WO2019171233A1 - 有機化合物、発光素子、発光装置、電子機器および照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器および照明装置 Download PDFInfo
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- WO2019171233A1 WO2019171233A1 PCT/IB2019/051702 IB2019051702W WO2019171233A1 WO 2019171233 A1 WO2019171233 A1 WO 2019171233A1 IB 2019051702 W IB2019051702 W IB 2019051702W WO 2019171233 A1 WO2019171233 A1 WO 2019171233A1
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- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 8
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- 238000000231 atomic layer deposition Methods 0.000 description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 description 8
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S2/00—Systems of lighting devices, not provided for in main groups F21S4/00 - F21S10/00 or F21S19/00, e.g. of modular construction
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S6/00—Lighting devices intended to be free-standing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- One embodiment of the present invention relates to an organic compound, a light-emitting element, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device.
- a light-emitting element e.g., a light-emitting element
- a display module e.g., a liquid crystal display
- a lighting module e.g., a liquid crystal display
- a display device e.g., a light-emitting device
- an electronic device e.g., a light-emitting device
- a lighting device e.g., a light-emitting device that is not limited to the above technical field.
- the technical field of one embodiment of the invention disclosed in this specification and the like relates to an object, a method, or a manufacturing method.
- one embodiment of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter).
- the technical field of one embodiment of the present invention disclosed in this specification more specifically includes a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a power storage device, a memory device, an imaging device, A driving method or a manufacturing method thereof can be given as an example.
- Such a light-emitting element is a self-luminous type, when used as a display pixel, it has advantages such as higher visibility and no need for a backlight compared to liquid crystal, and is suitable as a flat panel display element.
- a display using such a light emitting element has a great advantage that it can be manufactured to be thin and light. Another feature is that the response speed is very fast.
- these light emitting elements can continuously form a light emitting layer in two dimensions, light emission can be obtained in a planar shape. This is a feature that is difficult to obtain with a point light source typified by an incandescent bulb or LED, or a line light source typified by a fluorescent lamp, and therefore has a high utility value as a surface light source applicable to illumination or the like.
- a display and a lighting device using a light-emitting element are suitable for application to various electronic devices.
- research and development are being pursued for a light-emitting element having better efficiency and lifetime.
- Patent Document 1 discloses a substance in which a pyrene skeleton has a plurality of carbazolyl groups having a condensed ring structure.
- an object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide a novel organic compound having a hole transporting property. Another object of one embodiment of the present invention is to provide a novel hole transport material. Another object of one embodiment of the present invention is to provide a novel light-emitting element. Another object is to provide a light-emitting element with favorable light emission efficiency. Another object is to provide a light-emitting element with favorable lifetime. Another object of the present invention is to provide a light-emitting element with low driving voltage.
- Another object of one embodiment of the present invention is to provide a highly reliable light-emitting device, electronic device, and display device. Another object of one embodiment of the present invention is to provide a light-emitting device, an electronic device, and a display device each with low power consumption.
- the present invention should solve any one of the above-mentioned problems.
- One embodiment of the present invention is an organic compound represented by General Formula (G1) below.
- L represents a substituted or unsubstituted naphthalene-1,4-diyl group or a substituted or unsubstituted naphthalene-1,5-diyl group.
- A represents a group represented by the following general formula (gA)
- B represents a group represented by the following general formula (gB).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 7 R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 11 to R 17 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl having 6 to 25 carbon atoms. Represents any of the groups. However, R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be condensed to form a benzene ring.
- Another embodiment of the present invention is the above structure, in which the L is an organic compound represented by the following general formula (gL-1).
- R 41 to R 46 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring. It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to be formed.
- L is an organic compound represented by the following general formula (gL-2).
- R 51 to R 56 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring. It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to be formed.
- the group represented by the general formula (gA) is condensed with at least one combination of R 4 and R 5 , or R 6 and R 7.
- Another embodiment of the present invention is an organic compound in which, in the above structure, the group represented by the general formula (gA) is a group represented by the following general formula (gA-1).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 5 and R 21 to R 24 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substitution having 6 to 25 carbon atoms. Or it represents either an unsubstituted aryl group.
- Another embodiment of the present invention is an organic compound in which, in the above structure, the group represented by the general formula (gA) is a group represented by the following general formula (gA-2).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 3 , R 6 , R 7 and R 25 to R 28 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a carbon atom. It represents either a substituted or unsubstituted aryl group of formulas 6 to 25.
- Another embodiment of the present invention is an organic compound in the above structure, in which the group represented by the general formula (gA) is a group represented by the following general formula (gA-3).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 3 and R 31 to R 38 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substitution having 6 to 25 carbon atoms. Or it represents either an unsubstituted aryl group.
- Another embodiment of the present invention is an organic compound in which the Ar 1 is a phenyl group in the above structure.
- Another embodiment of the present invention is an organic compound in which the group represented by the general formula (gA) and the group represented by the general formula (gB) have the same structure in the above structure.
- Another embodiment of the present invention is an organic compound in which, in the above structure, the group represented by the general formula (gB) is a group represented by the following general formula (gB-1).
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring.
- R 11 to R 17 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Represents one of the following.
- Another embodiment of the present invention is an organic compound in which the Ar 2 is a phenyl group in the above structure.
- Another embodiment of the present invention is an organic compound represented by the following general formula (G2).
- Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 7 R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- R 11 to R 17 may be condensed to form a benzene ring, and the rest
- R 41 to R 46 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 6 to 13 carbon atoms forming a ring. Or a substituted or unsubstituted aryl group.
- Another embodiment of the present invention is an organic compound in which, in the above structure, R 4 and R 5 and R 14 and R 15 are condensed in each combination to form a benzene ring.
- Another embodiment of the present invention is an organic compound in which R 6 and R 7 and R 16 and R 17 are condensed in each combination to form a benzene ring in the above structure.
- Another embodiment of the present invention is an organic compound in which Ar 1 and Ar 2 are phenyl groups in the above structure.
- Another embodiment of the present invention is a light-emitting element material including an organic compound having the above structure.
- Another embodiment of the present invention is a light-emitting element including the organic compound having the above structure.
- Another embodiment of the present invention is a light-emitting element including an organic compound having the above structure between an anode and a light-emitting layer.
- Another embodiment of the present invention is a light-emitting element including an organic compound having the above structure in a light-emitting layer.
- Another embodiment of the present invention is a light-emitting device including the light-emitting element having the above structure and a transistor or a substrate.
- Another embodiment of the present invention is an electronic device including the light-emitting device and a sensor, an operation button, a speaker, or a microphone.
- Another embodiment of the present invention is a lighting device including the light-emitting device having the above structure and a housing.
- the light-emitting device in this specification includes an image display device using a light-emitting element.
- a connector for example, an anisotropic conductive film or TCP (Tape Carrier Package) attached to a light emitting element, a module provided with a printed wiring board at the end of TCP, or a COG (Chip On Glass) method for a light emitting element.
- the light emitting device also includes a module on which an IC (integrated circuit) is directly mounted.
- a lighting fixture or the like may include a light emitting device.
- a novel organic compound can be provided in one embodiment of the present invention.
- a novel organic compound having a hole transporting property can be provided.
- one embodiment of the present invention can provide a novel hole transport material.
- a novel light-emitting element can be provided.
- a light-emitting element with favorable lifetime can be provided.
- a light-emitting element with favorable light emission efficiency can be provided.
- a highly reliable light-emitting device, electronic device, and display device can be provided.
- a light-emitting device, an electronic device, and a display device with low power consumption can be provided.
- FIGS. 4A to 4C are schematic views of light-emitting elements.
- 1 is a conceptual diagram of an active matrix light emitting device.
- FIGS. 4A to 4C each illustrate an electronic device.
- FIGS. 4A to 4C each illustrate an electronic device.
- FIG. 2 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 1.
- the luminance-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2. 4 shows current-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2.
- FIG. The emission spectra of the light-emitting element 2 and the comparative light-emitting element 2.
- Luminance-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4. 4 shows current-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4.
- FIG. The emission spectrum of the light emitting element 4 and the comparative light emitting element 4. Normalized luminance-time change characteristics of the light-emitting element 4 and the comparative light-emitting element 4.
- any one of a benzocarbazole skeleton, a dibenzocarbazole skeleton, or a tribenzocarbazole skeleton, and any one of a carbazole skeleton, a benzocarbazole skeleton, and a dibenzocarbazole skeleton, or a tribenzocarbazole skeleton are naphthalene-1, It is an organic compound bonded through a 4-diyl group or a naphthalene-1,5-diyl group. Each of these skeletons or groups may have a substituent.
- the organic compound of one embodiment of the present invention having such a structure has a favorable hole transport property, and is a material that forms a hole injection layer of a light emitting element, a material that forms a hole transport layer, and a light emitting layer. It is a very suitable material as a host material.
- the organic compound of one embodiment of the present invention that does not include a polyacene skeleton as a substituent is also effective as a material for forming the electron blocking layer, and contributes to improvement in efficiency and lifetime of the light-emitting element.
- the organic compound can be represented by the following general formula (G1).
- L represents a substituted or unsubstituted naphthalene-1,4-diyl group or a substituted or unsubstituted naphthalene-1,5-diyl group.
- L in the general formula (G1) can also be represented by the following general formula (gL-1) or (gL-2).
- R 41 to R 46 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring. It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to be formed.
- R 51 to R 56 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring. It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to be formed.
- the raw material is It is preferable because it is easily available, the synthesis is simple, and the reduction potential is high.
- the raw material is It is preferable because it is easily available, the synthesis is simple, the reduction potential is shallow, and the like.
- A represents a group represented by the following general formula (gA)
- B represents a group represented by the following general formula (gB).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 7 R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 of the group represented by the general formula (gA) are condensed in at least one combination to form a benzene ring. Is preferred.
- a structure in which any of R 4 and R 5 , or R 6 and R 7 is condensed to form a benzene ring is preferable because of its high resistance to reduction.
- the group represented by the general formula (gA) is preferably a group represented by the following general formula (gA-1).
- a light-emitting element using the organic compound can be a light-emitting element with favorable emission efficiency.
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 5 and R 21 to R 24 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substitution having 6 to 25 carbon atoms. Or it represents either an unsubstituted aryl group.
- the group represented by the general formula (gA) is preferably a group represented by the following general formula (gA-2).
- a light-emitting element using the organic compound can have a long lifetime.
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 3 , R 6 , R 7 and R 25 to R 28 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a carbon atom. It represents either a substituted or unsubstituted aryl group of formulas 6 to 25.
- the group represented by the general formula (gA) is preferably a group represented by the following general formula (gA-3) because the thermophysical property is high. .
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 3 and R 31 to R 38 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substitution having 6 to 25 carbon atoms. Or it represents either an unsubstituted aryl group.
- Ar 1 is a phenyl group for easy synthesis and good sublimation. This is preferable.
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.
- R 11 to R 17 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl having 6 to 25 carbon atoms. Represents any of the groups. However, R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be condensed to form a benzene ring.
- the group represented by the general formula (gB) is preferably a group represented by the following general formula (gB-1).
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring.
- R 11 to R 17 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Represents one of the following.
- Ar 2 is preferably a phenyl group from the viewpoint of easy synthesis and good sublimation properties.
- organic compound of one embodiment of the present invention can be represented by the following general formula (G2).
- Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- these are both phenyl groups from the viewpoint of easy synthesis and sublimation.
- R 1 to R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- R 11 to R 17 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Represents one of the following. Of these, R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be condensed to form a benzene ring.
- R 41 to R 46 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 6 to 13 carbon atoms forming a ring. Or a substituted or unsubstituted aryl group.
- a light-emitting element using an organic compound in which R 4 and R 5 and R 14 and R 15 are condensed in each combination to form a benzene ring is a light-emitting element with a long lifetime. This is preferable because it can be performed.
- a light-emitting element using an organic compound in which R 6 and R 7 and R 16 and R 17 are condensed in each combination to form a benzene ring is a light-emitting element with favorable efficiency. This is preferable because it can be performed.
- R 1 to R 7 , R 11 to R 17 , R 21 to R 24 , R 25 to R 28 and R 31 to R 38 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or 3 carbon atoms.
- a group that does not contain three or more polyacenes is preferable.
- substituted or unsubstituted aryl group having 6 to 25 carbon atoms has a substituent
- substituents include an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms.
- an aryl group having 6 to 13 carbon atoms can be used.
- Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a hexyl group, a cyclopropyl group, a cyclohexyl group, a phenyl group, a tolyl group, a naphthyl group, and a biphenyl group.
- a methyl group an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a hexyl group, a cyclopropyl group, a cyclohexyl group, a phenyl group, a tolyl group, a naphthyl group, and a biphenyl group.
- R 1 to R 7 Specific examples of substituents applied to R 1 to R 7 , R 11 to R 17 , R 21 to R 24 , R 25 to R 28 and R 31 to R 38 include the following: The group can be mentioned.
- R 41 to R 46 and R 51 to R 56 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or the number of carbon atoms forming a ring.
- the substituent when a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring has a substituent, the substituent includes an alkyl group having 1 to 6 carbon atoms, 3 to 3 carbon atoms
- a cycloalkyl group having 6 carbon atoms or an aryl group having 6 to 13 carbon atoms can be used. Specific examples thereof include methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, hexyl group, cyclopropyl group, cyclohexyl group, phenyl group, tolyl group, naphthyl group and biphenyl group. be able to.
- substituents applied to R 41 to R 46 and R 51 to R 56 include the following groups.
- Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, and specifically includes a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group. Dimethylfluorenyl group, diphenylfluorenyl group, tert-butylphenyl group, tolyl group, trimethylphenyl group and the like.
- substituent applied to Ar 1 and Ar 2 include the following groups.
- a light-emitting element with a low driving voltage can be manufactured by using them as a host material or a material for a hole transport layer.
- a light-emitting element with favorable light emission efficiency can be manufactured.
- the organic compound as described above can be synthesized by, for example, the following synthesis scheme.
- the organic compound of one embodiment of the present invention includes a halide of a naphthalene derivative or a trifluoromethanesulfonic acid compound (Compound 1) and a carbazole derivative or a condensed polycyclic carbazole as represented by the following synthesis scheme (A-1).
- the target compound can be obtained by coupling a derivative organic boron compound or boronic acid (compounds 2 and 3) by the Suzuki-Miyaura reaction.
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 7 R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring.
- R 11 to R 17 R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be condensed to form a benzene ring, and the rest
- R 60 and R 61 and R 62 and R 63 may be bonded to each other to form a ring.
- X 1 and X 2 represent a halogen or a trifluoromethanesulfonyl group.
- the Suzuki-Miyaura reaction is a chemical reaction in which an organoboron compound and an aryl halide are cross-coupled by the action of a palladium catalyst and a nucleophilic species such as a base to obtain an asymmetric biaryl (biphenyl derivative).
- the catalyst examples include palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) dichloride and the like, and the ligand of the palladium catalyst includes tri (ortho- Tolyl) phosphine, triphenylphosphine, tricyclohexylphosphine, and the like.
- the base examples include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate and sodium carbonate.
- compound 2 and compound 3 are organic boron compounds or boronic acids, but these may be organic aluminum compounds, organic zirconium compounds, organic zinc compounds, or organic tin compounds.
- an organoboron compound or boronic acid of a carbazole derivative is reacted with a halide of a naphthalene derivative.
- an organoboron compound or boronic acid of a naphthalene derivative may be reacted with a halide of a carbazole derivative. good.
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms to form a ring.
- R 1 to R 7 R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 are condensed in at least one combination to form a benzene ring.
- the rest each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. .
- Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring.
- R 11 to R 17 R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be condensed to form a benzene ring, and the rest
- X 3 and X 4 represent a halogen, and iodine, bromine and chlorine are more preferable as the halogen.
- the Hartwick-Buchwald reaction is a chemical reaction in which an aromatic halide and an amine are combined in the presence of a palladium catalyst and a base.
- the palladium catalyst include bis (dibenzylideneacetone) palladium (0) and palladium acetate.
- the ligand include tri (tert-butyl) phosphine, tri (n-hexyl) phosphine, tricyclohexylphosphine, and the like.
- the base include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate. When a solvent is used, toluene, xylene, benzene, tetrahydrofuran and the like can be mentioned.
- reaction represented by the above synthesis scheme (A-2) can be performed by an Ullmann reaction or the like in addition to the Hartwick-Buchwald reaction.
- FIG. 1 illustrates a light-emitting element of one embodiment of the present invention.
- the light-emitting element of one embodiment of the present invention includes the first electrode 101, the second electrode 102, and the EL layer 103, and the hole transport material containing the above organic compound is used for the EL layer.
- the EL layer 103 includes a light emitting layer 113 and may include a hole transport layer 112.
- the light-emitting layer 113 includes a light-emitting material and a host material, and the light-emitting element of one embodiment of the present invention emits light from the light-emitting material.
- the organic compound of one embodiment of the present invention may be contained in any part of the EL layer 103, but is preferably used as a material for the light-emitting layer 113 and the hole-transport layer 112.
- FIG. 1 shows a hole injection layer 111, an electron transport layer 114, and an electron injection layer 115, but the structure of the light-emitting element is not limited thereto.
- the organic compound of one embodiment of the present invention can also be used as a host material for dispersing a light-emitting substance in a light-emitting layer.
- a structure may be employed in which an exciplex of the electron transport material and the organic compound of one embodiment of the present invention is formed by co-evaporation with the electron transport material.
- the organic compound of one embodiment of the present invention has favorable hole-transport properties, it is effective to be used for the hole-transport layer 112 or the electron blocking layer provided between the hole-transport layer 112 and the light-emitting layer 113. It is.
- the light-emitting element of one embodiment of the present invention includes the EL layer 103 including a plurality of layers between the pair of electrodes of the first electrode 101 and the second electrode 102 as described above.
- the EL layer 103 includes at least a light emitting layer 113.
- the layer included in the EL layer 103 is not particularly limited, and has various functions such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier block layer, an exciton block layer, and a charge generation layer.
- Various layer structures can be applied depending on the layers they have.
- the first electrode 101 is preferably formed using a metal, an alloy, a conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
- a metal an alloy, a conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
- ITO Indium Tin Oxide
- IWZO indium oxide-tin oxide
- These conductive metal oxide films are usually formed by a sputtering method, but may be formed by applying a sol-gel method or the like.
- indium oxide-zinc oxide is formed by a sputtering method using a target in which 1 to 20 wt% of zinc oxide is added to indium oxide.
- indium oxide (IWZO) containing tungsten oxide and zinc oxide is formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide.
- Graphene can also be used. Note that by using a composite material described later for a layer in contact with the first electrode 101 in the EL layer 103, an electrode material can be selected regardless of a work function.
- a structure including a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 as shown in FIG.
- FIG. 1B two types of configurations including a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116 are provided. 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 acceptor property.
- a substance having an acceptor property Either an organic or inorganic substance may be used as the acceptor substance, but the acceptor organic compound tends to be easily deposited and handled, and the inorganic compound has a strong acceptor and hole injection. There are substances with excellent properties.
- 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-tetrafluoroquinodi.
- Methane abbreviation: F4-TCNQ
- chloranil 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene
- HAT-CN 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene
- F6-TCNNQ 3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane
- F6-TCNNQ [2- (7-dicyanomethylene-1,3,4,5,6,8,9 , 10-octafluoro-7H-pyrene-2-ylidene) malononitrile] and the like.
- a compound in which an electron withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms such as HAT-CN is preferable because it is thermally stable.
- Radialene derivatives having an electron-withdrawing group are preferable because of their very high electron-accepting properties.
- ⁇ , ⁇ ′, ⁇ ′′ ⁇ 1,2,3-cyclopropanetriylidenetris (4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile), ⁇ , ⁇ ′, ⁇ ′′ -1,2,3-cyclopropanetriylidenetris [2,6-dichloro-3,5-difluoro-4- (trifluoromethyl) benzeneacetonitrile], ⁇ , ⁇ ′, ⁇ ′′ -1,2,3-cyclopropanetriylidentris (2,3,4) , 5,6-pentafluorobenzeneacetonitrile) and the like.
- molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used.
- phthalocyanine compounds such as phthalocyanine (abbreviation: H 2 Pc) and copper phthalocyanine (CuPC), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N′-bis ⁇ 4- [bis (3-methylphenyl) amino] phenyl ⁇ -N, N′-diphenyl- (1,1′-biphenyl) -4,4′-diamine (abbreviation:
- the hole injection layer 111 can also be formed by an aromatic amine compound such as DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT /
- a composite material in which an acceptor substance is contained in a substance having a hole-transport property can be used for the hole-injecting layer 111.
- a composite material in which a substance having an acceptor property is included in a substance having a hole-transporting property restriction on selection of an electrode formation material due to a work function can be relieved significantly. That is, not only a material with a high work function but also a material with a low work function can be used for the first electrode 101.
- the organic compound which has the above acceptor property, and a transition metal oxide can be mentioned. Alternatively, an oxide of a metal belonging to Groups 4 to 8 in the periodic table can be used.
- vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, and the like have high electron accepting properties. Therefore, it is preferable.
- molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.
- the hole-transporting substance used for the composite material various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and high molecular compounds (oligomers, dendrimers, polymers, and the like) can be used.
- the hole-transporting substance used for the composite material is preferably a substance having a hole mobility of 10 ⁇ 6 cm 2 / Vs or higher.
- organic compounds that can be used as the hole transporting substance in the composite material are specifically listed.
- N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4′-bis [ N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N′-bis ⁇ 4- [bis (3-methylphenyl) amino] phenyl ⁇ -N, N′-diphenyl -(1,1′-biphenyl) -4,4′-diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B) And the like.
- DTDPPA 4,4′-bis [ N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl
- DNTPD 1,
- carbazole derivative examples include 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N— (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9-phenylcarbazol-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- (10-phenylanthracen-9-yl) phenyl]
- aromatic hydrocarbon examples include 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di (1-naphthyl).
- pentacene, coronene, and the like can also be used. It may have a vinyl skeleton.
- aromatic hydrocarbon having a vinyl group for example, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.
- DPVBi 4,4′-bis (2,2-diphenylvinyl) biphenyl
- DPVPA 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene
- the organic compound of one embodiment of the present invention can also be used.
- 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: Polymer compounds such as Poly-TPD can also be used.
- the hole injecting layer 111 By forming the hole injecting layer 111, the hole injecting property is improved and a light emitting element with a low driving voltage can be obtained.
- the hole transport layer 112 is formed including a hole transport material.
- the hole transport material preferably has a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher.
- the hole-transport layer 112 preferably contains the organic compound of one embodiment of the present invention. By including the organic compound described in Embodiment 1 in the hole-transport layer 112, a light-emitting element with a long lifetime can be obtained. In addition, a light-emitting element with favorable light emission efficiency can be obtained.
- the light emitting layer 113 is a layer containing a host material and a light emitting material.
- the light emitting material may be a fluorescent light emitting material, a phosphorescent light emitting material, a material exhibiting thermally activated delayed fluorescence (TADF), or another light emitting material. Moreover, even if it is a single layer, it may consist of a plurality of layers containing different light emitting materials. Note that one embodiment of the present invention can be more suitably applied to the case where the light-emitting layer 113 is a layer that emits fluorescent light, particularly a layer that emits blue fluorescent light.
- the organic compound of one embodiment of the present invention can also be used as a host material, and is particularly suitable as a host material for a blue fluorescent material.
- Examples of materials that can be used as the fluorescent light-emitting substance in the light-emitting layer 113 include the following. Other fluorescent materials can also be used.
- condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferable because they have high hole trapping properties and are excellent in luminous efficiency and reliability.
- Examples of materials that can be used as the phosphorescent material in the light-emitting layer 113 include the following.
- a rare earth metal complex such as tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: [Tb (acac) 3 (Phen)]) can be given. These are compounds that mainly emit green phosphorescence, and have an emission peak at 500 nm to 600 nm. Note that an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because of its outstanding reliability and luminous efficiency.
- a known phosphorescent light emitting material may be selected and used.
- TADF material fullerene and its derivatives, acridine and its derivatives, eosin derivatives and the like can be used.
- metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like can be given.
- the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (SnF 2 (Proto IX)), a mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)) represented by the following structural formula, and hematoporphyrin.
- the heterocyclic compound has a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring, both the electron transport property and the hole transport property are high, which is preferable.
- a substance in which a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring are directly bonded increases both the donor property of the ⁇ -electron rich heteroaromatic ring and the acceptor property of the ⁇ -electron deficient heteroaromatic ring. Since the energy difference between the S 1 level and the T 1 level is small, it is particularly preferable because thermally activated delayed fluorescence can be obtained efficiently.
- an aromatic ring to which an electron withdrawing group such as a cyano group is bonded may be used.
- various carrier transport materials such as a material having an electron transport property and a material having a hole transport property can be used.
- NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
- TPD 4,4′-bis [N- (spiro-9,9′-bifluoren-2-yl) ) -N-phenylamino] biphenyl
- BSPB 4,4′-bis [N- (spiro-9,9′-bifluoren-2-yl) ) -N-phenylamino] biphenyl
- BSPB 4,4′-bis [N- (spiro-9,9′-bifluoren-2-yl) ) -N-phenylamino] biphenyl
- BPAFLP 4-phenyl-4 '-(9-phenylfluoren-9-yl) triphenylamine
- mBPAFLP 4-phenyl-4 ′-(9-phenyl-9H-carbamate
- bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ), 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), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4 -Oxadiazole (abbreviation: PBD), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylpheny
- a heterocyclic compound having a diazine skeleton and a heterocyclic compound having a pyridine skeleton are preferable because of their good reliability.
- a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has a high electron transporting property and contributes to a reduction in driving voltage.
- a material having an anthracene skeleton is preferable as the host material.
- a substance having an anthracene skeleton is used as a host material for a fluorescent light-emitting substance, a light-emitting layer with favorable emission efficiency and durability can be realized.
- a substance having an anthracene skeleton used as a host material 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 because hole injection / transport properties are improved.
- the HOMO is shallower by about 0.1 eV than carbazole.
- the host material includes a dibenzocarbazole skeleton, HOMO is shallower than carbazole by about 0.1 eV, which facilitates the entrance of holes, and also has excellent hole transportability and high heat resistance. .
- 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 more preferable as a host material.
- a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.
- Examples of such a substance include 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA), 3- [4- (1-naphthyl)- Phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 7- [4- (10- Phenyl-9-anthryl) phenyl] -7H-dibenzo [c, g] carbazole (abbreviation: cgDBCzPA), 6- [3- (9,10-diphenyl-2-anthryl) phenyl] -benzo [b] naphtho [1 , 2-d] furan (abbreviation: 2 mBnfPPA), 9-phenyl-10-
- CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferable choices because they exhibit very good characteristics.
- the organic compound of one embodiment of the present invention is extremely suitable as a material for a hole transport layer adjacent to a light-emitting layer of a fluorescent light-emitting element using any of these host materials.
- the host material may be a material in which a plurality of types of substances are mixed.
- a mixed host material it is preferable to mix a material having an electron transporting property and a material having a hole transporting property. .
- the exciplex selects a combination that forms an exciplex that emits light that overlaps with the wavelength of the absorption band on the lowest energy side of the light-emitting material, energy transfer becomes smooth and light can be emitted efficiently. preferable. Further, it is preferable to use the structure because the driving voltage is also reduced.
- the electron transport layer 114 is a layer containing a substance having an electron transport property.
- the substance having an electron transporting property those exemplified as the substance having an electron transporting property that can be used for the host material can be used.
- an alkali metal or an alkali such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or the like is used as the electron injection layer 115.
- a layer containing an earth metal or a compound thereof may be provided.
- the electron injecting layer 115 a layer made of a substance having an electron transporting property, an alkali metal, an alkaline earth metal, or a compound thereof, or electride may be used. Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum.
- 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 that can inject holes into a layer in contact with the cathode side of the layer and inject electrons into a layer in contact with the anode side by applying a potential.
- the charge generation layer 116 includes at least a P-type layer 117.
- the P-type layer 117 is preferably formed using the composite material mentioned as the material that can form the hole injection layer 111 described above. Further, the P-type layer 117 may be formed by stacking the above-described film containing an acceptor material and a film containing a hole transport material as a material constituting the composite material. By applying a potential to the P-type layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the second electrode 102 which is a cathode, so that the light-emitting element operates.
- the charge generation layer 116 is preferably provided with one or both of an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117.
- the electron relay layer 118 includes at least a substance having an electron transporting property, and has a function of smoothly transferring electrons by preventing the interaction between the electron injection buffer layer 119 and the P-type layer 117.
- the LUMO level of the substance having an electron transporting property contained in the electron relay layer 118 is the LUMO level of the acceptor substance in the P-type layer 117 and the substance contained in the layer in contact with the charge generation layer 116 in the electron transporting layer 114. It is preferably between the LUMO levels.
- the specific energy level of the LUMO level in the substance having an electron transporting property used for the electron relay layer 118 is ⁇ 5.0 eV or more, preferably ⁇ 5.0 eV or more and ⁇ 3.0 eV or less. Note that as the substance having an electron transporting property used for the electron relay layer 118, a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand is preferably used.
- the electron injection buffer layer 119 includes an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (including an alkali metal compound (including an oxide such as lithium oxide, a halide, and a carbonate such as lithium carbonate and cesium carbonate).
- Alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates) can be used. It is.
- the electron injection buffer layer 119 is formed to include an electron transporting substance and a donor substance, an alkali metal, an alkaline earth metal, a rare earth metal, or 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, carbonates
- rare earth metal compounds In addition to (including oxides, halides, and carbonates), organic compounds such as tetrathianaphthacene (abbreviation: TTN), nickelocene, and decamethyl nickelocene can also be used.
- TTN tetrathianaphthacene
- nickelocene nickelocene
- decamethyl nickelocene can also be used.
- the substance having an electron transporting property can be formed using a material similar to the material of the electron transport layer 114 described above.
- a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) can be used as a material for forming the second electrode 102.
- cathode materials 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 include elements belonging to Group 2, and alloys containing these (MgAg, AlLi), europium (Eu), ytterbium (Yb), and other rare earth metals, and alloys containing these.
- indium oxide-tin oxide containing Al, Ag, ITO, silicon or silicon oxide regardless of the work function.
- Various conductive materials such as the above can be used for the second electrode 102. These conductive materials can be formed by a dry method such as a vacuum evaporation method or a sputtering method, an inkjet method, a spin coating method, or the like. Alternatively, a sol-gel method may be used for a wet method, or a metal material paste may be used for a wet method.
- a formation method of 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 ink jet method, a spin coating method, or the like may be used.
- each electrode or each layer described above may be formed by using different film forming methods.
- the structure of the layers provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, in order to suppress quenching caused by the proximity of the light emitting region and the metal used for the electrode and the carrier injection layer, holes and electrons are separated from the first electrode 101 and the second electrode 102. A structure in which a light-emitting region in which is recombined is provided is preferable.
- This light emitting element is a light emitting element having a plurality of light emitting units between an anode and a cathode.
- One light-emitting unit has substantially the same structure as the EL layer 103 shown in FIG. That is, the light-emitting element illustrated in FIG. 1C is a light-emitting element having a plurality of light-emitting units, and the light-emitting element illustrated in FIG. 1A or 1B is a light-emitting element having one light-emitting unit. It can be said that there is.
- a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between an anode 501 and a cathode 502, and the first light-emitting unit 511 and the second light-emitting unit 512 are stacked.
- a charge generation layer 513 is provided between the two.
- 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 materials as those described in the description of FIG. Further, 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 What is necessary is just to inject holes into the light emitting unit 512.
- the charge generation layer 513 is preferably formed with a structure similar to that of the charge generation layer 116 described with reference to FIG. Since the composite material of an organic compound and a metal oxide is excellent in carrier injecting property and carrier transporting property, low voltage driving and low current driving can be realized. Note that in the case where the surface of the light emitting unit on the anode side is in contact with the charge generation layer 513, the charge generation layer 513 can also serve as a hole injection layer of the light emission unit. It does not have to be provided.
- the electron injection buffer layer 119 plays a role of the electron injection layer in the light emitting unit on the anode side. There is no need to form.
- FIG. 1C illustrates a light-emitting element having two light-emitting units
- the present invention can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked.
- a plurality of light-emitting units are partitioned and arranged between the pair of electrodes by the charge generation layer 513, thereby enabling high-luminance light emission while keeping the current density low.
- a long-life device can be realized.
- a light-emitting device that can be driven at a low voltage and has low power consumption can be realized.
- light emission of a desired color can be obtained as the whole light emitting element.
- a light-emitting element having two light-emitting units a light-emitting element that emits white light as a whole is obtained by obtaining red and green light-emitting colors with a first light-emitting unit and blue light-emitting color with a second light-emitting unit. It is also possible to obtain.
- each layer and electrode such as the EL layer 103, the first light emitting unit 511, the second light emitting unit 512, and the charge generation layer described above may be formed by, for example, a vapor deposition method (including a vacuum vapor deposition method) or a droplet discharge method (inkjet). Or a coating method, a gravure printing method, or the like. They may also include low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), or polymeric materials.
- FIGS. 2A is a top view illustrating the light-emitting device
- FIG. 2B is a cross-sectional view taken along lines AB and CD of FIG. 2A.
- This light-emitting device includes a drive circuit portion (source line drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate line drive circuit) 603 indicated by dotted lines, which control light emission of the light-emitting elements.
- Reference numeral 604 denotes a sealing substrate
- reference numeral 605 denotes a sealing material
- the inside surrounded by the sealing material 605 is a space 607.
- the lead wiring 608 is a wiring for transmitting a signal input to the source line driver circuit 601 and the gate line driver circuit 603, and a video signal, a clock signal, an FPC (flexible printed circuit) 609 serving as an external input terminal, Receives start signal, reset signal, etc.
- FPC flexible printed circuit
- a printed wiring board PWB
- the light-emitting device in this specification includes not only a light-emitting device body but also a state in which an FPC or a PWB is attached thereto.
- a driver circuit portion and a pixel portion are formed over the element substrate 610.
- a source line driver circuit 601 that is a driver circuit portion and one pixel in the pixel portion 602 are illustrated.
- the element substrate 610 is manufactured using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like. That's fine.
- FRP Fiber Reinforced Plastics
- PVF polyvinyl fluoride
- the structure of the transistor used for the pixel or the driver circuit there is no particular limitation on the structure of the transistor used for the pixel or the driver circuit.
- an inverted staggered transistor or a staggered transistor may be used.
- a top-gate transistor or a bottom-gate transistor may be used.
- the semiconductor material used for the transistor is not particularly limited, and for example, silicon, germanium, silicon carbide, gallium nitride, or the like can be used.
- an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In—Ga—Zn-based metal oxide, may be used.
- crystallinity of a semiconductor material used for the transistor there is no particular limitation on the crystallinity of a semiconductor material used for the transistor, and any of an amorphous semiconductor and a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor partially including a crystal region) is used. May be used. It is preferable to use a crystalline semiconductor because deterioration of transistor characteristics can be suppressed.
- an oxide semiconductor is preferably used for a semiconductor device such as a transistor used in a touch sensor described below.
- an oxide semiconductor having a wider band gap than silicon is preferably used.
- the oxide semiconductor preferably contains at least indium (In) or zinc (Zn).
- the oxide semiconductor includes 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.
- the semiconductor layer has a plurality of crystal parts, and the crystal part has a c-axis oriented perpendicular to the formation surface of the semiconductor layer or the top surface of the semiconductor layer, and a grain boundary between adjacent crystal parts. It is preferable to use an oxide semiconductor film which does not contain any oxide.
- the transistor having the above semiconductor layer can hold charge accumulated in the capacitor through the transistor for a long time due to the low off-state current.
- the driving circuit can be stopped while maintaining the gradation of an image displayed in each display region. As a result, an electronic device with extremely low power consumption can be realized.
- a base film In order to stabilize the characteristics of the transistor, it is preferable to provide a base film.
- an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film can be used, which can be formed as a single layer or a stacked layer.
- the base film is formed by sputtering, CVD (Chemical Vapor Deposition) (plasma CVD, thermal CVD, MOCVD (Metal Organic CVD), etc.), ALD (Atomic Layer Deposition), coating, printing, etc. it can. Note that the base film is not necessarily provided if not necessary.
- the FET 623 indicates one of the transistors formed in the drive circuit portion 601.
- the driving circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits.
- CMOS circuits complementary metal-oxide-semiconductor
- PMOS circuits PMOS circuits
- NMOS circuits NMOS circuits.
- a driver integrated type in which a driver circuit is formed over a substrate is shown; however, this is not necessarily required, and the driver circuit can be formed outside the substrate.
- the pixel portion 602 is formed by a plurality of pixels including the switching FET 611, the current control FET 612, and the first electrode 613 electrically connected to the drain thereof, but is not limited thereto.
- the pixel portion may be a combination of two or more FETs and a capacitor.
- an insulator 614 is formed so as to cover an end portion of the first electrode 613.
- a positive photosensitive acrylic resin film can be used.
- a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614 in order to improve the coverage of an EL layer or the like to be formed later.
- a curvature radius 0.2 ⁇ m to 3 ⁇ m.
- the insulator 614 either a negative photosensitive resin or a positive photosensitive resin can be used.
- An EL layer 616 and a second electrode 617 are formed over the first electrode 613.
- a material used for the first electrode 613 functioning as an anode a material having a high work function is preferably used.
- a stack of a titanium nitride film and a film containing aluminum as a main component, a three-layer structure including a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film can be used. Note that with a stacked structure, resistance as a wiring is low, good ohmic contact can be obtained, and a function as an anode can be obtained.
- the EL layer 616 is formed by various methods such as an evaporation method using an evaporation mask, an inkjet method, and a spin coating method.
- the EL layer 616 includes the structure described in Embodiment 1. Further, as another material forming the EL layer 616, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) may be used.
- the second electrode 617 formed over the EL layer 616 and functioning as a cathode a material having a low work function (Al, Mg, Li, Ca, or an alloy or compound thereof (MgAg, MgIn, AlLi etc.) is preferred.
- the second electrode 617 includes a thin metal film and a transparent conductive film (ITO, 2 to 20 wt% oxidation).
- ITO transparent conductive film
- a stack of indium oxide containing zinc, indium tin oxide containing silicon, zinc oxide (ZnO), or the like is preferably used.
- a light-emitting element is formed using the first electrode 613, the EL layer 616, and the second electrode 617.
- the light-emitting element is the light-emitting element described in Embodiment 2.
- the pixel portion includes a plurality of light-emitting elements, the light-emitting device in this embodiment includes both the light-emitting elements described in Embodiment 2 and light-emitting elements having other structures. It may be.
- the sealing substrate 604 is bonded to the element substrate 610 with the sealant 605, whereby the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. Yes.
- the space 607 is filled with a filler and may be filled with a sealing material in addition to the case of being filled with an inert gas (such as nitrogen or argon).
- an inert gas such as nitrogen or argon.
- a recess is formed in the sealing substrate, and a desiccant is provided therein, whereby deterioration due to the influence of moisture can be suppressed, which is a preferable configuration.
- an epoxy resin or glass frit is preferably used for the sealant 605. Moreover, it is desirable that these materials are materials that do not transmit moisture and oxygen as much as possible.
- a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as a material used for the sealing substrate 604.
- 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 sealant 605. The protective film can be provided so as to cover the exposed side surfaces of the surface and side surfaces of the pair of substrates, the sealing layer, the insulating layer, and the like.
- the protective film a material that hardly permeates impurities such as water can be used. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.
- oxide, nitride, fluoride, sulfide, ternary compound, metal or polymer can be used as a material constituting the protective film.
- oxide, nitride, fluoride, sulfide, ternary compound, metal or polymer can be used.
- the protective film is preferably formed by using a film formation method having good step coverage (step coverage).
- a film formation method having good step coverage there is an atomic layer deposition (ALD: Atomic Layer Deposition) method.
- a material that can be formed by an ALD method is preferably used for the protective film.
- ALD method a dense protective film with reduced defects such as cracks and pinholes or a uniform thickness can be formed.
- damage to the processed member when forming the protective film can be reduced.
- a protective film that is uniform and has few defects can be formed on the surface having a complicated uneven shape, and the top surface, side surface, and back surface of the touch panel.
- the light-emitting device described in Embodiment 2 is used for the light-emitting device in this embodiment, a light-emitting device having favorable characteristics can be obtained. Specifically, since the light-emitting element described in Embodiment 2 is a light-emitting element with a long lifetime, a light-emitting device with favorable reliability can be obtained. In addition, since the light-emitting device using the light-emitting element described in Embodiment 2 has favorable light emission efficiency, it can be a light-emitting device with low power consumption.
- FIG. 3 shows an example of a light-emitting device in which a light-emitting element that emits white light is formed and a full color is obtained by providing a colored layer (color filter) or the like.
- 3A shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, and a pixel portion.
- a driver circuit portion 1041 light emitting element first electrodes 1024W, 1024R, 1024G, and 1024B, a partition wall 1025, an EL layer 1028, a light emitting element second electrode 1029, a sealing substrate 1031, a sealant 1032, and the like are illustrated. ing.
- colored layers are provided over a transparent base material 1033.
- a black matrix 1035 may be further provided.
- the transparent base material 1033 provided with the coloring layer and the black matrix is aligned and fixed to the substrate 1001. Note that the coloring layer and the black matrix 1035 are covered with an overcoat layer 1036.
- there are a light emitting layer that emits light without passing through the colored layer and a light emitting layer that emits light through the colored layer of each color, and passes through the colored layer. Since the light that does not pass is white, and the light that passes through the colored layer is red, green, and blue, an image can be expressed by pixels of four colors.
- FIG. 3B illustrates an example in which a colored layer (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020.
- the coloring layer may be provided between the substrate 1001 and the sealing substrate 1031.
- a light-emitting device having a structure in which light is extracted to the substrate 1001 side where the FET is formed bottom emission type
- a structure in which light is extracted to the sealing substrate 1031 side top-emission type
- FIG. 1 A cross-sectional view of a top emission type light emitting device is shown in FIG.
- a substrate that does not transmit light can be used as the substrate 1001.
- the connection electrode for connecting the FET and the anode of the light emitting element is manufactured, it is formed in the same manner as the bottom emission type light emitting device.
- a third interlayer insulating film 1037 is formed so as to cover the electrode 1022. This insulating film may play a role of planarization.
- the third interlayer insulating film 1037 can be formed using other known materials in addition to the same material as the second interlayer insulating film.
- the first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes here, but may be cathodes. In the case of a top emission type light emitting device as shown in FIG. 4, the first electrode is preferably a reflective electrode.
- the EL layer 1028 has a structure as described for the EL layer 103 in Embodiment 1 and an element structure in which white light emission can be obtained.
- sealing can be performed with a sealing substrate 1031 provided with colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B).
- a black matrix 1035 may be provided on the sealing substrate 1031 so as to be positioned between the pixels.
- the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) and black matrix may be covered with an overcoat layer 1036.
- the sealing substrate 1031 is a light-transmitting substrate.
- full-color display is performed with four colors of red, green, blue, and white
- full-color with four colors of red, yellow, green, and blue, and three colors of red, green, and blue. Display may be performed.
- a microcavity structure can be suitably applied.
- a light-emitting element having a microcavity structure is obtained by using a first electrode as a reflective electrode and a second electrode as a semi-transmissive / semi-reflective electrode. Between the reflective electrode and the semi-transmissive / semi-reflective electrode, at least an EL layer is provided, and at least a light-emitting layer serving as a light emitting region is provided.
- the reflective electrode is a film having a visible light reflectance of 40% to 100%, preferably 70% to 100%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less.
- the semi-transmissive / semi-reflective electrode is a film having a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ cm or less. .
- the light emitted from the light emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode and resonates.
- the light-emitting element 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 composite material, the carrier transporting material, or the like. Thereby, between the reflective electrode and the semi-transmissive / semi-reflective electrode, it is possible to intensify the light having a resonating wavelength and attenuate the light having a wavelength not resonating.
- the light (first reflected light) reflected and returned by the reflective electrode causes a large interference with the light (first incident light) directly incident on the semi-transmissive / semi-reflective electrode from the light emitting layer, it is reflected.
- the optical distance between the electrode and the light emitting layer is 2n-1) ⁇ / 4 (where n is a natural number of 1 or more and ⁇ is the wavelength of light emission to be amplified).
- the EL layer may have a structure having a plurality of light emitting layers or a structure having a single light emitting layer.
- a plurality of EL layers may be provided in one light-emitting element with a charge generation layer interposed therebetween, and one or a plurality of light-emitting layers may be formed in each EL layer.
- microcavity structure By having a microcavity structure, it becomes possible to increase the light emission intensity in the front direction of a specific wavelength, so that power consumption can be reduced.
- a microcavity structure that matches the wavelength of each color in all sub-pixels, in addition to the effect of improving luminance by yellow light emission.
- a light-emitting device having favorable characteristics can be obtained.
- the light-emitting device described in Embodiment 2 is used for the light-emitting device in this embodiment, a light-emitting device having favorable characteristics can be obtained. Specifically, since the light-emitting element described in Embodiment 2 is a light-emitting element with a long lifetime, a light-emitting device with favorable reliability can be obtained. In addition, since the light-emitting device using the light-emitting element described in Embodiment 2 has favorable light emission efficiency, it can be a light-emitting device with low power consumption.
- FIG. 5 shows a passive matrix light-emitting device manufactured by applying the present invention.
- 5A is a perspective view illustrating the light-emitting device
- FIG. 5B is a cross-sectional view taken along line XY in FIG. 5A.
- an EL layer 955 is provided over the substrate 951 between the electrode 952 and the electrode 956.
- An end portion of the electrode 952 is covered with an insulating layer 953.
- a partition layer 954 is provided over 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 approaches the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 has a trapezoidal shape, and the bottom side (the side facing the insulating layer 953 in the same direction as the surface direction of the insulating layer 953) is the top side (the surface of the insulating layer 953).
- the direction is the same as the direction and is shorter than the side not in contact with the insulating layer 953. In this manner, by providing the partition layer 954, defects in the light-emitting element due to static electricity or the like can be prevented.
- a passive matrix light-emitting device also uses the light-emitting element described in Embodiment 2 and can be a light-emitting device with high reliability or low power consumption.
- the light-emitting device described above is a light-emitting device that can be suitably used as a display device that expresses an image because it can control a large number of minute light-emitting elements arranged in a matrix.
- FIGS. 6B is a top view of the lighting device
- FIG. 6A is a cross-sectional view taken along line ef in FIG. 6B.
- a first electrode 401 is formed over a light-transmitting substrate 400 which is a support.
- the first electrode 401 corresponds to the first electrode 101 in Embodiment 1.
- the first electrode 401 is formed using a light-transmitting 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 over the first electrode 401.
- the EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 1, or a structure in which the light-emitting units 511 and 512 and the charge generation layer 513 are combined. For these configurations, refer to the description.
- a second electrode 404 is formed so as to cover the EL layer 403.
- the second electrode 404 corresponds to the second electrode 102 in Embodiment 1.
- the second electrode 404 is formed using a highly reflective material.
- a voltage is supplied to the second electrode 404 by being connected to the pad 412.
- the lighting device described in this embodiment includes a light-emitting element including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting element is a light-emitting element with high emission efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.
- the substrate 400 on which the light-emitting element having the above structure is formed and the sealing substrate 407 are fixed using sealing materials 405 and 406 and sealed, whereby the lighting device is completed. Either one of the sealing materials 405 and 406 may be used.
- a desiccant can be mixed in the inner sealing material 406 (not shown in FIG. 6B), so that moisture can be adsorbed and reliability can be improved.
- an external input terminal can be obtained.
- an IC chip 420 mounted with a converter or the like may be provided thereon.
- the lighting device described in this embodiment uses the light-emitting element described in Embodiment 2 as an EL element, and thus can be a light-emitting device with favorable reliability. Further, a light-emitting device with low power consumption can be obtained.
- Embodiment 5 examples of electronic devices each including the light-emitting element described in Embodiment 2 will be described.
- the light-emitting element described in Embodiment 2 has a long lifetime and is a highly reliable light-emitting element.
- the electronic device described in this embodiment can be an electronic device having a highly reliable light-emitting portion.
- a television device also referred to as a television or a television receiver
- a monitor for a computer a digital camera, a digital video camera, a digital photo frame
- a mobile phone a mobile phone
- Large-sized game machines such as portable telephones, portable game machines, portable information terminals, sound reproduction apparatuses, and pachinko machines. Specific examples of these electronic devices are shown below.
- FIG. 7A illustrates an example of a television device.
- a display portion 7103 is incorporated in a housing 7101.
- a structure in which the housing 7101 is supported by a stand 7105 is shown.
- Images can be displayed on the display portion 7103, and the display portion 7103 is formed by arranging the light-emitting elements described in Embodiment 2 in a matrix.
- the television device can be operated with an operation switch included in the housing 7101 or a separate remote controller 7110.
- Channels and volume can be operated with an operation key 7109 provided in the remote controller 7110, and an image displayed on the display portion 7103 can be operated.
- the remote controller 7110 may be provided with a display portion 7107 for displaying information output from the remote controller 7110.
- the television device is provided with a receiver, a modem, and the like.
- General TV broadcasts can be received by a receiver, and connected to a wired or wireless communication network via a modem, so that it can be unidirectional (sender to receiver) or bidirectional (sender and receiver). It is also possible to perform information communication between each other or between recipients).
- FIG. 7B1 illustrates a computer, which includes a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. Note that this computer is manufactured by using the light-emitting elements described in Embodiment 2 for the display portion 7203 in a matrix.
- the computer shown in FIG. 7B1 may have a form as shown in FIG.
- a computer in FIG. 7B2 includes a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206.
- the second display portion 7210 is a touch panel type, and input can be performed by operating a display for input displayed on the second display portion 7210 with a finger or a dedicated pen.
- the second display portion 7210 can display not only an input display but also other images.
- the display portion 7203 may also be a touch panel.
- FIG. 7D illustrates an example of a mobile terminal.
- the mobile phone includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like.
- the cellular phone 7400 includes a display portion 7402 which is manufactured by arranging the light-emitting elements described in Embodiment 2 in a matrix.
- the portable terminal illustrated in FIG. 7C can have a structure in which information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call or creating a mail can be performed by touching the display portion 7402 with a finger or the like.
- the first mode is a display mode mainly for displaying an image.
- the first is a display mode mainly for displaying images, and the second is an input mode mainly for inputting information such as characters.
- the third is a display + input mode in which the display mode and the input mode are mixed.
- the display portion 7402 may be set to a character input mode mainly for inputting characters, and an operation for inputting characters displayed on the screen may be performed. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402.
- the orientation (portrait or horizontal) of the mobile terminal is determined, and the screen display of the display portion 7402 is automatically displayed. Can be switched automatically.
- the screen mode is switched by touching the display portion 7402 or operating the operation button 7403 of the housing 7401. Further, switching can be performed depending on the type of image displayed on the display portion 7402. For example, if the image signal to be displayed on the display unit is moving image data, the mode is switched to the display mode, and if it is text data, the mode is switched to the input mode.
- the screen mode is switched from the input mode to the display mode. You may control.
- the display portion 7402 can function as an image sensor. For example, personal authentication can be performed by touching the display portion 7402 with a palm or a finger and capturing an image of a palm print, a fingerprint, or the like. In addition, if a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display portion, finger veins, palm veins, and the like can be imaged.
- the applicable range of the light-emitting device including the light-emitting element described in Embodiment 2 is so wide that the light-emitting device can be applied to electronic devices in various fields.
- a highly reliable electronic device can be obtained by using the light-emitting element described in Embodiment 2.
- FIG. 8A is a schematic diagram illustrating an example of a cleaning robot.
- the cleaning robot 5100 includes a display 5101 disposed on the upper surface, a plurality of cameras 5102 disposed on the side surface, brushes 5103, and operation buttons 5104. Although not shown, the lower surface of the cleaning robot 5100 is provided with a tire, a suction port, and the like. In addition, the cleaning robot 5100 includes various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, an optical sensor, and a gyro sensor. Moreover, the cleaning robot 5100 includes a wireless communication unit.
- the cleaning robot 5100 is self-propelled, can detect the dust 5120, and can suck the dust from the suction port provided on the lower surface.
- the cleaning robot 5100 can analyze an image captured by the camera 5102 and determine whether there is an obstacle such as a wall, furniture, or a step. In addition, when an object that is likely to be entangled with the brush 5103 such as wiring is detected by image analysis, the rotation of the brush 5103 can be stopped.
- the display 5101 can display the remaining battery level, the amount of dust sucked, and the like.
- the route on which the cleaning robot 5100 has traveled may be displayed on the display 5101.
- 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.
- An image captured 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 away from home.
- the display on the display 5101 can be confirmed with a portable electronic device such as a smartphone.
- the light-emitting device of one embodiment of the present invention can be used for the display 5101.
- a robot 2100 illustrated in FIG. 8B includes an arithmetic 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 speaking voice, environmental sound, and the like.
- 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 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 an information terminal that can be removed, and is installed at a fixed position of the robot 2100 to enable charging and data transfer.
- the upper camera 2103 and the lower camera 2106 have a function of imaging the surroundings of the robot 2100.
- the obstacle sensor 2107 can detect the presence or absence of an obstacle in the traveling direction when the robot 2100 moves forward using the moving mechanism 2108.
- the robot 2100 can recognize the surrounding environment using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107, and can move safely.
- the light-emitting device of one embodiment of the present invention can be used for the display 2105.
- FIG. 8C illustrates 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, operation keys 5005 (including a power switch or an operation switch), a connection terminal 5006, and a sensor 5007 (force, displacement, position, speed). , Acceleration, angular velocity, number of revolutions, distance, light, liquid, magnetism, temperature, chemical, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell, or infrared
- the light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the second display portion 5002.
- FIG. 9 illustrates an example in which the light-emitting element described in Embodiment 2 is used for a table lamp which is a lighting device.
- the desk lamp illustrated in FIG. 9 includes a housing 2001 and a light source 2002, and the lighting device described in Embodiment 3 may be used as the light source 2002.
- FIG. 10 illustrates an example in which the light-emitting element described in Embodiment 2 is used as an indoor lighting device 3001. Since the light-emitting element described in Embodiment 2 is a highly reliable light-emitting element, a highly reliable lighting device can be obtained. Further, since the light-emitting element described in Embodiment 2 can have a large area, the light-emitting element can be used as a large-area lighting device. Further, since the light-emitting element described in Embodiment 2 is thin, it can be used as a thin lighting device.
- the light-emitting element described in Embodiment 2 can be mounted on a windshield or a dashboard of an automobile.
- FIG. 11 illustrates one mode in which the light-emitting element described in Embodiment 2 is used for a windshield or a dashboard of an automobile.
- Display regions 5200 to 5203 are displays provided using the light-emitting element described in Embodiment 2.
- a display region 5200 and a display region 5201 are display devices on which the light-emitting elements described in Embodiment 2 provided on a windshield of an automobile are mounted.
- the light-emitting element described in Embodiment 2 can be a display device in a so-called see-through state in which a first electrode and a second electrode are formed using a light-transmitting electrode so that opposite sides can be seen through. . If it is a see-through display, it can be installed without obstructing the field of view even if it is installed on the windshield of an automobile. Note that in the case where a transistor for driving or the like is provided, a light-transmitting transistor such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.
- a display region 5202 is a display device on which the light-emitting element described in Embodiment 2 provided in a pillar portion is mounted.
- the field of view blocked by the pillar can be complemented by projecting an image from the imaging means provided on the vehicle body.
- the display area 5203 provided in the dashboard portion compensates for the blind spot by projecting the image from the imaging means provided outside the vehicle from the field of view blocked by the vehicle body, and improves safety. Can do. By displaying the video so as to complement the invisible part, it is possible to check the safety more naturally and without a sense of incongruity.
- the display area 5203 can provide various information by displaying navigation information, a speedometer, a tachometer, a travel distance, a fuel gauge, a gear state, an air conditioner setting, and the like.
- the display items and layout can be appropriately changed according to the user's preference. Note that these pieces of information can also be provided in the display areas 5200 to 5202.
- the display areas 5200 to 5203 can also be used as lighting devices.
- FIG. 12A and 12B show a foldable portable information terminal 5150.
- FIG. A foldable portable information terminal 5150 includes a housing 5151, a display region 5152, and a bent portion 5153.
- FIG. 12A shows the portable information terminal 5150 in a developed state.
- FIG. 12B illustrates the portable information terminal in a folded state. Although the portable information terminal 5150 has a large display area 5152, the portable information terminal 5150 is compact and excellent in portability when folded.
- the display region 5152 can be folded in half by a bent portion 5153.
- the bent portion 5153 includes an extendable member and a plurality of support members. When the bent portion 5153 is folded, the extendable member is extended, and the bent portion 5153 is folded with a radius of curvature of 2 mm or more, preferably 3 mm or more. It is.
- the display area 5152 may be a touch panel (input / output device) that controls a touch sensor (input device).
- the light-emitting device of one embodiment of the present invention can be used for the display region 5152.
- FIG. 13A to 13C show a foldable portable information terminal 9310.
- FIG. 13A illustrates the portable information terminal 9310 in a developed state.
- FIG. 13B illustrates the portable information terminal 9310 in a state in which the state is changing from one of the developed state or the folded state to the other.
- FIG. 13C illustrates the portable information terminal 9310 in a folded state.
- the portable information terminal 9310 is excellent in portability in the folded state and excellent in display listability due to a seamless wide display area in the expanded state.
- the display 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).
- the display panel 9311 can be reversibly deformed from a developed state to a folded state by bending the two housings 9315 through the hinge 9313.
- the light-emitting device of one embodiment of the present invention can be used for the display panel 9311.
- the side of the display panel 9311 can display information icons, frequently used applications, program shortcuts, and the like, so that information can be confirmed and applications can be activated smoothly.
- PaBC2N 8,8 ′-(naphthalene-1,4-diyl) bis (11-phenyl-11H-benzo [a] carbazole)
- the method will be described in detail.
- the structural formula of PaBC2N is shown below.
- a synthesis scheme is shown below.
- Sublimation purification of 0.83 g of the obtained powder was performed by a train sublimation method.
- the sublimation purification was performed by heating at 330 ° C. under conditions of a pressure of 3.3 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.71 g of white powder was obtained with a recovery rate of 85%.
- FIG. 14 shows a 1 H NMR chart of the obtained compound, and numerical data are shown below.
- An ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of PaBC2N and a solid thin film were measured.
- absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of PaBC2N and a solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100) was used.
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- FIG. 15 shows the absorption spectrum and emission spectrum of the toluene solution
- FIG. 16 shows the absorption spectrum and emission spectrum of the thin film.
- the thin film of PaBC2N is a good film quality that hardly aggregates even in the air and has little change in form.
- the HOMO level and LUMO level of PaBC2N were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below.
- an electrochemical analyzer manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C
- DMF dehydrated dimethylformamide
- tetra-n-butylammonium perchlorate supporting electrolyte
- n-Bu 4 NClO 4 tetra-n-butylammonium perchlorate
- T0836 tetra-n-butylammonium perchlorate
- a platinum electrode manufactured by BAS Co., Ltd., PTE platinum electrode
- a platinum electrode manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)
- Ag / Ag + electrode manufactured by BAS Co., Ltd., RE7 non-aqueous solvent system reference electrode
- the measurement was performed at room temperature (20 to 25 ° C.). Further, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured.
- Ea was an intermediate potential of the oxidation-reduction wave
- Ec was an intermediate potential of the reduction-oxidation wave.
- the potential energy with respect to the vacuum level of the reference electrode used in this example is ⁇ 4.94 [eV]
- the HOMO level [eV] ⁇ 4.94 ⁇ Ea
- LUMO the HOMO level and the LUMO level can be obtained respectively.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- Sublimation purification of 0.60 g of the obtained white solid was performed by a train sublimation method.
- the sublimation purification was performed by heating at 340 ° C. under conditions of a pressure of 3.4 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.50 g of a pale yellow solid was obtained with a recovery rate of 83%.
- FIG. 17 shows a 1 H NMR chart of the obtained pale yellow solid, and numerical data are shown below.
- the absorption spectrum and emission spectrum of the toluene solution of PacDBC2N and the solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate.
- the thin film of PacDBC2N is a good film quality that hardly aggregates even in the air and has little change in form.
- the HOMO level and LUMO level of PacDBC2N were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- the obtained methanol suspension of the oily substance was irradiated with ultrasonic waves, and the solid was collected by suction filtration.
- the obtained solid was purified by high performance liquid chromatography (HPLC) to give an oil. Methanol was added to the resulting oily matter and the precipitated solid was recovered, and the target white powder was obtained in a yield of 0.68 g and a yield of 53%.
- HPLC high performance liquid chromatography
- 0.65 g of the obtained white powder was purified by sublimation by a train sublimation method. Sublimation purification was performed by heating at 370 ° C. under conditions of a pressure of 3.2 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.45 g of white powder was obtained with a recovery rate of 69%.
- FIG. 20 shows a 1 H NMR chart of the obtained white powder, and numerical data is shown below.
- the absorption spectrum and emission spectrum of the toluene solution of PcBC2N and the solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG.
- the horizontal axis represents wavelength
- the vertical axis represents absorption intensity and emission intensity.
- the measurement result of the absorption spectrum and emission spectrum of a solid thin film is shown in FIG.
- the toluene solution of PcBC2N showed absorption peaks at around 368 nm and 333 nm, and similarly, the emission wavelength peaks were 376 nm and 400 nm (excitation wavelength: 335 nm). Further, from FIG. 22, the PcBC2N thin film showed an absorption peak at around 374 nm and 338 nm, and similarly, the emission wavelength peak was seen at around 430 nm (excitation wavelength: 355 nm). It was confirmed that PcBC2N emitted blue light.
- the thin film of PcBC2N is a good film quality that hardly aggregates even in the air and has little change in form.
- the HOMO level and LUMO level of PcBC2N were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- PCNPaBC 11-phenyl-8- [4- (9-phenylcarbazol-3-yl) -1-naphthyl] benzo [a] carbazole (abbreviation: PCNPaBC) which is an organic compound of one embodiment of the present invention is used.
- PCNPaBC carbazole
- the mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen.
- 0.12 g (0.53 mmol) of palladium (II) acetate was added, and the mixture was stirred at 100 ° C. for 23 hours under a nitrogen stream.
- the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene.
- the obtained extracted solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate.
- the obtained mixture was naturally filtered, and the filtrate was concentrated to obtain an oily substance.
- the obtained solid was purified by high performance liquid chromatography (developing solvent: chloroform) and recrystallized with a mixed solvent of ethyl acetate and methanol. As a result, 1.7 g of the target white solid was obtained in a yield of 58%. Obtained.
- a synthesis scheme is shown below.
- Sublimation purification of 1.7 g of the obtained white solid was performed by a train sublimation method. Sublimation purification was performed by heating at 320 ° C. under conditions of a pressure of 5.0 Pa and an argon flow rate of 10 mL / min. After purification by sublimation, 0.64 g of white solid was obtained with a recovery rate of 38%.
- FIG. 23 shows a 1 H NMR chart of the obtained white powder, and numerical data is shown below.
- the absorption spectrum and emission spectrum of the toluene solution of PCNPaBC and the solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate.
- T / (100-% R)] where% T represents transmittance,% R represents reflectance
- the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG.
- the horizontal axis represents wavelength
- the vertical axis represents absorption intensity and emission intensity.
- the measurement result of the absorption spectrum and emission spectrum of a solid thin film is shown in FIG.
- the toluene solution of PCNPaBC showed absorption peaks around 358 nm, 317 nm, and 300 nm, and the emission wavelength peak was 415 nm (excitation wavelength: 323 nm).
- the PCNPaBC thin film showed absorption peaks around 372 nm, 362 nm, and 319 nm, and the emission wavelength peak was found around 423 nm (excitation wavelength: 340 nm).
- the compound of one embodiment of the present invention can also be used as a host material or a hole transport material of a light-emitting substance or a fluorescent light-emitting substance in the visible range.
- the PCNPaBC thin film is a good film quality that hardly aggregates in the air and has little change in form.
- the HOMO level and LUMO level of PCNPaBC were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- Step 1 Synthesis of 10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl] benzo [c] carbazole>
- 2.0 g (4.5 mmol) of 3- (4-bromo-1-naphthyl) -9-phenyl-9H-carbazole, 2- (benzo [c] carbazol-10-yl) -4, 4,5,5-tetramethyl-1,3,2-dioxaborolane 1.9 g (5.4 mmol), tris (2-methylphenyl) phosphine 0.28 g (0.91 mmol), potassium carbonate 1.5 g (11 mmol) , 45 mL of toluene, 6 mL of ethanol, and 6 mL of water were added.
- the mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen.
- the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene.
- the obtained extraction solvent and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate.
- the obtained mixture was naturally filtered, and the filtrate was concentrated to obtain an oily substance.
- the synthesis scheme of Step 1 is shown below.
- FIG. 26 shows a 1 H NMR chart of the obtained white solid, and numerical data are shown below.
- the mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen.
- 0.40 mL (0.13 mmol) of a 10 wt% tritert-butylphosphine hexane solution and 0.074 g (0.13 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was added at 150 ° C. under a nitrogen stream at 14 ° C. Stir for hours. After stirring, water was added to the resulting mixture to separate the organic layer and the aqueous layer, and then the aqueous layer was extracted with toluene.
- the obtained extracted solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate.
- the obtained mixture was naturally filtered, and the filtrate was concentrated to obtain an oily substance.
- the synthesis scheme of Step 2 is shown below.
- Sublimation purification of 1.8 g of the obtained white solid was performed by a train sublimation method. Sublimation purification was performed by heating at 340 ° C. under conditions of a pressure of 5.0 Pa and an argon flow rate of 10 mL / min. After purification by sublimation, 1.1 g of a white solid was obtained with a recovery rate of 61%.
- FIG. 27 shows a 1 H NMR chart of the obtained white solid, and numerical data is shown below.
- the absorption spectrum and emission spectrum of the toluene solution of PCNPcBC and the solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate.
- T / (100-% R)] where% T represents transmittance,% R represents reflectance
- the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- FIG. 29 shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film.
- the PCNPcBC thin film is a good film quality that hardly aggregates in the air and has little change in form.
- the HOMO level and LUMO level of PCNPcBC were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- Step 1 Synthesis of 10- [5- (9-phenylcarbazol-3-yl) -1-naphthyl] benzo [c] carbazole>
- the mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen.
- the aqueous layer of the obtained mixture was extracted with toluene.
- the obtained extracted solution and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate.
- the obtained mixture was naturally filtered, and the filtrate was concentrated to obtain an oily substance.
- the obtained oily substance was purified by silica gel column chromatography (toluene) and further recrystallized with a mixed solvent of ethyl acetate and methanol to obtain 2.0 g of the objective white solid in a yield of 80%.
- the synthesis scheme of Step 1 is shown below.
- FIG. 30 shows a 1 H NMR chart of the obtained white solid, and numerical data are shown below.
- the mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen.
- the obtained extracted solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate.
- the obtained mixture was gravity filtered, and the filtrate was concentrated to obtain an oily substance.
- the white solid was obtained in a yield of 1.9 g and a yield of 84%.
- the synthesis scheme of Step 2 is shown below.
- Sublimation purification of 1.9 g of the obtained white solid was performed by a train sublimation method. Sublimation purification was performed by heating at 340 ° C. under conditions of a pressure of 5.0 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 1.1 g of a white solid was obtained with a recovery rate of 58%.
- FIG. 31 shows a 1 H NMR chart of the obtained white solid, and numerical data is shown below.
- an absorption spectrum and an emission spectrum of a toluene solution of 1,5PCNPcBC and a solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate.
- T / (100-% R)] where% T represents transmittance,% R represents reflectance
- the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- FIG. 32 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution.
- the horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.
- the measurement result of the absorption spectrum and emission spectrum of a solid thin film is shown in FIG.
- the toluene solution of 1,5PCNPcBC had absorption peaks near 369 nm, 332 nm, and 323 nm, and the emission wavelength peaks were 375 nm and 395 nm (excitation wavelength: 333 nm). Further, as shown in FIG. 33, the 1,5PCNPcBC thin film showed absorption peaks at around 372 nm and 334 nm, and the emission wavelength peaks were seen at around 385 nm and 407 nm (excitation wavelength: 330 nm).
- the 1,5PCNPcBC thin film is a good film quality that hardly aggregates in the air and has little change in form.
- the HOMO level and LUMO level of 1,5PCNPcBC were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- a light-emitting element 1 which is a light-emitting element of one embodiment of the present invention described in Embodiment Mode and a comparative light-emitting element 1 which is a light-emitting element of a comparative example will be described in detail.
- Structural formulas of organic compounds used in the light-emitting element 1 and the comparative light-emitting element 1 are shown below.
- indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, whereby the anode 101 was formed.
- the film thickness was 70 nm
- the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
- the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.
- the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
- the substrate on which the anode 101 is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the anode 101 is formed is downward, and vapor deposition using resistance heating is performed on the anode 101.
- 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq ⁇ ) represented by the above structural formula (iv) is formed over the light-emitting layer 113.
- II) is deposited to a thickness of 15 nm
- 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (v) Was deposited to a thickness of 10 nm to form the electron transport layer 114.
- lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injection layer 115, and then aluminum is deposited to a thickness of 200 nm to form a cathode. 102 was formed to manufacture the light-emitting element 1.
- the comparative light-emitting element 1 includes 3,3 ′-(naphthalene-1,4-diyl) represented by the above structural formula (vi) in which PaBC2N used for the hole injection layer 111 and the hole transport layer 112 in the light-emitting element 1 is represented.
- the light-emitting element 1 was manufactured in the same manner as the light-emitting element 1 except that bis (9-phenyl-9H-carbazole) (abbreviation: PCzN2) was used.
- the luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1 are shown in FIG. 34, the current efficiency-luminance characteristics in FIG. 35, the brightness-voltage characteristics in FIG. 36, and the current-voltage characteristics in FIG.
- the luminance characteristics are shown in FIG. 38, and the emission spectrum is shown in FIG.
- Table 2 summarizes element characteristics in the vicinity of luminance of 1000 cd / m 2 .
- the light-emitting element 1 of one embodiment of the present invention using PaBC2N was a light-emitting element with better light emission efficiency than the comparative light-emitting element 1 using PCzN2.
- a light-emitting element 2 which is a light-emitting element of one embodiment of the present invention described in Embodiment Mode and a comparative light-emitting element 2 which is a light-emitting element of a comparative example will be described in detail.
- Structural formulas of organic compounds used in the light-emitting element 2 and the comparative light-emitting element 2 are shown below.
- indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, whereby the anode 101 was formed.
- the film thickness was 70 nm
- the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
- the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.
- the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
- the substrate on which the anode 101 is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the anode 101 is formed is downward, and vapor deposition using resistance heating is performed on the anode 101.
- PcBC2N 7-phenylbenzo [c] carbazole
- VI molybdenum oxide
- cgDBCzPA is vapor-deposited on the light emitting layer 113 so as to have a film thickness of 15 nm, and 2,9-di (2-naphthyl) -4,7-diphenyl-1,10 represented by the structural formula (v) is formed.
- -Phenanthroline abbreviation: NBPhen
- NBPhen was deposited to a thickness of 10 nm to form the electron transport layer 114.
- lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injection layer 115, and then aluminum is deposited to a thickness of 200 nm to form a cathode. 102 was formed to manufacture the light-emitting element 2.
- the comparative light-emitting element 2 is a 3,3 ′-(naphthalene-1,4-diyl) represented by the structural formula (vi) above in which PcBC2N used for the hole injection layer 111 and the hole transport layer 112 in the light-emitting element 2 is represented.
- the light-emitting element 2 was manufactured in the same manner as in the light-emitting element 2 except that it was changed to bis (9-phenyl-9H-carbazole) (abbreviation: PCzN2).
- the luminance-current density characteristics of the light-emitting element 2 and the comparative light-emitting element 2 are shown in FIG. 40, the current efficiency-luminance characteristics in FIG. 41, the brightness-voltage characteristics in FIG. 42, and the current-voltage characteristics in FIG.
- the luminance characteristics are shown in FIG. 44, and the emission spectrum is shown in FIG.
- Table 4 summarizes element characteristics around a luminance of 1000 cd / m 2 .
- the light-emitting element 2 of one embodiment of the present invention using PcBC2N exhibits a good blue color with a chromaticity of (0.14, 0.17), but the external quantum efficiency is It was found that the light-emitting element had a highly efficient characteristic of 11.3%.
- FIG. 46 shows a graph showing a change in luminance with respect to driving time at a current density of 50 mA / cm 2 .
- the light-emitting element 2 which is a light-emitting element of one embodiment of the present invention is a light-emitting element with a small lifetime due to accumulation of driving time and a favorable lifetime.
- the light-emitting element 3 which is a light-emitting element of one embodiment of the present invention described in Embodiment Mode and the comparative light-emitting element 3 which is a light-emitting element of a comparative example will be described in detail.
- Structural formulas of organic compounds used in the light-emitting element 3 and the comparative light-emitting element 3 are shown below.
- indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, whereby the anode 101 was formed.
- the film thickness was 70 nm
- the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
- the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.
- the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
- the substrate on which the anode 101 is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the anode 101 is formed is downward, and vapor deposition using resistance heating is performed on the anode 101.
- 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq ⁇ ) represented by the above structural formula (iv) is formed over the light-emitting layer 113.
- II) is deposited to a thickness of 15 nm
- 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (v) Was deposited to a thickness of 10 nm to form the electron transport layer 114.
- lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injection layer 115, and then aluminum is deposited to a thickness of 200 nm to form a cathode. 102 was formed to manufacture the light-emitting element 3.
- Comparative light-emitting element 3 is obtained by using 3,3 ′-(naphthalene-1,4-diyl) represented by the above structural formula (vi) for PCNPaBC used in hole injection layer 111 and hole transport layer 112 in light-emitting element 3.
- the light-emitting element 3 was manufactured in the same manner as in the light-emitting element 3 except that it was changed to bis (9-phenyl-9H-carbazole) (abbreviation: PCzN2).
- the luminance-current density characteristics of the light-emitting element 3 and the comparative light-emitting element 3 are shown in FIG. 47, the current efficiency-luminance characteristics in FIG. 48, the brightness-voltage characteristics in FIG. 49, and the current-voltage characteristics in FIG.
- the luminance characteristics are shown in FIG. 51, and the emission spectrum is shown in FIG.
- Table 6 summarizes element characteristics around a luminance of 1000 cd / m 2 .
- a light-emitting element 4 which is a light-emitting element of one embodiment of the present invention described in Embodiment Mode and a comparative light-emitting element 4 which is a light-emitting element of a comparative example will be described in detail.
- Structural formulas of organic compounds used in the light-emitting element 4 and the comparative light-emitting element 4 are shown below.
- indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, whereby the anode 101 was formed.
- the film thickness was 70 nm
- the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
- the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.
- the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
- the substrate on which the anode 101 is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the anode 101 is formed is downward, and vapor deposition using resistance heating is performed on the anode 101.
- cgDBCzPA is vapor-deposited on the light emitting layer 113 so as to have a film thickness of 15 nm, and 2,9-di (2-naphthyl) -4,7-diphenyl-1,10 represented by the structural formula (v) is formed.
- -Phenanthroline abbreviation: NBPhen
- NBPhen was deposited to a thickness of 10 nm to form the electron transport layer 114.
- lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injection layer 115, and then aluminum is deposited to a thickness of 200 nm to form a cathode. 102 was formed to manufacture the light-emitting element 4.
- the comparative light-emitting element 4 is a 3,3 ′-(naphthalene-1,4-diyl) represented by the above structural formula (vi) of PCNPcBC used for the hole injection layer 111 and the hole transport layer 112 in the light-emitting element 4.
- the light-emitting element 4 was manufactured in the same manner as in the light-emitting element 4 except that it was changed to bis (9-phenyl-9H-carbazole) (abbreviation: PCzN2).
- the luminance-current density characteristics of the light-emitting element 4 and the comparative light-emitting element 4 are shown in FIG. 53, the current efficiency-luminance characteristics in FIG. 54, the brightness-voltage characteristics in FIG. 55, and the current-voltage characteristics in FIG.
- the luminance characteristics are shown in FIG. 57 and the emission spectrum is shown in FIG. Table 8 summarizes element characteristics in the vicinity of luminance of 1000 cd / m 2 .
- the light-emitting element 4 of one embodiment of the present invention using PCNPcBC was a light-emitting element having favorable light emission efficiency equivalent to that of the comparative light-emitting element 4 using PCzN2.
- FIG. 59 shows a graph showing a change in luminance with respect to driving time at a current density of 50 mA / cm 2 .
- the light-emitting element 4 which is a light-emitting element of one embodiment of the present invention is a light-emitting element with a small lifetime due to accumulation of driving time and a favorable lifetime.
- the obtained solid was purified by high performance liquid chromatography (developing solvent: chloroform) and further recrystallized from toluene / hexane to obtain 1.5 g of the objective yellow solid in a yield of 58%.
- a synthesis scheme is shown below.
- Sublimation purification of 1.4 g of the obtained yellow solid was performed by a train sublimation method. Sublimation purification is performed by heating 2,2 ′-(naphthalene-1,4-diyl) bis (5-phenyl-5H-benzo [b] carbazole) at 355 ° C. under conditions of a pressure of 3.9 Pa and an argon flow rate of 6 mL / min. I went there. 0.75 g of a yellow solid after sublimation purification was obtained with a recovery rate of 52%.
- FIG. 60 shows a 1 H NMR chart of the obtained yellow solid, and numerical data are shown below.
- the absorption spectrum and emission spectrum of the toluene solution of PbBC2N and the solid thin film were measured.
- the solid thin film was produced on a quartz substrate by a vacuum deposition method.
- an ultraviolet-visible spectrophotometer solution: manufactured by JASCO Corporation, V-550, thin film: manufactured by Hitachi High-Technologies Corporation, U-4100
- the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured only by putting toluene in a quartz cell, and the absorption spectrum of the thin film was the absorbance ( ⁇ log 10 [%] obtained from the transmittance and reflectance including the substrate. T / (100-% R)], where% T represents transmittance,% R represents reflectance, and the emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics). Using.
- FIG. 62 shows the measurement results of the absorption spectrum and emission spectrum of the solid thin film.
- an absorption peak was observed in the vicinity of 397 nm, 378 nm, 335 nm, and 327 nm in the toluene solution of PbBC2N.
- the emission wavelength peaks were 409 nm and 434 nm (excitation wavelength: 335 nm).
- the PbBC2N thin film showed absorption peaks in the vicinity of 404 nm, 382 nm, 336 nm, and 325 nm, and similarly from FIG. 62, the emission wavelength peaks were observed in the vicinity of 421 nm and 447 nm (excitation wavelength: 350 nm).
- the compound of one embodiment of the present invention can also be used as a host material for a light-emitting substance or a fluorescent light-emitting substance in the visible range.
- the thin film of PbBC2N is a good film quality that hardly aggregates even in the air and has little change in form.
- the HOMO level and LUMO level of PbBC2N were calculated based on cyclic voltammetry (CV) measurement. Since the calculation method is the same as that of the first embodiment, duplicate description is omitted.
- CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.
- a light-emitting element 5 which is a light-emitting element of one embodiment of the present invention described in Embodiment Mode will be described in detail. Structural formulas of organic compounds used in the light-emitting element 5 are shown below.
- indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, whereby the anode 101 was formed.
- the film thickness was 70 nm
- the electrode area was 4 mm 2 (2 mm ⁇ 2 mm).
- the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.
- the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁇ 4 Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.
- the substrate on which the anode 101 is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the anode 101 is formed is downward, and vapor deposition using resistance heating is performed on the anode 101.
- PbBC2N is 20 nm on the hole injection layer 111, and then 3,3 ′-(naphthalene-1,4-diyl) bis (9-phenyl-9H-carbazole) represented by the structural formula (vi). ) (Abbreviation: PCzN2) was deposited to a thickness of 10 nm to form the hole transport layer 112.
- 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq) represented by the above structural formula (iv) is formed over the light-emitting layer 113.
- -II) is deposited to a thickness of 15 nm
- 2,9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (v) ) was deposited to 10 nm to form the electron transport layer 114.
- LiF is deposited to a thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a thickness of 200 nm to form the cathode 102.
- a light-emitting element 5 was manufactured.
- the element structure of the light-emitting element 5 is summarized in the following table.
- FIG. 63 shows the luminance-current density characteristics of the light-emitting element 5
- FIG. 64 shows the current efficiency-luminance characteristics
- FIG. 65 shows the luminance-voltage characteristics
- FIG. 66 shows the current-voltage characteristics
- FIG. 67 the emission spectrum is shown in FIG.
- Table 10 summarizes element characteristics around a luminance of 1000 cd / m 2 .
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Abstract
Description
本発明の一態様は、ベンゾカルバゾール骨格、ジベンゾカルバゾール骨格またはトリベンゾカルバゾール骨格のいずれか一と、カルバゾール骨格、ベンゾカルバゾール骨格およびジベンゾカルバゾール骨格またはトリベンゾカルバゾール骨格のいずれか一が、ナフタレン−1,4−ジイル基またはナフタレン−1,5−ジイル基で結合する有機化合物である。これらの骨格または基は各々置換基を有していても良い。
これら導電性材料は、真空蒸着法やスパッタリング法などの乾式法、インクジェット法、スピンコート法等を用いて成膜することが可能である。また、ゾル−ゲル法を用いて湿式法で形成しても良いし、金属材料のペーストを用いて湿式法で形成してもよい。
本実施の形態では、実施の形態2に記載の発光素子を用いた発光装置について説明する。
本実施の形態では、実施の形態2に記載の発光素子を照明装置として用いる例を図6を参照しながら説明する。図6(B)は照明装置の上面図、図6(A)は図6(B)におけるe−f断面図である。
本実施の形態では、実施の形態2に記載の発光素子をその一部に含む電子機器の例について説明する。実施の形態2に記載の発光素子は寿命が良好であり、信頼性の良好な発光素子である。その結果、本実施の形態に記載の電子機器は、信頼性の良好な発光部を有する電子機器とすることが可能である。
本実施例では、本発明の一態様の有機化合物である8,8’−(ナフタレン−1,4−ジイル)ビス(11−フェニル−11H−ベンゾ[a]カルバゾール)(略称:PaBC2N)の合成方法について詳しく説明する。PaBC2Nの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である12,12’−(ナフタレン−1,4−ジイル)ビス(9−フェニル−9H−ジベンゾ[a,c]カルバゾール)(略称:PacDBC2N)の合成方法について詳しく説明する。PacDBC2Nの構造式を以下に示す。
得られたトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図18に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、固体薄膜の吸収スペクトルおよび発光スペクトルの測定結果を図19に示す。
本実施例では、本発明の一態様の有機化合物である10,10’−(ナフタレン−1,4−ジイル)ビス(7−フェニルベンゾ[c]カルバゾール)(略称:PcBC2N)の合成方法について詳しく説明する。PcBC2Nの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である11−フェニル−8−[4−(9−フェニルカルバゾール−3−イル)−1−ナフチル]ベンゾ[a]カルバゾール(略称:PCNPaBC)の合成方法について詳しく説明する。PCNPaBCの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である7−フェニル−10−[4−(9−フェニルカルバゾール−3−イル)−1−ナフチル]ベンゾ[c]カルバゾール(略称:PCNPcBC)の合成方法について詳しく説明する。PCNPcBCの構造式を以下に示す。
200mLの3口フラスコに3−(4−ブロモ−1−ナフチル)−9−フェニル−9H−カルバゾール2.0g(4.5mmol)、2−(ベンゾ[c]カルバゾール−10−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン1.9g(5.4mmol)、トリス(2−メチルフェニル)ホスフィン0.28g(0.91mmol)、炭酸カリウム1.5g(11mmol)、トルエン45mL、エタノール6mL、水6mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に酢酸パラジウム(II)0.070g(0.31mmol)を加え、窒素気流下、80℃で6時間、90℃で8時間撹拌した。撹拌後、有機層と水層を分離してから水層をトルエンで抽出した。得られた抽出溶媒と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルクロマトグラフィー(トルエン:ヘキサン=11:9)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を収量2.0g、収率76%で得た。ステップ1の合成スキームを以下に示す。
100mLの3口フラスコに10−[4−(9−フェニルカルバゾール−3−イル)−1−ナフチル]ベンゾ[c]カルバゾール2.0g(3.3mmol)、ヨードベンゼン0.75mL(6.7mmol)、ナトリウムtert−ブトキシド0.68g(7.0mmol)、キシレン17mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物にトリtert−ブチルホスフィン10wt%ヘキサン溶液0.40mL(0.13mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.074g(0.13mmol)を加え、窒素気流下、150℃で14時間撹拌した。撹拌後、得られた混合物に水を加え、有機層と水層を分離した後、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルクロマトグラフィー(トルエン:ヘキサン=1:2)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を1.8g、収率84%で得た。ステップ2の合成スキームを以下に示す。
本実施例では、本発明の一態様の有機化合物である7−フェニル−10−[5−(9−フェニルカルバゾール−3−イル)−1−ナフチル]ベンゾ[c]カルバゾール(略称:1,5PCNPcBC)の合成方法について詳しく説明する。1,5PCNPcBCの構造式を以下に示す。
300mLの3口フラスコに3−(5−ブロモ−1−ナフチル)−9−フェニルカルバゾール2.0g(4.4mmol)、2−(ベンゾ[c]カルバゾール−10−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン1.8g(5.2mmol)、トリス(2−メチルフェニル)ホスフィン0.13g(0.44mmol)、炭酸カリウム1.5g(11mmol)、トルエン43mL、エタノール5mL、水5mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に酢酸パラジウム(II)0.036g(0.16mmol)を加え、窒素気流下、100℃で11時間撹拌した。撹拌後、得られた混合物の水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィー(トルエン)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を2.0g、収率80%で得た。ステップ1の合成スキームを以下に示す。
100mLの3口フラスコに10−[5−(9−フェニルカルバゾール−3−イル)−1−ナフチル]ベンゾ[c]カルバゾール2.0g(3.5mmol)、ヨードベンゼン0.80mL(7.1mmol)、ナトリウムtert−ブトキシド0.68g(7.1mmol)、キシレン18mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物にトリ−tert−ブチルホスフィン10wt%ヘキサン溶液0.30mL(0.098mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.043g(0.075mmol)を加え、窒素気流下、150℃で7時間撹拌した。撹拌後、得られた混合物に水を加え、有機層と水層を分離した後、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィー(トルエン:ヘキサン=1:1)で精製し、さらに酢酸エチルとメタノールとの混合溶媒と、トルエンとヘキサンの混合溶媒で2回再結晶したところ、目的物の白色固体を収量1.9g、収率84%で得た。ステップ2の合成スキームを以下に示す。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子1は、発光素子1における正孔注入層111および正孔輸送層112に用いたPaBC2N)を上記構造式(vi)で表される3,3’−(ナフタレン−1,4−ジイル)ビス(9−フェニル−9H−カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子1と同様に作製した。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子2は、発光素子2における正孔注入層111および正孔輸送層112に用いたPcBC2Nを上記構造式(vi)で表される3,3’−(ナフタレン−1,4−ジイル)ビス(9−フェニル−9H−カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子2と同様に作製した。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子3は、発光素子3における正孔注入層111および正孔輸送層112に用いたPCNPaBCを上記構造式(vi)で表される3,3’−(ナフタレン−1,4−ジイル)ビス(9−フェニル−9H−カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子3と同様に作製した。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子4は、発光素子4における正孔注入層111および正孔輸送層112に用いたPCNPcBCを上記構造式(vi)で表される3,3’−(ナフタレン−1,4−ジイル)ビス(9−フェニル−9H−カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子4と同様に作製した。
本実施例では、本発明の一態様の有機化合物である2,2’−(ナフタレン−1,4−ジイル)ビス(5−フェニル−5H−ベンゾ[b]カルバゾール)(略称:PbBC2N)の合成方法について詳しく説明する。PbBC2Nの構造式を以下に示す。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
Claims (22)
- 下記一般式(G1)で表される有機化合物。
- 請求項1乃至請求項3のいずれか一項において、
前記一般式(gA)で表される基のR4およびR5、R5およびR6、並びにR6およびR7の少なくとも一つの組み合わせにおいて縮合してベンゼン環が形成されている有機化合物。 - 請求項1乃至請求項3のいずれか一項において、
前記一般式(gA)で表される基の、R4およびR5、または、R6およびR7の少なくとも一つの組み合わせで縮合してベンゼン環が形成されている有機化合物。 - 請求項1乃至請求項8のいずれか一項において、
前記Ar1がフェニル基である有機化合物。 - 請求項1乃至請求項9のいずれか一項において、
前記一般式(gA)で表される基と、前記一般式(gB)で表される基が同一の構造を有する有機化合物。 - 請求項1乃至請求項11のいずれか一項において、
前記Ar2がフェニル基である有機化合物。 - 下記一般式(G2)で表される有機化合物。
- 請求項13においてR4およびR5並びにR14およびR15が各々の組み合わせで縮合してベンゼン環を形成する有機化合物。
- 請求項13においてR6およびR7並びにR16およびR17が各々の組み合わせで縮合してベンゼン環を形成する有機化合物。
- 請求項13乃至請求項15のいずれか一項において、
Ar1およびAr2がフェニル基である有機化合物。 - 請求項1乃至請求項16のいずれか一項に記載の有機化合物を含む発光素子。
- 請求項1乃至請求項16のいずれか一項に記載の有機化合物を陽極と発光層の間に含む発光素子。
- 請求項1乃至請求項16のいずれか一項に記載の有機化合物を発光層に含む発光素子。
- 請求項17乃至請求項19のいずれか一項に記載の発光素子と、
センサ、操作ボタン、スピーカ、または、マイクと、
を有する電子機器。 - 請求項17乃至請求項19のいずれか一項に記載の発光素子と、
トランジスタ、または、基板と、
を有する発光装置。 - 請求項21に記載の発光装置と、
筐体と、
を有する照明装置。
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JP2010195708A (ja) * | 2009-02-25 | 2010-09-09 | Toyo Ink Mfg Co Ltd | カルバゾリル基を有する化合物およびその用途 |
KR20110066766A (ko) * | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
WO2012014500A1 (ja) * | 2010-07-30 | 2012-02-02 | 保土谷化学工業株式会社 | インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
CN103936653A (zh) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | 苯并咔唑类oled材料及其制备方法与应用 |
JP2016508131A (ja) * | 2012-12-24 | 2016-03-17 | ドクサンネオルクス シーオー., エルティーディー.Duk San Neolux Co., Ltd. | 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2016508131A (ja) * | 2012-12-24 | 2016-03-17 | ドクサンネオルクス シーオー., エルティーディー.Duk San Neolux Co., Ltd. | 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 |
CN103936653A (zh) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | 苯并咔唑类oled材料及其制备方法与应用 |
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