hydrocarbon group and the case where such a hydrocarbon group has a substituent are shown in the following structural formulas (1-41) to (1-50).
  • the organic compound of one aspect of the present invention having the above-mentioned structure is an organic compound having high carrier transportability.
  • it has high hole transportability, and even if it is formed as a thick film, the drive voltage does not increase much, and a light emitting device having good characteristics can be obtained.
  • the organic compound having the above structure can be suitably used as a hole injection layer and a hole transport layer of a light emitting device.
  • the general formula (G1-1a) is a molecular structure in which A is the general formula (g1) and the molecular structure of (g1) is fluorene-2-amine in the general formula (G1).
  • the organic compound represented by the general formula (G1-1a) can be synthesized as in the following synthesis schemes (a-1) and (a-2).
  • a fluorenylamine compound (Compound 3) can be obtained by coupling an arylamine compound (Compound 1) and a fluorene compound (Compound 2) according to the reaction formula (a-1).
  • a fluorenylamine compound Compound 3
  • a fluorene compound Compound 2
  • a-2 benzonaphthofuran compound
  • G1-1a target benzonaphthofuranylamine compound
  • Q is an oxygen atom or a sulfur atom.
  • B and R 1 to R 8 and R 11 to R 14 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a cyano. It represents a group, a halogen, a haloalkyl group having 1 to 6 carbon atoms and either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and 1 carbon group.
  • X 1 to X 2 are each independently chlorine, bromine, iodine, triflate group.
  • an organic base such as sodium tert-butoxide, an inorganic base such as potassium carbonate, cesium carbonate, and sodium carbonate can be used.
  • an inorganic base such as potassium carbonate, cesium carbonate, and sodium carbonate
  • toluene, xylene, benzene, tetrahydrofuran, dioxane and the like can be used as the solvent.
  • the reagents that can be used in the reaction are not limited to the reagents. Further, a compound in which an organic tin group is bonded to an amino group can be used instead of compound 1 or compound 3.
  • the Ullmann reaction using copper or a copper compound can also be carried out.
  • Copper or a copper compound can be used in the reaction.
  • the base used include inorganic bases such as potassium carbonate.
  • the solvent that can be used in the reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone (DMPU), toluene, xylene, benzene and the like.
  • DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone
  • it is preferable to use DMPU or xylene having a high boiling point because the desired product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 ° C. or higher.
  • the reaction temperature is more preferably 150 ° C. or higher, DMPU is more preferably used.
  • the reagents that can be used in the reaction are not limited to the reagents.
  • the synthesis of compound 3 can also be carried out by coupling an aryl compound (compound 5) and a fluorenylamine compound (compound 6) as in the following synthesis scheme (a-3).
  • R 11 to R 14 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a cyano group.
  • Halogen a haloalkyl group having 1 to 6 carbon atoms and either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and 1 carbon group.
  • organic compound represented by the above general formula (G1-1a) can also be synthesized as in the following synthesis schemes (b-1) and (b-2).
  • the benzonaphthofuranylamine compound (Compound 7) can be obtained by coupling the arylamine compound (Compound 1) and the benzonaphthofuran compound (Compound 4) according to the reaction formula (b-1).
  • the target benzonaphthofuranylamine compound (G1-1a) is obtained by coupling the benzonaphthofuranylamine compound (Compound 7) and the fluorene compound (Compound 2) according to the reaction formula (b-2). You can get it.
  • the synthetic schemes (b-1) and (b-2) are shown below.
  • Q is an oxygen atom or a sulfur atom.
  • B and R 1 to R 8 and R 11 to R 14 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a cyano. It represents a group, a halogen, a haloalkyl group having 1 to 6 carbon atoms and either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and 1 carbon group.
  • the synthesis of compound 7 can also be carried out by coupling an aryl compound (compound 5) and a benzonaphthofuranylamine compound (compound 6) as in the following synthesis scheme (b-3).
  • Q is an oxygen atom or a sulfur atom.
  • B and R 1 to R 8 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a carbon number of carbon atoms.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • organic compound represented by the above general formula (G1-1a) can also be synthesized as in the following synthesis schemes (c-1) and (c-2).
  • the benzonaphthofuranylamine compound (Compound 8) can be obtained by coupling the fluorenylamine compound (Compound 6) and the benzonaphthofuran compound (Compound 4) according to the reaction formula (c-1). ..
  • the target benzonaphthofuranylamine compound (G1-1a) is obtained by coupling the benzonaphthofuranylamine compound (Compound 8) and the allyl compound (Compound 5) according to the reaction formula (c-2). You can get it.
  • the synthetic schemes (c-1) and (c-2) are shown below.
  • Q is an oxygen atom or a sulfur atom.
  • B and R 1 to R 8 and R 11 to R 14 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a cyano. It represents a group, a halogen, a haloalkyl group having 1 to 6 carbon atoms and either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and 1 carbon group.
  • Q is an oxygen atom or a sulfur atom.
  • B and R 1 to R 8 and R 11 to R 14 are hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a cyano. It represents a group, a halogen, a haloalkyl group having 1 to 6 carbon atoms and either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.
  • R 9 and R 10 are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and 1 carbon atom. Represents a haloalkyl group of to 6 and either a substituted or unsubstituted phenyl group.
  • X 1 independently represents a chlorine, bromine, iodine and triflate group.
  • the same reaction conditions as those of the synthetic schemes (a-1) and (a-2) can be used in the synthetic scheme (c-3).
  • the method for synthesizing the organic compound represented by the general formula (G1-1a) is the above-mentioned synthesis schemes (a-1) and (a-3), synthesis schemes (b-1) and (b-3), and synthesis scheme (c). It is not limited to -1) and (c-3).
  • the benzonaphthofuran-6-amine compound of the present invention is used as a raw material by using a compound having a substituent at the 6-position of benzonaphthofuran as a raw material. Can be obtained.
  • FIG. 1A shows a diagram showing a light emitting device according to an aspect of the present invention.
  • the light emitting device of one aspect of the present invention has a first electrode 101, a second electrode 102, and an EL layer 103. Further, the EL layer 103 has the organic compound shown in the first embodiment.
  • the EL layer 103 has a light emitting layer 113, and the light emitting layer 113 contains a light emitting material.
  • a hole injection layer 111 and a hole transport layer 112 are provided between the light emitting layer 113 and the first electrode 101. Since the organic compound according to the first embodiment has high carrier transportability, particularly hole transportability, it is preferable to use the hole injection layer 111 or the hole transport layer 112.
  • the light emitting layer 113 may include the organic compound and the electron transporting material according to the first embodiment together with the light emitting material. Further, at this time, the organic compound according to the first embodiment and the electron transporting material may form an excited complex. By forming an excitation complex having an appropriate emission wavelength, it is possible to realize effective energy transfer to a light emitting material and provide a light emitting device having high efficiency and good lifetime.
  • the electron transport layer 114 and the electron injection layer 115 are shown on the EL layer 103, but the configuration of the light emitting device Is not limited to these. It is not necessary to form any of these layers, or it may have a layer having another function.
  • the light emitting device of one aspect of the present invention has an EL layer 103 composed of a plurality of layers between the pair of electrodes of the first electrode 101 and the second electrode 102, and the EL layer 103 Any portion contains the organic compound disclosed in Embodiment 1.
  • the first electrode 101 is preferably formed by using a metal having a large work function (specifically, 4.0 eV or more), an alloy, a conductive compound, a mixture thereof, or the like.
  • a metal having a large work function specifically, 4.0 eV or more
  • an alloy e.g., aluminum, copper, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium
  • indium oxide-zinc oxide may be formed by a sputtering method using a target in which 1 to 20 wt% zinc oxide is added to indium oxide.
  • Indium oxide (IWZO) containing tungsten oxide and zinc oxide is formed by a sputtering method using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide. You can also do it.
  • nitride of a metallic material for example, titanium nitride
  • the electrode material can be selected regardless of the work function.
  • the EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited, and is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a carrier block layer. , Exciton block layer, charge generation layer, and various other layer structures can be applied.
  • FIG. 1A a configuration having an electron transport layer 114 and an electron injection layer 115 in addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, and FIG. 1B are shown.
  • two types of configurations having the electron transport layer 114 and the charge generation layer 116 in addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113 will be described.
  • the materials constituting each layer are specifically shown below.
  • the hole injection layer 111 is a layer containing a substance having an accepting property.
  • a substance having an accepting property both an organic compound and an inorganic compound can be used.
  • a compound having an electron-withdrawing group (halogen group or cyano group) can be used, and 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane.
  • F 4 -TCNQ chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1, 3,4,5,7,8-Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2- (7-dicyanomethylene-1,3,4,5,6,8,9,10) ⁇ Octafluoro-7H-pyrene-2-ylidene) Malononitrile and the like can be mentioned.
  • a compound such as HAT-CN in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of complex atoms is thermally stable and preferable.
  • the [3] radialene derivative having an electron-withdrawing group is preferable because it has very high electron acceptability, and specifically, ⁇ , ⁇ ', ⁇ ''-.
  • 1,2,3-Cyclopropanetriylidentris [4-cyano-2,3,5,6-tetrafluorobenzene acetonitrile], ⁇ , ⁇ ', ⁇ ''-1,2,3-cyclopropanetriiridentris [2,6-dichloro-3,5-difluoro-4- (trifluoromethyl) benzene acetonitrile], ⁇ , ⁇ ', ⁇ ''-1,2,3-cyclopropanthrylilidentris [2,3,4 , 5,6-Pentafluorobenzene acetonitrile] and the like.
  • molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide and the like can be used in addition to the organic compounds described above.
  • phthalocyanine (abbreviation: H 2 Pc) or copper phthalocyanine (CuPc) complex phthalocyanine-based compound such as 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) :
  • the hole injection layer 111 is also formed by an aromatic amine compound such as DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrene
  • a composite material in which the accepting substance is contained in a material having a hole transporting property can also be used.
  • a material forming an electrode can be selected regardless of the work function. That is, not only a material having a large work function but also a material having a small work function can be used as the first electrode 101.
  • the material having a hole transport property used for the composite material various organic compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a polymer compound (oligomer, dendrimer, polymer, etc.) can be used.
  • the hole-transporting material used for the composite material is preferably a substance having a hole mobility of 1 ⁇ 10-6 cm 2 / Vs or more. In the following, organic compounds that can be used as materials having hole transport properties in composite materials are specifically listed.
  • DTDPPA N'-di (p-tolyl) -N, N'-diphenyl-
  • carbazole derivative examples include 3- [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1) and 3,6-bis [N- (9-Phenylcarbazole-3-yl) -9-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9-phenylcarbazole-3-yl) Amino] -9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene ( Abbreviation: TCPB), 9- [4- (N-carbazolyl)] benzene ( Abbre
  • aromatic hydrocarbon examples include 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA) and 2-tert-butyl-9,10-di (1-naphthyl).
  • pentacene, coronene and the like can also be used. It may have a vinyl skeleton.
  • aromatic hydrocarbons having a vinyl group include 4,4'-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi) and 9,10-bis [4- (2,2-2)].
  • 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: A polymer compound such as Poly-TPD) can also be used.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N'-[4- (4-diphenylamino) Phenyl] phenyl-N'-phenylamino ⁇ phenyl) methacrylamide]
  • the hole-transporting material used for the composite material it is more preferable to have any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton.
  • a carbazole skeleton a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton.
  • an aromatic amine having a substituent containing a dibenzofuran ring or a dibenzothiophene ring an aromatic monoamine having a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group.
  • these second organic compounds are substances having an N, N-bis (4-biphenyl) amino group because a light emitting device having a good life can be produced.
  • Specific examples of the second organic compound as described above include N- (4-biphenyl) -6, N-diphenylbenzo [b] naphtho [1,2-d] furan-8-amine (abbreviation: abbreviation:).
  • BnfABP N, N-bis (4-biphenyl) -6-phenylbenzo [b] naphtho [1,2-d] furan-8-amine
  • BBABnf 4,4'-bis (6-phenyl) Benzo [b] naphtho [1,2-d] furan-8-yl) -4''-phenyltriphenylamine
  • BnfBB1BP 4,4'-bis (6-phenyl) Benzo [b] naphtho [1,2-d] furan-8-yl) -4''-phenyltriphenylamine
  • BnfBB1BP N, N-bis (4-biphenyl) benzo [b] naphtho [1] , 2-d] furan-6-amine
  • BBABnf N, N-bis (4-biphenyl) benzo [b] naphtho [1,2-d] furan-8-amine
  • BBABnf (8)
  • the hole-transporting material used for the composite material is more preferably a substance having a relatively deep HOMO level of ⁇ 5.7 eV or more and ⁇ 5.4 eV or less. Since the hole-transporting material used for the composite material has a relatively deep HOMO level, it is easy to inject holes into the hole-transporting layer 112, and a light-emitting device having a good life can be obtained. Becomes easier.
  • the organic compound according to the first embodiment can be suitably used as a material having a hole transporting property used in the composite material.
  • the refractive index of the layer can be lowered by further mixing fluoride of an alkali metal or an alkaline earth metal with the composite material (preferably, the atomic ratio of fluorine atoms in the layer is 20% or more). It can. This also makes it possible to form a layer having a low refractive index inside the EL layer 103, and improve the external quantum efficiency of the light emitting device.
  • the hole injection layer 111 By forming the hole injection layer 111, the hole injection property is improved, and a light emitting device having a small driving voltage can be obtained. Further, the organic compound having acceptability is an easy-to-use material because it is easy to deposit and form a film.
  • the hole transport layer 112 is formed containing a material having a hole transport property.
  • the material having hole transportability it is preferable that the material has a hole mobility of 1 ⁇ 10-6 cm 2 / Vs or more.
  • the material having hole transporting property include 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and N, N'-bis (3-methylphenyl).
  • Tri (dibenzothiophene) (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-Phenyldibenzoti Compounds with a thiophene skeleton such as offen (abbreviation: DBTFLP-IV) and 4,4', 4''- (benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 4 Examples thereof include compounds having a furan skeleton such as ⁇ ⁇ 3- [3- (9-phenyl-9H-fluorene-9-yl) phenyl] phenyl ⁇ dibenzofuran (abbre
  • compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferable because they have good reliability, high hole transportability, and contribute to reduction of driving voltage.
  • the substance mentioned as the material having hole transportability used for the composite material of the hole injection layer 111 can also be suitably used as the material constituting the hole transport layer 112. Since the organic compound according to the first embodiment has high hole transportability, it can be very preferably used as a material constituting the hole transport layer 112. Further, since the organic compound according to the first embodiment has high hole transportability, even if the hole transport layer 112 is formed by thickening the hole transport layer 112 to 100 nm or more, the drive voltage rise is small and good device characteristics are obtained.
  • a light emitting device having a light emitting device can be provided. By thickening the hole transport layer 112, the optical path length between the electrodes can be easily adjusted, so that the microcavity structure can be appropriately configured.
  • the light emitting layer 113 has a light emitting substance and a host material.
  • the light emitting layer 113 may contain other materials at the same time. Further, two layers having different compositions may be laminated.
  • the luminescent substance may be a fluorescent luminescent substance, a phosphorescent luminescent substance, a substance exhibiting thermal activated delayed fluorescence (TADF), or another luminescent substance.
  • TADF thermal activated delayed fluorescence
  • Examples of the material that can be used as the fluorescent light emitting substance in the light emitting layer 113 include 5,6-bis [4- (10-phenyl-9-anthryl) phenyl] -2,2'-bipyridine (abbreviation: PAP2BPy).
  • condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn, 1,6mmemFLPARn, and 1,6BnfAPrn-03 are preferable because they have high hole trapping properties and excellent luminous efficiency and reliability. Further, other fluorescent light emitting substances can also be used.
  • a phosphorescent luminescent substance is used as the luminescent substance in the light emitting layer 113, as a material that can be used, for example, Tris ⁇ 2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) ) -4H-1,2,4-triazol-3-yl- ⁇ N2] Phenyl- ⁇ C ⁇ Iridium (III) (abbreviation: [Ir (mpptz-dmp) 3 ]), Tris (5-methyl-3,4- Diphenyl-4H-1,2,4-triazolate) Iridium (III) (abbreviation: [Ir (Mptz) 3 ]), Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1, Organic metal iridium complex having a 4H-triazole skeleton such as 2,4-triazolate] iridium (III) (abbreviation: [Ir (iPrp
  • organometallic iridium complex having a pyrimidine skeleton is particularly preferable because it is remarkably excellent in reliability and luminous efficiency.
  • a known phosphorescent luminescent substance may be selected and used.
  • TADF material fullerene and its derivative, acridine and its derivative, eosin derivative and the like can be used.
  • metal-containing porphyrin include protoporphyrin-tin fluoride complex (ShF 2 (Proto IX)), mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)), and hematoporphyrin represented by the following structural formulas.
  • 2- (biphenyl-4-yl) -4,6-bis (12-phenylindro [2,3-a] carbazole-11-yl) -1,3,5-l shown in the following structural formula Triazine (abbreviation: PIC-TRZ) and 9- (4,6-diphenyl-1,3,5-triazine-2-yl) -9'-phenyl-9H, 9'H-3,3'-bicarbazole (Abbreviation: PCCzTzn), 2- ⁇ 4- [3- (N-phenyl-9H-carbazole-3-yl) -9H-carbazole-9-yl] phenyl ⁇ -4,6-diphenyl-1,3,5 -Triazine (abbreviation: PCCzPTzn), 2- [4- (10H-phenoxazine-10-yl) phenyl] -4,6-diphenyl-1,3,5-triazine (abbreviation: PIC-
  • Heterocyclic compounds having one or both rings can also be used. Since the heterocyclic compound has a ⁇ -electron excess type heteroaromatic ring and a ⁇ -electron deficiency type heteroaromatic ring, both electron transportability and hole transportability are high, which is preferable.
  • the skeletons having a ⁇ -electron deficient heteroaromatic ring the pyridine skeleton, the diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferable because they are stable and have good reliability.
  • the benzoflopyrimidine skeleton, the benzothienopyrimidine skeleton, the benzoflopyrazine skeleton, and the benzothienopyrazine skeleton are preferable because they have high acceptability and good reliability.
  • the skeletons having a ⁇ -electron excess type heteroaromatic ring the acrydin skeleton, the phenoxazine skeleton, the phenothiazine skeleton, the furan skeleton, the thiophene skeleton, and the pyrrole skeleton are stable and have good reliability, and therefore at least one of the skeletons. It is preferable to have.
  • the furan skeleton is preferably a dibenzofuran skeleton
  • the thiophene skeleton is preferably a dibenzothiophene skeleton.
  • the pyrrole skeleton an indole skeleton, a carbazole skeleton, an indolecarbazole skeleton, a bicarbazole skeleton, and a 3- (9-phenyl-9H-carbazole-3-yl) -9H-carbazole skeleton are particularly preferable.
  • the substance in which the ⁇ -electron-rich heteroaromatic ring and the ⁇ -electron-deficient heteroaromatic ring are directly bonded has both the electron donating property of the ⁇ -electron-rich heteroaromatic ring and the electron acceptability of the ⁇ -electron-deficient heteroaromatic ring. This is particularly preferable because the energy difference between the S1 level and the T1 level becomes stronger and the energy difference between the S1 level and the T1 level becomes smaller, so that thermal activation delayed fluorescence can be efficiently obtained.
  • an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used.
  • an aromatic amine skeleton, a phenazine skeleton, or the like can be used.
  • Aromatic rings or heteroaromatic rings having a group or a cyano group, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton and the like can be used.
  • a ⁇ -electron-deficient skeleton and a ⁇ -electron-rich skeleton can be used instead of at least one of the ⁇ -electron-deficient heteroaromatic ring and the ⁇ -electron-rich heteroaromatic ring.
  • the TADF material is a material having a small difference between the S1 level and the T1 level and having a function of converting energy from triplet excitation energy to singlet excitation energy by intersystem crossing. Therefore, the triplet excited energy can be up-converted to the singlet excited energy by a small amount of heat energy (intersystem crossing), and the singlet excited state can be efficiently generated. In addition, triplet excitation energy can be converted into light emission.
  • an excited complex also referred to as an exciplex, an exciplex or an Exciplex
  • an excited complex that forms an excited state with two kinds of substances has an extremely small difference between the S1 level and the T1 level, and the triplet excitation energy is the singlet excitation energy. It has a function as a TADF material that can be converted into.
  • a phosphorescent spectrum observed at a low temperature may be used.
  • a TADF material a tangent line is drawn at the hem on the short wavelength side of the fluorescence spectrum, the energy of the wavelength of the extraline is set to the S1 level, and a tangent line is drawn at the hem on the short wavelength side of the phosphorescent spectrum, and the extrapolation is performed.
  • the difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.
  • the S1 level of the host material is preferably higher than the S1 level of the TADF material.
  • the T1 level of the host material is preferably higher than the T1 level of the TADF material.
  • various carrier transport materials such as a material having an electron transport property, a material having a hole transport property, and the TADF material can be used.
  • an organic compound having an amine skeleton or a ⁇ -electron excess type heteroaromatic ring skeleton is preferable.
  • NPB 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • TPD N, N'-bis (3-methylphenyl) -N, N'-diphenyl-[ 1,1'-biphenyl] -4,4'-diamine
  • TPD 1,1'-biphenyl] -4,4'-diamine
  • BSPB 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl
  • BPAFLP 4-phenyl-4'-(9-phenylfluoren-9-yl) triphenylamine
  • BPAFLP 4-phenyl-3'-(9-phenylfluoren-9-yl) tri Phenylamine
  • electron-transporting material examples include bis (10-hydroxybenzo [h] quinolinato) berylium (II) (abbreviation: BeBq 2 ) and bis (2-methyl-8-quinolinolato) (4-phenylphenolato).
  • Aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), Metal complexes such as bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) and organic compounds having a ⁇ -electron-deficient heteroaromatic ring skeleton are preferable.
  • Examples of the organic compound having a ⁇ -electron-deficient heterocyclic skeleton include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD).
  • a heterocyclic compound having a diazine skeleton and a heterocyclic compound having a pyridine skeleton are preferable because they have good reliability.
  • a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has high electron transportability and contributes to reduction of driving voltage.
  • the TADF material that can be used as the host material
  • those listed above as the TADF material can also be used in the same manner.
  • the triplet excitation energy generated by the TADF material is converted to singlet excitation energy by inverse intersystem crossing, and the energy is further transferred to the luminescent material, thereby increasing the emission efficiency of the light emitting device. be able to.
  • the TADF material functions as an energy donor, and the luminescent material functions as an energy acceptor.
  • the S1 level of the TADF material is preferably higher than the S1 level of the fluorescent light emitting substance.
  • the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent light emitting substance. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent substance.
  • a TADF material that emits light so as to overlap the wavelength of the absorption band on the lowest energy side of the fluorescent light emitting substance.
  • the fluorescent luminescent substance has a protecting group around the luminescent group (skeleton that causes luminescence) of the fluorescent luminescent substance.
  • a substituent having no ⁇ bond is preferable, a saturated hydrocarbon is preferable, specifically, an alkyl group having 3 or more and 10 or less carbon atoms, and a substituted or unsubstituted cyclo having 3 or more and 10 or less carbon atoms. Examples thereof include an alkyl group and a trialkylsilyl group having 3 or more and 10 or less carbon atoms, and it is more preferable that there are a plurality of protecting groups.
  • Substituents that do not have a ⁇ bond have a poor function of transporting carriers, so that the distance between the TADF material and the luminous group of the fluorescent luminescent material can be increased with almost no effect on carrier transport or carrier recombination. ..
  • the luminescent group refers to an atomic group (skeleton) that causes light emission in a fluorescent luminescent substance.
  • the luminescent group preferably has a skeleton having a ⁇ bond, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring.
  • the condensed aromatic ring or the condensed heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, and a phenothiazine skeleton.
  • a fluorescent substance having a naphthalene skeleton, anthracene skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, and naphthobisbenzofuran skeleton is preferable because of its high fluorescence quantum yield.
  • a material having an anthracene skeleton is suitable as the host material.
  • a substance having an anthracene skeleton is used as a host material for a fluorescent light emitting substance, it is possible to realize a light emitting layer having good luminous efficiency and durability.
  • a diphenylanthracene skeleton, particularly a substance having a 9,10-diphenylanthracene skeleton is preferable because it is chemically stable.
  • the host material has a carbazole skeleton
  • the injection / transportability of holes is enhanced, but when the host material contains a benzocarbazole skeleton in which a benzene ring is further condensed with carbazole, the HOMO is about 0.1 eV shallower than that of carbazole.
  • the HOMO is about 0.1 eV shallower than that of carbazole, holes are easily entered, and the hole transport property is excellent and the heat resistance is high, which is preferable. ..
  • a substance having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton) at the same time is further preferable as a host material.
  • a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.
  • examples of such substances are 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA), 3- [4- (1-naphthyl)-.
  • Phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 9- [4- (10-phenyl-9-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] Fran (abbreviation: 2mBnfPPA), 9-Phenyl-10- ⁇ 4- (9-phenyl-9H-fluoren-9-yl) biphenyl-4'-yl ⁇ anthracene (abbreviation: FLPPA), 9- Examples thereof include (1-naphthyl) -10- [4- (2
  • the host material may be a material obtained by mixing a plurality of kinds of substances, and when a mixed host material is used, it is preferable to mix a material having an electron transporting property and a material having a hole transporting property. ..
  • a material having an electron transporting property By mixing the material having electron transportability and the material having hole transportability, the transportability of the light emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled.
  • the organic compound according to the first embodiment can be preferably used as the material having electron transportability in the mixed host material.
  • a phosphorescent light emitting substance can be used as a part of the mixed materials.
  • the phosphorescent luminescent material can be used as an energy donor that provides excitation energy to the fluorescent luminescent material when the fluorescent luminescent material is used as the luminescent material.
  • At least one of the materials forming the excitation complex may be a phosphorescent substance.
  • the HOMO level of the material having hole transportability is equal to or higher than the HOMO level of the material having electron transportability.
  • the LUMO level of the material having hole transportability is equal to or higher than the LUMO level of the material having electron transportability.
  • the LUMO level and HOMO level of the material can be derived from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV) measurement.
  • the emission spectrum of the material having hole transporting property, the emission spectrum of the material having electron transporting property, and the emission spectrum of the mixed film in which these materials are mixed are compared, and the emission spectrum of the mixed film is compared.
  • the transient photoluminescence (PL) of the material having hole transportability, the transient PL of the material having electron transportability, and the transient PL of the mixed membrane in which these materials are mixed are compared, and the transient PL lifetime of the mixed membrane is determined.
  • transient PL may be read as transient electroluminescence (EL). That is, by comparing the transient EL of the material having hole transportability, the transient EL of the material having electron transportability, and the transient EL of the mixed membrane of these, and observing the difference in the transient response, the formation of the excited complex can be formed. You can check.
  • EL transient electroluminescence
  • the electron transport layer 114 is a layer containing a substance having an electron transport property.
  • substance having electron transportability those listed as the substance having electron transportability that can be used for the host material can be used.
  • the electron transport layer 114 preferably has an electron mobility of 1 ⁇ 10-7 cm 2 / Vs or more and 5 ⁇ 10-5 cm 2 / Vs or less when the square root of the electric field strength [V / cm] is 600. By reducing the electron transportability of the electron transport layer 114, the amount of electrons injected into the light emitting layer can be controlled, and the light emitting layer can be prevented from being in a state of excess electrons. Further, the electron transport layer preferably contains a material having electron transport property and an alkali metal or a simple substance, compound or complex of an alkali metal.
  • the hole injection layer is formed as a composite material
  • the HOMO level of the material having hole transportability in the composite material is -5.7 eV or more and -5.4 eV or less, which is a relatively deep HOMO level. It is particularly preferable that the substance has a good life. At this time, it is preferable that the HOMO level of the material having electron transportability is ⁇ 6.0 eV or more.
  • the material having electron transport property is preferably an organic compound having an anthracene skeleton, and more preferably an organic compound containing both an anthracene skeleton and a heterocyclic skeleton.
  • the heterocyclic skeleton is preferably a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton, and these heterocyclic skeletons include a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring. It is particularly preferable to have a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton containing two heteroatoms in the ring.
  • the alkali metal or the alkali metal simple substance, the compound or the complex preferably contains an 8-hydroxyquinolinato structure.
  • 8-hydroxyquinolinato-lithium abbreviation: Liq
  • 8-hydroxyquinolinato-sodium abbreviation: Naq
  • a monovalent metal ion complex particularly a lithium complex
  • Liq is more preferable.
  • it contains an 8-hydroxyquinolinato structure its methyl-substituted product (for example, 2-methyl-substituted product or 5-methyl-substituted product) can also be used.
  • the alkali metal or the alkali metal simple substance, the compound or the complex has a concentration difference (including the case where it is 0) in the thickness direction thereof.
  • lithium fluoride LiF
  • cesium fluoride CsF
  • calcium fluoride CaF 2
  • 8-hydroxyquinolinato-lithium A layer containing an alkali metal or alkaline earth metal such as (abbreviation: Liq) or a compound thereof may be provided.
  • an alkali metal, an alkaline earth metal, or a compound thereof contained in a layer made of a substance having an electron transporting property, or an electlide may be used.
  • the electride include a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum.
  • the electron-injected layer 115 contains an electron-transporting substance (preferably an organic compound having a bipyridine skeleton) containing fluoride of the above-mentioned alkali metal or alkaline earth metal in a concentration or more (50 wt% or more) of being in a microcrystalline state. It is also possible to use an alkaline layer. Since the layer has a low refractive index, it is possible to provide a light emitting device having better external quantum efficiency.
  • an electron-transporting substance preferably an organic compound having a bipyridine skeleton
  • fluoride of the above-mentioned alkali metal or alkaline earth metal in a concentration or more (50 wt% or more) of being in a microcrystalline state. It is also possible to use an alkaline layer. Since the layer has a low refractive index, it is possible to provide a light emitting device having better external quantum efficiency.
  • a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1B).
  • the charge generation layer 116 is a layer capable of injecting holes into the layer in contact with the cathode side and electrons into the layer in contact with the anode side by applying an electric potential.
  • the charge generation layer 116 includes at least a P-type layer 117.
  • the P-type layer 117 is preferably formed by using the composite material mentioned as a material capable of forming the hole injection layer 111 described above. Further, the P-type layer 117 may be formed by laminating a film containing the above-mentioned acceptor material and a film containing a hole transport material as a material constituting the composite material.
  • the organic compound according to one aspect of the present invention is an organic compound having a low refractive index, a light emitting device having good external quantum efficiency can be obtained by using it for the P-type layer 117.
  • the charge generation layer 116 is provided with either one or both of the electron relay layer 118 and the electron injection buffer layer 119 in addition to the P-type layer 117.
  • the electron relay layer 118 contains at least a substance having electron transportability, and has a function of preventing the interaction between the electron injection buffer layer 119 and the P-type layer 117 and smoothly transferring electrons.
  • the LUMO level of the electron-transporting substance contained in the electron relay layer 118 is the LUMO level of the accepting substance in the P-type layer 117 and the substance contained in the layer in contact with the charge generating layer 116 in the electron-transporting layer 114. It is preferably between the LUMO level.
  • the specific energy level of the LUMO level in the electron-transporting substance used for the electron relay layer 118 is preferably -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less.
  • As the electron transporting substance used in the electron relay layer 118 it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.
  • the electron injection buffer layer 119 includes alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (including oxides such as lithium oxide, halides, and carbonates such as lithium carbonate and cesium carbonate). , Alkali earth metal compounds (including oxides, halides and carbonates), or rare earth metal compounds (including oxides, halides and carbonates)) and other highly electron-injectable substances can be used. Is.
  • the donor substance includes an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (as a donor substance).
  • Alkali metal compounds including oxides such as lithium oxide, halides, carbonates such as lithium carbonate and cesium carbonate
  • alkaline earth metal compounds including oxides, halides and carbonates
  • rare earth metal compounds In addition to (including oxides, halides, and carbonates), organic compounds such as tetrathianaphthalene (abbreviation: TTN), nickerosen, and decamethyl nickerosen can also be used.
  • TTN tetrathianaphthalene
  • nickerosen nickerosen
  • decamethyl nickerosen can also be used.
  • the material having electron transportability it can be formed by using the same material as the material constituting the electron transport layer 114 described above.
  • a metal having a small work function (specifically, 3.8 eV or less), an alloy, an electrically conductive compound, a mixture thereof, or the like
  • a cathode material include alkali metals such as lithium (Li) and cesium (Cs), and Group 1 of the periodic table of elements such as magnesium (Mg), calcium (Ca), and strontium (Sr). Examples thereof include elements belonging to Group 2, rare earth metals such as alloys containing them (MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
  • indium-tin oxide containing Al, Ag, ITO, silicon or silicon oxide is provided regardless of the magnitude of the work function.
  • Various conductive materials such as, etc. can be used as the second electrode 102. These conductive materials can be formed into a film by using a dry method such as a vacuum vapor deposition method or a sputtering method, an inkjet method, a spin coating method, or the like. Further, it may be formed by a wet method using a sol-gel method, or may be formed by a wet method using a paste of a metal material.
  • a method for forming the EL layer 103 various methods can be used regardless of a dry method or a wet method.
  • a vacuum deposition method, a gravure printing method, an offset printing method, a screen printing method, an inkjet method, a spin coating method, or the like may be used.
  • each electrode or each layer described above may be formed by using a different film forming method.
  • the structure of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, holes and electrons are formed in a portion away from the first electrode 101 and the second electrode 102 so that the quenching caused by the proximity of the light emitting region to the metal used for the electrode or the carrier injection layer is suppressed. It is preferable to provide a light emitting region in which the electrons recombine.
  • the hole transport layer and the electron transport layer in contact with the light emitting layer 113 suppresses energy transfer from excitons generated in the light emitting layer, so that the band gap thereof.
  • a light emitting device also referred to as a laminated element or a tandem type element having a configuration in which a plurality of light emitting units are laminated
  • This light emitting device is a light emitting device having a plurality of light emitting units between the anode and the cathode.
  • One light emitting unit has substantially the same configuration as the EL layer 103 shown in FIG. 1A. That is, it can be said that the light emitting device shown in FIG. 1C is a light emitting device having a plurality of light emitting units, and the light emitting device shown in FIG. 1A or FIG. 1B is a light emitting device having one light emitting unit.
  • a first light emitting unit 511 and a second light emitting unit 512 are laminated between the anode 501 and the cathode 502, and between the first light emitting unit 511 and the second light emitting unit 512. Is provided with a charge generation layer 513.
  • the anode 501 and the cathode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1A, respectively, and the same ones as described in the description of FIG. 1A can be applied.
  • the first light emitting unit 511 and the second light emitting unit 512 may have the same configuration or different configurations.
  • the charge generation layer 513 has a function of injecting electrons into one light emitting unit and injecting holes into the other light emitting unit when a voltage is applied to the anode 501 and the cathode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 injects electrons into the first light emitting unit 511 and the second light emitting unit. Anything that injects holes into 512 may be used.
  • the charge generation layer 513 is preferably formed in the same configuration as the charge generation layer 116 described with reference to FIG. 1B. Since the composite material of the organic compound and the metal oxide is excellent in carrier injection property and carrier transport property, low voltage drive and low current drive can be realized. When the surface of the light emitting unit on the anode side is in contact with the charge generating layer 513, the charge generating layer 513 can also serve as the hole injection layer of the light emitting unit, so that the light emitting unit uses the hole injection layer. It does not have to be provided.
  • the electron injection buffer layer 119 plays the role of the electron injection layer in the light emitting unit on the anode side, so that the light emitting unit on the anode side is not necessarily provided with the electron injection layer. There is no need to form.
  • FIG. 1C a light emitting device having two light emitting units has been described, but the same can be applied to a light emitting device in which three or more light emitting units are stacked.
  • a light emitting device in which three or more light emitting units are stacked.
  • each light emitting unit by making the emission color of each light emitting unit different, it is possible to obtain light emission of a desired color as the entire light emitting device. For example, in a light emitting device having two light emitting units, a light emitting device that emits white light as a whole by obtaining red and green light emitting colors in the first light emitting unit and blue light emitting colors in the second light emitting unit. It is also possible to obtain.
  • each layer or electrode such as the EL layer 103, the first light emitting unit 511, the second light emitting unit 512, and the charge generation layer can be, for example, a vapor deposition method (including a vacuum vapor deposition method) or a droplet ejection method (inkjet). It can be formed by using a method such as a method), a coating method, or a gravure printing method. They may also include low molecular weight materials, medium molecular weight materials (including oligomers, dendrimers), or high molecular weight materials.
  • FIG. 2A is a top view showing the light emitting device
  • FIG. 2B is a cross-sectional view of FIG. 2A cut by AB and CD.
  • This light emitting device includes a drive circuit unit (source line drive circuit) 601, a pixel unit 602, and a drive circuit unit (gate line drive circuit) 603 shown by dotted lines to control the light emission of the light emitting device.
  • 604 is a sealing substrate
  • 605 is a sealing material
  • the inside surrounded by the sealing material 605 is a space 607.
  • the routing wiring 608 is a wiring for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and is a video signal, a clock signal, and a video signal and a clock signal from the FPC (flexible print circuit) 609 which is an external input terminal. Receives start signal, reset signal, etc. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to the FPC.
  • the light emitting device in the present specification includes not only the light emitting device main body but also a state in which an FPC or PWB is attached to the light emitting device main body.
  • a drive circuit unit and a pixel unit are formed on the element substrate 610, and here, a source line drive circuit 601 which is a drive circuit unit and one pixel in the pixel unit 602 are shown.
  • the element substrate 610 is manufactured by using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc., as well as a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, etc. do it.
  • FRP Fiber Reinforced Plastics
  • PVF polyvinyl fluoride
  • the structure of the transistor used for the pixel and the drive circuit is not particularly limited. For example, it may be an inverted stagger type transistor or a stagger type transistor. Further, a top gate type transistor or a bottom gate type transistor may be used.
  • the semiconductor material used for the transistor is not particularly limited, and for example, silicon, germanium, silicon carbide, gallium nitride and the like can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In—Ga—Zn-based metal oxide, may be used.
  • the crystallinity of the semiconductor material used for the transistor is not particularly limited, and either an amorphous semiconductor or a crystalline semiconductor (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or semiconductor having a partially crystalline region). May be used. It is preferable to use a semiconductor having crystallinity because deterioration of transistor characteristics can be suppressed.
  • an oxide semiconductor in addition to the transistors provided in the pixels and the drive circuit, it is preferable to apply an oxide semiconductor to a semiconductor device such as a transistor used in a touch sensor or the like described later. In particular, it is preferable to apply an oxide semiconductor having a bandgap wider than that of silicon. By using an oxide semiconductor having a bandgap wider than that of silicon, the current in the off state of the transistor can be reduced.
  • the oxide semiconductor preferably contains at least indium (In) or zinc (Zn). Further, the oxide semiconductor contains an oxide represented by an In—M—Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf). Is more preferable.
  • M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf. Is more preferable.
  • the semiconductor layer has a plurality of crystal portions, and the c-axis of the crystal portion is oriented perpendicular to the surface to be formed of the semiconductor layer or the upper surface of the semiconductor layer, and grain boundaries are formed between adjacent crystal portions. It is preferable to use an oxide semiconductor film that does not have.
  • the transistor having the above-mentioned semiconductor layer can retain the electric charge accumulated in the capacitance through the transistor for a long period of time due to its low off current.
  • the transistor having the above-mentioned semiconductor layer can retain the electric charge accumulated in the capacitance through the transistor for a long period of time due to its low off current.
  • a base film for stabilizing the characteristics of the transistor As the base film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxide film, or a silicon nitride film can be used, and can be produced as a single layer or laminated.
  • the base film is formed by using a sputtering method, a CVD (Chemical Vapor Deposition) method (plasma CVD method, thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. it can.
  • the base film may not be provided if it is not necessary.
  • the FET 623 represents one of the transistors formed in the drive circuit unit 601.
  • the drive circuit may be formed of various CMOS circuits, MOSFET circuits or NMOS circuits.
  • the driver integrated type in which the drive circuit is formed on the substrate is shown, but it is not always necessary, and the drive circuit can be formed on the outside instead of on the substrate.
  • the pixel unit 602 is formed by a plurality of pixels including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain thereof, but the pixel portion 602 is not limited to 3
  • a pixel unit may be a combination of two or more FETs and a capacitive element.
  • An insulator 614 is formed so as to cover the end portion of the first electrode 613.
  • it can be formed by using a positive type photosensitive acrylic resin film.
  • a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614.
  • a positive photosensitive acrylic resin is used as the material of the insulator 614
  • a negative type photosensitive resin or a positive type photosensitive resin can be used as the insulator 614.
  • An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively.
  • the material used for the first electrode 613 that functions as an anode it is desirable to use a material having a large work function.
  • a laminated structure of a titanium nitride film and a film containing aluminum as a main component a three-layer structure of a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film can be used.
  • the resistance as wiring is low, good ohmic contact can be obtained, and the structure can further function as an anode.
  • the EL layer 616 is formed by various methods such as a thin-film deposition method using a thin-film deposition mask, an inkjet method, and a spin coating method.
  • the EL layer 616 includes a configuration as described in the second embodiment.
  • the other material constituting the EL layer 616 may be a low molecular weight compound or a high molecular weight compound (including an oligomer and a dendrimer).
  • the material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode a material having a small work function (Al, Mg, Li, Ca, or an alloy or compound thereof (MgAg, MgIn, etc.) It is preferable to use AlLi etc.)).
  • the second electrode 617 is a thin metal thin film and a transparent conductive film (ITO, 2 to 20 wt% oxide). It is preferable to use a laminate with indium oxide containing zinc, indium tin oxide containing silicon, zinc oxide (ZnO), etc.).
  • a light emitting device is formed by the first electrode 613, the EL layer 616, and the second electrode 617.
  • the light emitting device is the light emitting device according to the second embodiment. Although a plurality of light emitting devices are formed in the pixel portion, in the light emitting device according to the present embodiment, both the light emitting device according to the second embodiment and the light emitting device having other configurations are mixed. You may be doing it.
  • the sealing substrate 604 by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light emitting device 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605.
  • the space 607 is filled with a filler, which may be filled with an inert gas (nitrogen, argon, etc.) or a sealing material.
  • an epoxy resin or glass frit for the sealing material 605. Further, it is desirable that these materials are materials that do not allow moisture or oxygen to permeate as much as possible. Further, as a material used for the sealing substrate 604, in addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin or the like can be used.
  • FRP Fiber Reinforced Plastics
  • PVF polyvinyl fluoride
  • polyester acrylic resin or the like
  • a protective film may be provided on the second electrode.
  • the protective film may be formed of an organic resin film or an inorganic insulating film. Further, a protective film may be formed so as to cover the exposed portion of the sealing material 605. Further, the protective film can be provided so as to cover the surface and side surfaces of the pair of substrates, the sealing layer, the insulating layer, and the exposed side surfaces.
  • the protective film a material that does not easily allow impurities such as water to permeate can be used. Therefore, it is possible to effectively prevent impurities such as water from diffusing from the outside to the inside.
  • oxides, nitrides, fluorides, sulfides, ternary compounds, metals, polymers and the like can be used, and for example, aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide and oxidation can be used.
  • the protective film is preferably formed by using a film forming method having good step coverage (step coverage).
  • a film forming method having good step coverage is the atomic layer deposition (ALD) method.
  • ALD atomic layer deposition
  • ALD method it is possible to form a protective film having a dense, reduced defects such as cracks and pinholes, or a uniform thickness.
  • damage to the processed member when forming the protective film can be reduced.
  • the protective film by using the ALD method, it is possible to form a protective film having a complicated uneven shape and a uniform and few defects on the upper surface, the side surface and the back surface of the touch panel.
  • a light emitting device manufactured by using the light emitting device according to the second embodiment can be obtained.
  • the light emitting device according to the present embodiment uses the light emitting device according to the second embodiment, it is possible to obtain a light emitting device having good characteristics. Specifically, since the light emitting device according to the second embodiment has good luminous efficiency, it can be a light emitting device having low power consumption.
  • FIG. 3 shows an example of a light emitting device in which a light emitting device exhibiting white light emission is formed and a colored layer (color filter) or the like is provided to achieve full color.
  • the circuit unit 1041, the first electrode of the light emitting device 1024W, 1024R, 1024G, 1024B, the partition wall 1025, the EL layer 1028, the second electrode 1029 of the light emitting device, the sealing substrate 1031, the sealing material 1032, and the like are shown.
  • the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) is provided on the transparent base material 1033. Further, a black matrix 1035 may be further provided. The transparent substrate 1033 provided with the colored layer and the black matrix is aligned and fixed to the substrate 1001. The colored layer and the black matrix 1035 are covered with the overcoat layer 1036. Further, in FIG. 3A, there is a light emitting layer in which light is emitted to the outside without passing through the colored layer and a light emitting layer in which light is transmitted through the colored layer of each color and emitted to the outside. Since the light transmitted through the white and colored layers is red, green, and blue, an image can be expressed by pixels of four colors.
  • FIG. 3B shows an example in which a colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020.
  • the colored layer may be provided between the substrate 1001 and the sealing substrate 1031.
  • the light emitting device has a structure that extracts light to the substrate 1001 side on which the FET is formed (bottom emission type), but has a structure that extracts light to the sealing substrate 1031 side (top emission type). ) May be used as a light emitting device.
  • a cross-sectional view of the top emission type light emitting device is shown in FIG.
  • the substrate 1001 can be a substrate that does not allow light to pass through. It is formed in the same manner as the bottom emission type light emitting device until the connection electrode for connecting the FET and the anode of the light emitting device is manufactured.
  • a third interlayer insulating film 1037 is formed so as to cover the electrode 1022. This insulating film may play a role of flattening.
  • the third interlayer insulating film 1037 can be formed by using the same material as the second interlayer insulating film and other known materials.
  • the first electrodes 1024W, 1024R, 1024G, and 1024B of the light emitting device are used as anodes here, but may be cathodes. Further, in the case of the top emission type light emitting device as shown in FIG. 4, it is preferable that the first electrode is a reflecting electrode.
  • the structure of the EL layer 1028 is the same as that described as the EL layer 103 in the second embodiment, and the element structure is such that white light emission can be obtained.
  • the sealing can be performed by the sealing substrate 1031 provided with the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B).
  • the sealing substrate 1031 may be provided with a black matrix 1035 so as to be located between the pixels.
  • the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) and the black matrix may be covered with the overcoat layer 1036.
  • a substrate having translucency is used as the sealing substrate 1031.
  • full-color display with four colors of red, green, blue, and white is shown here, it is not particularly limited, and full-color with four colors of red, yellow, green, and blue, and three colors of red, green, and blue. It may be displayed.
  • the microcavity structure can be preferably applied.
  • a light emitting device having a microcavity structure can be obtained by using a first electrode as a reflective electrode and a second electrode as a semitransmissive / semireflective electrode.
  • An EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light emitting layer serving as a light emitting region is provided.
  • the reflecting electrode is a film having a visible light reflectance of 40% to 100%, preferably 70% to 100%, and a resistivity of 1 ⁇ 10-2 ⁇ cm or less.
  • the semi-transmissive / semi-reflective electrode is a film having a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1 ⁇ 10-2 ⁇ cm or less. ..
  • the light emitted from the light emitting layer included in the EL layer is reflected by the reflecting electrode and the semitransparent / semi-reflecting electrode and resonates.
  • the light emitting device can change the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode by changing the thickness of the transparent conductive film, the above-mentioned composite material, the carrier transport material, and the like. As a result, it is possible to strengthen the light having a resonating wavelength and attenuate the light having a wavelength that does not resonate between the reflecting electrode and the semitransmissive / semi-reflecting electrode.
  • the light reflected by the reflecting electrode and returned causes a large interference with the light directly incident on the semitransparent / semi-reflecting electrode from the light emitting layer (first incident light), and is therefore reflected.
  • the EL layer may have a structure having a plurality of light emitting layers or a structure having a single light emitting layer.
  • the tandem type light emitting device in combination with the above-mentioned configuration of the tandem type light emitting device, one It may be applied to a configuration in which a plurality of EL layers are provided on one light emitting device with a charge generation layer interposed therebetween, and a single or a plurality of light emitting layers are formed on each EL layer.
  • the microcavity structure By having the microcavity structure, it is possible to enhance the emission intensity in the front direction of a specific wavelength, so that it is possible to reduce power consumption.
  • the microcavity structure that matches the wavelength of each color can be applied to all the sub-pixels in addition to the effect of improving the brightness by emitting yellow light. It can be a light emitting device having good characteristics.
  • the light emitting device according to the present embodiment uses the light emitting device according to the second embodiment, it is possible to obtain a light emitting device having good characteristics. Specifically, since the light emitting device according to the second embodiment has good luminous efficiency, it can be a light emitting device having low power consumption.
  • FIG. 5 shows a passive matrix type light emitting device manufactured by applying the present invention.
  • 5A is a perspective view showing the light emitting device
  • FIG. 5B is a cross-sectional view of FIG. 5A cut by XY.
  • an EL layer 955 is provided between the electrodes 952 and the electrodes 956 on the substrate 951.
  • the end of the electrode 952 is covered with an insulating layer 953.
  • a partition layer 954 is provided on the insulating layer 953.
  • the side wall of the partition wall layer 954 has an inclination such that the distance between one side wall and the other side wall becomes narrower as it gets closer to the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 is trapezoidal, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is the upper side (the surface of the insulating layer 953). It faces in the same direction as the direction, and is shorter than the side that does not contact the insulating layer 953).
  • the passive matrix type light emitting device also uses the light emitting device according to the second embodiment, and can be a highly reliable light emitting device or a light emitting device having low power consumption.
  • the light emitting device described above can control a large number of minute light emitting devices arranged in a matrix, it is a light emitting device that can be suitably used as a display device for expressing an image.
  • FIG. 6B is a top view of the lighting device
  • FIG. 6A is a cross-sectional view taken along the line ef in FIG. 6B.
  • the first electrode 401 is formed on the translucent substrate 400 which is a support.
  • the first electrode 401 corresponds to the first electrode 101 in the second embodiment.
  • the first electrode 401 is formed of a translucent material.
  • a pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400.
  • the EL layer 403 is formed on the first electrode 401.
  • the EL layer 403 corresponds to the configuration of the EL layer 103 in the second embodiment, or the configuration in which the light emitting units 511 and 512 and the charge generation layer 513 are combined. Please refer to the description for these configurations.
  • the EL layer 403 is covered to form the second electrode 404.
  • the second electrode 404 corresponds to the second electrode 102 in the second embodiment.
  • the second electrode 404 is formed of a material having high reflectance. A voltage is supplied by connecting the second electrode 404 to the pad 412.
  • the lighting device showing the light emitting device having the first electrode 401, the EL layer 403, and the second electrode 404 in the present embodiment has. Since the light emitting device is a light emitting device having high luminous efficiency, the lighting device in the present embodiment can be a lighting device having low power consumption.
  • the illumination device is completed by fixing the substrate 400 on which the light emitting device having the above configuration is formed and the sealing substrate 407 using the sealing materials 405 and 406 and sealing them. Either one of the sealing materials 405 and 406 may be used.
  • a desiccant can be mixed with the inner sealing material 406, whereby moisture can be adsorbed, which leads to improvement in reliability.
  • an IC chip 420 or the like on which a converter or the like is mounted may be provided on the IC chip 420.
  • the lighting device according to the present embodiment uses the light emitting device according to the second embodiment for the EL element, and can be a light emitting device having low power consumption.
  • the light emitting device according to the second embodiment is a light emitting device having good luminous efficiency and low power consumption.
  • the electronic device described in the present embodiment can be an electronic device having a light emitting unit having low power consumption.
  • Examples of electronic devices to which the above light emitting device is applied include television devices (also referred to as televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (mobile phones, etc.). (Also referred to as a mobile phone device), a portable game machine, a mobile information terminal, a sound reproduction device, a large game machine such as a pachinko machine, and the like. Specific examples of these electronic devices are shown below.
  • FIG. 7A shows an example of a television device.
  • the display unit 7103 is incorporated in the housing 7101. Further, here, a configuration in which the housing 7101 is supported by the stand 7105 is shown. An image can be displayed by the display unit 7103, and the display unit 7103 is configured by arranging the light emitting devices according to the second embodiment in a matrix.
  • the operation of the television device can be performed by an operation switch provided in the housing 7101 or a separate remote control operation device 7110.
  • the operation keys 7109 included in the remote controller 7110 can be used to control the channel and volume, and the image displayed on the display unit 7103 can be operated.
  • the remote controller 7110 may be provided with a display unit 7107 for displaying information output from the remote controller 7110.
  • the television device is configured to include a receiver, a modem, and the like.
  • the receiver can receive general television broadcasts, and by connecting to a wired or wireless communication network via a modem, it can be unidirectional (sender to receiver) or bidirectional (sender and receiver). It is also possible to perform information communication between (or between recipients, etc.).
  • FIG. 7B1 is a computer, which includes a main body 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like.
  • This computer is manufactured by arranging the light emitting devices according to the second embodiment in a matrix and using the light emitting devices in the display unit 7203.
  • the computer of FIG. 7B1 may have a form as shown in FIG. 7B2.
  • the computer of FIG. 7B2 is provided with a second display unit 7210 instead of the keyboard 7204 and the pointing device 7206.
  • the second display unit 7210 is a touch panel type, and input can be performed by operating the input display displayed on the second display unit 7210 with a finger or a dedicated pen.
  • the second display unit 7210 can display not only the input display but also other images. Further, the display unit 7203 may also be a touch panel. By connecting the two screens with a hinge, it is possible to prevent troubles such as damage or damage to the screens during storage or transportation.
  • FIG. 7C shows an example of a mobile terminal.
  • the mobile phone includes an operation button 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like, in addition to the display unit 7402 incorporated in the housing 7401.
  • the mobile phone 7400 has a display unit 7402 manufactured by arranging the light emitting devices according to the second embodiment in a matrix.
  • the mobile terminal shown in FIG. 7C may be configured so that information can be input by touching the display unit 7402 with a finger or the like. In this case, operations such as making a phone call or composing an e-mail can be performed by touching the display unit 7402 with a finger or the like.
  • the screen of the display unit 7402 mainly has three modes. The first is a display mode mainly for displaying an image, and the second is an input mode mainly for inputting information such as characters. The third is a display + input mode in which two modes, a display mode and an input mode, are mixed.
  • the display unit 7402 may be set to a character input mode mainly for inputting characters, and the characters displayed on the screen may be input. In this case, it is preferable to display the keyboard or the number button on the screen of the display unit 7402.
  • the orientation (vertical or horizontal) of the mobile terminal is determined, and the screen display of the display unit 7402 is automatically displayed. Can be switched.
  • the screen mode can be switched by touching the display unit 7402 or by operating the operation button 7403 of the housing 7401. It is also possible to switch depending on the type of image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is moving image data, the display mode is switched, and if the image signal is text data, the input mode is switched.
  • the input mode the signal detected by the optical sensor of the display unit 7402 is detected, and when there is no input by the touch operation of the display unit 7402 for a certain period of time, the screen mode is switched from the input mode to the display mode. You may control it.
  • the display unit 7402 can also function as an image sensor.
  • the person can be authenticated by touching the display unit 7402 with a palm or a finger and taking an image of a palm print, a fingerprint, or the like.
  • a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display unit, finger veins, palmar veins, and the like can be imaged.
  • FIG. 8A is a schematic view showing an example of a cleaning robot.
  • the cleaning robot 5100 has a display 5101 arranged on the upper surface, a plurality of cameras 5102 arranged on the side surface, a brush 5103, and an operation button 5104. Although not shown, the lower surface of the cleaning robot 5100 is provided with tires, suction ports, and the like.
  • the cleaning robot 5100 also includes various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, an optical sensor, and a gyro sensor. Further, the cleaning robot 5100 is provided with wireless communication means.
  • the cleaning robot 5100 is self-propelled, can detect dust 5120, and can suck dust from a suction port provided on the lower surface.
  • the cleaning robot 5100 can analyze the image taken by the camera 5102 and determine the presence or absence of obstacles such as walls, furniture, and steps. Further, when an object such as wiring that is likely to be entangled with the brush 5103 is detected by image analysis, the rotation of the brush 5103 can be stopped.
  • the display 5101 can display the remaining amount of the battery, the amount of dust sucked, and the like.
  • the route traveled by the cleaning robot 5100 may be displayed on the display 5101. Further, the display 5101 may be a touch panel, and the operation buttons 5104 may be provided on the display 5101.
  • the cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone.
  • the image taken by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when he / she is out. Further, the display of the display 5101 can be confirmed by a portable electronic device such as a smartphone.
  • the light emitting device of one aspect of the present invention can be used for the display 5101.
  • the robot 2100 shown in FIG. 8B includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.
  • the microphone 2102 has a function of detecting a user's voice, environmental sound, and the like. Further, the speaker 2104 has a function of emitting sound.
  • the robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.
  • the display 2105 has a function of displaying various information.
  • the robot 2100 can display the information desired by the user on the display 2105.
  • the display 2105 may be equipped with a touch panel. Further, the display 2105 may be a removable information terminal, and by installing the display 2105 at a fixed position of the robot 2100, charging and data transfer are possible.
  • the upper camera 2103 and the lower camera 2106 have a function of photographing the surroundings of the robot 2100. Further, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the traveling direction when the robot 2100 advances by using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely by using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107.
  • the light emitting device of one aspect of the present invention can be used for the display 2105.
  • FIG. 8C is a diagram showing an example of a goggle type display.
  • the goggle type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, an operation key 5005 (including a power switch or an operation switch), a connection terminal 5006, and a sensor 5007 (force, displacement, position, speed). , Acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, voice, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell, or infrared rays. It includes a measuring function), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, and the like.
  • the light emitting device of one aspect of the present invention can be used for the display unit 5001 and the display unit 5002.
  • FIG. 9 shows an example in which the light emitting device according to the second embodiment is used for a desk lamp which is a lighting device.
  • the desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002, and the lighting device described in the third embodiment may be used as the light source 2002.
  • FIG. 10 shows an example in which the light emitting device according to the second embodiment is used as an indoor lighting device 3001. Since the light emitting device according to the second embodiment is a light emitting device having high luminous efficiency, it can be a lighting device having low power consumption. Further, since the light emitting device according to the second embodiment can have a large area, it can be used as a large area lighting device. Further, since the light emitting device according to the second embodiment is thin, it can be used as a thin lighting device.
  • the light emitting device according to the second embodiment can also be mounted on a windshield or a dashboard of an automobile.
  • FIG. 11 shows an aspect in which the light emitting device according to the second embodiment is used for a windshield or a dashboard of an automobile.
  • the display area 5200 to the display area 5203 are displays provided by using the light emitting device according to the second embodiment.
  • the display area 5200 and the display area 5201 are display devices equipped with the light emitting device according to the second embodiment provided on the windshield of an automobile.
  • the light emitting device according to the second embodiment can be a so-called see-through display device in which the opposite side can be seen through by manufacturing the first electrode and the second electrode with electrodes having translucency. .. If the display is in a see-through state, even if it is installed on the windshield of an automobile, it can be installed without obstructing the view.
  • a transistor for driving it is preferable to use a transistor having translucency, such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor.
  • the display area 5202 is a display device provided with the light emitting device according to the second embodiment provided in the pillar portion.
  • the display area 5203 provided on the dashboard portion compensates for blind spots and enhances safety by projecting an image from an imaging means provided on the outside of the automobile with a view blocked by the vehicle body. Can be done. By projecting the image so as to complement the invisible part, it is possible to confirm the safety more naturally and without discomfort.
  • the display area 5203 can also provide various information by displaying navigation information, a speedometer or tachometer, a mileage, a fuel gauge, a gear state, an air conditioning setting, and the like.
  • the display items and layout of the display can be changed as appropriate according to the user's preference. It should be noted that such information can also be provided in the display area 5200 to the display area 5202. Further, the display area 5200 to the display area 5203 can also be used as a lighting device.
  • FIGS. 12A and 12B show a foldable portable information terminal 5150.
  • the foldable personal digital assistant 5150 has a housing 5151, a display area 5152, and a bent portion 5153.
  • FIG. 12A shows the mobile information terminal 5150 in the expanded state.
  • FIG. 12B shows a mobile information terminal in a folded state.
  • the portable information terminal 5150 has a large display area 5152, it is compact and excellent in portability when folded.
  • the display area 5152 can be folded in half by the bent portion 5153.
  • the bent portion 5153 is composed of a stretchable member and a plurality of support members, and when folded, the stretchable member stretches.
  • the bent portion 5153 is folded with a radius of curvature of 2 mm or more, preferably 3 mm or more.
  • the display area 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device).
  • the light emitting device of one aspect of the present invention can be used in the display area 5152.
  • FIGS. 13A to 13C show a foldable mobile information terminal 9310.
  • FIG. 13A shows the mobile information terminal 9310 in the expanded state.
  • FIG. 13B shows a mobile information terminal 9310 in a state of being changed from one of the expanded state or the folded state to the other.
  • FIG. 13C shows a mobile information terminal 9310 in a folded state.
  • the mobile information terminal 9310 is excellent in portability in the folded state, and is excellent in display listability due to a wide seamless display area in the unfolded state.
  • the display panel 9311 is supported by three housings 9315 connected by hinges 9313.
  • the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Further, the display panel 9311 can be reversibly deformed from the unfolded state to the folded state of the portable information terminal 9310 by bending between the two housings 9315 via the hinge 9313.
  • the light emitting device of one aspect of the present invention can be used for the display panel 9311.
  • the configurations shown in the present embodiment can be used by appropriately combining the configurations shown in the first to fourth embodiments.
  • the range of application of the light emitting device provided with the light emitting device according to the second embodiment is extremely wide, and this light emitting device can be applied to electronic devices in all fields.
  • an electronic device having low power consumption can be obtained.
  • Step 1 Synthesis of N- (1,1'-biphenyl-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine> 5.2 g (15 mmol) of 6-iodo-benzo [b] naphtho [1,2-d] flask, 2.5 g (15 mmol) of 2-biphenylamine, and 0.12 g (0.30 mmol) of 2- Dicyclohexylphosphino-2', 6'-dimethoxybiphenyl was placed in a 200 mL three-necked flask equipped with a reflux tube, and the inside of the flask was replaced with nitrogen.
  • step 1 2.9 g (30 mmol) of sodium tert-butoxide and 110 mL of xylene were added to the flask, and vacuum degassing and nitrogen substitution were performed three times each. 86 mg (0.15 mmol) of bis (bis (dibenzylideneacetone) palladium) (0) was added to the flask, and the mixture was stirred at 110 ° C. for 3 hours. After stirring, insoluble matter was removed from the mixture obtained by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, washed with saturated brine, and dried over anhydrous magnesium sulfate. The resulting mixture was naturally filtered to remove anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain 5.5 g of the desired brown solid in a yield of 95%.
  • the synthesis scheme of step 1 is shown below.
  • Step 2 N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-2-yl) benzo [b] naphtho [1,2-d] furan- Synthesis of 6-amine (abbreviation: oFBiBnf (6))> 2. 2.0 g (5.2 mmol) of N- (1,1'-biphenyl-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine obtained in step 1 and 1.
  • step 2 The synthesis scheme of step 2 is shown below.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of oFBiBnf (6) and the solid thin film were measured.
  • the solid thin film was formed on a quartz substrate by a vacuum deposition method.
  • An ultraviolet-visible spectrophotometer (solution: JASCO Corporation, V-550, thin film: Hitachi High-Technologies Corporation, U-4100) 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 the quartz cell, and the absorption spectrum of the thin film was the absorbance (-log 10 [%) obtained from the transmittance and reflectance including the substrate. It was calculated from T / (100-% R)]). Note that% T represents the transmittance and% R represents the reflectance.
  • a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for the measurement of the emission spectrum.
  • the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution are shown in FIG.
  • the measurement results of the absorption spectrum and the emission spectrum of the solid thin film are shown in FIG. From the results of FIG. 15, in the toluene solution of oFBiBnf (6), an absorption peak including a shoulder peak was observed near 382 nm, 337 nm, and 311 nm, and an emission wavelength peak was observed at 429 nm (excitation wavelength 377 nm). Further, from the results of FIG.
  • HOMO and LUMO levels of oFBiBnf (6) were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.
  • An electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used as the measuring device.
  • dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number; 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) was used.
  • a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) is used as the working electrode, and a platinum electrode (manufactured by BAS Co., Ltd., Pt counter electrode for VC-3) is used as the auxiliary electrode. 5 cm)) was used as a reference electrode, and an Ag / Ag + electrode (RE7 non-aqueous solvent system reference electrode manufactured by BAS Co., Ltd.) was used. The measurement was performed at room temperature (20 or more and 25 ° C. or less).
  • the scan speed at the time of 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 the intermediate potential of the oxidation-reduction wave
  • Ec was the intermediate potential of the reduction-oxidation wave.
  • the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV]
  • the HOMO level [eV] -4.94-Ea, LUMO.
  • the CV measurement was repeated 100 times, and the oxidation-reduction wave in the measurement in the 100th cycle was compared with the oxidation-reduction wave in the first cycle to examine the electrical stability of the compound.
  • the differential scanning calorimetry (DSC measurement) of oFBiBnf (6) was measured using Pyris1DSC manufactured by PerkinElmer.
  • the temperature is raised from -10 ° C to 270 ° C at a heating rate of 40 ° C / min, held at the same temperature for 1 minute, and then cooled to -10 ° C at a temperature lowering rate of 100 ° C / min.
  • the operation was performed twice in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of oFBiBnf (6) was 119 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis Thermogravimetric-Differential Thermal Analysis of oFBiBnf (6) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 366 ° C, and the substance had good sublimation properties. It has been shown.
  • the organic compound according to one aspect of the present invention can provide an organic optical device (light emitting device and light receiving device) having both high heat resistance and good sublimation property and high heat resistance, and can also be used for production of device fabrication. It was confirmed that the sex can be improved.
  • Step 1 Synthesis of N- (1,1'-biphenyl-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine> Synthesis of Example 1 Synthesis was carried out in the same manner as in Step 1 in Example 1.
  • Step 2 N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-4-yl) benzo [b] naphtho [1,2-d] furan- Synthesis of 6-amine (abbreviation: oFBi (4) Bnf (6))> 2. 2.0 g (5.2 mmol) of N- (1,1'-biphenyl-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine obtained in step 1 and 1.
  • the obtained 1.4 g of white solid was sublimated and purified by the train sublimation method.
  • Sublimation purification was carried out by heating the white solid at a pressure of 3.6 Pa and 205 ° C. for 15 hours while flowing argon at 15 mL / min. After sublimation purification, 1.1 g of the target white solid was obtained with a recovery rate of 78%.
  • the synthesis scheme is shown below.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of oFBi (4) Bnf (6) and the solid thin film were measured. Since the measuring method and the measuring device are the same as those in the first embodiment, the repeated description will be omitted.
  • FIG. 19 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. From the results shown in FIG. 18, in the toluene solution of oFBi (4) Bnf (6), absorption peaks including shoulder peaks were observed near 357 nm, 328 nm, and 301 nm, and emission wavelength peaks were observed at 405 nm (excitation wavelength 353 nm). It was. Further, from the results of FIG.
  • oFBi (4) Bnf (6) were calculated based on cyclic voltammetry (CV) measurements. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • the differential scanning calorimetry (DSC measurement) of oFBi (4) Bnf (6) was measured using Pyris1DSC manufactured by PerkinElmer.
  • the temperature is raised from -10 ° C to 253 ° C at a heating rate of 40 ° C / min, held at the same temperature for 1 minute, and then cooled to -10 ° C at a temperature lowering rate of 100 ° C / min.
  • the operation was performed twice in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of oFBi (4) Bnf (6) was 114 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis (Thermogravimetric-Differential Thermal Analysis) of oFBi (4) Bnf (6) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 343 ° C, and the substance had good sublimation properties. It has been shown.
  • the organic compound according to one aspect of the present invention can provide an organic optical device (light emitting device and light receiving device) having both high heat resistance and good sublimation property and high heat resistance, and can also be used for production of device fabrication. It was confirmed that the sex can be improved.
  • Step 1 Synthesis of N- (9,9-dimethyl-9H-fluorene-4-yl) t-butoxycarbonylamine> 5.4 g (20 mmol) of 4-bromo-9,9-dimethyl-9H-fluorene, 2.3 g (20 mmol) of tert-butyl carbamate, and 0.23 g (0.40 mmol) of 4,5-bis.
  • Step 2 Synthesis of 9,9-dimethyl-9H-fluorene-4-amine> 5.5 g (18 mmol) of N- (9,9-dimethyl-9H-fluorene-4-yl) t-butoxycarbonylamine obtained in step 1 and 100 mL of dichloromethane were placed in a 1000 mL eggplant flask and placed in a flask. Was placed under a nitrogen stream. To this solution, 5.2 mL (8.1 g, 71 mmol) of trifluoroacetic acid was added dropwise from the dropping funnel over 5 minutes, and then the mixture was stirred at room temperature for about 16 hours.
  • step 2 After stirring, the eggplant flask was bathed in ice and then neutralized by adding 100 mL of potassium hydroxide solution (0.7 mmol). The resulting mixture was separated into an organic phase and an aqueous phase using a 500 mL separatory funnel, and the organic phase was washed 3 times with about 100 mL of water. The water used for washing was extracted three times with 200 mL of toluene, and the obtained extract and the organic phase were combined and washed with about 200 mL of saturated brine. Anhydrous magnesium sulfate was added to the organic phase obtained after washing, and the mixture was allowed to stand for 1 hour, followed by natural filtration, and the obtained filtrate was concentrated. When the obtained compound was vacuum dried, 3.2 g of the desired white solid was obtained in a yield of 86%. The synthesis scheme of step 2 is shown below.
  • Step 3 Synthesis of N- (9,9-dimethyl-9H-fluorene-4-yl) benzo [b] naphtho [1,2-d] furan-6-amine> 1.5 g (7.2 mmol) of 9,9-dimethyl-9H-fluoren-4-amine obtained in step 2 and 2.5 g (7.2 mmol) of 6-iodobenzo [b] naphtho [1, 2] -D] furan, 0.18 g (0.4 mmol) of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (sphos), and 1.5 g (15 mmol) of t-butoxysodium in a reflux tube.
  • the water used for washing was extracted three times with about 100 mL of toluene, and the obtained extract and the organic phase were combined and washed with about 200 mL of saturated brine.
  • Anhydrous magnesium sulfate was added to the obtained organic phase and the mixture was left to stand for 1 hour, and then the mixture was naturally filtered and the obtained filtrate was concentrated to obtain 3.5 g of a dark brown compound.
  • the synthesis scheme of step 3 is shown below.
  • Step 4 N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H-fluorene-4-yl) benzo [b] naphtho [1,2-d] furan- Synthesis of 6-amine (abbreviation: FBi (4) Bnf (6))> With 1.8 g (4.1 mmol) of N- (9,9-dimethyl-9H-fluorene-4-yl) benzo [b] naphtho [1,2-d] furan-6-amine obtained in step 3.
  • step 4 The synthesis scheme of step 4 is shown below.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of FBi (4) Bnf (6) and the solid thin film were measured. Since the measuring method and the measuring device are the same as those in the first embodiment, the repeated description will be omitted.
  • FIG. 22 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. From the results of FIG. 21, in the toluene solution of FBi (4) Bnf (6), absorption peaks including shoulder peaks were observed near 371 nm, 336 nm, 307 nm, and 283 nm, and the emission wavelength peak was found at 428 nm (excitation wavelength 370 nm). Was seen. Further, from the results of FIG.
  • the HOMO and LUMO levels of FBi (4) Bnf (6) were calculated based on cyclic voltammetry (CV) measurements.
  • the calculation method is shown below. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • the differential scanning calorimetry (DSC measurement) of FBi (4) Bnf (6) was measured using Pyris1DSC manufactured by PerkinElmer.
  • the temperature is raised from -10 ° C to 280 ° C at a heating rate of 40 ° C / min, held at the same temperature for 1 minute, and then cooled to -10 ° C at a temperature lowering rate of 100 ° C / min.
  • the operation was performed twice in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of FBi (4) Bnf (6) was 134 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis Thermogravimetric-Differential Thermal Analysis of FBi (4) Bnf (6) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 390 ° C, and the substance had good sublimation properties. It has been shown.
  • the organic compound according to one aspect of the present invention can provide an organic optical device (light emitting device and light receiving device) having both high heat resistance and good sublimation property and high heat resistance, and can also be used for production of device fabrication. It was confirmed that the sex can be improved.
  • Step 1 Synthesis of N- (9,9-dimethyl-9H-fluorene-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine> 2.1 g (10 mmol) of 9,9-dimethyl-9H-fluorene-2-amine and 3.4 g (10 mmol) of 6-iodobenzo [b] naphtho [1,2-d] furan and 0.84 mg ( 0.2 mmol) 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (sphos) and 2.0 g (20 mmol) t-butoxysodium were placed in a 200 mL three-necked flask equipped with a reflux tube and placed in the flask.
  • step 1 The mixture was filtered through alumina, Florisil (Wako Pure Chemical Industries, Ltd., Catalog No .: 066-05265) and Celite (Wako Pure Chemical Industries, Ltd., Catalog No .: 537-02305) at the same temperature.
  • the solid obtained by concentrating the obtained filtrate was recrystallized from 300 mL of ethanol to obtain 2.5 g of the desired white solid in a yield of 58%.
  • the synthesis scheme of step 1 is shown below.
  • Step 2 N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H-fluorene-2-yl) -benzo [b] naphtho [1,2-d] furan Synthesis of -6-amine (abbreviation: FBiBnf (6))> 1.1 g (2.5 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) benzo [b] naphtho [1,2-d] furan-6-amine obtained in step 1 and 0.58 g (2.5 mmol) of 4-bromobiphenyl and 0.86 mg (0.2 mmol) of 2-di-tert-butylphosphino-2', 4', 6'-triisopropylbiphenyl (tBuxphos) , 0.52 g (5.0 mmol) of t-butoxysodium was placed in a 200 mL three-necked flask equipped with a reflux
  • the mixture was filtered through alumina, Florisil (Wako Pure Chemical Industries, Ltd., Catalog No .: 066-05265) and Celite (Wako Pure Chemical Industries, Ltd., Catalog No .: 537-02305) at the same temperature.
  • step 2 The synthesis scheme of step 2 is shown below.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of FBiBnf (6) and the solid thin film were measured. Since the measuring method and the measuring device are the same as those in the first embodiment, the repeated description will be omitted.
  • FIG. 25 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. From the results shown in FIG. 24, in the toluene solution of FBiBnf (6), absorption peaks including shoulder peaks were observed near 389 nm, 352 nm, 340 nm and 313 nm, and emission wavelength peaks were observed at 438 nm (excitation wavelength 360 nm). Further, from the result of FIG.
  • the HOMO and LUMO levels of FBiBnf (6) were calculated based on cyclic voltammetry (CV) measurements.
  • the calculation method is shown below. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • the differential scanning calorimetry (DSC measurement) of FBiBnf (6) was measured using Pyris1DSC manufactured by PerkinElmer.
  • the temperature is raised from -10 ° C to 300 ° C at a heating rate of 40 ° C / min, held at the same temperature for 1 minute, and then cooled to -10 ° C at a temperature lowering rate of 100 ° C / min.
  • the operation was performed twice in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of FBiBnf (6) was 128 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis Thermogravimetric-Differential Thermal Analysis of FBiBnf (6) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 352 ° C, and the substance had good sublimation properties. It has been shown.
  • the organic compound according to one aspect of the present invention can provide an organic optical device (light emitting device and light receiving device) having both high heat resistance and good sublimation property and high heat resistance, and can also be used for production of device fabrication. It was confirmed that the sex can be improved.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 70 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H-fluorene-2) represented by the above structural formula (i) by a vapor deposition method using resistance heating.
  • FBiBnf (6) is deposited on the hole injection layer 111 so as to have a film thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl) represented by the above structural formula (ii).
  • PCzN2 bis (9-phenyl-9H-carbazole)
  • 2- [3'-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-) represented by the above structural formula (v). II) is formed at 15 nm, and 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) has a thickness of 10 nm.
  • the electron transport layer 114 was formed by vapor deposition.
  • lithium fluoride (LiF) is vapor-deposited at 1 nm to form an electron injection layer 115, and then aluminum is vapor-deposited to a film thickness of 200 nm to form a second electrode 102. Was formed to produce the light emitting device 1 of this example.
  • the light emitting device 2 was produced in the same manner as the light emitting device 1 except that the film thickness of FBiBnf (6) in the hole transport layer of the light emitting device 1 was changed from 20 nm to 120 nm.
  • the comparative light emitting device 2 was produced in the same manner as the light emitting device 2 except that the FBiBnf (6) in the light emitting device 2 was changed to BBABnf.
  • the element structure of the light emitting device is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the brightness-current density characteristics of the light emitting device 1 and the comparative light emitting device 1 are shown in FIG. 26, the current efficiency-luminance characteristics are shown in FIG. 27, the brightness-voltage characteristics are shown in FIG. 28, the current-voltage characteristics are shown in FIG. -Brightness characteristics are shown in FIG. 30, emission spectra are shown in FIG. 31, brightness-current density characteristics of the light emitting device 2 and comparative light emitting device 2 are shown in FIG. 32, current efficiency-luminance characteristics are shown in FIG. 33, and brightness-voltage characteristics are shown in FIG. 34 shows the current-voltage characteristic in FIG. 35, the external quantum efficiency-luminance characteristic in FIG. 36, and the emission spectrum in FIG. 37.
  • the main characteristics of each light emitting device near 1000 cd / m 2 are shown below.
  • the light emitting device 1 of one aspect of the present invention is an EL device having good luminous efficiency.
  • the light emitting device 2 and the comparative light emitting device 2 are devices in which FBiBnf (6) and BBABnf in the hole transport layer are thickened to 120 nm, but the light emitting device 2 of one aspect of the present invention is thickened.
  • the element has a small voltage rise.
  • FBiBnf (6) which is an organic compound according to one aspect of the present invention, is an organic compound having good carrier transportability, particularly hole transportability.
  • FIGS. 38 and 39 graphs showing the change in luminance with respect to the driving time at a current density of 50 mA / cm 2 are shown in FIGS. 38 and 39.
  • the light emitting device 1 and the light emitting device 2 which are the light emitting devices of one aspect of the present invention are light emitting devices having a good life like the comparative light emitting device 1 and the comparative light emitting device 2. I found out.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 70 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-2) represented by the above structural formula (viii) by a vapor deposition method using resistance heating -Il) benzo [b] naphtho [1,2-d] furan-6-amine (abbreviation: oFBiBnf (6)) and ALD-MP001Q (Analysis Studio Co., Ltd., material serial number: 1S20180314) by weight ratio.
  • oFBiBnf (6) is deposited on the hole injection layer 111 so as to have a film thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl) represented by the above structural formula (ii).
  • PCzN2 bis (9-phenyl-9H-carbazole)
  • 2- [3'-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-) represented by the above structural formula (v). II) is formed at 15 nm, and 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) has a thickness of 10 nm.
  • the electron transport layer 114 was formed by vapor deposition.
  • lithium fluoride (LiF) is vapor-deposited at 1 nm to form an electron injection layer 115, and then aluminum is vapor-deposited to a film thickness of 200 nm to form a second electrode 102. Was formed to produce the light emitting device 3 of this example.
  • the comparative light emitting device 3 uses the oFBiBnf (6) in the light emitting device 3 as N, N-bis (4-biphenyl) -6-phenylbenzo [b] naphtho [1,2-] represented by the above structural formula (vii). d] It was produced in the same manner as the light emitting device 3 except that it was changed to furan-8-amine (abbreviation: BBABnf).
  • the light emitting device 4 was produced in the same manner as the light emitting device 3 except that the film thickness of oFBiBnf (6) in the hole transport layer of the light emitting device 3 was changed from 20 nm to 120 nm.
  • the comparative light emitting device 4 was produced in the same manner as the light emitting device 4 except that the oFBiBnf (6) in the light emitting device 4 was changed to BBABnf.
  • the element structure of the light emitting device is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the brightness-current density characteristics of the light emitting device 3 and the comparative light emitting device 3 are shown in FIG. 40, the current efficiency-luminance characteristics are shown in FIG. 41, the brightness-voltage characteristics are shown in FIG. 42, the current-voltage characteristics are shown in FIG. 43, and the external quantum efficiency. -Brightness characteristics are shown in FIG. 44, emission spectra are shown in FIG. 45, brightness-current density characteristics of the light emitting device 4 and the comparative light emitting device 4 are shown in FIG. 46, current efficiency-luminance characteristics are shown in FIG. 47, and brightness-voltage characteristics are shown in FIG. 48 shows the current-voltage characteristic in FIG. 49, the external quantum efficiency-luminance characteristic in FIG. 50, and the emission spectrum in FIG. 51.
  • the main characteristics of each light emitting device near 1000 cd / m 2 are shown below.
  • the light emitting device 3 according to one aspect of the present invention is an EL device having good luminous efficiency.
  • the light emitting device 4 and the comparative light emitting device 4 are devices in which oFBiBnf (6) and BBABnf in the hole transport layer are thickened to 120 nm, but the light emitting device according to one aspect of the present invention.
  • No. 4 is an element having a small voltage rise even if the film is thickened.
  • oFBiBnf (6) which is an organic compound according to one aspect of the present invention, is an organic compound having good carrier transportability, particularly hole transportability.
  • FIGS. 52 and 53 graphs showing the change in luminance with respect to the driving time at a current density of 50 mA / cm 2 are shown in FIGS. 52 and 53.
  • the light emitting device 3 and the light emitting device 4 which are the light emitting devices of one aspect of the present invention are light emitting devices having a good life like the comparative light emitting device 3 and the comparative light emitting device 4. I found out.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 70 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-4) represented by the above structural formula (ix) by a vapor deposition method using resistance heating.
  • oFBi (4) Bnf (6) is deposited on the hole injection layer 111 so as to have a film thickness of 20 nm, and then 3,3'-(naphthalene-1) represented by the above structural formula (ii). , 4-Diyl) bis (9-phenyl-9H-carbazole) (abbreviation: PCzN2) was vapor-deposited to 10 nm to form a hole transport layer 112.
  • 2- [3'-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-) represented by the above structural formula (v). II) is formed at 15 nm, and 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) has a thickness of 10 nm.
  • the electron transport layer 114 was formed by vapor deposition.
  • lithium fluoride (LiF) is vapor-deposited at 1 nm to form an electron injection layer 115, and then aluminum is vapor-deposited to a film thickness of 200 nm to form a second electrode 102. Was formed to produce the light emitting device 5 of this example.
  • the element structure of the light emitting device is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the luminance-current density characteristics of the light emitting device 5 and the light emitting device 6 are shown in FIG. 54, the current efficiency-luminance characteristic is shown in FIG. 55, the brightness-voltage characteristic is shown in FIG. 56, the current-voltage characteristic is shown in FIG. 57, and the external quantum efficiency- The luminance characteristics are shown in FIG. 58, and the emission spectrum is shown in FIG. 59.
  • the main characteristics of each light emitting device near 1000 cd / m 2 are shown below.
  • the light emitting device 5 and the light emitting device 6 of one aspect of the present invention are EL devices having good luminous efficiency.
  • Step 1 Synthesis of FBiBnf (8)> 1.6 g (6.3 mmol) of 8-chloro-benzo [b] naphtho [1,2-d] flask and 2.3 g (6.3 mmol) of 2- (4-biphenylyl) amino-9,9- Dimethylfluorene, 1.2 g (13 mol) of sodium tert-butoxide, and 44 mg (0.13 mmol) of di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (commonly known as cBRIDP (regR)).
  • FIG. 60B is a graph showing an enlarged range of 7.0 ppm to 9.0 ppm in FIG. 60A. As a result, it was found that FBiBnf (8) was obtained.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of FBiBnf (8) and the solid thin film were measured.
  • the solid thin film was formed on a quartz substrate by a vacuum deposition method.
  • An ultraviolet-visible spectrophotometer (solution: JASCO Corporation, V-550, thin film: Hitachi High-Technologies Corporation, U-4100) 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 the quartz cell, and the absorption spectrum of the thin film was the absorbance (-log 10 [%) obtained from the transmittance and reflectance including the substrate. It was calculated from T / (100-% R)]). Note that% T represents the transmittance and% R represents the reflectance.
  • a fluorometer (JASCO FP-8600) was used for the measurement of the emission spectrum.
  • FIG. 62 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • HOMO and LUMO levels of FBiBnf (8) were calculated based on cyclic voltammetry (CV) measurements. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • differential scanning calorimetry (DSC measurement) of FBiBnf (8) was measured using DSC8231-SL manufactured by Rigaku Co., Ltd.
  • the differential scanning calorimetry is an operation in which the temperature is raised from 0 ° C. to 290 ° C. at a heating rate of 10 ° C./min, held at the same temperature for 1 minute, and then cooled to 0 ° C. at a temperature lowering rate of 10 ° C./min. was performed three times in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of FBiBnf (8) was 118 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis Thermogravimetric-Differential Thermal Analysis of FBiBnf (8) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 422 ° C, and the substance had good sublimation properties. It has been shown.
  • Step 1 N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-2-yl) benzo [b] naphtho [1,2-d] furan- Synthesis of 8-amine (abbreviation: oFBiBnf (8))> 1.6 g (6.3 mmol) of 8-chloro-benzo [b] naphtho [1,2-d] flask and 2.3 g (6.3 mmol) of 2- (2-biphenylyl) amino-9,9- Dimethylfluorene, 1.2 g (13 mol) of sodium tert-butoxide, and 44 mg (0.13 mmol) of di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (commonly known as cBRIDP (regR)).
  • cBRIDP di-tert-butyl (1-methyl-2,2-diphenylcycloprop
  • the obtained 1.2 g of white solid was sublimated and purified by the train sublimation method.
  • Sublimation purification was carried out by heating the solid at a pressure of 4.0 Pa and 225 ° C. for 16 hours while flowing argon at 15 mL / min. After sublimation purification, 1.1 g of the target white solid was obtained with a recovery rate of 92%.
  • FIG. 63B is an enlarged graph showing the range of 6.6 ppm to 9.0 ppm in FIG. 63A. As a result, it was found that oFBiBnf (8) was obtained.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of oFBiBnf (8) and the solid thin film were measured. Since the measuring method and the apparatus are the same as those in the seventh embodiment, the repeated description will be omitted.
  • FIG. 65 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • oFBiBnf (8) The HOMO and LUMO levels of oFBiBnf (8) were calculated based on cyclic voltammetry (CV) measurements. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • differential scanning calorimetry (DSC measurement) of oFBiBnf (8) was measured using DSC8231-SL manufactured by Rigaku Co., Ltd.
  • the differential scanning calorimetry is an operation in which the temperature is raised from 0 ° C. to 220 ° C. at a heating rate of 10 ° C./min, held at the same temperature for 1 minute, and then cooled to 0 ° C. at a temperature lowering rate of 10 ° C./min. was performed three times in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of oFBiBnf (8) was 114 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis Thermogravimetric-Differential Thermal Analysis of oFBiBnf (8) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from thermogravimetric analysis was -5% at the start of measurement was 364 ° C, and the substance had good sublimation properties. It has been shown.
  • Step 1 Synthesis of FBi (4) Bnf (8)> 1.5 g (5.8 mmol) of 8-chloro-benzo [b] naphtho [1,2-d] flask and 2.0 g (5.8 mmol) of 4- (4-biphenylyl) amino-9,9- Dimethylfluorene, 1.1 g (12 mol) of sodium tert-butoxide, 60 mg (0.15 mmol) of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (commonly known as Flas), and 30 mL of xylene.
  • the flask was placed in a 500 mL three-necked flask equipped with a reflux tube, and the inside of the flask was replaced with nitrogen. 33 mg (58 ⁇ mol) of bis (dibenzylideneacetone) palladium (0) was added to the flask, and the mixture was heated at 160 ° C. for 7 hours.
  • the obtained 1.7 g of white solid was sublimated and purified by the train sublimation method.
  • Sublimation purification was carried out by heating the solid at a pressure of 3.8 Pa and 245 ° C. for 19 hours while flowing argon at 15 mL / min. After sublimation purification, 1.4 g of the target white solid was obtained with a recovery rate of 82%.
  • FIG. 66B is a graph showing an enlarged range of 6.8 ppm to 8.8 ppm in FIG. 66A. As a result, it was found that FBi (4) Bnf (8) was obtained.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of FBi (4) Bnf (8) and the solid thin film were measured. Since the measuring method and the measuring device are the same as those in the seventh embodiment, the repeated description will be omitted.
  • FIG. 68 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • the HOMO and LUMO levels of FBi (4) Bnf (8) were calculated based on cyclic voltammetry (CV) measurements. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • differential scanning calorimetry (DSC measurement) of FBi (4) Bnf (8) was measured using DSC8231-SL manufactured by Rigaku Co., Ltd.
  • the differential scanning calorimetry is an operation in which the temperature is raised from 0 ° C. to 290 ° C. at a heating rate of 10 ° C./min, held at the same temperature for 1 minute, and then cooled to 0 ° C. at a temperature lowering rate of 10 ° C./min. was performed three times in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of FBi (4) Bnf (8) was 118 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis (Thermogravimetric-Differential Thermal Analysis) of FBi (4) Bnf (8) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 394 ° C, and the substance had good sublimation properties. It has been shown.
  • Step 1 Synthesis of oFBi (4) Bnf (8)> 1.6 g (6.3 mmol) of 8-chloro-benzo [b] naphtho [1,2-d] flask and 2.3 g (6.3 mmol) of 4- (2-biphenylyl) amino-9,9- Dimethylfluorene, 1.2 g (13 mol) of sodium tert-butoxide, and 44 mg (0.13 mmol) of di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (commonly known as cBRIDP (regR)).
  • the obtained 1.1 g of white solid was sublimated and purified by the train sublimation method.
  • Sublimation purification was carried out by heating the solid at a pressure of 5.2 Pa and 220 ° C. for 16 hours while flowing argon at 10 mL / min. After sublimation purification, 0.78 g of the target white solid was obtained with a recovery rate of 71%.
  • the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of oFBi (4) Bnf (8) and the solid thin film were measured. Since the measuring method and the measuring device are the same as those in the seventh embodiment, the repeated description will be omitted.
  • FIG. 70 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.
  • the horizontal axis represents wavelength
  • the vertical axis represents absorption intensity and emission intensity.
  • HOMO and LUMO levels of oFBi (4) Bnf (8) were calculated based on cyclic voltammetry (CV) measurements. Since the calculation method, the measurement method, and the measurement device are the same as those in the first embodiment, the repeated description will be omitted.
  • differential scanning calorimetry (DSC measurement) of oFBi (4) Bnf (8) was measured using DSC8231-SL manufactured by Rigaku Co., Ltd.
  • the differential scanning calorimetry is an operation in which the temperature is raised from 0 ° C. to 250 ° C. at a heating rate of 10 ° C./min, held at the same temperature for 1 minute, and then cooled to 0 ° C. at a temperature lowering rate of 10 ° C./min. was performed three times in a row. From the results of the DSC measurement in the second cycle, it was clarified that the glass transition point of oFBi (4) Bnf (8) was 101 ° C., indicating that the substance has extremely high heat resistance.
  • differential thermal analysis (Thermogravimetric-Differential Thermal Analysis) of oFBi (4) Bnf (8) was performed.
  • a high vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS Corporation) was used for the measurement. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 ° C./min and a nitrogen stream (flow velocity of 200 mL / min).
  • Thermogravimetric analysis-In differential thermal analysis it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric analysis was -5% at the start of measurement was 343 ° C, and the substance had good sublimation properties. It has been shown.
  • the organic compound according to one aspect of the present invention can provide an organic optical device (light emitting device and light receiving device) having both high heat resistance and good sublimation property and high heat resistance, and can also be used for production of device fabrication. It was confirmed that the sex can be improved.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 110 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluorene-2) represented by the above structural formula (xii) by a vapor deposition method using resistance heating.
  • -Il) -benzo [b] naphtho [1,2-d] furan-8-amine abbreviation: oFBiBnf (8)
  • ALD-MP001Q Analytical Studio Co., Ltd., material serial number: 1S20180314
  • oFBiBnf (8) is deposited on the hole injection layer 111 so as to have a film thickness of 20 nm, and then N, N-bis [4- (dibenzofuran-4- (dibenzofuran-4-)) represented by the above structural formula (xiii).
  • phenyl] -4-amino-p-terphenyl (abbreviation: DBfBB1TP) was vapor-deposited to a thickness of 10 nm to form a hole transport layer 112.
  • the electron transport layer 114 was formed by co-depositing so as to have a weight ratio of 1: 1 and a film thickness of 15 nm.
  • the light emitting device 8 describes oFBiBnf (8) in the light emitting device 7 as N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H) represented by the above structural formula (xvii).
  • -Fluorene-2-yl) -benzo [b] naphtho [1,2-d] furan-8-amine (abbreviation: FBiBnf (8)) was used in the same manner as in the light emitting device 7.
  • the element structure of the light emitting device is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the luminance-current density characteristics of the light emitting device 7 and the light emitting device 8 are shown in FIG. 71, the current efficiency-luminance characteristic is shown in FIG. 72, the brightness-voltage characteristic is shown in FIG. 73, the current-voltage characteristic is shown in FIG. 74, and the external quantum efficiency- The luminance characteristics are shown in FIG. 75, and the emission spectrum is shown in FIG. 76.
  • the main characteristics of each light emitting device near 1000 cd / m 2 are shown below.
  • the light emitting device 7 and the light emitting device 8 of one aspect of the present invention are EL devices having good luminous efficiency.
  • FIG. 77 shows a graph showing the change in brightness with respect to the driving time at a current density of 50 mA / cm 2. As shown in FIG. 77, it was found that the light emitting device 7 and the light emitting device 8 which are the light emitting devices of one aspect of the present invention are both light emitting devices having a good life.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 110 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H-fluorene-2) represented by the above structural formula (xvii) by a vapor deposition method using resistance heating -Il) -benzo [b] naphtho [1,2-d] furan-8-amine (abbreviation: FBiBnf (8)) and ALD-MP001Q (Analytical Studio Co., Ltd., material serial number: 1S20180314) in weight ratio.
  • FBiBnf (8) is deposited on the hole injection layer 111 so as to have a film thickness of 90 nm, and then 3,3'-(naphthalene-1,4-diyl) represented by the above structural formula (ii).
  • PCzN2 bis (9-phenyl-9H-carbazole)
  • 2- [3'-(9,9-dimethyl-9H-fluorene-2-yl) -1,1'-biphenyl-3-yl represented by the above structural formula (xv) ] -4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzhn) is formed at 10 nm, and further represented by ALD-MC057Q (Analytical Studio Co., Ltd., material serial number: 1S20190330) and the above structural formula (xvii).
  • 8-Kinolinolatritium (abbreviation: Liq) to be produced was co-deposited so as to have a weight ratio of 1: 1 and a film thickness of 15 nm to form an electron transport layer 114.
  • Liq is vapor-deposited to a thickness of 1 nm to form an electron injection layer 115, and aluminum is vapor-deposited to a film thickness of 200 nm to form a second electrode 102.
  • the light emitting device 9 of the example was produced.
  • the element structure of the light emitting device is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the brightness-current density characteristics of the light emitting device 9 and the comparative light emitting device 5 are shown in FIG. 78, the current efficiency-luminance characteristics are shown in FIG. 79, the brightness-voltage characteristics are shown in FIG. 80, the current-voltage characteristics are shown in FIG. -The luminance characteristic is shown in FIG. 82, and the emission spectrum is shown in FIG. 83.
  • the main characteristics of each light emitting device near 1000 cd / m 2 are shown below.
  • the light emitting device 9 of one aspect of the present invention is an EL device having good light emitting efficiency and also showing good light emitting efficiency even in a low luminance region.
  • FIG. 84 shows a graph showing the change in brightness with respect to the driving time at a current density of 50 mA / cm 2. As shown in FIG. 84, it was found that both the light emitting device 9 and the comparative light emitting device 5 are light emitting devices having a good life.
  • indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by a sputtering method to form a first electrode 101.
  • the film thickness was 110 nm, and the electrode area was 2 mm ⁇ 2 mm.
  • the surface of the substrate was washed with water, fired at 200 ° C. for 1 hour, and then UV ozone treatment was performed for 370 seconds.
  • the substrate was introduced into a vacuum vapor deposition apparatus whose internal pressure was reduced to about 10-4 Pa, vacuum fired at 170 ° C. for 30 minutes in a heating chamber inside the vacuum vapor deposition apparatus, and then the substrate was released for about 30 minutes. It was chilled.
  • N- (1,1'-biphenyl-4-yl) -N- (9,9-dimethyl-9H-fluorene-4) represented by the above structural formula (xx) by a vapor deposition method using resistance heating.
  • FBi (4) Bnf (8) is deposited on the hole injection layer 111 so as to have a film thickness of 90 nm, and then 3,3'-(naphthalene-1) represented by the above structural formula (ii).
  • PCzN2 4-Diyl) bis (9-phenyl-9H-carbazole)
  • the electron transport layer 114 was formed by co-depositing so as to have a weight ratio of 1: 1 and a film thickness of 15 nm.
  • Liq is vapor-deposited to a thickness of 1 nm to form an electron injection layer 115, and aluminum is vapor-deposited to a film thickness of 200 nm to form a second electrode 102.
  • the light emitting device 10 of the example was produced.
  • the element structure of the light emitting device 10 is summarized in the table below.
  • the work of sealing the light emitting device with a glass substrate in a glove box having a nitrogen atmosphere so that the light emitting device is not exposed to the atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80 ° C. at the time of sealing. After performing heat treatment for 1 hour), the initial characteristics were measured.
  • the luminance-current density characteristic of the light emitting device 10 is shown in FIG. 85, the current efficiency-luminance characteristic is shown in FIG. 86, the luminance-voltage characteristic is shown in FIG. 87, the current-voltage characteristic is shown in FIG. 89, the emission spectrum is shown in FIG. 90.
  • the main characteristics of the light emitting device 10 in the vicinity of 1000 cd / m 2 are shown below.
  • the light emitting device 10 which is the light emitting device of one aspect of the present invention is an EL device having good luminous efficiency.
  • Electron injection buffer layer 400: Substrate, 401: First electrode, 403: EL layer, 404: Second electrode, 405: Sealing material, 406: Sealing material, 407: Encapsulating substrate, 412: Pad, 420: IC chip, 501: Electrode, 502: Electrode, 511: First light emitting unit, 512: Second light emitting unit, 513: Charge Generation layer, 601: Drive circuit part (source line drive circuit), 602: Pixel part, 603: Drive circuit part (gate line drive circuit), 604: Sealing substrate, 605: Sealing material, 607: Space, 608: Wiring , 609: FPC (Flexible Print Circuit),

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