Light emitting element

Abstract

To provide a new organic compound that is effective in improving element characteristics and reliability.SOLUTION: An organic compound has an anthracene skeleton and a carbazole skeleton and is represented by the following general formula (G1).SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one embodiment of the present invention is not limited to the above technical fields. The present invention relates to an object, a method, a manufacturing method, or a driving method. process, machine, manufacture, or composition of matter Specifically, the present invention relates to a semiconductor device, a display device, a liquid crystal display device, etc. It is possible. [Background technology]

[0002] Light-emitting elements (also called organic EL elements) are thin, lightweight, and have an EL layer sandwiched between a pair of electrodes. These features include high-speed response to input signals and low power consumption. This display is attracting attention as the next generation of flat panel displays.

[0003] The light-emitting element is a device that emits light by applying a voltage between a pair of electrodes, and the electrons injected from each electrode are The electrons and holes recombine in the EL layer, and the luminescent material (organic compound) contained in the EL layer becomes excited. When the excited state returns to the ground state, light is emitted. , singlet excited state (S * ) and triplet excited states (T * ) and emission from the singlet excited state. The light emitted from the triplet excited state is called fluorescence, and the light emitted from the triplet excited state is called phosphorescence. The statistical generation ratio of these is S * :T * =1:3. From luminous materials The emission spectrum obtained is specific to the luminescent material, and different types of organic compounds emit By using it as an optical substance, it is possible to obtain light-emitting elements that emit light of various colors.

[0004] Regarding such light-emitting devices, in order to improve the device characteristics, improvements in the device structure and material development have been carried out. Developments in this field are being actively pursued (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2010-182699 A Summary of the Invention [Problem to be solved by the invention]

[0006] In the development of light-emitting devices, the organic compounds used in the light-emitting devices are Therefore, in one aspect of the present invention, a novel organic compound is provided. That is, the present invention provides a novel organic compound that is effective in improving device characteristics and reliability. In one embodiment of the present invention, a novel organic compound that can be used in a light-emitting element is provided. In one embodiment, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a novel highly efficient and reliable emitter using a novel organic compound according to one embodiment of the present invention is The present invention also provides a novel light emitting device, a novel electronic device, or a novel lighting device. The description of these issues does not preclude the existence of other issues. An embodiment of the invention does not necessarily have to solve all of these problems. Other problems will be obvious from the description, drawings, claims, etc. It is possible to extract other issues from the detailed description, drawings, claims, etc. [Means for solving the problem]

[0007] One embodiment of the present invention has an anthracene skeleton and a carbazole skeleton and is represented by the following general formula (G1 ) is an organic compound represented by the formula:

[0008] [ka]

[0009] In general formula (G1), Ar is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. When the arylene group has substituents, the substituents are bonded to each other to form a ring. Cz may represent a substituted or unsubstituted carbazole skeleton. R 1 ~R 9 , and R 11 ~R 17 each independently represents hydrogen, a substituted or unsubstituted carbon atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or R represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings is a fused ring. It's fine to do so.

[0010] Another embodiment of the present invention is a compound represented by the formula (G1), It is an organic compound in which the 9th, 3rd or 2nd position is bonded to the carbazole skeleton.

[0011] In another aspect of the present invention, Ar in the general formula (G1) is a substituted or unsubstituted fluorine-containing compound. The organic compound is a phenylene group, or a substituted or unsubstituted biphenyldiyl group.

[0012] Another aspect of the present invention is that R 5 However, substituted or unsubstituted carbon It is an organic compound that is an aryl group with prime numbers of 6 to 13.

[0013] The organic compound according to one embodiment of the present invention has an anthracene skeleton and a carbazole skeleton. In addition, organic compounds having an anthracene skeleton are bipolar fluorescent phosphatase. Many organic compounds have been developed as anthracene materials. Since it has a carbazole skeleton in addition to the anthracene skeleton, it is composed only of an anthracene skeleton. It is a fluorescent host material that exhibits better hole transport properties than organic compounds.

[0014] In addition, the organic compound according to one embodiment of the present invention has an anthracene skeleton and a bicarbazole skeleton. In the case of such organic compounds, the HOMO orbital is The HOMO orbital is in the carbazole skeleton, and compared to the HOMO orbital in the anthracene skeleton, The HOMO level tends to be shallower. When used, the difference in HOMO level between the light-emitting layer and the hole transport layer formed in contact with the light-emitting layer becomes small, The barrier for holes to be injected from the hole transport layer to the light emitting layer is relaxed, so that light is emitted from the hole transport layer. This improves the hole injection into the layer, thereby reducing the driving voltage and improving the light emission efficiency. can be done.

[0015] In addition, the organic compound according to one embodiment of the present invention may have an anthracene skeleton and a carbazole skeleton. The 2-position of the first carbazole skeleton is bonded to the anthracene skeleton, and By adjusting the bonding position of the second carbazole skeleton bonded to the first Compared with the case where the 3-position of the carbazole skeleton is bonded to the second carbazole skeleton, Since the phase shift is small and the singlet excitation energy is high, it is possible to use shorter wavelength This facilitates energy transfer to the substrate material, thereby improving the luminous efficiency of the light-emitting element. In addition, the reliability of the element can be improved. The organic compound is a compound having a structure in which the first carbazole skeleton is bonded to the anthracene skeleton at the 2-position and the second carbazole skeleton is bonded to the anthracene skeleton at the 3-position. The 9-, 3-, or 2-position of the carbazole skeleton of 2 is bonded, making the synthesis easy. This is preferable because

[0016] Another aspect of the present invention is a compound represented by the following structural formula (200), (220), (221), or (222): It is an organic compound represented by formula (252) or structural formula (253).

[0017] [ka]

[0018] Another aspect of the present invention is to provide an organic compound having an anthracene skeleton and a carbazole skeleton. In addition to the above organic compounds, a light-emitting element having a guest material is also used in this invention. Included in the invention.

[0019] Another embodiment of the present invention is a light-emitting element using the organic compound according to any one of the above embodiments of the present invention. In addition, the EL layer between the pair of electrodes and the light-emitting layer included in the EL layer may include the The present invention also includes a light-emitting element formed using a certain organic compound. In addition to the element, a light-emitting device having a transistor, a substrate, etc. is also included in the scope of the invention. In addition to these light-emitting devices, microphones, cameras, operation buttons, external connectors, housings, covers, etc. The scope of the invention also includes electronic devices and lighting devices having a speaker, a support stand, or the like.

[0020] Another embodiment of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device. Therefore, the term "light-emitting device" in this specification includes a light-emitting device such as an image display device. It also refers to a light source (including lighting equipment) that has a connector, such as F PC (Flexible Printed Circuit) or TCP (Tape A module with a Carrier Package attached, and a printer at the end of the TCP A module with a printed wiring board or a light-emitting element with COG (Chip On Glass) s) All modules in which an IC (integrated circuit) is directly mounted using this method are included in the light-emitting device. Let us assume that. Effect of the Invention

[0021] One embodiment of the present invention can provide a novel organic compound. It is possible to provide a novel organic compound that is effective in improving the reliability of the present invention. In this manner, a novel organic compound that can be used in a light-emitting element can be provided. In one embodiment of the present invention, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a highly efficient and reliable photocatalytic reaction can be achieved by using a novel organic compound according to one embodiment of the present invention. It is possible to provide a novel light emitting element having high reliability. In addition, the description of these effects may be used in other applications. However, this does not necessarily prevent the existence of the effects of the above. It is not necessary for the invention to have all of the above effects. Effects other than these effects may be included in the description, drawings, claims, etc. These will become apparent from the description, drawings, claims, etc. It is possible to extract effects other than those mentioned above. [Brief description of the drawings]

[0022] [Figure 1] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 2] 1A and 1B are diagrams illustrating a light-emitting device. [Diagram 3] 1A and 1B are diagrams illustrating a light-emitting device. [Figure 4] 1A to 1C are diagrams illustrating electronic devices. [Diagram 5] 1A to 1C are diagrams illustrating electronic devices. [Figure 6] FIG. [Figure 7] 1A and 1B are diagrams illustrating a lighting device. [Figure 8] 1A and 1B are diagrams illustrating a lighting device. [Figure 9] 1H-NMR chart of the organic compound shown in structural formula (200). [Figure 10] UV-visible absorption and emission spectra of the organic compound shown in structural formula (200). [Figure 11] 1H-NMR chart of the organic compound shown in structural formula (221). [Figure 12] UV-visible absorption and emission spectra of the organic compound shown in structural formula (221). [Figure 13] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Figure 14] FIG. 13 shows current density-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 15]FIG. 13 shows voltage-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 16] FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 17] FIG. 13 shows voltage-current characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 18] FIG. 1 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 19] 13 shows the reliability of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 20] 1H-NMR chart of the organic compound shown in structural formula (252). [Figure 21] UV-visible absorption and emission spectra of the organic compound shown in structural formula (252). [Figure 22] 1H-NMR chart of the organic compound shown in structural formula (253). [Diagram 23] UV-visible absorption and emission spectra of the organic compound shown in structural formula (253). [Figure 24] 1H-NMR chart of the organic compound shown in structural formula (220). [Diagram 25] UV-visible absorption and emission spectra of the organic compound shown in structural formula (220). [Figure 26] FIG. 13 shows current density-luminance characteristics of the light-emitting element 3. [Figure 27] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 3. [Figure 28] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 3. [Figure 29] FIG. 13 shows voltage-current characteristics of the light-emitting element 3. [Diagram 30] FIG. 2 shows an emission spectrum of the light-emitting element 3. [Diagram 31] 1H-NMR chart of 9-chloro-7H-benzo[c]carbazole. [Diagram 32] 1H-NMR chart of PCcBCz. [Diagram 33] 1H-NMR chart of PCcBCz-02. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0023] Hereinafter, the embodiment of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details are not limited thereto without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the above embodiment. It is not to be construed as being limited to the following:

[0024] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily shown in order to facilitate understanding. The actual position, size, range, etc. may not be shown. The present invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings, etc.

[0025] In addition, in this specification and the like, when explaining the configuration of the invention using drawings, The reference numerals are used commonly among different drawings.

[0026] (Embodiment 1) In this embodiment, an organic compound which is one embodiment of the present invention will be described.

[0027] Note that the organic compound described in this embodiment has an anthracene skeleton and a carbazole skeleton. It has a structure represented by the following general formula (G1).

[0028] [ka]

[0029] In general formula (G1), Ar is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. When the arylene group has substituents, the substituents are bonded to each other to form a ring. Cz may represent a substituted or unsubstituted carbazole skeleton. R 1 ~R 9 , and R 11 ~R 17 each independently represents hydrogen, a substituted or unsubstituted carbon atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or R represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings is a fused ring. It's fine to do so.

[0030] In the above general formula (G1), a substituted or unsubstituted arylene having 6 to 13 carbon atoms group, a substituted or unsubstituted carbazole skeleton, a substituted or unsubstituted arsenic skeleton having 1 to 6 carbon atoms alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, substituted or unsubstituted When any of the aryl groups having 6 to 13 carbon atoms has a substituent, the substituent is preferably methyl. ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl Alkyl groups with 1 to 6 carbon atoms, such as butyl, tert-butyl, pentyl, and hexyl groups cyclopentyl, cyclohexyl, cycloheptyl, 1-norbornyl, 2 -Cycloalkyl groups with 5 to 7 carbon atoms, such as norbornyl groups, phenyl groups, and biphenyl groups. Examples of aryl groups include aryl groups having 6 to 12 carbon atoms such as the group.

[0031] In addition, in the above general formula (G1), a substituted or unsubstituted arylene having 6 to 13 carbon atoms Specific examples of the group include a phenylene group, a 2,5-dimethyl-1,4-phenylene group, and a naphtha group. Diphenyldiyl group, biphenyldiyl group, 9,9-dimethylfluorenediyl group, 9,9-di Examples thereof include a phenylfluorenediyl group and a 9,9'-spirobifluorenediyl group.

[0032] In addition, specific examples of the substituted or unsubstituted carbazole skeleton in the above general formula (G1) are The following are examples of benzo[a]carbazole, benzo[b]carbazole, and benzo[c]carbazole: dibenzo[a,c]carbazole, dibenzo[a,g]carbazole, dibenzo[ c,g]carbazole, dibenzo[b,g]carbazole, naphtho[2,3-c]carbazole azole, naphtho[1,2-c]carbazole, and the like.

[0033] In the above general formula (G1), Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a sec -butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec -pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-Methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethyl Examples of the alkyl group include a butyl group.

[0034] In addition, in the above general formula (G1), a substituted or unsubstituted aryl group having 6 to 13 carbon atoms Specific examples of the alkyl group include a phenyl group, a naphthyl group (1-naphthyl group, 2-naphthyl group), a trialkyl group, tolyl groups (o-tolyl group, m-tolyl group, p-tolyl group), biphenyl group (biphenyl-2- biphenyl-3-yl group, biphenyl-4-yl group, etc.

[0035] The organic compound of one embodiment of the present invention represented by the general formula (G1) has an anthracene skeleton and a carbene skeleton. Organic compounds with an anthracene skeleton have bipolar properties. Many fluorescent host materials have been developed, including the organic compound represented by the general formula (G1). Since it has an anthracene skeleton and a carbazole skeleton, It is a fluorescent host material that exhibits good hole transport properties compared to organic compounds composed of do.

[0036] The organic compound of one embodiment of the present invention represented by General Formula (G1) has an anthracene skeleton and The fluorescent host material has a bicarbazole skeleton. In this case, the HOMO orbital is in the bicarbazole skeleton and the HOMO orbital is in the anthracene skeleton. In this case, the HOMO level tends to be shallower than in the case of When a host material is used in the light-emitting layer, the HOMO equilibrium with the hole-transporting layer formed in contact with the light-emitting layer is The potential difference between the hole transport layer and the light emitting layer is reduced, and the barrier to hole injection from the hole transport layer to the light emitting layer is alleviated. The hole injection from the hole transport layer to the light emitting layer is improved. This leads to a reduction in the driving voltage and light emission. Efficiency can be improved.

[0037] In addition, the organic compound according to one embodiment of the present invention has an anthracene skeleton and a carbazole skeleton. The second phenylcarbazole bonded to the 3-position of the first phenylcarbazole bonded to the anthracene skeleton has By adjusting the bonding position of the phenylcarbazole in 2 to a desired position, the luminescence efficiency and The reliability of the light-emitting element using the first phenylcarbazole can be improved. The bonding position of the second phenylcarbazole bonded to the 3-position of the As such, it is preferable to have the 2-position of the second phenylcarbazole.

[0038] Next, specific structural formulas of the organic compounds according to embodiments of the present invention are shown below. However, the present invention is not limited to these.

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] The organic compounds represented by the above structural formulas (200) to (260) are represented by the above general formula (G1) The organic compound according to one embodiment of the present invention is an example of the organic compound represented by the formula: Not limited to.

[0048] Next, an example of a method for synthesizing an organic compound represented by general formula (G1), which is one embodiment of the present invention, will be described. We will explain about this.

[0049] <Method for synthesizing organic compound represented by general formula (G1)> First, an example of a method for synthesizing an organic compound represented by the following general formula (G1) will be described.

[0050] [ka]

[0051] In general formula (G1), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms. When the arylene group has substituents, the substituents are bonded to each other to form a ring. Cz may represent a substituted or unsubstituted carbazole skeleton. 1 ~ R 9 , and R 11 ~R 17 are each independently hydrogen or a substituted or unsubstituted group having 1 to 1 6 alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or substituted or unsubstituted or an unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings is fused. That's fine.

[0052] The organic compound represented by the above general formula (G1) can be synthesized according to the following synthesis scheme (A-1): That is, a halide of an anthracene derivative (compound 1) and Carbazole derivatives or condensed polycyclic carbazole derivatives, organoboron compounds or boron compounds The compound (compound 2) is coupled with uronic acid via the Suzuki-Miyaura reaction to give the compound of the general formula (G The organic compound represented by formula 1) can be obtained.

[0053] [ka]

[0054] In the above synthesis scheme (A-1), Ar is a substituted or unsubstituted alkyl group having 6 to 6 carbon atoms. 13 represents an arylene group, and when the arylene group has a substituent, the substituents are bonded to each other. Cz may be a substituted or unsubstituted carbazole skeleton. Also, R 1 ~R 9 , and R 11 ~R 17 are each independently hydrogen, a substituent or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least One of the rings may be condensed. 50 and R 51 is hydrogen or carbon number 1-6 In addition, R 50 and R 51 are bonded together to form a ring Also, X 1 represents a halogen or a triflate group.

[0055] In the above synthesis scheme (A-1), the palladium catalyst that can be used is acetic acid. Palladium(II) acid, Tetrakis(triphenylphosphine)palladium(0), bis (triphenylphosphine)palladium(II) dichloride, etc. The palladium catalysts that can be used are not limited to those shown in the following synthesis scheme (A-1). In the above, the ligand of the palladium catalyst that can be used is tri(ortho-tolyl) ) phosphine, triphenylphosphine, tricyclohexylphosphine, etc. The ligands of the palladium catalyst that can be used are not limited to these. In the synthesis scheme (A-1), examples of the base that can be used include sodium tert-butyl ether. Examples of the base include organic bases such as t-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate. However, the bases that can be used are not limited to these. In 1), the solvent that can be used is a mixed solvent of toluene and water, toluene and Mixtures of alcohols such as ethanol and water, mixtures of xylene and water, and mixtures of xylene and ethanol Mixtures of alcohol and water, such as alcohol and water, mixed solvents of benzene and water, benzene and ethanol, etc. Mixtures of alcohol and water, ethers such as ethylene glycol dimethyl ether and water However, the solvents that can be used are not limited to these. Also, mixed solvents of toluene and water, toluene, ethanol and water, ethylene glycol A mixed solvent of water and an ether such as glycerol dimethyl ether is more preferred.

[0056] In addition, the compound 2 in the above synthesis scheme (A-1) is an organic boron compound or a boron In addition to acids, organic aluminum compounds, organic zirconium compounds, organic zinc compounds, Organotin compounds and the like can be used.

[0057] In addition, as a coupling reaction other than the reaction shown in the synthetic scheme (A-1), The coupling reaction shown in (A-2) can also be used. In the coupling reaction shown in -2), a halide of an anthracene derivative (compound 3) and A carbazole derivative (compound 4) is reacted with a metal catalyst, a metal, or a metal compound in the presence of a base. By coupling with a coupling agent, an organic compound represented by general formula (G1) is obtained. This can be done.

[0058] [ka]

[0059] In the above synthesis scheme (A-2), Ar is a substituted or unsubstituted aryl group having 6 to 6 carbon atoms. 13 represents an arylene group, and when the arylene group has a substituent, the substituents are bonded to each other. Cz may be a substituted or unsubstituted carbazole skeleton. Also, R 1 ~R 9 , and R 11 ~R 17 are each independently hydrogen, a substituent or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least The other one may be a condensed ring. 2 represents a halogen, and the halogen is iodine. and bromine and chlorine are more preferred.

[0060] In the above synthesis scheme (A-2), when the Hartwig-Buchwald reaction is carried out, The palladium catalyst that can be used is bis(dibenzylideneacetone)palladium. Examples of suitable palladium(0) acetate include palladium(II) acetate. The ligand of the palladium catalyst that can be used in the present invention is tri(tert-butyl) Phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, etc. In the synthesis scheme (A-2), examples of the base that can be used include sodium Examples of bases include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate. In addition, in the synthesis scheme (A-2), examples of the solvent that can be used include toluene. Examples of the solvent include benzene, xylene, benzene, and tetrahydrofuran. In addition to the Buchwald reaction, the Ullmann reaction may also be used, but is not limited thereto. isn't it.

[0061] The above is an embodiment of the present invention, and relates to a method for synthesizing an organic compound represented by general formula (G1). However, the present invention is not limited to this, and other synthesis methods may be used. stomach.

[0062] Note that the organic compound according to one embodiment of the present invention has an electron-transport property and a hole-transport property. Therefore, it can be used as a host material in the light-emitting layer, or in the electron transport layer or hole transport layer. It can also be used as a host material in combination with a fluorescent material that emits fluorescence. In addition, since it exhibits fluorescent emission, it can be used as a light-emitting material for a light-emitting element. Therefore, a light-emitting element including such an organic compound is also included in one embodiment of the present invention. can be.

[0063] In addition, by using the organic compound which is one embodiment of the present invention, a light-emitting element and a light-emitting In addition, a light emitting device having low power consumption can be realized. It is possible to realize a device, a light-emitting device, an electronic device, or a lighting device.

[0064] Note that one embodiment of the present invention has been described in this embodiment. In the following, one embodiment of the present invention will be described. However, the present invention is not limited to the above. That is, various inventive aspects are described in this and other embodiments. Therefore, one embodiment of the present invention is not limited to a specific embodiment.

[0065] The configuration described in this embodiment may be used in appropriate combination with the configurations described in other embodiments. can be done.

[0066] (Embodiment 2) In this embodiment mode, a light-emitting element using the organic compound shown in Embodiment Mode 1 will be described with reference to FIG. I will explain this in more detail.

[0067] <Basic structure of light-emitting element> First, the basic structure of a light-emitting element will be described. Specifically, the light-emitting element has a first electrode 101 and a second electrode 1 EL layer 103 is sandwiched between the insulating layer 102 and the insulating film 103 .

[0068] In addition, in FIG. 1B, a plurality of EL layers (two layers in FIG. 1B) are disposed between a pair of electrodes. a, 103b), and a stacked structure (tandem structure) having a charge generating layer 104 between the EL layers. The light-emitting element of the tandem structure is an emission element that can be driven at a low voltage and consumes low power. Optical devices can be realized.

[0069] When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer 104 Electrons are injected into one EL layer (103a or 103b) and the other EL layer (103b or 1B, the first electrode 1 When a voltage is applied to the charge generating layer 101 so that the potential of the charge generating layer 101 becomes higher than that of the second electrode 102, Electrons are injected from the electrode 4 into the EL layer 103a, and holes are injected into the EL layer 103b. .

[0070] The charge generating layer 104 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the transmittance of visible light through the charge generating layer 104 is 40% or more.) In addition, the charge generating layer 104 has a lower conductivity than the first electrode 101 and the second electrode 102. But it still works.

[0071] FIG. 1C shows a stacked structure of an EL layer 103 of a light-emitting element according to one embodiment of the present invention. In this case, however, the first electrode 101 functions as an anode. The EL layer 103 On the first electrode 101, a hole injection layer 111, a hole transport layer 112, The light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115 are laminated in this order. Even in the case of a tandem structure having multiple EL layers as shown in FIG. The L layer is laminated in the above order from the anode side. If the first electrode 102 is the cathode and the second electrode 102 is the anode, the stacking order is reversed.

[0072] The light-emitting layers 113 included in the EL layers (103, 103a, 103b) each contain a light-emitting material or It has a combination of multiple substances and emits fluorescent or phosphorescent light of a desired color. In addition, the light-emitting layer 113 may have a laminated structure with different luminescent colors. In this case, the luminescent material and other materials used in each of the laminated luminescent layers may be the same as those used in the laminated luminescent layers. Different materials may be used for each of the EL layers. 3b) may be used to obtain different luminescent colors. The luminescent material and other materials used may be different materials.

[0073] In the light-emitting element according to one embodiment of the present invention, for example, the first electrode 1 The first electrode 101 is a reflective electrode, the second electrode 102 is a semi-transmissive and semi-reflective electrode, and a micro-optical resonator (microcavity) is formed. By forming a closed cavity structure, the light emitting layer 113 included in the EL layer 103 can be used as a light emitting layer. The emitted light can be resonated between the two electrodes, and the light emitted from the second electrode 102 can be strengthened. do.

[0074] The first electrode 101 of the light-emitting element is made of a conductive material having reflectivity and a conductive material having light-transmitting property. In the case of a reflective electrode having a laminated structure with a conductive material (transparent conductive film), the thickness of the transparent conductive film is controlled. Specifically, the light emitting layer 113 can be optically adjusted by controlling the light emitting layer 113. The distance between the first electrode 101 and the second electrode 102 is mλ / 2, where λ is the wavelength of light. It is preferable to adjust the value so that it is close to m (where m is a natural number).

[0075] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, , are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). The light-emitting region here is preferably a region in which holes in the light-emitting layer 113 and The recombination region with electrons is shown.

[0076] By carrying out such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be adjusted. This narrows the line width and allows light emission with good color purity to be obtained.

[0077] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is necessary to strictly define the reflection area of ​​the first electrode 101 or the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, It is assumed that the above-mentioned effect can be obtained by assuming the ray domain. The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 101 / 100 . The optical distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained is called the optical distance. However, it is possible to change the reflecting area of ​​the first electrode 101 and the emitting area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light source is assumed to be the reflection region, and any position on the light-emitting layer where the desired light is obtained is assumed to be the light-emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0078] The light-emitting element shown in FIG. 1C has a microcavity structure and therefore has the same EL layer. Therefore, it is possible to obtain different emission colors. This eliminates the need for separate coloring (e.g., RGB) for the purpose of achieving high resolution. It is easy to combine with a colored layer (color filter). It is possible to increase the emission intensity in the front direction of a fixed wavelength, which leads to lower power consumption. can.

[0079] The light-emitting element shown in FIG. 1E is an example of the light-emitting element having the tandem structure shown in FIG. 1B. As shown in the figure, three EL layers (103a, 103b, 103c) are disposed on the charge generating layer (10 The three EL layers (103a, 104a, 104b) are sandwiched between the EL layers. Each of the light-emitting layers (113a, 113b, 113c) has a light-emitting layer (113a, 113b, 113c). Therefore, the emission colors of the light emitting layers can be freely combined. The light-emitting layer 113b is red, green, or yellow, and the light-emitting layer 113c is blue. However, the light-emitting layer 113a can be red, and the light-emitting layer 113b can be blue, green, or yellow. Either of the light-emitting layers 113c may be red.

[0080] In the light-emitting element according to one embodiment of the present invention, the first electrode 101 and the second electrode At least one of the electrodes 102 is a light-transmitting electrode (transparent electrode, semi-transmitting / semi-reflective electrode, etc.). When the electrode having light transmission is a transparent electrode, the visible light transmittance of the transparent electrode shall be 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the visible light reflectance of the semi-transmissive / semi-reflective electrode is The ratio is 20% or more and 80% or less, preferably 40% or more and 70% or less. , resistivity is 1×10 -2 It is preferable to set it to Ωcm or less.

[0081] In the above-described light-emitting element which is one embodiment of the present invention, the first electrode 101 and the second electrode When one of the electrodes 102 is a reflective electrode, the possibility of the reflective electrode The reflectance of visible light is set to 40% or more and 100% or less, and preferably 70% or more and 100% or less. In addition, this electrode has a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.

[0082] <Specific structure and manufacturing method of light-emitting element> Next, a specific structure and a manufacturing method of a light-emitting element according to one embodiment of the present invention will be described with reference to FIG. In this example, the tandem structure shown in FIG. 1(B) is used. A light-emitting device having a T-structure will also be described with reference to FIG. 1(D). When the optical element has a microcavity structure, the first electrode 101 is formed as a reflective electrode. The second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. The second electrode 1 may be formed as a single layer or a multilayer structure using one or more of the above. After the EL layer 103b is formed, the material is selected in the same manner as above and the EL layer 103b is formed. These electrodes can be fabricated by sputtering or vacuum deposition.

[0083] <First Electrode and Second Electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from those having the above-mentioned functions of both electrodes. If the requirements are met, the following materials can be used in combination. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (IT SO), In-Zn oxide, and In-W-Zn oxide. Aluminum (Al), Titanium (Ti), Chromium (Cr), Manganese (Mn), Iron (Fe), Cobalt (Co), Nickel (Ni), Copper (Cu), Gallium (Ga), Zinc (Zn), Indium (In), Tin (Sn), Molybdenum (Mo), Tantalum (Ta), Tungsten Tin (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium The material used is alloys containing metals such as yttrium (Y), neodymium (Nd), and other suitable combinations. In addition, elements belonging to Group 1 or 2 of the periodic table that are not listed above may be used. Elements (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr) Rare earth metals such as strontium (Sr), europium (Eu), and ytterbium (Yb) An alloy containing these in appropriate combination, graphene, etc. may also be used.

[0084] In the light-emitting element shown in FIG. 1D, when the first electrode 101 is an anode, The hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are formed on the substrate 101 by vacuum deposition. After the EL layer 103a and the charge generating layer 104 are formed, On the generating layer 104, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are formed in the same manner. are successively laminated.

[0085] <Hole injection layer and hole transport layer> The hole injection layer (111, 111a, 111b) is connected to the first electrode 101 which is an anode and the charge generating This layer injects holes from the layer 104 to the EL layer (103, 103a, 103b). The layer contains a material with high hole injection properties.

[0086] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. Examples of transition metal oxides include oxides of tungsten, manganese, and other oxides. Phthalocyanine (abbreviation: H 2 Pc) and copper phthalocyanine (abbreviation: CuPC) The nin-series compound, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl N,N'-bis{4-[bis(3-methylphenyl)amino]biphenyl (abbreviation: DPAB), phenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4, Aromatic amine compounds such as 4'-diamine (abbreviation: DNTPD) or poly(3,4-ene Poly(ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS ) and other polymers can be used.

[0087] In addition, materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptors). A composite material containing an acceptor material can also be used. In this case, the positive Electrons are extracted from the hole transport material and holes are transported in the hole injection layer (111, 111a, 111b). are generated and are transported through the hole transport layers (112, 112a, 112b) to the light emitting layers (113, 113 Holes are injected into the hole injection layers (111, 111a, 111b). The single-layered semiconductor device is made of a composite material containing a hole transport material and an acceptor material (electron acceptor material). Alternatively, a hole transport material and an acceptor material (electron accepting material) may be formed in layers. Each of these layers may be formed by laminating different layers.

[0088] The hole transport layer (112, 112a, 112b) is The holes injected from the first electrode 101 and the charge generating layer 104 are transported to the light emitting layer (11 3, 113a, 113b). The hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. The hole transport material used in b) is HO, particularly the hole injection layer (111, 111a, 111b). It is preferable to use a material having a HOMO level that is the same as or close to the MO level.

[0089] The acceptor material used in the hole injection layer (111, 111a, 111b) is an element Oxides of metals belonging to Groups 4 to 8 of the periodic table can be used. are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tantalum oxide. Among them, molybdenum oxide is particularly It is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. The organic acceptors, such as chloranil derivatives and hexaazatriphenylene derivatives, Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetracyano Trifluoroquinodimethane (abbreviation: F4 -TCNQ), Chloranil, 2,3,6,7,1 0,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation In particular, HAT-CN, which contains multiple heteroatoms, can be used. Compounds having a condensed aromatic ring to which an electron-withdrawing group is bonded are preferred because they are thermally stable. In addition, the radicals [3] contain electron-withdrawing groups (especially halogen groups such as fluoro groups and cyano groups). The olefin derivatives are preferred because they have a very high electron-accepting property. ,2,3-Cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluoroethylene] Fluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane trihydrate Ylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) Benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene [2,3,4,5,6-pentafluorobenzeneacetonitrile] and can be.

[0090] The hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 As the hole transport material used in 2b), 10 -6 cm 2 / Vs or higher hole mobility In addition, other materials that have a higher hole transporting property than an electron transporting property are also usable. can be used.

[0091] As hole transport materials, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives, Indole derivatives) and aromatic amine compounds are preferred. Specific examples include 4,4'-bis [N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-N PD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'- Biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro- 9,9'-Bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSP B) 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl) Triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl- 9H-Carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[ 4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9 -Phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'- Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl) Phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) , 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl) PCBBi1BP, 4-(1-naphthyl)-4'-(9-phenyl) (phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl) PCBNBB, 9,9-dimethyl-N-phenyl-N -[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene-2- Amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carba 9,9'-bifluoren-2-amine (abbreviation: P CBASF), 4,4',4''-tris(carbazol-9-yl)triphenylamine TCTA, 4,4',4''-tris(N,N-diphenylamino)triphenylphosphine phenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl Aromatic compounds such as [Nyl]-N-phenylamino]triphenylamine (abbreviation: MTDATA) A compound with an amine skeleton, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3 ,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3' -Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(9-phenyl 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-phenyl Phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4-(N-carbazole 9-[4-(10-phenyl-9-azolyl)phenyl]benzene (abbreviation: TCPB), Carbazoles such as [9H-carbazole]-9H-phenyl-(abbreviation: CzPA) Compounds with the skeleton, 4,4',4''-(benzene-1,3,5-triyl)tri(di Benzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9 -phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DB TFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl Thiophenes such as [1-phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Compounds with the skeleton 4,4',4''-(benzene-1,3,5-triyl)tri(di Benzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H- Fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLB i-II) and other compounds having a furan skeleton.

[0092] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylphosphine) nylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl Amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis (phenyl)benzidine (abbreviation: Poly-TPD) and other polymer compounds. It is also possible.

[0093] However, the hole transport material is not limited to the above, and one or more of various known materials may be used. In combination, the hole injection layer (111, 111a, 111b) and the hole transport layer (111, 111a, 111b) serve as hole transport materials. It can be used for the hole transport layer (112, 112a, 112b). Each of the layers 112, 112a, and 112b may be formed of multiple layers. For example, a first hole transport layer and a second hole transport layer may be laminated.

[0094] In the light-emitting element shown in FIG. 1D, a light-emitting layer 112 is formed on the hole transport layer 112a of the EL layer 103a. The EL layer 103a and the charge generating layer 104 are formed by vacuum deposition. After the formation of the hole transport layer 112b of the EL layer 103b, a light emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by vacuum deposition. It is formed by:

[0095] <Light-emitting layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing a light-emitting substance. Luminescent materials include blue, purple, blue-purple, green, yellow-green, yellow, orange, and red. In addition, a material exhibiting different properties is appropriately used for the light-emitting layers (113a, 113b, 113c). By using luminescent materials having different luminescent colors (for example, complementary colors), It is possible to obtain white light by combining different luminescent colors. A laminated structure having different light emitting materials may also be used.

[0096] The light-emitting layers (113, 113a, 113b, 113c) contain a light-emitting material (guest material). In addition, one or more organic compounds (host material, assist material) may be included. In addition, the one or more organic compounds may be a hole-transporting compound described in this embodiment. Either or both of a conductive material and an electron transporting material can be used.

[0097] The luminescent material that can be used in the luminescent layers (113, 113a, 113b, 113c) As examples, there are luminescent materials that convert singlet excitation energy into visible light, and triplet excitation A luminescent material that converts electromotive energy into light emission in the visible light region can be used.

[0098] Examples of other light-emitting substances include the following:

[0099] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples of such derivatives include pyrene derivatives, anthracene derivatives, triphenylene derivatives, and fluoro derivatives. Oleno derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives In particular, pyrene derivatives are The photon yield is high, which is preferable. Specific examples of pyrene derivatives include N,N'-bis(3- Methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl (dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation Name: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N '-Diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( Pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura N,N'-(pyrene-1,6-diamine) (abbreviation: 1,6BnfAPrn), yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[ (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation :1,6BnfAPrn-03).

[0100] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-Anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-cal 4'-(10-phenyl-9-anthryl)-4'-(10-phenyl-9-benzol-9-yl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo PCAPA, 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA) ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1- phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation Name: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-phenyl] N-(2-phenyl)-9H-carbazol-3-amine (abbreviation: 2PCAPPA), -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) etc. can be used. do.

[0101] In addition, examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials. Materials that exhibit thermally activated delayed fluorescence (thermally activated delayed fluorescence) tivated delayed fluorescence (TADF) materials are can be.

[0102] Phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since each substance has a different emission color (emission peak), it is necessary to select the appropriate one as needed. Select and use.

[0103] Blue or green, with a peak wavelength of 450 nm or more and 570 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0104] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp) 3 ]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz) 3 ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrPrp tz-3b) 3 ]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl [Ir(iPr5 btz) 3 ]), organometallic complexes with a 4H-triazole skeleton such as tris[3- Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato ]Iridium(III) (abbreviation: [Ir(Mptz1-mp) 3 ]), Tris(1-methyl 1H-1,2,4-triazolato)iridium(II I) (abbreviation: [Ir(Prptz1-Me) 3 ]) Organometallic complexes, fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl] [phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] [Phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me) 3 Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluorophenyl] (O-phenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1-pyrazo aryl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pi Lysinato-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), S(2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’ }Iridium(III) picolinate (abbreviation: [Ir(CF3 ppy) 2 (pic)] , bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium (III) Acetylacetonate (abbreviation: FIr(acac)) Examples of such a complex include an organometallic complex having a phenylpyridine derivative as a ligand.

[0105] It has a green or yellow color and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0106] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(mppm) 3 ]), tris(4-t-butyl-6-phenylpyrimidinato)i Iridium(III) (abbreviation: [Ir(tBuppm) 3 ]), (acetylacetonato)bi Bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm) 2 (acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) 2 (a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Ir(nbppm) 2 (acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl Rupyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm) 2 (acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation :[Ir(dmppm-dmp) 2 (acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III)(abbreviation: [Ir(dppm) 2 ( Organometallic iridium complexes with pyrimidine skeletons such as (acetylated acac)] cetonato)bis(3,5-dimethyl-2-phenylpyrazinate)iridium(III)( Abbreviation: [Ir(mppr-Me) 2 (acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinate)iridium(III)(abbreviation: [Ir(mppr-iPr) 2 Organometallic compounds with pyrazine skeletons such as (acac)] Iridium complex, tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (Abbreviation: [Ir(ppy) 3 ]), bis(2-phenylpyridinato-N,C 2’ ) Iridi Ir(III) acetylacetonate (abbreviation: [Ir(ppy) 2 (acac)]), (benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq) 2 (acac)]), tris(benzo[h]quinolinato)iridium(II I) (Abbreviation: [Ir(bzq) 3 ]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3 ]), bis(2-phenylquinolinato- N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2 (a Organometallic iridium complexes with pyridine skeletons such as bis(2,4-diphenyl ether (cac)]) Phenyl-1,3-oxazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(dpo) 2 (acac)]), bis{2-[4'-(perfluoro Phenyl)phenyl]pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir(p-PF-ph) 2 (acac)]), bis(2-phenylbenzo[2- Thiazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir( bt) 2 In addition to organometallic complexes such as tris(acetylacetonato) (mono Nophenanthroline)terbium(III) (abbreviation: [Tb(acac) 3 (Phen) ]) are examples of rare earth metal complexes.

[0107] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0108] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinium] dinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), S[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(5mdppm) 2 (dpm)]), (dipivaloyl Thanato)bis[4,6-di(naphthalene-1-yl)pyrimidinato]iridium(III )(Abbreviation: [Ir(d1npm) 2 (dpm)]) Metal Complex, (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridide Ir(tppr) 2 (acac)]), bis(2,3,5-tetrahydrofuran Triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr) 2 (dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethyl {5-phenyl-2-pyrazinyl-κN}phenyl-κC}(2,6-diphenyl Tyl-3,5-heptanedionate-κ 2 O,O') Iridium(III) (abbreviation: [Ir (dmdppr-P) 2 (dibm)]), bis{4,6-dimethyl-2-[5-(4- Cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazine {2,2,6,6-tetramethyl-3,5-heptanedioic acid} Nat-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2 (dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxa Nat-N,C 2’ ]Iridium(III) (abbreviation: [Ir(mpq) 2 (acac)]) , (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ ) Ili Ir(dpq) 2 (acac)]), (acetylacetonate ) Bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (Abbreviation: [Ir(Fdpq)2 Organometallic compounds with pyrazine skeletons such as (acac)] Complexes and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium (III) (abbreviation Title: [Ir(piq) 3 ]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridi Ir(III) acetylacetonate (abbreviation: [Ir(piq) 2 (acac)]) Organometallic complexes with pyridine skeletons such as 2,3,7,8,12,13,17,18- octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: [PtOEP]) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monofena Europium(III) (abbreviation: [Eu(DBM) 3 (Phen)]), Tris[1-(2-phenanthroyl)-3,3,3-trifluoroacetonato](monophenanthroyl) Europium(III) (abbreviation: [Eu(TTA) 3 (Phen)] Rare earth metal complexes are included.

[0109] The organic compounds (host materials, The host material has an energy gap larger than that of the light-emitting material (guest material). One or more substances having a Gap may be selected and used.

[0110] When the light-emitting substance is a fluorescent material, the host material has an energy level of 100 nm in the singlet excited state. It is preferable to use an organic compound having a large triplet excited state energy level and a small triplet excited state energy level. For example, it is preferable to use anthracene derivatives or tetracene derivatives. Phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl- 9H-Carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracene 7-[4-(10-phenyl)phenyl]-9H-carbazole (abbreviation: CzPA), [c,g]carbazole (abbreviation: cg DBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-be Benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-1 0-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}a 5,12-diphenyltetracene (abbreviation: FLPPA), 5,12-diphenyltetracene, 5,12-bis( (biphenyl-2-yl)tetracene.

[0111] When the light-emitting material is a phosphorescent material, the host material is a material that has a triplet excitation energy of the light-emitting material. (energy difference between the ground state and the triplet excited state) In this case, in addition to zinc and aluminum-based metal complexes, Oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline Dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives Conductors, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline In addition to anthroline derivatives, aromatic amines and carbazole derivatives can be used. .

[0112] More specifically, the host material may be, for example, the following hole transporting material and electron transporting material: can be used.

[0113] Examples of such host materials with high hole transport properties include N,N'-di(p-tolyl)-N ,N'-Diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis [N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: D PAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N ,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTP) D) 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamine Examples of aromatic amine compounds include aromatic amine compounds such as diphenyl ether (DPA3B) and diphenyl ether (DPA3B).

[0114] Also, 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl Nylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylamine PCzDPA 2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)a 3-[N-(9-phenylamino)-9-phenylcarbazole (abbreviation: PCzTPN2), [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-phenyl Examples of the carbazole derivatives include PCzPCN1 and PCzPCN2. Another example of a carbazole derivative is 4,4'-di(N-carbazolyl)biphene. Nyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzoyl Zene (abbreviation: TCPB), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3 , 5,6-tetraphenylbenzene, etc. can also be used.

[0115] In addition, examples of host materials with high hole transport properties include 4,4'-bis[N-(1-naphthalene) (abbreviation: NPB or α-NPD) and N,N' -Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4 ,4'-diamine (abbreviation: TPD), 4,4',4''-tris(carbazole-9-yl) N-(1-phenyl)triphenylamine (TCTA), 1'-TNATA), 4, 4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDA TA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino ]triphenylamine (abbreviation: m-MTDATA), 4,4'-bis[N-(spiro-9 ,9'-Bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB ), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine ( Abbreviated name: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl) tetrahydrofuran mBPAFLP, N-(9,9-dimethyl-9H-fluorene) N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-diphenyl-2-yl)-N- Methyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenyl DFLADFL, N-(9,9-dimethyl-2-diphenylamino- 9H-Fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4- diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene ( Abbreviation: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazole-3- 4,4'-diphenyl-4''-yl)triphenylamine (abbreviation: PCBA1BP), (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBB i1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3- 4,4'-di(1-naphthyl)-4 ''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P CBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl N,N'-bis(9-phenylcarbazole-3- yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N, N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazole- 3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-biphenyl N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H -Carbazole-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4- yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9, 9-Dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 9,9-dimethyl -N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] N-phenyl-N-[4-(9-fluorophenyl]fluorene-2-amine (abbreviation: PCBAF), (phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene 2-Amine (abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl )-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2, 7-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro-9 ,9'-Bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazole-9- N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), ,N'-Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9 Aromatic amines such as 9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) Compounds such as 3-[4-(1-naphthyl)-phenyl]-9- Phenyl-9H-carbazole (abbreviation: PCPN), 3-[4-(9-phenanthryl) -phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3,3'-biphenyl (9-phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis(N-carbazole) 3,6-bis(3,5-diphenylphenyl)- 9-Phenylcarbazole (abbreviation: CzTP), 4-{3-[3-(9-phenyl-9H -fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFL Bi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzo furan) (abbreviation: DBF3P-II), 1,3,5-tri(dibenzothiophene-4-yl) 2,8-diphenyl-4-[4-(9-phenyl)-benzene (abbreviation: DBT3P-II) (phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTF LP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4-[3-(triphenyl (phenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II), etc. Carbazole compounds, thiophene compounds, furan compounds, fluorene compounds, triphenyl compounds, Nylene compounds, phenanthrene compounds, etc. can be used.

[0116] An example of a host material with high electron transport properties is tris(8-quinolinolato)aluminum. Aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (III) (Abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)be Lilium(II) (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4- Phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolin Zn(II) (abbreviation: Znq) and other quinols with quinoline or benzoquinoline skeletons. In addition, bis[2-(2-benzoxazolyl)phenolato] ]Zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolate ]Zinc(II) (abbreviation: ZnBTZ) and other oxazole and thiazole ligands Metal complexes such as 2-(4-biphenyl) (aryl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation : PBD) and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-phenylenediamine] oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl -1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11) and 3-(4-biphenylyl)-4-phenyl TAZ ) and triazole derivatives such as 2,2',2''-(1,3,5-benzenetriyl ) Tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3- (Dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazol Compounds with imidazole skeletons (especially benzoyl) such as mDBTBIm-II zoimidazole derivatives) and 4,4'-bis(5-methylbenzoxazol-2-yl Compounds with an oxazole skeleton, such as stilbene (abbreviation: BzOs) (especially benzoyl compounds) xazole derivatives), bathophenanthroline (abbreviated as Bphen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1, Phenanthroline derivatives such as 10-phenanthroline (NBphen) and 2- [3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline ( Abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl] phenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq- II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibene 2-[4-(3,6-diphenyl (f,h)quinoxaline Name: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl ]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3 -(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation : 6mDBTPDBq-II), 4,6-bis[3-(phenanthren-9-yl)phenyl 4,6-bis[3-(4-dibenzo[p- ... 4,6-Bi(phenyl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6mCz Heterocyclic compounds with diazine skeletons such as 2-{4-[3-(N-phenyl (9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4 ,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) Heterocyclic compounds with a carbazole skeleton and 3,5-bis[3-(9H-carbazol-9-yl) phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridin Heterocyclic compounds having a pyridine skeleton, such as triphenylphenylbenzene (abbreviation: TmPyPB) Also usable are poly(2,5-pyridinediyl) (abbreviation: PPy), poly Li[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5- poly[(9,9-dioctylfluorene-2,7-diyl)] (abbreviation: PF-Py), PF-BPy) It is also possible to use polymer compounds such as the following.

[0117] In addition, examples of the host material include anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Condensed polycyclic aromatic compounds such as chrysene derivatives and dibenzo[g,p]chrysene derivatives are included. Specifically, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N- Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carba CzA1PA, 4-(10-phenyl-9-anthryl) Triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl -N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H -Carbazole-3-amine (abbreviation: PCAPBA), 2PCAPA, 6,12-dimeth Diphenylchrysene, DBC1, 9-[4-(10-phenyl-9- 3,6-Diphenyl)-9H-carbazole (abbreviation: CzPA), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene ( DPPA), 9,10-di(2-naphthyl)anthracene (DNA), 2- tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA ), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'- Diphenylphenanthrene (DPNS), 9,9'-(stilbene-4,4'-di 1,3,5-tri(1-pyrenyl)benzoate (abbreviation: DPNS2), Zen (abbreviation: TPB3) etc. can be used.

[0118] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), Two types of compounds (a first compound and a second compound) that form an exciplex, and an organometallic In this case, various organic compounds may be used in appropriate combination. However, in order to efficiently form an exciplex, a compound that easily accepts holes ( A compound that easily accepts electrons (a hole-transporting material) is combined with a compound that easily accepts electrons (an electron-transporting material). Specific examples of the hole transport material and the electron transport material are as follows: The materials shown in this embodiment mode can be used. This structure provides high efficiency, low voltage, and long life. You can achieve both lives at the same time.

[0119] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the light into a singlet state (reverse intersystem crossing), and efficiently emit light (fluorescence) from the singlet excited state. The conditions for efficiently obtaining thermally activated delayed fluorescence are as follows: The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably In addition, the delayed fluorescence in TADF materials is The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of -6 seconds or more, preferably 10 -3 More than seconds.

[0120] Examples of TADF materials include fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium (Cd) Cd, Sn, Pt, In, or Palladium Examples of metal-containing porphyrins include those containing Pd. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Proto IX) , mesoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Meso IX)), Hematopoietin Lufirin-Tin Fluoride Complex (abbreviation: SnF 2 (Hemato IX), Coproporf Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF 2 (Copro III- 4Me), Octaethylporphyrin-Tin Fluoride Complex (abbreviation: SnF 2 (OEP) , etioporphyrin-tin fluoride complex (abbreviation: SnF 2 (Etio I)), Octae Tyrporphyrin-Platinum Chloride Complex (abbreviation: PtCl 2 OEP) etc.

[0121] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl 4,6-diphenyl-1,3,5-triazine (abbreviation Name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4 -(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5- Diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-di Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACR XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a Clidine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having an excess type heteroaromatic ring and a π-electron deficient type heteroaromatic ring can be used. In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded is The donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings are both strong. This is particularly preferred because it reduces the energy difference between the singlet excited state and the triplet excited state. stomach.

[0122] In addition, when using a TADF material, it can also be used in combination with other organic compounds.

[0123] In the light-emitting device shown in FIG. 1D, an electron transport layer is provided on the light-emitting layer 113a of the EL layer 103a. The EL layer 103a and the charge generating layer 104 are formed by vacuum deposition. After the formation of the electron transport layer 114b, the electron transport layer 114b is formed on the light emitting layer 113b of the EL layer 103b by vacuum deposition. It is formed by:

[0124] <Electron transport layer> The electron transport layer (114, 114a, 114b) is b) transfers electrons injected from the second electrode 102 and the charge generating layer 104 to the light emitting layer (11 3, 113a, 113b). The electron transport layer (114, 114a, 114b) is a layer containing an electron transport material. The electron transport material used in b) is 1×10 -6 cm 2 / Vs or higher electron mobility In addition, other materials that have a higher electron transporting property than a hole transporting property may be used. It can be used.

[0125] Electron transport materials include quinoline ligands, benzoquinoline ligands, and oxazole ligands. or a metal complex having a thiazole ligand, an oxadiazole derivative, or a triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. In addition, the use of π-electron-deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds It is also possible.

[0126] Specifically, Alq 3 , tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: B eBq 2 ), BAlq, bis[2-(2-hydroxyphenyl)benzoxazolato] Lead(II) (abbreviation: Zn(BOX) 2 ), bis[2-(2-hydroxyphenyl)benzo Thiazolato]zinc(II) (abbreviation: Zn(BTZ) 2 ), metal complexes such as 2-(4-biphenyl (phenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( Abbreviation: PBD), OXD-7, 3-(4'-tert-butylphenyl)-4-phenyl -5-(4''-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4 -tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl )-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation :Bphen), Bathocuproine (abbreviation:BCP), 4,4'-bis(5-methylphenyl) Heteroaromatic compounds such as 2-benzoxazolyl stilbene (abbreviation: BzOs), -[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (Abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl) Biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq -II), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl ]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(di Benzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7m DBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibe Quinoxaline such as quinoxaline [f,h] quinoxaline (abbreviation: 6mDBTPDBq-II) Alternatively, dibenzoquinoxaline derivatives can be used.

[0127] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl Fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' -bipyridine-6,6'-diyl) (abbreviation: PF-BPy) You can also be there.

[0128] In addition, the electron transport layer (114, 114a, 114b) may be a single layer or may be made of the above-mentioned material. The layer may have a structure in which two or more layers made of the above are laminated.

[0129] In the light-emitting element shown in FIG. 1D, electrons are injected onto the electron transport layer 114a of the EL layer 103a. The charge generating layer 115a is formed by vacuum deposition. Then, the EL layer 103a and the charge generating layer 115b are After the electron transport layer 114b of the EL layer 103b is formed, the electron injection layer 104 is formed. The insulating layer 115b is formed by vacuum deposition.

[0130] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing a substance with high electron injection properties. The electron injection layers (115, 115a, 115b) are made of lithium fluoride (LiF), cerium fluoride (CeF), CsF, Calcium Fluoride (CaF 2 ), lithium oxide (LiO x ) etc. Such alkali metals, alkaline earth metals, or compounds thereof can be used. Erbium fluoride (ErF 3 ) can be used. In addition, an electride may be used for the electron injection layer (115, 115a, 115b). For example, a mixed oxide of calcium and aluminum with high electron doping is used as a tritride. In addition, the above-mentioned electron transport layer (114, 114a, 114b) It is also possible to use a substance constituting the above.

[0131] In addition, the electron injection layer (115, 115a, 115b) contains an organic compound and an electron donor (donor A composite material containing the above-mentioned compound may be used. Since electrons are generated in the organic compound, the organic compound has excellent electron injection and transport properties. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, for example, the electron transporting layer (114, 114a, 114b) described above may be used Materials such as metal complexes and heteroaromatic compounds can be used as electron donors. Any substance that exhibits electron donating properties to organic compounds is acceptable. The lithium earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, Erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metals Metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Alternatively, a Lewis base such as magnesium oxide can be used. Organic compounds such as thiafulvalene (abbreviation: TTF) can also be used.

[0132] For example, when the light obtained from the light emitting layer 113b is to be amplified, the second electrode 102 The optical distance between the light emitting layer 113b and the light emitting layer 113b is less than λ / 4 with respect to the wavelength of the light emitted by the light emitting layer 113b. In this case, it is preferable to form the electron transport layer 114b or the electron injection layer 114c so that the electron transport layer 114b is filled with the electron This can be adjusted by changing the film thickness of 115b.

[0133] <Charge generation layer> The charge generating layer 104 generates a charge between the first electrode (anode) 101 and the second electrode (cathode) 102. When pressure is applied, electrons are injected into the EL layer 103a and holes are injected into the EL layer 103b. The charge generation layer 104 has a function of forming a hole transporting material with an electron acceptor (acceptor ) is added to the electron transport material, Alternatively, both of these configurations may be laminated. By forming the charge generating layer 104 using the material, when the EL layer is laminated, The increase in driving voltage can be suppressed.

[0134] In the case where the charge generating layer 104 is configured such that an electron acceptor is added to a hole transporting material, As the hole transporting material, the material shown in this embodiment mode can be used. The receptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinoline. Dimethane (abbreviation: F 4 -TCNQ), chloranil, etc. Examples of the oxides of metals belonging to Groups 4 to 8 in the table include: Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples of the oxide include tin, manganese oxide, and rhenium oxide.

[0135] In the case where the charge generating layer 104 has a structure in which an electron donor is added to an electron transporting material, As the electron transporting material, the materials shown in this embodiment mode can be used. The donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or an element of the periodic table. Metals belonging to Groups 2 and 13 in the table and their oxides and carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium Ca, Yb, In, Lithium oxide, Cesium carbonate It is preferable to use organic compounds such as tetrathianaphthalene. It may also be used as a donor.

[0136] The EL layer 103c in FIG. 1(E) is the same as the EL layer (103, 103a, 103b) described above. The charge generating layers 104a and 104b may have the same structure as described above. The charge generating layer 104 may have a similar structure.

[0137] <Substrate> The light-emitting element shown in this embodiment mode can be formed on various substrates. The type of substrate is not limited to a specific one. An example of the substrate is a semiconductor substrate (e.g. Single crystal substrate or silicon substrate), SOI substrate, glass substrate, quartz substrate, plastic substrate , metal substrate, stainless steel substrate, substrate with stainless steel foil, tantalum Tungsten substrate, substrate with tungsten foil, flexible substrate, lamination film, Examples of the material include paper containing fibrous materials and base films.

[0138] Examples of the glass substrate include barium borosilicate glass and aluminoborosilicate glass. Glass or soda lime glass. Flexible substrates, lamination films, etc. Examples of base films include polyethylene terephthalate (PET), polyethylene Plastics such as polyolefin naphthalate (PEN) and polyethersulfone (PES) Synthetic resins such as acrylic, polypropylene, polyester, polyvinyl fluoride, Vinyl chloride, polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, or paper Examples include:

[0139] Note that the light-emitting element shown in this embodiment mode can be manufactured by a vacuum process such as a deposition method or a spin-coil method. Solution processes such as the inkjet method and the ink-jet method can be used. In this case, sputtering, ion plating, ion beam deposition, molecular beam deposition, Physical vapor deposition (PVD) methods such as air vapor deposition and chemical vapor deposition (CVD) methods can be used. In particular, the functional layer (hole injection layer (111, 111a, 111)) included in the EL layer of the light-emitting element can be formed. b), hole transport layer (112, 112a, 112b), light emitting layer (113, 113a, 113 b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 1 15a, 115b), and the charge generating layer (104, 104a, 104b), Vacuum deposition method (vacuum deposition method, etc.), coating method (dip coating method, die coating method, bar coating method, stripping method, etc.) Pin coat method, spray coat method, etc.), printing method (inkjet method, screen (stencil printing offset (lithographic printing), flexography (letterpress printing), gravure, microcompression The film can be formed by a method such as a contact method.

[0140] The EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are Each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), electron injection layer (115, 115a, 115b)), charge generation layer ( 104, 104a, 104b) are not limited to the above-mentioned materials and may be other materials. However, as long as the functions of each layer can be fulfilled, they can be used in combination. The following compounds are considered to be suitable for use: high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds, Compounds in the intermediate range between polymers and molecules: molecular weight 400-4000), inorganic compounds (quantum dot materials As the quantum dot material, colloidal quantum dots can be used. Materials, alloy-type quantum dot materials, core-shell-type quantum dot materials, core-type quantum dot materials, etc. etc. can be used.

[0141] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments. It is possible.

[0142] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light emitting device shown in FIG. 1 comprises a transistor (FET) 202 and a light emitting element (2 03R, 203G, 203B, 203W) are electrically connected to form an active matrix. A light-emitting device of the type having a plurality of light-emitting elements (203R, 203G, 203B, 203W) 204, and the electrodes of each light-emitting element are electrically connected to each other according to the color of the light emitted by each light-emitting element. The optical path length of the EL layer 204 is adjusted to obtain a microcavity structure. The emitted light is reflected by the color filters (206R, 206G, 206 It is a top-emission type light-emitting device in which light is emitted through a

[0143] In the light-emitting device shown in FIG. 2A, the first electrode 207 is formed to function as a reflective electrode. In addition, the second electrode 208 is formed so as to function as a semi-transmissive and semi-reflective electrode. In other embodiments, the electrode material for forming the first electrode 207 and the second electrode 208 may be Please refer to the description and use it as appropriate.

[0144] In addition, in FIG. 2A, for example, the light emitting element 203R is a red light emitting element, and the light emitting element 203 G is a green light emitting element, the light emitting element 203B is a blue light emitting element, and the light emitting element 203W is a white light emitting element. In this case, the light-emitting element 203R has a first electrode 207 and a second electrode 208 as shown in FIG. The light emitting element 203G is adjusted so that the optical distance between the light emitting element 203G and the pole 208 is 200R. The optical distance between the first electrode 207 and the second electrode 208 is adjusted to 200G. 03B is arranged so that the optical distance between the first electrode 207 and the second electrode 208 is 200B. As shown in FIG. 2B, the conductive layer 207R in the light-emitting element 203R is adjusted. A conductive layer 207G is laminated on the first electrode 207 in the light emitting element 203G. This allows optical adjustment.

[0145] Color filters (206R, 206G, 206B) are formed on the second substrate 205. A color filter allows a specific wavelength range of visible light to pass through and blocks a specific wavelength range. Therefore, as shown in FIG. 2A, the filter overlaps with the light emitting element 203R. A color filter 206R that passes only the red wavelength region is provided at the position Red light can be obtained from the light emitting element 203R. By providing a color filter 206G that transmits only the wavelength range of the light emitting element 203 Green light can be obtained from G. Also, a blue wavelength region is obtained at a position overlapping with the light emitting element 203B. By providing a color filter 206B that transmits only blue light, the light emitting element 203B However, the light emitting element 203W does not need to be provided with a color filter. It is possible to obtain white light emission. A color filter (206R) may be provided. , 206G, 206B) and the black layer 209 are covered with an overcoat layer made of a transparent material. It is okay if it is.

[0146] In FIG. 2A, a structure (top emission type) in which light is extracted on the second substrate 205 side is used. A light emitting device is shown, but as shown in FIG. 2(C), a first substrate on which a FET 202 is formed The light emitting device may have a structure in which light is extracted from the 201 side (bottom emission type). In the case of a bottom emission type light emitting device, the first electrode 207 is a semi-transmissive and semi-reflective electrode. The first electrode 206 is formed to function as a reflecting electrode, and the second electrode 208 is formed to function as a reflecting electrode. The first substrate 201 is at least a light-transmitting substrate. (206R', 206G', 206B') are light emitting elements (203 R, 203G, and 203B) on the first substrate 201 side.

[0147] In addition, in FIG. 2(A), the light emitting elements are red light emitting elements, green light emitting elements, blue light emitting elements, Although the case of a white light-emitting element has been described, the light-emitting element which is one embodiment of the present invention is not limited to this structure. The light emitting element may be a yellow light emitting element or an orange light emitting element. In order to manufacture these light-emitting devices, EL layers (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, etc.) are For the materials used in the layer (e.g., the electron injection layer, the charge generation layer, etc.), see the description of other embodiments. In this case, the color filter may be appropriately selected according to the color of the light emitted by the light emitting element. The filter must be selected appropriately.

[0148] By adopting the above-mentioned configuration, a light-emitting device having light-emitting elements that emit light of a plurality of colors can be obtained. can be obtained.

[0149] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible to do so.

[0150] (Embodiment 4) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0151] By applying the element configuration of the light-emitting element according to one embodiment of the present invention, It is possible to manufacture a light-emitting device or a passive matrix type light-emitting device. A matrix type light emitting device is a device that combines light emitting elements and transistors (FETs). Therefore, the light emitting device may be a passive matrix type light emitting device or an active matrix type light emitting device. Note that the light-emitting device described in this embodiment can also include other The light emitting element described in the embodiment can be applied.

[0152] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG.

[0153] 3A is a top view showing the light emitting device, and FIG. 3B is a top view showing the light emitting device along the dashed line AA in FIG. The active matrix type light emitting device has a first substrate 301 and a second substrate 302. A pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate The pixel section 302 and the driver circuit section (304a, 304b) are connected to the pixel section 302. The first substrate 301 and the second substrate 302 are connected by a seal material 305. It is sealed between the plate 306 .

[0154] Moreover, on the first substrate 301, a lead wiring 307 is provided. The external input terminal is connected to the FPC 308. The FPC 308 is a drive circuit section. (303, 304a, 304b) receive external signals (e.g., video signals, clock signals , start signal, reset signal, etc.) and electric potential. A printed wiring board (PWB) may be attached. Note that if these FPCs or PWBs are installed, The attached state is included in the light emitting device.

[0155] Next, a cross-sectional structure is shown in FIG.

[0156] The pixel section 302 includes a FET (switching FET) 311 and a FET (current control FET). 312, and a plurality of pixels having a first electrode 313 electrically connected to the FET 312. The number of FETs in each pixel is not particularly limited, and may be any number. It can be provided appropriately as needed.

[0157] The FETs 309, 310, 311, and 312 are not particularly limited, and may be, for example, staggered. In addition, top-gate and bottom-gate transistors can be used. The transistor may have a structure such as a Tom-gate type.

[0158] The semiconductors that can be used for these FETs 309, 310, 311, and 312 are The crystallinity is not particularly limited, and may be an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, Any of polycrystalline semiconductors, single crystal semiconductors, and semiconductors having crystalline regions in some parts may be used. By using a crystalline semiconductor, the deterioration of transistor characteristics can be suppressed. This is preferable.

[0159] In addition, these semiconductors include, for example, Group 14 elements, compound semiconductors, and oxide semiconductors. , organic semiconductors, etc. can be used. Representative examples include semiconductors containing silicon, gallium, etc. A semiconductor containing arsenic, an oxide semiconductor containing indium, or the like can be used.

[0160] The driving circuit section 303 includes a FET 309 and a FET 310. The ET310 is a circuit that contains transistors of one polarity (either N-type or P-type only). Alternatively, the transistor may be a CMOS circuit including an N-type transistor and a P-type transistor. Alternatively, a configuration having an external driver circuit may be used.

[0161] The end of the first electrode 313 is covered with an insulator 314. , organic compounds such as negative photosensitive resins and positive photosensitive resins (acrylic resins), and acids. Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride can be used. It is preferable that the upper end or the lower end of the edge 314 has a curved surface having a curvature. This allows the film formed on the upper layer of the insulator 314 to have good coverage.

[0162] An EL layer 315 and a second electrode 316 are stacked on the first electrode 313. 315 is a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. Yes.

[0163] Note that the structure of the light-emitting element 317 in this embodiment mode may be the same as that described in the other embodiment modes or materials. Although not shown here, the second electrode 316 is connected to an external input. It is electrically connected to the terminal FPC308.

[0164] In addition, although only one light emitting element 317 is shown in the cross-sectional view shown in FIG. 02, a plurality of light emitting elements are arranged in a matrix. 2, light-emitting elements capable of emitting three kinds of light (R, G, B) are selectively formed, and It is possible to form a light-emitting device capable of displaying three colors (R, G, B). In addition to the light-emitting element from which light is obtained, for example, white (W), yellow (Y), magenta (M For example, a light-emitting element that can emit light of three colors (R, A light-emitting element capable of emitting the above-mentioned several types of light is added to a light-emitting element capable of emitting the light of G and B. This can improve color purity and reduce power consumption. By combining it with a filter, a light emitting device capable of full color display may be formed. The color filters are red (R), green (G), blue (B), cyan (C), and magenta (M). Colors such as ink (M), yellow (Y), etc. can be used.

[0165] The FETs (309, 310, 311, 312) and the light-emitting element 317 on the first substrate 301 are The second substrate 306 and the first substrate 301 are bonded together with a sealant 305. A space 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305 is formed. The space 318 is filled with an inert gas (nitrogen, argon, etc.) It may be filled with an organic material (including a sealant 305).

[0166] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material for the cooling material 305 that is as impermeable to moisture and oxygen as possible. In addition, the second substrate 306 may be made of the same material as the first substrate 301. Therefore, the various substrates described in the other embodiments can be used appropriately. In addition to glass and quartz substrates, FRP (Fiber-Reinforced Plastics) is also used as the substrate. ed Plastics), PVF (Polyvinyl Fluoride), polyester or acrylic A plastic substrate made of glass frit can be used as a sealing material. When using a glass substrate, the first substrate 301 and the second substrate 306 are preferably made of a glass substrate from the viewpoint of adhesion. It is preferably a plate.

[0167] In this manner, an active matrix light emitting device can be obtained.

[0168] In addition, when an active matrix type light emitting device is formed on a flexible substrate, The FET and the light emitting element may be formed directly, or the FET and the light emitting element may be formed on a separate substrate having a release layer. After forming the semiconductor, the FET and the light emitting element are separated from each other by applying heat, force, laser irradiation, etc. The peeling layer may be, for example, a thin film. Inorganic films such as tungsten and silicon oxide films, and organic resin films such as polyimide are used. In addition, as the flexible substrate, a substrate on which a transistor can be formed can be used. In addition to plates, paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, Fabric substrates (natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester, etc.) , leather substrate, or rubber substrate. By using these substrates, durability It has excellent heat resistance and can be made lighter and thinner.

[0169] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0170] (Embodiment 5) In this embodiment, a light-emitting device according to one embodiment of the present invention and a light-emitting element according to one embodiment of the present invention will be described. Examples of various electronic devices and automobiles completed using the display device will be described below.

[0171] The electronic device shown in FIG. 4(A) to FIG. 4(E) includes a housing 7000, a display unit 7001, and a speaker 7002. 003, LED lamp 7004, operation key 7005 (power switch or operation switch ), a connection terminal 7006, a sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, Rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, Includes functions to measure power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays ), microphones 7008, 7019, etc.

[0172] FIG. 4A shows a mobile computer, which includes, in addition to the above, a switch 7009, a red It may have an outside line port 7010, etc.

[0173] FIG. 4B shows a portable image reproducing device (for example, a DVD reproducing device) equipped with a recording medium. In addition to the above, it has a second display unit 7002, a recording medium reading unit 7011, etc. This can be done.

[0174] FIG. 4C shows a goggle-type display. In addition to the above, a second display unit 7002 , a support 7012, an earphone 7013, etc.

[0175] FIG. 4(D) shows a digital camera with a television receiving function, which, in addition to the above, has an antenna 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0176] FIG. 4E shows a mobile phone (including a smartphone), and a display unit 70 is provided in a housing 7000. 01, microphone 7019, speaker 7003, camera 7020, external connection part 702 1, operation buttons 7022, etc.

[0177] Figure 4(F) shows a large television set (also called a television or television receiver). The display device may include a housing 7000, a display unit 7001, a speaker 7003, and the like. In addition, here, a configuration in which the housing 7000 is supported by a stand 7018 is shown.

[0178] The electronic devices shown in FIG. 4(A) to FIG. 4(F) can have various functions. For example, Function to display various information (still images, videos, text images, etc.) on the display, touch panel Functions such as displaying calendars, dates, or times, and various software (programs) ) to control processing, wireless communication function, and wireless communication function to connect various computers It has a function to connect to a data network, and a wireless communication function to transmit or receive various data. The function of reading out a program or data recorded on a recording medium and displaying it on the display unit. Furthermore, in an electronic device having multiple display units, One display section is used mainly to display image information, and the other display section is used mainly to display text information. A function that displays a stereoscopic image by displaying an image that takes parallax into account on multiple displays. Furthermore, in electronic devices having an image receiving unit, the function of displaying static electricity can be It has the functions of taking still images, taking videos, and automatically or manually correcting the captured images. The function of storing the captured image on a recording medium (external or built-in to the camera) The display unit can have a function of displaying information on the display unit. The functions that an electronic device can have are not limited to these, and it may have a variety of functions. can.

[0179] FIG. 4G shows a smart watch, which includes a housing 7000, a display unit 7001, and operation buttons. 7022, 7023, a connection terminal 7024, a band 7025, a clasp 7026, etc. .

[0180] A display unit 7001 mounted on a housing 7000 that also serves as a bezel has a non-rectangular display area. The display unit 7001 has an icon 7027 representing the time, other icons 702 8, etc. The display unit 7001 is equipped with a touch sensor (input device). The display may be a touch panel (input / output device) mounted thereon.

[0181] The smartwatch shown in FIG. 4G can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display unit, Functions such as displaying calendars, dates, or times, and various software (programs) The function of controlling processing by the wireless communication function, It has a function to connect to a data network, and a wireless communication function to transmit or receive various data. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It may have the function of

[0182] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, degree, rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays. ), a microphone, etc.

[0183] Note that a light-emitting device according to one embodiment of the present invention and a display device having a light-emitting element according to one embodiment of the present invention The device can be used for each display portion of the electronic devices described in this embodiment, and has good color purity. This becomes possible.

[0184] In addition, as an electronic device to which a light-emitting device is applied, a folding type as shown in Figs. 5A shows a portable information terminal 931 in an unfolded state. 0. Also, FIG. 5(B) shows the state of the unfolded or folded state. The mobile information terminal 9310 is shown in a state in the middle of changing. The portable information terminal 9310 is in a folded state. The FOMA terminal is highly portable, and when unfolded, it has a seamless, wide display area that provides excellent visibility of the display. can be.

[0185] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the gap between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device according to one embodiment of the present invention can be reversibly transformed into a display portion 931. In addition, it is possible to display with good color purity. The display area 9312 is a display area located on the side of the portable information terminal 9310 in the folded state. The display area 9312 displays information icons and frequently used apps and programs. Shortcuts can be displayed, making it easy to check information and launch apps. can be carried out.

[0186] In addition, an automobile to which a light emitting device is applied is shown in FIG. The device can be integrated with the automobile. Outer lights 5101 (including the rear of the vehicle), tire wheels 5102, doors 5103 It can be applied to a part or the whole of the car. A display unit 5104, a handle 5105, a shift lever 5106, a seat 5107, an inner - It can be applied to rear view mirrors 5108, etc. It can also be applied to some glass windows. You may do so.

[0187] As described above, electronic devices and automobiles to which the light-emitting device or the display device according to one embodiment of the present invention is applied can be used. In this case, a display with good color purity is possible. The electronic devices and automobiles that can be used are not limited to those shown in the present embodiment, but can be used in any field. It is possible to apply

[0188] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0189] (Embodiment 6) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is used. The structure of a lighting device manufactured using this will be described with reference to FIG.

[0190] 7(A), (B), (C), and (D) show examples of cross-sectional views of a lighting device. (A) and (B) are bottom emission type lighting devices that extract light from the substrate side. C) and (D) are top-emission type lighting devices that extract light from the encapsulation substrate side.

[0191] A lighting device 4000 shown in FIG. 7A has a light-emitting element 4002 on a substrate 4001. The light emitting element 4002 has a substrate 4003 having projections and recesses on the outer side of the substrate 4001. It has a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0192] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0193] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light emitting element 4002. It is preferable that the substrate 4003 has the unevenness as shown in FIG. This can improve the efficiency of extracting the light generated in 02.

[0194] In addition, instead of the substrate 4003, as in the illumination device 4100 of FIG. 7(B), A diffuser plate 4015 may be provided on the outside.

[0195] A lighting device 4200 in FIG. 7C has a light-emitting element 4202 over a substrate 4201. The element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. .

[0196] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0197] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 421 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has projections and recesses as shown in FIG. The extraction efficiency of the light generated by the light emitting element 4202 can be improved.

[0198] In addition, instead of the sealing substrate 4211, a light-emitting element 4 is provided as in a lighting device 4300 of FIG. A diffuser plate 4215 may be provided on top of 202 .

[0199] As described in this embodiment, a light-emitting device according to one embodiment of the present invention or a part thereof By using a light-emitting element having such a characteristic, a lighting device having a desired chromaticity can be provided.

[0200] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0201] (Embodiment 7) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is used. An application example of a lighting device manufactured using this will be described with reference to FIG.

[0202] As an indoor lighting device, it can be used as a ceiling light 8001. The 8001 lighting fixture is available in ceiling-mounted and ceiling-embedded types. It is constructed by combining the optical device with a case and a cover. It can also be applied to a ceiling-hanging type (cord hanging type).

[0203] In addition, the footlights 8002 can irradiate the floor surface with light, improving safety at the feet. For example, it is effective to use it in bedrooms, stairs, and corridors. In that case, depending on the size and structure of the room, The size and shape can be changed as needed. It is also possible to configure the lighting device as a stationary type.

[0204] The sheet-like lighting 8003 is a thin sheet-like lighting device. It is attached to a wall surface. Since it uses a small space, it can be used for a wide range of purposes. It can also be used on curved walls or housings.

[0205] It is also possible to use a lighting device 8004 in which light from a light source is controlled to only a desired direction. do.

[0206] In addition to the above, a light-emitting device according to one embodiment of the present invention may be attached to a part of furniture in a room. By applying the light-emitting element that is a part of the device, it becomes a lighting device that also functions as furniture. It is possible.

[0207] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0208] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible. EXAMPLES

[0209] <Synthesis Example 1> In this example, an organic compound represented by structural formula (200) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 9'-phenyl-9'-[4-(10-phenyl-9-anthryl)phenyl]- Explain the synthesis method of 2,3'-bi-9H-carbazole (abbreviation: PCCPA-02) The structure of PCCPA-02 is shown below.

[0210] [ka]

[0211] Add 1 mL of 9-(4-bromophenyl)-10-phenylanthracene to a 200 mL three-neck flask. .2g (3.0mmol), 9'-phenyl-2,3'-bi-9H-carbazole 1.2 g (3.0 mmol), sodium tert-butoxide 0.60 g (6.2 mmol ) was added and the atmosphere in the flask was replaced with nitrogen. 30 mL of xylene was added to this mixture and cooled under reduced pressure. The mixture was degassed by stirring. 0.4 mL of tri(tert-butyl)phosphine was added to the mixture. bis(dibenzylideneacetone)palladium(0) 48 mg (83 μmol) was added, The mixture was refluxed at 150° C. for 6 hours under a nitrogen stream.

[0212] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried over magnesium sulfate. The resulting mixture was gravity filtered, and the filtrate was concentrated to obtain a solid. The liquid was filtered through Celite and alumina with suction, and the filtrate was concentrated to obtain a solid. When recrystallized from toluene, the target pale yellow solid was obtained in an amount of 1.1 g and a yield of 49%. The synthesis scheme of the above synthesis method is shown in the following formula (a).

[0213] [ka]

[0214] The resulting pale yellow solid (1.1 g) was purified by train sublimation. The preparation was carried out under the conditions of a pressure of 3.1 Pa and an argon flow rate of 5.0 mL / min. -[4-(10-phenyl-9-anthryl)phenyl]-2,3'-bi-9H-carba The sol was heated at 335°C. After purification by sublimation, 1.0g of a pale yellow solid was obtained, with a recovery rate of 92%. I got it at.

[0215] Nuclear magnetic resonance spectroscopy of the resulting yellow solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR charts are shown in Figures 9(A) and 9(B). Note that Figure 9(B) is the same as Figure 9(A). This is a chart showing an enlarged range of 7.0 ppm to 9.0 ppm in the In this embodiment, the organic compound represented by the above structural formula (200) according to one embodiment of the present invention is It was found that a compound, PCCPA-02, was obtained.

[0216] 1 H NMR (CDCl 3 ,300MHz):δ=7.29-7.81(m, 27H), 7.85-7.94(m, 5H), 8.24(d, J=7.8Hz, 2H), 8.30( d, J=7.8Hz, 1H), 8.48(d, J=1.2Hz, 1H).

[0217] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of PCCPA-02 (hereafter referred to as The solid thin film was placed on a quartz substrate. The absorption spectrum was measured using a UV-Vis spectrophotometer (solution: JASCO Corporation, V-550, Thin film: Hitachi High-Technologies Corporation, U-410 The absorption spectrum of the solution was measured by placing only toluene in the quartz cell. The absorption spectrum of the thin film is calculated by subtracting the transmittance and reflection spectrum of the substrate. Absorbance calculated from reflectance (-log 10 It was calculated from [%T / (100-%R)]. %T represents transmittance and %R represents reflectance. A fluorescence spectrometer (( The FS920 manufactured by Hamamatsu Photonics was used.

[0218] The absorption and emission spectra of the obtained toluene solution are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The results of the measurement of the absorption and emission spectra are shown in FIG. 10(B). The horizontal axis is the wavelength, and the vertical axis is the absorption Intensity and luminescence intensity are shown.

[0219] From the results of FIG. 10(A), the toluene solution of PCCPA-02 had the peaks at 396 nm and 376 nm. Absorption peaks were observed at 422 nm, 433 nm (excitation The emission wavelength peak was observed at a wavelength of 377 nm. For solid thin films of CPA-02, 399 nm, 377 nm, 353 nm, 325 nm, 30 An absorption peak is seen around 4 nm, and an emission peak is seen around 445 nm (excitation wavelength 380 nm). A peak was seen.

[0220] It was confirmed that PCCPA-02 emitted blue light. The compound PCCPA-02 can also be used as a host for luminescent and visible fluorescent materials. In addition, the thin film of PCCPA-02 has good film quality that is difficult to aggregate even in the atmosphere. I discovered something.

[0221] The HOMO and LUMO levels of PCCPA-02 were measured by cyclic voltammetry (C V) was calculated based on the measurements. The calculation method is shown below.

[0222] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Co., Ltd., 99.8%, Catalog No. 227 05-6) was used as the supporting electrolyte, tetra-n-butylammonium perchlorate (nB u 4 NClO 4 ) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target was then dissolved in water to a concentration of 2 mmol / L. The mixture was then dissolved and prepared.

[0223] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) as the reference electrode, and Ag / Ag+ Electrode (B.A.S. Co., Ltd., RE7 The measurements were performed at room temperature (20°C to 25°C). went.

[0224] In addition, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation rate relative to the reference electrode was The potential Ea [V] and reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave and Here, Ec is the midpoint potential of the reduction-oxidation wave. The potential energy for the position is known to be -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, and the LUMO level [eV] = -4.94-E From the equation c, the HOMO level and the LUMO level can be calculated.

[0225] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was The electrical stability of the compounds was examined by comparing the oxidation-reduction waves in the first cycle.

[0226] As a result, the HOMO level of PCCPA-02 was -5 On the other hand, in the measurement of the reduction potential Ec [V], the LUMO The level was found to be -2.72 eV. In addition, repeated measurements of the oxidation-reduction wave When comparing the waveforms after the first and 100th cycles, the Ea measurement showed a In the Ec measurement, the peak intensity remained at 87%, indicating that PCCPA-02 is an acid. It was confirmed that the resistance to oxidation and reduction was very good. EXAMPLES

[0227] <Synthesis Example 2> In this example, an organic compound represented by structural formula (221) in Embodiment 1, which is one embodiment of the present invention, Compound, 9-phenyl-9'-[4-(10-phenyl-9-anthryl)phenyl]-2 This article describes the synthesis method of 2'-bi-9H-carbazole (abbreviation: PCCPA-03). The structure of PCCPA-03 is shown below.

[0228] [ka]

[0229] Add 100 mL of 9-(4-bromophenyl)-10-phenylanthracene to a 3-neck flask. .2g (3.0mmol), 9-phenyl-2,2'-bi-9H-carbazole 1.3g (3.1mmol), sodium tert-butoxide 0.59g (6.1mmol) The mixture was added with 30 mL of xylene and stirred under reduced pressure. The mixture was degassed by stirring. 10 wt% of tri(tert-butyl)phosphine was added to the mixture. 0.4 mL of hexane solution, 85 mg of bis(dibenzylideneacetone)palladium(0) ( 0.15 mmol) was added, and the mixture was refluxed at 140° C. for 6 hours under a nitrogen stream.

[0230] After stirring, the resulting mixture was washed with water, a saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride. The organic layer was dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated. The oily product was purified by silica gel column chromatography (toluene:hexane = 1:2). The product was then recrystallized from toluene to give a pale yellow solid (1.6 g, yield 71%). The synthesis scheme of the above synthesis method is shown in the following formula (b).

[0231] [ka]

[0232] The resulting pale yellow solid (1.6 g) was purified by train sublimation. The preparation was carried out at 320℃ for 18 hours under the conditions of a pressure of 3.2 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 1.4 g of a pale yellow solid was obtained with a recovery rate of 93%.

[0233] Nuclear magnetic resonance spectroscopy of the resulting pale yellow solid ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 11(A) and 11(B). 1(A) is an enlarged chart showing the range from 7.0 ppm to 8.5 ppm. From these results, in this example, the compound represented by the above structural formula (221) according to one embodiment of the present invention was It was found that a certain organic compound, PCCPA-03, had been obtained.

[0234] 1 H NMR (1,1,2,2-tetrachloroethane-d2, 300MHz): δ = 7. 31-7.95(m, 32H), 8.19(d, J=7.5Hz, 1H), 8.23-8 .28(m, 3H).

[0235] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of PCCPA-03 (hereafter referred to as The solid thin film was placed on a quartz substrate. The absorption spectrum was measured using a spectrophotometer (solution: JASCO V-550 manufactured by Hitachi High-Technologies Corporation, thin film: U-4100 manufactured by Hitachi High-Technologies Corporation The absorption spectrum of the solution was measured by putting only toluene in a quartz cell. The absorption spectrum of the thin film is calculated from the transmittance and reflectance including the substrate. The absorbance (-log 10 It was calculated from [%T / (100-%R)]. Note that %T is the transparency. The transmittance and %R represent the reflectance. The emission spectrum was measured using a fluorescence spectrometer (Hamamatsu A Photonics FS920 was used.

[0236] The results of measuring the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. 12(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The results of the measurement of the absorption and emission spectra are shown in FIG. 12(B). The horizontal axis is the wavelength, and the vertical axis is the absorption Intensity and luminescence intensity are shown.

[0237] From the results of FIG. 12(A), the toluene solution of PCCPA-03 has the peaks at 396 nm, 375 nm, An absorption peak is observed around 326 nm, and an emission peak is observed at 423 nm (excitation wavelength 376 nm). In addition, the results in Fig. 12(B) show that in the solid thin film of PCCPA-03, Absorption peaks are seen around 401 nm, 380 nm, 356 nm, and 335 nm, and 446 nm. An emission wavelength peak was observed around m (excitation wavelength 360 nm).

[0238] It was confirmed that PCCPA-03 emits blue light. It can also be used as a host for photoluminescent materials and visible fluorescent materials. The thin film of 3 was found to have good film quality and was resistant to aggregation even in air. EXAMPLES

[0239] In this example, the PCCPA described in Example 1 is used as a light-emitting element which is one embodiment of the present invention. A light-emitting device 1 using -02 (structural formula (200)) in the light-emitting layer, and an organic compound for comparison, PCC Regarding comparative light-emitting element 2, which uses PA (structural formula (300)) in the light-emitting layer, The element structure of the light-emitting element used in this embodiment will be described. The structure is shown in FIG. 13, and the specific configuration is shown in Table 1. The academic formula is shown below.

[0240] [Table 1]

[0241] [ka]

[0242] <Fabrication of light-emitting element> The light emitting device shown in this embodiment has a first electrode 9 formed on a substrate 900 as shown in FIG. 01, a hole injection layer 911, a hole transport layer 912, a light emitting layer 913, an electron transport layer 914, and an electron A structure in which an electron injection layer 915 is laminated in this order, and a second electrode 903 is laminated on the electron injection layer 915. has.

[0243] First, a first electrode 901 was formed on a substrate 900. The electrode area was 4 mm 2 (2mm x 2 The thickness of the first electrode 901 was 1 mm. The substrate 900 was a glass substrate. , Indium tin oxide containing silicon oxide (ITSO) was sputtered to a thickness of 70 nm. The film was formed to a thickness of 100 nm.

[0244] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 60 minutes in the heating chamber. After that, the substrate was allowed to cool for about 30 minutes.

[0245] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by vacuum evaporation. 10 -4 After reducing the pressure to 100 Pa, 3-[4-(9-phenanthryl)-phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum oxide were mixed to form PC The mass ratio of PPn:molybdenum oxide was 4:2, and the film thickness was 10 nm. It was formed by co-evaporation.

[0246] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was made of PCP Pn was used and formed by vapor deposition to a film thickness of 30 nm.

[0247] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0248] In the case of the light-emitting element 1, the light-emitting layer 913 is formed by using PCCPA-02 as a host material and The material used was N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl 1,6-diaminopyrene-1,6-diamine (abbreviation: 1H-fluoren-9-yl)phenyl ,6mMemFLPAPrn) was used, and the weight ratio was PCCPA-02:1,6mMemFL The deposition was carried out so that PAPrn was 1:0.03. The film thickness was 25 nm.

[0249] In the case of the comparative light-emitting element 2, the light-emitting layer 913 uses PCCPA as a host material and The material used was 1.6mMemFLPAPrn, with a weight ratio of PCCPA:1.6mMem The deposition was carried out so that FLPAPrn=1:0.03. The film thickness was set to 25 nm. .

[0250] Next, an electron transport layer 914 was formed on the light-emitting layer 913. In the case of PCCPA-02, the thickness of the film is 10 nm, and bathophenanthroline (abbreviation: Bphe n) were successively deposited to a thickness of 15 nm. The film thickness of PCCPA is 10 nm, and the film thickness of bathophenanthroline (abbreviation: Bphen) is The layers were deposited in sequence to a thickness of 15 nm.

[0251] Next, the electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was made of fluoride. Lithium (LiF) was used and the film was formed by vapor deposition to a thickness of 1 nm.

[0252] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. The aluminum was deposited by vapor deposition to a thickness of 200 nm. Thus, the second electrode 903 functions as a cathode.

[0253] Through the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 900. In addition, the hole injection layer 911, the hole transport layer 912, the light emitting layer 913, and the electrode layer 914 described in the above steps were The electron transport layer 914 and the electron injection layer 915 are functional layers constituting the EL layer in one embodiment of the present invention. In addition, in the deposition process in the above-mentioned manufacturing method, the deposition method is all performed by resistance heating. Used.

[0254] Moreover, the light emitting element manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. Then, another substrate (not shown) is fixed onto the substrate 900 using a sealing material, and the sealing material is It is applied around the light-emitting element formed on 00, and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 The irradiation was performed by heating at 80°C for 1 hour.

[0255] <Operation characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting devices were measured. The measurements were carried out at room temperature. The results are shown in Figs. 14 to 17.

[0256] Also, 1000cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 2 below. .

[0257] [Table 2]

[0258] From the above results, it can be seen that the light-emitting element 1 fabricated in this example has good current efficiency and high external quantum efficiency. From these results, it can be seen that the first carbazole bonded to the anthracene skeleton The bonding position of the carbazole skeleton and the second carbazole skeleton bonded to the first carbazole skeleton is changed. This allows for smooth energy transfer to the light-emitting material, resulting in good device characteristics. It can be seen that...

[0259] Furthermore, the light-emitting element 1 and the comparative light-emitting element 2 were subjected to an electric current of 12.5 mA / cm 2 A current is passed with a current density of The emission spectra of the light-emitting element 1 and the comparative light-emitting element are shown in FIG. The emission spectrum of the element 2 has a peak at about 466 nm. This suggests that this is due to the emission of 1,6mMemFLPAPrn contained in 3.

[0260] Next, a reliability test was performed on the light-emitting element 1 and the comparative light-emitting element 2. Results of the reliability test This is shown in FIG. 19. In FIG. 19, the vertical axis represents the normalized brightness (%) when the initial brightness is 100%. The horizontal axis indicates the operation time (h) of the element. The reliability test was performed at a constant current of 2 mA. A current drive test was carried out.

[0261] These results show that the light-emitting element (light-emitting element 1) of one embodiment of the present invention has excellent current efficiency and external In terms of photoluminescence efficiency, the comparative light-emitting element shows better characteristics than the comparative light-emitting element 2. The light-emitting element according to one embodiment of the present invention (light-emitting element 1) is also superior in reliability. I found out. EXAMPLES

[0262] <Synthesis Example 3> In this example, an organic compound represented by structural formula (252) in Embodiment 1, which is one embodiment of the present invention, Compound, 7-[4-(10-phenyl-9-anthryl)phenyl]-9-(9-phenyl -9H-carbazol-3-yl)-7H-benzo[c]carbazole (abbreviation: PCcB The synthesis method of PCcBCzPA is explained below. The structure of PCcBCzPA is shown below.

[0263] [ka]

[0264] Add 100 mL of 9-(4-bromophenyl)-10-phenylanthracene to a 3-neck flask. .8g (4.4mmol), 9-(9-phenyl-9H-carbazol-3-yl)-7 H-benzo[c]carbazole 2.0g (4.4mmol), sodium tert-butyl 0.85 g (8.8 mmol) of tungsten oxide was added, and the atmosphere in the flask was replaced with nitrogen. 22 mL of xylene, 0 mL of a 10 wt% hexane solution of tri(tert-butyl)phosphine 0.9mL was added and the mixture was degassed by stirring under reduced pressure. Add 0.13 g (0.22 mmol) of palladium(0) in acetone and stir under a nitrogen stream for 16 The mixture was refluxed at 0° C. for 6 hours.

[0265] After stirring, water was added to the mixture and the solid was filtered. The mixture was filtered through ethyl acetate, alumina, and Florisil, and the filtrate was concentrated to obtain a solid. The solid was purified by silica gel column chromatography (toluene) and then re-extracted with toluene. Upon crystallization, the target product was obtained as a pale yellow solid in an amount of 2.2 g and a yield of 63%. The synthesis scheme is shown in formula (c) below.

[0266] [ka]

[0267] The resulting pale yellow solid (0.95 g) was purified by train sublimation. The purification was carried out at a pressure of 1.3 x 10 -2 The pale yellow solid was heated at 300°C under conditions of 10 Pa. After purification by sublimation, 0.74 g of a pale yellow solid was obtained with a recovery rate of 78%.

[0268] Nuclear magnetic resonance spectroscopy of the resulting pale yellow solid ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 20(A) and 20(B). 0(A) is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm. From this result, in this example, the compound represented by the above structural formula (252) according to one embodiment of the present invention was It was found that a certain organic compound, PCcBCzPA, had been obtained.

[0269] 1 H NMR (CDCl 3 ,300MHz):δ=7.29-7.97(m, 32H), 8.03(d, J=1.5Hz, 1H), 8.08(d, J=7.8Hz, 1H), 8. 25(d, J=7.8Hz, 1H), 8.51(d, J=1.5Hz, 1H), 8.79 (d, J=8.4Hz, 1H), 8.95(d, J=8.1Hz, 1H).

[0270] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of PCcBCzPA (hereafter referred to as The solid thin film was placed on a quartz substrate. The absorption spectrum was measured using a UV-Vis spectrophotometer (solution: JASCO Corporation, V-550, Thin film: Hitachi High-Technologies Corporation, U-410 The absorption spectrum of the solution was measured by placing only toluene in the quartz cell. The absorption spectrum of the thin film is calculated by subtracting the transmittance and reflection spectrum of the substrate. Absorbance calculated from reflectance (-log 10 It was calculated from [%T / (100-%R)]. %T represents transmittance and %R represents reflectance. A fluorescence spectrometer (( The FS920 manufactured by Hamamatsu Photonics was used.

[0271] The results of measuring the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The results of the measurement of the absorption and emission spectra are shown in FIG. Intensity and luminescence intensity are shown.

[0272] From the results of FIG. 21(A), the toluene solution of PCcBCzPA had peaks of 396 nm and 375 nm. Absorption peaks were observed at 422 nm, 434 nm (excitation The emission wavelength peak was observed at a wavelength of 375 nm. For solid thin films of cBCzPA, the An absorption peak is seen around 5 nm, and an emission peak is seen around 446 nm (excitation wavelength 370 nm). A peak was seen.

[0273] It was confirmed that PCcBCzPA emits blue light. The compound PCcBCzPA can also be used as a host for luminescent and visible fluorescent materials. In addition, thin films of PCcBCzPA are less likely to aggregate even in the atmosphere, and their morphology does not change. It was found that the film had good quality and small.

[0274] The HOMO and LUMO levels of PCcBCzPA were measured by cyclic voltammetry (C V) was calculated based on the measurements. The calculation method is shown below.

[0275] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Co., Ltd., 99.8%, Catalog No. 227 05-6) was used as the supporting electrolyte, tetra-n-butylammonium perchlorate (nB u 4 NClO 4 ) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target was then dissolved in water to a concentration of 2 mmol / L. The mixture was then dissolved and prepared.

[0276] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) as the reference electrode, and Ag / Ag + Electrode (B.A.S. Co., Ltd., RE7 The measurements were performed at room temperature (20°C to 25°C). went.

[0277] In addition, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation rate relative to the reference electrode was The potential Ea [V] and reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave and Here, Ec is the midpoint potential of the reduction-oxidation wave. The potential energy for the position is known to be -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, and the LUMO level [eV] = -4.94-E From the equation c, the HOMO level and the LUMO level can be calculated.

[0278] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was The electrical stability of the compounds was examined by comparing the oxidation-reduction waves in the first cycle.

[0279] As a result, in the measurement of the oxidation potential Ea [V] of PCcBCzPA, the HOMO level was -5 On the other hand, in the measurement of the reduction potential Ec [V], the LUMO The level was found to be -2.73 eV. In addition, repeated measurements of the oxidation-reduction wave When comparing the waveforms after the first and 100th cycles, the Ea measurement showed a In the Ec measurement, the peak intensity remained at 71%, indicating that PCcBCzPA is an acid. It was confirmed that the resistance to oxidation and reduction was very good. EXAMPLES

[0280] <Synthesis Example 4> In this example, an organic compound represented by structural formula (253) in Embodiment 1, which is one embodiment of the present invention, Compound, 7-[4-(10-phenyl-9-anthryl)phenyl]-9-(9-phenyl -9H-carbazol-2-yl)-7H-benzo[c]carbazole (abbreviation: PCcB The synthesis method of PCcBCzPA-02) is explained below. As shown below.

[0281] [ka]

[0282] 0.05 mL of 9-(4-bromophenyl)-10-phenylanthracene in a 100 mL three-neck flask. .80g (2.0mmol), 9-(9-phenyl-9H-carbazol-2-yl)- 7H-benzo[c]carbazole 0.90g (2.0mmol), sodium tert 0.38 g (4.0 mmol) of 1,2-butoxide was added, and the atmosphere in the flask was replaced with nitrogen. The mixture was mixed with 10 mL of xylene and 10 wt% of tri(tert-butyl)phosphine in hexane. 0.4 mL of the liquid was added and the mixture was degassed by stirring under reduced pressure. Add 58 mg (0.10 mmol) of palladium(0) to the flask and 1 The mixture was refluxed at 50°C for 6 hours.

[0283] After stirring, the mixture was filtered and the solid was washed with water. The filtrate was washed with saturated saline solution, The organic layer was dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated. The oil and solid were combined and purified by silica gel column chromatography (toluene:hexane = The product was purified with a toluene / hexane mixture (1:2) and then recrystallized with toluene / hexane to obtain the desired white solid. The yield was 0.70 g and the yield was 59%. The synthesis scheme of the above synthesis method is shown in the following formula (d). .

[0284] [ka]

[0285] The resulting white solid (0.50 g) was purified by train sublimation. The pressure is 3.2 x 10 -2 After sublimation purification, the yellow A yellow solid was obtained, 0.40 g, 80% recovery.

[0286] Nuclear magnetic resonance spectroscopy of the resulting yellow solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR charts are shown in Figures 22(A) and 22(B). This is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm in (A). From the results, in this example, the compound represented by the above structural formula (253) according to one embodiment of the present invention was It was found that an organic compound, PCcBCzPA-02, was obtained.

[0287] 1 H NMR (CDCl 3 ,300MHz):δ=7.28-7.91(m, 31H), 7.95(d, J=9.3Hz, 1H), 7.99(d, J=1.5Hz, 1H), 8. 08(d, J=7.8Hz, 1H), 8.18(d, J=7.5Hz, 1H), 8.26 (d, J=7.8Hz, 1H), 8.73(d, J=8.1Hz, 1H), 8.91(d , J=8.7Hz, 1H).

[0288] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of PCcBCzPA-02 The absorption spectrum (hereafter simply referred to as the "absorption spectrum") and emission spectrum were measured. The solution was prepared on a silicon substrate by vacuum deposition. The absorption spectrum was measured using a spectrophotometer (solution: V-550, manufactured by Nippon Bunko Co., Ltd.; Thin film: U-4100, manufactured by Hitachi High-Technologies Corporation The absorption spectrum of the solution was measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film was calculated by subtracting the transmittance and reflectance including the substrate. Absorbance calculated from the rate (-log 10 Calculated from [%T / (100-%R)]. T is the transmittance and %R is the reflectance. The emission spectrum was measured using a fluorometer (Kabushiki Kaisha, Ltd.). ) Hamamatsu Photonics FS920) was used.

[0289] The results of measuring the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The results of the measurement of the absorption and emission spectra are shown in FIG. Intensity and luminescence intensity are shown.

[0290] From the results of FIG. 23(A), the toluene solution of PCcBCzPA-02 has a peak at 396 nm and a peak at 376 nm. Absorption peaks were observed at 422 nm (excitation The emission wavelength peak was observed at 376 nm. For solid thin films of CcBCzPA-02, 401nm, 381nm, 358nm, 343nm m, an absorption peak is seen around 323 nm, and an emission peak is seen around 445 nm (excitation wavelength 370 nm). Peaks of light wavelengths were observed.

[0291] It was confirmed that PCcBCzPA-02 emitted blue light. The materials can also be used as hosts for luminescent and visible fluorescent materials. It was found that the thin film of CzPA-02 has good film quality that is resistant to aggregation even in the atmosphere. Ta.

[0292] The HOMO and LUMO levels of PCcBCzPA-02 were measured by cyclic voltammetry. The calculation method is shown below.

[0293] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Co., Ltd., 99.8%, Catalog No. 227 05-6) was used as the supporting electrolyte, tetra-n-butylammonium perchlorate (nB u 4 NClO 4 ) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target was then dissolved in water to a concentration of 2 mmol / L. The mixture was then dissolved and prepared.

[0294] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) as the reference electrode, and Ag / Ag + Electrode (B.A.S. Co., Ltd., RE7 The measurements were performed at room temperature (20°C to 25°C). went.

[0295] In addition, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation rate relative to the reference electrode was The potential Ea [V] and reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave and Here, Ec is the midpoint potential of the reduction-oxidation wave. The potential energy for the position is known to be -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, and the LUMO level [eV] = -4.94-E From the equation c, the HOMO level and the LUMO level can be calculated.

[0296] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was The electrical stability of the compounds was examined by comparing the oxidation-reduction waves in the first cycle.

[0297] As a result, in the measurement of the oxidation potential Ea [V] of PCcBCzPA-02, the HOMO level On the other hand, in the measurement of the reduction potential Ec [V], L The UMO level was found to be -2.74 eV. In addition, repeated measurements of the oxidation-reduction wave When comparing the waveforms after the first cycle and 100 cycles, the Ea measurement PCcBCzPA-02 was found to be resistant to oxidation, as it maintained 78% of its peak intensity. was confirmed to be very good. EXAMPLES

[0298] <Synthesis Example 5> In this example, an organic compound represented by structural formula (220) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 9-[4-(10-phenyl-9-anthryl)phenyl]-2,9'-bi-9H The synthesis method of Cz-carbazole (abbreviation: CzCzPA-02) will be described. The structure of CzPA-02 is shown below.

[0299] [ka]

[0300] 0.05 mL of 9-(4-bromophenyl)-10-phenylanthracene in a 100 mL three-neck flask. 0.65g (1.6mmol), 2,9'-bi-9H-carbazole 0.54g (1.6m mol) and sodium tert-butoxide 0.32g (3.3mmol), and The atmosphere in the flask was replaced with nitrogen. 10 mL of xylene was added to the mixture, and the mixture was stirred under reduced pressure. The mixture was degassed. A 10 wt% solution of tri(tert-butyl)phosphine in hexane was added to the mixture. 0.4 mL, bis(dibenzylideneacetone)palladium(0) 34 mg (59 μmol ) was added, and the mixture was stirred at 120° C. for 6 hours under a nitrogen stream.

[0301] After stirring, the resulting mixture was washed with water and saturated saline, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated. The oily product was purified by silica gel column chromatography. HPLC (toluene:hexane = 1:2) and HPLC (eluent) The product was purified in a solvent of chloroform and then recrystallized in toluene to obtain the desired white solid. The yield was 0.66 g and the yield was 63%. The synthesis scheme of the above synthesis method is shown in the following formula (e). .

[0302] [ka]

[0303] The resulting white solid (0.69 g) was purified by train sublimation. The preparation was carried out at 300℃ for 22 hours under the conditions of a pressure of 3.4 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 0.61 g of a pale yellow solid was obtained with a recovery rate of 88%.

[0304] Nuclear magnetic resonance spectroscopy of the resulting pale yellow solid ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 24(A) and 24(B). 4(A) is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm. From this result, in this example, the compound represented by the above structural formula (220) according to one embodiment of the present invention was It was found that a certain organic compound, CzCzPA-02, had been obtained.

[0305] 1 H NMR (DMSO-d6,300MHz): δ=7.31(dt, J=0.9Hz , 7.8Hz, 2H), 7.40-7.76(m, 23H), 7.82(d, J=1.5 Hz, 1H), 8.02(d, J=8.4Hz, 2H), 8.28(d, J=7.8Hz , 2H), 8.45(d, J=7.5Hz, 1H), 8.61(d, J=8.1Hz, 1 H).

[0306] Next, the UV-visible absorption spectra (absorption The absorption spectrum and emission spectrum were measured. The solid thin film was formed on a quartz substrate by vacuum deposition. The absorption spectrum was measured using a spectrophotometer (solution: V-5, manufactured by JASCO Corporation). 50, thin film: Hitachi High-Technologies Corporation, U-4100) was used. The absorption spectrum was obtained by subtracting the absorption spectrum measured by putting only toluene in the quartz cell. The absorption spectrum of the thin film is calculated by the absorbance (-l og 10 It was calculated from [%T / (100-%R)]. %T is the transmittance and %R is the reflectance. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS 920) was used.

[0307] The results of measuring the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The results of the measurement of the absorption and emission spectra are shown in FIG. 25(B). The horizontal axis is the wavelength, and the vertical axis is the absorption Intensity and luminescence intensity are shown.

[0308] From the results of FIG. 25(A), the toluene solution of CzCzPA-02 has a wavelength of 396 nm and 376 nm Absorption peaks were observed at 356 nm, 334 nm, and 322 nm, and at 419 nm and 434 nm. The emission wavelength peak was observed at 376 nm (excitation wavelength). Therefore, in the solid thin film of CzCzPA-02, the wavelengths are around 402 nm, 380 nm, and 335 nm. An absorption peak is observed, and an emission wavelength peak is observed around 440 nm (excitation wavelength 345 nm). It was.

[0309] It was confirmed that CzCzPA-02 emitted blue light. It can also be used as a host for luminescent materials and visible fluorescent materials. It was found that the -02 thin film has good film quality and is resistant to aggregation even in air. EXAMPLES

[0310] In this example, the CzCzP light-emitting element described in Example 6 is used as a light-emitting element according to one embodiment of the present invention. A light-emitting device 3 was fabricated using A-02 (structural formula (220)) in the light-emitting layer, and its characteristics were The measurement results are shown below.

[0311] The element structure of the light-emitting element used in this embodiment is the same as that shown in FIG. 13 in the third embodiment. However, the specific configuration of each layer constituting the element structure is as shown in Table 3. The chemical formulas of the materials used in this example are shown below.

[0312] [Table 3]

[0313] [ka]

[0314] <Operation characteristics of light-emitting element> The operating characteristics of the fabricated light-emitting element 3 were measured. The measurements were carried out at room temperature. The results are shown in Figures 26 to 29.

[0315] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting elements in the vicinity are shown in Table 4 below.

[0316] [Table 4]

[0317] From the above results, it can be seen that the light-emitting element 3 fabricated in this embodiment can be driven at a low voltage and has good chromaticity. It can be seen that the device is blue in color but has good efficiency.

[0318] In addition, the light-emitting element 3 is supplied with 12.5 mA / cm 2 Emission spectrum when a current is applied at a current density of 30. As shown in FIG. 30, the emission spectrum of the light-emitting element is This suggests that this is due to the emission of luminescent substances. EXAMPLES

[0319] In this example, the compound used in the synthesis of PCcBCzPA (structural formula (252)) shown in Example 4 was 9-(9-phenyl-9H-carbazol-3-yl)-7H-benzo[c]carbazol (PCcBCz (Structural formula (400))) and PCcBCzPA-0 shown in Example 5 9-(9-phenyl-9H-carbazole-2, used in the synthesis of 2 (structural formula (253)) -yl)-7H-benzo[c]carbazole (PCcBCz-02 (Structural formula (401)) The synthesis method of PCcBCz and PCcBCz-02 is as follows. As shown below.

[0320] [ka]

[0321] <Step 1: Synthesis of 9-chloro-7H-benzo[c]carbazole> 2.9g of 1-(4-chlorophenyl)-2-nitronaphthalene in a 200mL three-neck flask (10mmol), triphenylphosphine 11g (40mmol), o-dichlorobenzene The mixture was stirred at 180° C. for 10 hours under a nitrogen stream. Purification by silica gel column chromatography (toluene:hexane = 1:1) The solid was washed with hexane to give the target white solid in a yield of 2.0 g. The synthesis scheme of step 1 is shown in formula (f-1) below.

[0322] [ka]

[0323] Nuclear magnetic resonance spectroscopy of the resulting white solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR charts are shown in Figures 31(A) and 31(B). This is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm in (A). From the results, it is possible to confirm that the target compound in the above formula (f-1), 9-chloro-7H-benzo[c] It was found that carbazole was obtained.

[0324] 1 H NMR (CDCl 3 , 300MHz): δ = 7.34 (dd, J 1 =9.0Hz, J 2 =1.8Hz,1H), 7.47-7.52(m, 1H), 7.54(d, J=2. 1Hz, 1H), 7.61(d, J=8.7Hz, 1H), 7.68-7.74(m, 1 H), 7.87(d, J=8.7Hz, 1H), 8.00(d, J=7.8Hz, 1H) , 8.43-8.46(m, 2H), 8.69(d, J=8.4Hz, 1H).

[0325] <Step 2-1: Synthesis of PCcBCz> In this step 2-1, 9-chloro-7H-benzo[c]carbamide synthesized in step 1 above is used. We will explain how to synthesize PCcBCz using rubazolyl.

[0326] In a 200 mL three-neck flask, add the 9-chloro-7H-benzo[c ]Carbazole 1.8g (7.1mmol), 9-phenyl-9H-carbazole-3- Boronic acid 2.2g (7.1mmol), di(1-adamantyl)-n-butylphosphine 0.25g (0.70mmol), tripotassium phosphate 4.6g (22mmol), ter 1.6 g (22 mmol) of t-butyl alcohol and diethylene glycol dimethyl 35 mL of ether was added and the mixture was stirred under reduced pressure to degas it.

[0327] To this mixture was added 79 mg (0.35 mmol) of palladium(II) acetate, and the mixture was then subjected to a nitrogen stream. The mixture was stirred at 160° C. for 13 hours under reduced pressure. After the reaction, the solid was removed from the mixture by suction filtration. The filtrate was then purified by silica gel column chromatography (chloroform:hexane=1 The solid was washed with hexane to obtain the target light brown solid. The yield was 2.0 g and the yield was 61%. The synthesis scheme of the above synthesis method is shown in the following formula (f-2-1): As shown in.

[0328] [ka]

[0329] Nuclear magnetic resonance spectroscopy of the resulting light brown solid ( 1 The results of analysis by H-NMR are shown below. Also, 1The H-NMR charts are shown in Figures 32(A) and 32(B). 2(A) is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm. From these results, it is understood that PCcBCz (structural formula (4) 00)) was obtained.

[0330] 1 H NMR (CDCl 3 ,300MHz):δ=7.30-7.36(m, 1H), 7 .44-7.53(m, 5H), 7.60-7.66(m, 5H), 7.71-7.81 (m, 3H), 7.86-7.89(m, 2H), 8.02(d, J=7.8Hz, 1H ), 8.23-8.25(m, 1H), 8.47-8.49(m, 2H), 8.63(d , J=8.1Hz, 1H), 8.82(d, J=8.4Hz, 1H).

[0331] <Step 2-2: Synthesis of PCcBCz-02> In this step 2-2, 9-chloro-7H-benzo[c]carbamide, which was synthesized in step 1 above, is used. A method for synthesizing PCcBCz-02 using rubazolium is described below.

[0332] In a 200 mL three-neck flask, add the 9-chloro-7H-benzo[c ]Carbazole 1.0g (4.0mmol), 9-phenyl-9H-carbazole-2- Boronic acid 1.2g (4.0mmol), di(1-adamantyl)-n-butylphosphine 29mg (0.080mmol), tripotassium phosphate 2.5g (12mmol), ter 0.90 g (12 mmol) of t-butyl alcohol and diethylene glycol dimethyl 20 mL of diethyl ether was added, and the mixture was stirred under reduced pressure and degassed.

[0333] To this mixture was added 9.0 mg (0.040 mmol) of palladium(II) acetate and nitrogen The mixture was stirred at 120°C for 20 hours under airflow. After the reaction, the solid was collected by suction filtration. The filtrate was purified by silica gel column chromatography (toluene:hexane = 1 The solid was washed with hexane to obtain the target light brown solid. The yield was 0.91 g and the yield was 50%. The synthesis scheme of the above synthesis method is shown in the following formula (f-2-2 ) as shown in

[0334] [ka]

[0335] Nuclear magnetic resonance spectroscopy of the resulting light brown solid ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 33(A) and 33(B). 3(A) is an enlarged chart showing the range from 7.0 ppm to 9.0 ppm. From this result, it was confirmed that the target product, PCcBCz-02 (structural formula (401)), was obtained. Understood.

[0336] 1 H NMR (CDCl 3 ,300MHz):δ=7.27-7.33(m, 1H), 7 .40-7.52(m, 4H), 7.61-7.73(m, 9H), 7.81(d, J= 1.5Hz, 1H), 7.86(d, J=8.7Hz, 1H), 7.99(d, J=8. 4Hz, 1H), 8.17(d, J=7.8Hz, 1H), 8.23(d, J=9.0H z, 1H), 8.41(s, 1H), 8.57(d, J=8.4Hz, 1H), 8.77 (d, J = 7.8 Hz, 1H). [Explanation of symbols]

[0337] 101 First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generating layer 111, 111a, 111b Hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b Light-emitting layer 114, 114a, 114b electron transport layer 115, 115a, 115b electron injection layer 201 First Substrate 202 Transistor (FET) 203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second Board 206R, 206G, 206B Color Filters 206R', 206G', 206B' Color filters 207 First Electrode 208 Second Electrode 209 Black layer (black matrix) 210R, 210G conductive layer 301 First Substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second Board 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulation 315 EL layer 316 Second Electrode 317 Light-emitting element 318 Space 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting Equipment 4001 Substrate 4002 Light emitting element 4003 Substrate 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4100 Lighting equipment 4200 Lighting Equipment 4201 Substrate 4202 Light emitting element 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 4300 Lighting Equipment 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rear view mirror 7000 Chassis 7001 Display section 7002 2nd display section 7003 Speaker 7004 LED Lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7012 Support part 7013 Earphones 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7019 Microphone 7020 Camera 7021 External connection part 7022, 7023 Operation buttons 7024 Connection terminal 7025 band, 7026 Clasp 7027 Time Icon 7028 Other Icons 8001 Lighting equipment 8002 Lighting equipment 8003 Lighting equipment 8004 Lighting equipment 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 Case

Claims

1. A light-emitting layer is disposed between a pair of electrodes, The light-emitting layer is a light-emitting element having a fluorescent material and an organic compound having an anthracene skeleton and a bicarbazole skeleton.

2. In claim 1, the organic compound has a first carbazole skeleton and a second carbazole skeleton, The light-emitting element has the second carbazole skeleton bonded to the second position of the first carbazole skeleton.

3. In claim 1, the organic compound has a first carbazole skeleton and a second carbazole skeleton, The light-emitting element has the 2-position of the first carbazole skeleton bonded to the 9-position, the 3-position or the 2-position of the second carbazole skeleton.

4. In any one of claims 1 to 3, The first carbazole skeleton is bonded to an anthracene skeleton via an arylene group.

5. In any one of claims 1 to 4, The organic compound is an organic compound represented by General Formula (G1). 【Chemistry 1】 (In the formula, Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R １ ~R ９ , and R １１ ~R １７ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

6. In any one of claims 1 to 4, The organic compound is an organic compound represented by General Formula (G1). 【Chemistry 2】 (In the formula, Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R １ ~R ９ , and R １１ ~R １７ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. １２ and R １３ , R １４ and R １５ , R １５ and R １６ , or R １６ and R １７ At least one of the rings is fused.)

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