Organometallic complex and light-emitting device

Abstract

To provide a new material for a light-emitting element, and a material for a light-emitting element which can simplify a process for manufacturing a light-emitting element, to provide a material for a light-emitting element which can reduce the cost for manufacturing a light-emitting element, and to provide a material for a light-emitting element which can achieve a light-emitting element having good light-emitting efficiency.SOLUTION: A material for a light-emitting element contains an organic compound which has a first skeleton having carrier transport property and a second skeleton having light-emitting property in one molecule, and has a molecular weight of 3,000 or less.SELECTED DRAWING: Figure 2

Description

[Technical Field]

[0001] One embodiment of the present invention relates to a light-emitting element, a display module, a lighting module, a display device, a light-emitting element, a display module ... The present invention relates to an optical device, an electronic device, and a lighting device. The technical field of one embodiment of the invention disclosed in the present specification and the like is related to an object, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture It is about cha, or composition of matter. More specifically, the technical field of one embodiment of the present invention disclosed in this specification is a semiconductor device, a display, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and the like A driving method or a manufacturing method thereof can be cited as an example. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting elements (organic EL elements) that utilize these elements is progressing. The basic structure of a liquid crystal display is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material between them. A voltage is applied to this element to inject carriers, and the recombination energy of the carriers is By utilizing this, light can be emitted from the light-emitting material.

[0003] Since such light-emitting elements are self-luminous, when they are used as pixels in a display, Compared to flat panel displays, it has advantages such as high visibility and no need for backlighting. The light-emitting element is suitable for use as a panel display element. Another major advantage of the sensor is that it can be made thin and lightweight. This is also one of its characteristics.

[0004] In addition, these light-emitting elements can have a light-emitting layer formed continuously in two dimensions, This is similar to point light sources such as incandescent bulbs and LEDs, or This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it can be used as a surface light source for lighting, etc. It is also highly useful.

[0005] Displays and lighting devices using such light-emitting elements are suitable for use in a variety of electronic devices. However, research and development is ongoing to develop light-emitting devices with better efficiency and life span.

[0006] Organic EL elements have a so-called functional separation, where different functions are assigned to different layers or materials. However, this has led to a dramatic improvement in the characteristics of the device. However, the number of layers to be stacked increased, and the rate of co-evaporation had to be controlled, and the size of the element also increased. The manufacturing process became extremely complicated. As a result, the manufacturing equipment became longer and the manufacturing time became longer. This has resulted in an increase in the number of projects and, ultimately, a significant increase in manufacturing costs.

[0007] Patent Document 1 describes a dendrimer having a carrier transport skeleton with iridium as the central metal. This information has been disclosed. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Laid-Open No. 2003-231692 Summary of the Invention [Problem to be solved by the invention]

[0009] In view of the above, an object of one embodiment of the present invention is to provide a novel material for a light-emitting element. In one embodiment of the present invention, a light-emitting element capable of simplifying a manufacturing process of a light-emitting element is provided. Another object of the present invention is to provide a material for a light-emitting element. The present invention aims to provide a material for a light-emitting element that can reduce the cost of manufacturing the light-emitting element. Alternatively, in one embodiment of the present invention, a light-emitting element with high emission efficiency can be realized. Another object of the present invention is to provide a material for a light emitting device having a long life. The object is to provide a material for a light-emitting device that can provide a device.

[0010] Another embodiment of the present invention aims to provide a light-emitting element that can be easily manufactured. Another aspect of the present invention is to provide a light-emitting element that can be manufactured at low cost. Another object of one embodiment of the present invention is to provide a light-emitting element with high emission efficiency. Another object of one embodiment of the present invention is to provide a light-emitting element having a long lifetime. The purpose is to

[0011] Alternatively, in another embodiment of the present invention, an inexpensive light-emitting device, an electronic device, and a display device are provided. Alternatively, it is an object of the present invention to provide a highly reliable light-emitting device, an electronic device, and a display device. Another object of the present invention is to provide a light-emitting device with low power consumption. Another object of the present invention is to provide an electronic device and a display device. The present invention aims to provide a light-emitting device, an electronic device, and a display device each having good display quality. do.

[0012] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0013] One embodiment of the present invention is a compound semiconductor device comprising a first skeleton having a carrier transport property and a second skeleton having a light-emitting property. in one molecule and has a molecular weight of 3000 or less. .

[0014] Alternatively, another embodiment of the present invention is a compound semiconductor device having the above structure, wherein the first skeleton has a hole transport property. It is a material for a light-emitting element.

[0015] Alternatively, another aspect of the present invention is a compound having the above structure, wherein the first skeleton has a HOMO. The material for a light-emitting device is described above.

[0016] Alternatively, another embodiment of the present invention is a compound semiconductor device having the above structure, wherein the first skeleton has an electron transport property. It is a material for a light-emitting element.

[0017] Alternatively, another aspect of the present invention is a compound having the above structure, wherein the first skeleton has a LUMO. It is a material for light-emitting devices.

[0018] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the first skeleton is It is a light-emitting element material that is directly bonded to

[0019] Alternatively, another aspect of the present invention is a method for manufacturing a semiconductor device according to the above-mentioned embodiment, wherein the first skeleton and the second skeleton are , a light-emitting element linked by a metaphenylene group or a biphenyl-3,3'-diyl group It is a material used.

[0020] Alternatively, another aspect of the present invention is a compound having a first skeleton having hole transport properties and a second skeleton having electron transport properties. The compound has a second skeleton and a third skeleton having luminescence in one molecule, and has a molecular weight of 3000 or less. The light-emitting element material contains an organic compound.

[0021] Alternatively, another aspect of the present invention is a compound having the above structure, wherein the first skeleton has a HOMO. It is a material for light-emitting devices.

[0022] Alternatively, another aspect of the present invention is a compound having the above structure, wherein the second skeleton has a LUMO. It is a material for light-emitting devices.

[0023] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the first skeleton and / or the The second skeleton is directly bonded to the third skeleton in the light-emitting device material.

[0024] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the first skeleton and / or the The second skeleton is a compound obtained by combining the third skeleton with a metaphenylene group or a biphenyl-3,3'-diyl group. The material is a light-emitting element material in which the aryl groups are linked together.

[0025] Alternatively, another embodiment of the present invention is a light-emitting device in which the organic compound emits fluorescence in the above structure. It is a material for devices.

[0026] Alternatively, another aspect of the present invention is a light-emitting device according to the above-described embodiment, wherein the organic compound emits delayed fluorescence. It is a material for light emitting devices.

[0027] Alternatively, another embodiment of the present invention is a light-emitting device having the above-described structure, wherein the organic compound emits phosphorescence. It is a material for optical elements.

[0028] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the organic compound further contains a central metal. The light-emitting element material is an organometallic complex having the above structure.

[0029] Alternatively, another aspect of the present invention is a semiconductor device having the above-described structure, wherein the central metal is iridium. It is a material for optical elements.

[0030] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a semiconductor device, comprising: The first skeleton having rear transport properties is a diphenyltriazine skeleton. .

[0031] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a semiconductor device, comprising: The compound has different ligands, one of which has a light-emitting backbone and the other has hole-transporting properties. The light-emitting element material has the following skeleton:

[0032] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a semiconductor device, comprising: The ligands have different structures, one of which has a light-emitting backbone and the other has electron-transporting properties. The light-emitting element material has the following skeleton:

[0033] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a semiconductor device, comprising: The structure has different ligands, one of which has a hole-transporting skeleton and the other has an electron-transporting skeleton. and at least one of the two different ligands has a luminescent skeleton. There is also a light-emitting element material having the above structure.

[0034] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device, comprising: The complex has a molecular weight of 1,300 or less.

[0035] Alternatively, another embodiment of the present invention is a light-emitting element material having the above structure, wherein the light-emitting element material is formed by a vapor deposition method. This is a light-emitting element in which a film is formed and used.

[0036] Alternatively, another embodiment of the present invention is a light-emitting element material according to any one of the above structures, The light-emitting device is formed by the method and used.

[0037] Another embodiment of the present invention is a light-emitting element comprising: a first organic compound; the above-described light-emitting element material; and a light-emitting device having a light-emitting layer containing the organic compound, the iridium complex, and the first skeleton having carrier transport properties of the iridium complex is the same as that of the first skeleton having carrier transport properties of the iridium complex. the same structure is contained in at least a part of the skeleton of the first organic compound. do.

[0038] Alternatively, another embodiment of the present invention is a light-emitting device having the above structure, wherein the light-emitting layer further contains a second organic compound. The light-emitting element further includes:

[0039] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the first skeleton is an amine skeleton. It is a light-emitting element.

[0040] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the first skeleton is diphenylamine. It is a light-emitting element that is the skeleton.

[0041] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0042] [ka]

[0043] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0044] [ka]

[0045] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0046] [ka]

[0047] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0048] [ka]

[0049] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0050] [ka]

[0051] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0052] [ka]

[0053] Another embodiment of the present invention is an organometallic complex represented by the following structural formula:

[0054] [ka]

[0055] Another embodiment of the present invention is a light-emitting element having any of the above structures, a transistor, or and a substrate.

[0056] Another embodiment of the present invention is a light-emitting device including the above-described light-emitting device, a sensor, an operation button, and a speaker. , or an electronic device having a microphone and.

[0057] Another embodiment of the present invention is a lighting device including a light-emitting device having the above structure and a housing. It is a location.

[0058] In this specification, the term "light-emitting device" includes an image display device using a light-emitting element. In addition, a connector, such as an anisotropic conductive film or TCP (Tape Carrier), is attached to the light emitting element. The module has a printed wiring board at the end of the TCP. The COG (Chip On Glass) method is used for the module or light emitting element. In some cases, a light emitting device also includes a module on which an IC (integrated circuit) is directly mounted. A lighting fixture or the like may include a light-emitting device. [Effects of the Invention]

[0059] According to one embodiment of the present invention, a novel material for a light-emitting element can be provided. In one embodiment, a material for a light-emitting element that can simplify the process for manufacturing a light-emitting element is provided. Alternatively, in one embodiment of the present invention, the cost for manufacturing a light-emitting element can be reduced. It is possible to provide a material for a light-emitting element that can reduce the In this case, it is possible to provide a material for a light-emitting element that can realize a light-emitting element with good luminous efficiency. Alternatively, in one embodiment of the present invention, a light-emitting element with a long lifetime can be provided. Thus, it is possible to provide a material for a light-emitting device.

[0060] Alternatively, in one embodiment of the present invention, a light-emitting element that can be easily manufactured can be provided. Alternatively, one embodiment of the present invention provides a light-emitting element that can be manufactured at low cost. Alternatively, one embodiment of the present invention can provide a light-emitting element with high emission efficiency. Alternatively, in one embodiment of the present invention, a light-emitting element with a long lifetime can be provided.

[0061] Alternatively, in another embodiment of the present invention, an inexpensive light-emitting device, an electronic device, and a display device are provided. Alternatively, a highly reliable light-emitting device, an electronic device, and a display device can be provided. Alternatively, in another embodiment of the present invention, a light-emitting device with low power consumption, an electronic device Alternatively, in another aspect of the present invention, a display device may be provided. It is possible to provide a light emitting device, an electronic device, and a display device with good quality.

[0062] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0063] [Figure 1] 1 is a conceptual diagram of a material for a light-emitting element of the present invention. [Figure 2] Schematic diagram of a light-emitting element. [Figure 3] 1A to 1C illustrate an example of a method for manufacturing a light-emitting element. [Figure 4] 1A to 1C illustrate an example of a method for manufacturing a light-emitting element. [Figure 5] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 6] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 7] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 8] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 9] FIG. [Figure 10] 1 is a diagram showing an electronic device. [Figure 11] FIG. [Figure 12] FIG. [Figure 13] FIG. [Figure 14] FIG. 2 is a diagram illustrating an in-vehicle display device and an illumination device. [Figure 15] 1 is a diagram showing an electronic device. [Figure 16] 1 is a diagram showing an electronic device. [Figure 17] 1H-NMR spectrum of [Ir(ppy)2(Czppy)] [Figure 18] Absorption and emission spectra of [Ir(ppy)2(Czppy)] [Figure 19] 1H-NMR spectrum of [Ir(ppy)(Czppy)2] [Figure 20] Absorption and emission spectra of [Ir(ppy)(Czppy)2] [Figure 21] 1 is a schematic diagram of the element structure of a light-emitting element. [Figure 22] 1 shows the luminance-current density characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1. [Figure 23] luminance-voltage characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1; [Figure 24] Current efficiency-luminance characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1. [Figure 25] Current-voltage characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1. [Figure 26] 1 shows emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1. [Figure 27]Luminance-current density characteristics of light-emitting element 3. [Figure 28] Current efficiency-luminance characteristics of light-emitting element 3. [Figure 29] Luminance-voltage characteristics of light-emitting element 3. [Figure 30] Current-voltage characteristics of light-emitting element 3. [Figure 31] External quantum efficiency-luminance characteristics of light-emitting element 3. [Figure 32] Emission spectrum of light-emitting element 3. [Figure 33] 1H-NMR spectrum of [Ir(czppm)2(ppy)]. [Figure 34] Absorption and emission spectra of [Ir(czppm)2(ppy)]. [Figure 35] 1H-NMR spectrum of [Ir(ppy)2(5dptznppy)]. [Figure 36] Absorption and emission spectra of [Ir(ppy)2(5dptznppy)]. [Figure 37] 1H-NMR spectrum of [Ir(5dptznppy)2(ppy)]. [Figure 38] Absorption and emission spectra of [Ir(5dptznppy)2(ppy)]. [Figure 39] 1H-NMR spectrum of [Ir(ppy)2(dpappy)]. [Figure 40] Absorption and emission spectra of [Ir(ppy)2(dpappy)]. [Figure 41] 1H-NMR spectrum of [Ir(dpappy)2(ppy)]. [Figure 42] Absorption and emission spectra of [Ir(dpappy)2(ppy)]. [Figure 43] 1H-NMR spectrum of [Ir(mdppy)2(5dptznmdppy)]. [Figure 44] Absorption and emission spectra of [Ir(mdppy)2(5dptznmdppy)]. [Figure 45]1H-NMR spectrum of [Ir(5dptznmdppy)2(mdppy)]. [Figure 46] Absorption and emission spectra of [Ir(5dptznmdppy)2(mdppy)]. [Figure 47] 1 shows luminance-current density characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 48] Current efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 49] luminance-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 50] Current-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 51] 1 shows the external quantum efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 52] 1 shows emission spectra of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 53] Normalized luminance vs. time change characteristics of the light-emitting element 4 and the comparative light-emitting element 2. [Figure 54] luminance-current density characteristics of light-emitting element 5. [Figure 55] Current efficiency-luminance characteristics of light-emitting element 5. [Figure 56] Luminance-voltage characteristics of light-emitting element 5. [Figure 57] Current-voltage characteristics of light-emitting element 5. [Figure 58] External quantum efficiency-luminance characteristics of light-emitting element 5. [Figure 59] Emission spectrum of light-emitting element 5. [Figure 60] A diagram showing the calculation results. DETAILED DESCRIPTION OF THE INVENTION

[0064] Hereinafter, embodiments 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 embodiments and details thereof may be modified without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications can be made to the above. The present invention should not be construed as being limited to the description of the embodiments.

[0065] (Embodiment 1) The light-emitting layer of an organic EL element is made up of a carrier transport material, which is a host material, and a light-emitting material, which is a guest material. The mainstream method is to mix the materials by co-evaporating them. To achieve this, it is necessary to have multiple evaporation sources in the evaporation chamber. It requires large-scale manufacturing equipment and a huge initial investment, making it difficult for new companies to enter the market. Moreover, complicated and lengthy manufacturing processes lead to increased product costs. there was.

[0066] In view of this, the present inventors have developed a carrier transport layer, which is a host material that has conventionally been vapor-deposited separately. For light-emitting devices that simultaneously have the function of a material and the function of a light-emitting material (guest material) in one molecule By using this material, it becomes easier to manufacture the element, and the cost can be reduced significantly by simplifying the manufacturing equipment. It was found that reduction was possible.

[0067] Specifically, as shown in FIG. 1(A), a first skeleton having carrier transport properties and a second skeleton having light-emitting properties are The light-emitting material has a second skeleton having a molecular weight of Although it is not a polymer, if it is given solubility, it can be dissolved in a solvent and processed by the wet method. Film formation by the method is also possible.

[0068] The light-emitting material has a structure in which a skeleton responsible for carrier transport and a skeleton responsible for light emission exist simultaneously in one molecule. Therefore, the light-emitting layer can be formed using only the light-emitting material. Therefore, a light-emitting layer with good characteristics can be obtained without using a relatively simple structure. It is possible to manufacture light-emitting elements with good characteristics using the same manufacturing equipment, and to produce light-emitting elements with low cost and good performance. It will be possible to provide.

[0069] As the first skeleton having a carrier transport property, a structure having a hole transport property as shown in FIG. 1(B) is used. The skeleton may be either a skeleton having a hole transporting property as shown in FIG. 1(C) or a skeleton having a hole transporting property as shown in FIG. Although not shown, a skeleton having bipolar properties may also be used. Even if a single molecule has both a skeleton with electron transport properties and a skeleton with hole transport properties, good.

[0070] Note that, for a light-emitting element, the first skeleton having a carrier transport property is a skeleton having a hole transport property. In the case of a material, the skeleton having hole transport properties is a skeleton having a HOMO in the material. It is also preferable that the first skeleton having carrier transport properties is a skeleton having electron transport properties. In the case of a material for a light-emitting device, the backbone having the electron transport property is the LUM of the material. It is preferable that the first skeleton having carrier transport properties is a skeleton having positive O. When the material for a light-emitting device has both a skeleton having hole transport properties and a skeleton having electron transport properties, In the materials, the HOMO is located in the skeleton with hole transport properties, and the LUM is located in the skeleton with electron transport properties. Preferably, O is present.

[0071] The first skeleton and the second skeleton may be bonded directly or via some group. The intermediate group may be a metaphenylene group or a biphenyl-3,3'-diyl group. This is a preferable configuration since it is difficult for the emission energy level to decrease.

[0072] Three skeletons: a skeleton with hole transport properties, a skeleton with electron transport properties, and a skeleton with light-emitting properties In the case where the material for a light-emitting element has a sufficient quality, the material for a light-emitting element is used to perform co-evaporation. and fabricating a light-emitting device with good luminous efficiency using an exciplex as an energy donor. In this case, the hole transporting property in the same molecule is The skeleton having electron transport property and the skeleton having electron transport property may interact to form an excited state, or one molecule may The skeleton having hole transport properties of one molecule and the skeleton having electron transport properties of another molecule form an exciplex. The excitation energy may be applied to an excited state or an exciplex of a molecule. Transfer to a luminescent backbone or transfer to a luminescent backbone of another ground-state molecule By doing so, efficient light emission can be obtained. In the exciplex, the S1 level and the T1 level are almost the same. Because of its position, it will not be in the T1 state unless it has some framework with a lower triplet energy. This facilitates intersystem crossing from the S1 level to the S1 level, increasing the probability of generating the S1 level. Therefore, it is expected that the luminous efficiency of the fluorescent light emitting device will be improved. A characteristic feature of this method is that delayed fluorescence is observed from the light-emitting element that produces the light.

[0073] Of course, the present invention can also be applied to phosphorescent light emitting devices. Representative examples of such materials are organometallic complexes with central metals such as iridium and platinum. The framework responsible for carrier transport and the framework responsible for light emission can be introduced as ligands. In the case of organometallic complexes with multiple ligands, each ligand has a different function (electron transport, The structure may have a skeleton that performs hole transporting, light emitting, etc., or a structure having a skeleton that performs light emitting and a A ligand having a skeleton with carrier transport properties may also be used. It is also possible to arrange the desired characteristics.

[0074] For example, in the case of an organometallic complex having two or more ligands, at least two different One of the ligands has a light-emitting backbone and the other has a hole-transporting backbone. One ligand has a luminescent skeleton and the other has an electron-transporting skeleton. One of the ligands has a skeleton with hole transport properties, and the other ligand has electron transport properties. The compound has a light-emitting skeleton and has the light-emitting property of at least one of the two different ligands. A structure further having a skeleton may be considered.

[0075] In addition, by having a skeleton with carrier transport properties and a skeleton with light-emitting properties in the same molecule, It is possible to control the positional relationship. It is possible to adjust the concentration of the light-emitting material (guest) and the carrier transport material (host). Even if it is possible to control the relative positions and arrangement of the molecules, the efficiency of energy transfer is , the molecular shape of the host, which is the energy donor, and the guest, which is the energy acceptor, It is known that the carrier transport property and the distance between the electrons are significantly dependent on the arrangement. By incorporating a luminescent skeleton into a single molecule, the distance and arrangement of the luminescent skeleton can be controlled to control the energy transfer. This allows the relative positions of the light sources to be kept in a good condition. A good light emitting element can be obtained.

[0076] Note that the molecular weight of the light-emitting element material according to one embodiment of the present invention is 1,300 or less. By having a molecular weight of 1300 or less, it is possible to easily perform vapor deposition of the polymer for the light emitting device. This makes it possible to prevent the decomposition of materials, resulting in a light-emitting element with a long life and high reliability. You can get it.

[0077] In addition, even if the material cannot be evaporated, it can be spin-coated by dissolving it in an appropriate solvent. The film can be formed by a wet method such as a stencil method or an ink-jet method.

[0078] Note that the light-emitting element material according to one embodiment of the present invention and a commonly used host material may be used. Alternatively, a guest material or the like may be mixed to form the light-emitting layer. The light-emitting material itself has high carrier transport properties, so the driving voltage of the device can be reduced. While maintaining high recombination efficiency, high efficiency and low driving voltage can be achieved at the same time. In this case, different organic compounds contained in the light-emitting layer, such as the host material and the guest material, An organic compound containing the same skeleton as the skeleton having carrier transport properties of the material for the light-emitting element. is preferred.

[0079] FIG. 2 shows an example of a light-emitting element using a light-emitting element material according to one embodiment of the present invention. A light-emitting element using the light-emitting element material of one embodiment of the present invention is also one embodiment of the present invention. The device has an anode 101, a cathode 102, and an EL layer 103, and the EL layer is made of the above-mentioned light-emitting element material. is used.

[0080] The EL layer 103 has at least a light-emitting layer 113, which is the light-emitting element described above. The light-emitting element material is formed using a material for a light-emitting element. It contains both a backbone responsible for rear transport and a backbone responsible for light emission, and can be successfully fabricated without co-evaporation. This allows the formation of a light-emitting layer having desirable characteristics. This simplifies the manufacturing process, reduces the initial investment, and enables light-emitting devices to be manufactured at low cost. You will be able to do it.

[0081] 2, the EL layer 103 includes a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, and a 112, the electron transport layer 114, and the electron injection layer 115 are shown in the figure, but the configuration of the light-emitting element The layer is not limited to these, and may be a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a cathode ... Various layer structures can be applied, such as carrier blocking layer, exciton blocking layer, and charge generating layer. can.

[0082] Next, examples of the detailed structure and materials of the light-emitting element will be described.

[0083] In this embodiment, the stacked structure of the EL layer 103 is as shown in FIG. In addition to the optical layer 113, the hole injection layer 111, the hole transport layer 112, the electron transport layer 114, and the electron 2B, the hole injection layer 111 and the hole transport layer 115 are formed. In addition to the layer 112 and the light-emitting layer 113, the structure includes an electron transport layer 114 and a charge generation layer 116. The materials that make up the electrodes and EL layer are described below in detail. Target.

[0084] The anode 101 is made of a metal, alloy, or conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound or a mixture thereof. , indium tin oxide (ITO), silicon or Indium oxide-tin oxide, indium oxide-zinc oxide, or silicon oxide-containing indium oxide-tin oxide Examples include tungsten oxide and indium oxide containing zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they can also be formed by the sol-gel method. It is also possible to manufacture it by applying the method described above. An example of the manufacturing method is indium oxide-zinc oxide. The film was formed by sputtering using a target containing indium oxide and 1 to 20 wt% zinc oxide. Also, there are methods for forming the film by tarnishing. The indium oxide (IWZO) film has a ratio of tungsten oxide to indium oxide of 0. Sputtering was performed using a target containing 5-5 wt% of zinc oxide and 0.1-1 wt% of zinc oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Nitrides of metallic materials (e.g., titanium nitride), copper (Cu), palladium (Pd), or Graphene can also be used. By using it in the layer 103 that contacts the anode 101, the electrode material You will be able to select.

[0085] The hole injection layer 111 is a layer containing a substance having acceptor properties. As a substance, a compound having an electron-withdrawing group (halogen group or cyano group) can be used. 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation Name: F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyano-naphtho Quinodimethane (abbreviation: F6-TCNNQ), 3,6-difluoro-2,5,7,7,8, 8-Hexacyanoquinodimethane, Chloranil, 2,3,6,7,10,11-Hexacyanoquinodimethane Organic aza-triphenylene (HAT-CN) Cepta, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide Inorganic oxides such as manganese oxide, phthalocyanine (abbreviated as H2Pc) and copper Phthalocyanine metal complexes such as phthalocyanine (CuPC), 4,4'-bis[N-( 4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) , N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'- Diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) Aromatic amine compounds or poly(3,4-ethylenedioxythiophene) / poly(styrene) Polymers such as poly(ethylenediaminetetraacetic acid) (PEDOT / PSS) can be used.

[0086] As organic acceptors, fused aromatic rings with multiple heteroatoms, such as HAT-CN, are used. Compounds with an attractive group bonded thereto are preferred because they are thermally stable. The compound attracts electrons from the adjacent hole transport layer (or hole transport material) by applying an electric field. It can be pulled out.

[0087] The hole injection layer 111 is formed by adding an acceptor substance to a substance having a hole transporting property. A composite material in which an acceptor substance is contained in a hole transporting substance can also be used. By using a composite material with this structure, it is possible to select a material for forming an electrode regardless of the work function. In other words, the anode 101 can be made of not only a material with a large work function but also a material with a small work function. As the acceptor material, the above-mentioned organic acceptor can be used. ceptors, transition metal oxides, and metals from groups 4 to 8 of the periodic table Oxides of metals belonging to groups 4 to 8 of the periodic table can be used. Examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and molybdenum oxide. tungsten oxide, manganese oxide, rhenium oxide, etc. are preferred because of their high electron-accepting properties. Among them, molybdenum oxide is particularly stable in the air, has low hygroscopicity, and is easy to handle. The organic acceptor is preferably 7,7,8,8-tetracyano-2,3,5,6- Tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, and the like are preferred.

[0088] The hole transporting material used in the composite material is -6 cm 2 Hole mobility above / Vs As the substance having hole transport properties, N,N'-di(p-to (aryl)-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4, 4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl {Nyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation :DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl] aromatic amines such as 3-[N-(9-phenylamino)benzene (abbreviation: DPA3B), N-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation Name: 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 Nylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl Nyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzoyl Zene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]- 9H-Carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl] carbazole derivatives such as 2-tert-butyl-2,3,5,6-tetraphenylbenzene, t-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2 -tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3 ,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl- 9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9, 10-Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene Helical anthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7 -Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) 10,10'-bis[(2,3,4,5,6-pentanthryl Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, pentacene Benzene, coronene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)pentane The aromatic hydrocarbon may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2- Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2- diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc. , 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: N PB), 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), 4,4 '-Diphenyl-4''-(9-phenyl-9-H-carbazol-3-yl)triphenyl PCBBi1BP, 4-(1-naphthyl)-4'-(9-phenyl -9H-carbazol-3-yl)-triphenylamine (abbreviation: PCBANB), 4, 4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl) Triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[ 4-(9-phenyl-9H-carbazol-3-yl)phenyl]-fluorene-2-a PCBAF, N-phenyl-N-[4-(9-phenyl-9H-carbazoline (3-yl)phenyl]-spiro-9,9'-bifluoren-2-amine (abbreviation: P Compounds with an aromatic amine skeleton, such as 1,3-bis(N-carbazolyl) ) benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: C BP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCC P), compounds with a carbazole skeleton such as 4,4',4''-(benzene-1,3, 5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl Phenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzo Thiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoro [6-phenyl-9-yl]phenyldibenzothiophene (abbreviation: DBTFLP- IV), compounds with a thiophene skeleton such as 4,4',4''-(benzene-1,3, 5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3- (9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran ( Compounds having a furan skeleton such as benzophenone (abbreviation: mmDBFFLBi-II) can be used. Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred. The material is preferred because it has good reliability, high hole transport properties, and contributes to reducing the driving voltage. Desirable.

[0089] The hole injection layer 111 can also be formed by a wet method. PEDOT / PSS (poly(oxythiophene) / poly(styrene sulfonic acid) aqueous solution), Aniline / camphorsulfonic acid aqueous solution (PANI / CSA), PTPDES, Et-P TPDEK, or PPBA, polyaniline / poly(styrene sulfonate) (PANI / A conductive polymer compound to which an acid such as PSS has been added can be used.

[0090] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. In addition, organic acceptors are easy to vapor-deposit and form into films. Therefore, it is an easy-to-use material.

[0091] The hole transport layer 112 may be made of any of the above-mentioned materials having hole transport properties or various other materials. Any suitable material having hole transport properties may be used.

[0092] The light-emitting layer 113 is formed using the above-described material for a light-emitting element according to one embodiment of the present invention. The light-emitting element of the present invention comprises a carrier transporting skeleton having a host function and a light-emitting Since the material for light emitting devices has the above skeleton in one molecule, it has good properties. A light-emitting layer can be formed.

[0093] As a carrier transporting skeleton having a host function, it is more preferable to use a light-emitting skeleton having a light-emitting function. A fused aromatic ring skeleton or a heterocyclic ring skeleton having high excitation energy can be used.

[0094] The host functions are broadly divided into hole transport, electron transport, and bipolar. The skeleton having hole transport function is a π-electron-rich heteroaromatic structure. Examples of the arylamine skeleton include a diphenylamine skeleton and a diphenylamine skeleton. A skeleton containing an amine structure, or a skeleton containing a pyrrole ring, a furan ring, or a thiophene ring, These rings may also be condensed with other aromatic rings. a dibenzofuran ring, a dibenzothiophene ring, or a heterocyclic ring having these ring structures Examples of skeletons with electron transport function include π-electron deficient heteroaromatic skeletons. More specifically, pyridine rings, diazine rings, triazine rings, etc. can be used. The ring may be condensed with another aromatic ring. Radizine ring, pyrimidine ring, pyrazine ring, triazine ring, quinoline ring, quinazoline ring, quinone ring It is a heteroaromatic ring having a cyclohexaline ring or these ring structures. As the skeleton, a condensed aromatic hydrocarbon ring such as anthracene or pyrene can be suitably used. do.

[0095] Examples of luminescent skeletons that have a luminescent function include an anthracene skeleton, a pyrene skeleton, and a perylene skeleton. or a partial structure in which aromatic ligands are orthometalated to iridium or platinum. Examples of the skeleton include:

[0096] The material for a light-emitting element according to one embodiment of the present invention does not require co-evaporation. When used in this way, it becomes possible to manufacture light-emitting devices without going through complicated manufacturing processes, This results in significant cost reduction effects.

[0097] In addition, when the light-emitting layer is formed using the material for the light-emitting element by a wet method, The materials are dissolved or dispersed in a suitable liquid medium and then applied by a wet process (spin coating, Strapping method, die coating method, blade coating method, roll coating method, inkjet method, printing method , spray coating, curtain coating, Langmuir-Blodgett method, etc.) After forming the film, the solvent may be removed or the film may be baked.

[0098] Examples of liquid media used in wet processes include methyl ethyl ketone and cyclohexane. Ketones such as Sanon, fatty acid esters such as ethyl acetate, halogens such as dichlorobenzene Aromatic hydrocarbons such as toluene, xylene, mesitylene, and cyclohexylbenzene Hydrogen fluorides, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, dimethylform Organic solvents such as dimethyl amide (DMF) and dimethyl sulfoxide (DMSO) can be used. do.

[0099] In the light-emitting layer, in order to adjust the carrier balance, and a carrier transport material having hole transport properties and / or electron transport properties. Alternatively, the light-emitting element material of one embodiment of the present invention may be mixed with other light-emitting materials. The carrier transport material may be a mixture of multiple substances. When a mixed host material is used, a material having an electron transporting property and a material having a hole transporting property are mixed. It is preferable to mix a material having an electron transporting property and a material having a hole transporting property. By mixing these, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region The region can be easily controlled. The ratio of the content of the material having hole transport properties to the material having electron transport properties is 1:9 to 9:1. This can be done as follows.

[0100] Furthermore, these mixed host materials may form an exciplex. The wavelength of the lowest energy absorption band of a fluorescent or phosphorescent substance overlaps with the wavelength of the lowest energy absorption band of the fluorescent or phosphorescent substance. By selecting a combination that forms an exciplex that emits light, energy transfer This configuration also reduces the driving voltage. This is a preferable configuration.

[0101] Among the carrier transport materials, the material having hole transport properties is 2-[N-(9-phenyl)-2-(phenyl)-2-(2- ... Nylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 4,4',4''-tris[N-(1-naphthyl)-N-phenyl] 2,7-bis[N-(4- Diphenylaminophenyl)-N-phenylamino]-spiro-9,9'-bifluorene (abbreviation: DPA2SF), N,N'-bis(9-phenylcarbazol-3-yl)-N ,N'-Diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N-(9,9- Dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation) N,N',N''-triphenyl-N,N',N''-tris(9-phenyl- (phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B ), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9, 9'-Bifluorene (abbreviation: DPASF), N,N'-bis[4-(carbazole-9- [N,N'-diphenyl-9,9-dimethylfluorene-2,7-diazomethane N,N'-bis(3-methylphenyl)-N,N'-amine (abbreviation: YGA2F), NPB, N,N'-bis(3-methylphenyl)-N,N'- -Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4, 4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), BSPB, 4-phenyl-4'-(9-phenylfluorene-9- 4-phenyl-3'-(9-phenylyl)triphenylamine (abbreviation: BPAFLP), mBPAFLP, N-(9,9 -dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-fluoren-2-yl] phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren Fluoren-7-yl}phenylamine (abbreviation: DFLADFL), PCzPCA1,3- [N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarba azole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), DN TPD, 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl) Amino]-9-phenylcarbazole (abbreviation: PCzTPN2), PCzPCA2, 4- Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carboxylate) PCBBi1BP, 4-(1-naphthyl)triphenylamine (9H-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9 H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 3-[N- (1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenyl PCzPCN1, 9,9-dimethyl-N-phenyl-N-[4 -(9-phenyl-9H-carbazol-3-yl)phenyl]-fluorene-2-amine PCBAF, N-phenyl-N-[4-(9-phenyl-9H-carbazol-2-yl)methyl] PC BASF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2 -yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole] -3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: P Compounds with aromatic amine skeletons such as 1,3-bis(N-carbazolidinediamine) and 1,3-bis(N-carbazolidinediamine) mCP, CBP, 3,6-bis(3,5-diphenylphenyl)benzene -9-phenylcarbazole (abbreviation: CzTP), 9-phenyl-9H-3-(9-phenyl Carbazoline, such as (9H-carbazol-3-yl)carbazole (abbreviation: PCCP) Compounds with a benzoyl skeleton and 4,4',4''-(benzene-1,3,5-triyl)trimethylsilyl Dibenzothiophene (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4 -(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated :DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl) phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV) Compounds with a phen skeleton and 4,4',4''-(benzene-1,3,5-triyl) Tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl -9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDB Examples include compounds with a furan skeleton such as FFLBi-II).

[0102] Among the carrier transport materials, the material having hole transport properties is bis(10-hydroxybenzophenone). Bis(2-methylbenzo[h]quinolinato)beryllium(II) (BeBq2) (4-phenyl-8-quinolinolato)aluminum(III) (abbreviation: B Alq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2- benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2 -benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ) and other metal complexes , 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-o PBD (Phenyldiazole), 3-(4-biphenylyl)-4-phenyl-5-(4 -tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3- Bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl] 9-[4-(5-phenyl-1,3,4-oxazolidinyl)benzene (abbreviation: OXD-7) azol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2', 2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazoline) 2-[3-(dibenzothiophen-4-yl)phenyl] -1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds with an azole skeleton and 2-[3-(dibenzothiophen-4-yl)phenyl] ... phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[ 3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]ky Noxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole -9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mCz BPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl] nyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3- (Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 7mDBTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl] 4,6-nyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP 2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl )phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm) Polycyclic compounds and 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9 H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazol- Heterocyclic compounds with triazine skeletons, such as PCCzPTzn (abbreviation: PCCzPTzn), and 3,5- Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzP Py), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPy PB) and other heterocyclic compounds having a pyridine skeleton.

[0103] The light-emitting material is tris{2-[5-(2-methylphenyl)-4-(2,6-dimethyl ... (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] [phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: Ir(iPr ptz-3b)3), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl Ir(iPr) tz)3), tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H- 1,2,4-Triazolate]iridium(III) (abbreviation: Ir(Mptz1-mp)3 ), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazola Iridium(III) (abbreviation: Ir(PrPrtZ1-Me)3), fac-tris[ 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridine Ir(iPrpmi)3, tris[3-(2,6-dimethylphenyl)- (phenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III ) (abbreviation: Ir(dmpimpt-Me)3), bis[2-(4',6'-difluoromethyl] Phenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl) Borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridina To-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), bis{2 -[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Ili Ir(CF3ppy)2(pic) -(4',6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) Acetylacetonate (abbreviation: FIr(acac)), tris(4-methyl-6-phenyl) Iridium(III) (abbreviation: Ir(mppm)3), tris(4-t -butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: Ir(tBupp m)3), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)yl Ir(mppm)2(acac) (acetylacetonate) Bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation : Ir(tBuppm)2(acac)), (acetylacetonato)bis[4-(2-acetylacetonato)bis( ... Iridium(III) (abbreviation: Ir(nbp) pm)2(acac)), (acetylacetonato)bis[5-methyl-6-(2-methyl Iridium(III) (abbreviation: Ir(mpmp) pm)2(acac)), (acetylacetonato)bis{4,6-dimethyl-2-[6- (2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridi Ir(dmppm-dmp)2(acac)), (acetylacetonate Nato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: Ir(d ppm)2(acac)), (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Nilpyrazinato)iridium(III) (abbreviation: Ir(mppr-Me)2(acac) ), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazine Nat(III) (abbreviation: Ir(mppr-iPr)2(acac)), tri Su(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: Ir(ppy )3), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetone Setonate (abbreviation: Ir(ppy)2(acac)), bis(benzo[h]quinolinato) Iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), Tris(benzo[h]quinolinato)iridium(III) (abbreviation: Ir(bzq)3), Tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: Ir(p q)3), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetyl Acetonate (abbreviation: Ir(pq)2(acac)), bis(2,4-diphenyl-1, 3-Oxazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: I r(dpo)2(acac)), bis{2-[4'-(perfluorophenyl)phenyl ]Pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: Ir( p-PF-ph)2(acac)), bis(2-phenylbenzothiazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: Ir(bt)2(acac)), (Diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato] Iridium(III) (abbreviation: Ir(5mdppm)2(dibm)), bis[4,6- Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(II) I) (abbreviation: Ir(5mdppm)2(dpm)), bis[4,6-di(naphthalene-1 -yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: Ir( d1npm)2(dpm)), (acetylacetonato)bis(2,3,5-triphenyl pyrazinato)iridium(III) (abbreviation: Ir(tppr)2(acac)), bis( 2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (Abbreviation: Ir(tppr)2(dpm)), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdp q) 2(acac)), tris(1-phenylisoquinolinato-N,C 2’ )iridium (III) (abbreviation: Ir(piq)3), bis(1-phenylisoquinolinato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac) ), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porph Phosphorescent compounds such as platinum(II) phosphate (PtOEP) and 2-(biphenyl- 4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazole-11 -yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N- Phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl }-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[ 4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3 ,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-di Hydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-tria PPZ-3TPT, 3-(9,9-dimethyl-9H-acridine-10 -yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9- Dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DP S), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene Thermally activated delayed fluorescence (TADF) materials such as N-10'-one (abbreviated as ACRSA) and ,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl] N,N'-phenyl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn) Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene -9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPr n), N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl] -N,N'-bis(4-tert-butylphenyl)-pyrene-1,6-diamine (abbreviation :1,6tBu-FLPAPrn), N,N'-bis[4-(9-phenyl-9H-fluro[ (Olen-9-yl)phenyl]-N,N'-diphenyl-3,8-dicyclohexylpyrene N,N'-bis[4-( 9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4 '-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-( 10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9 H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)tri Phenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl)- [phenyl-9-anthrylphenyl]-9H-carbazol-3-amine (abbreviation: PCA PA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: T BP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-cal N,N''-(2-(2-benzol-3-yl)triphenylamine (abbreviation: PCBAPA) tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N, N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N ,9-Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]- 9H-Carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-di (phenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenyl Nylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N' '',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetradecane Tolamine (abbreviation: DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthracene) tolyl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA ), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N ,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4- Phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl)] N,N',N'-triphenyl-1,4-phenyl)-2-anthryl Diamine (abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2 -yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylan thracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen DPhAPhA, Coumarin 6, Coumarin 545T, N,N' -Diphenylquinacridone (abbreviation: DPQd), rubrene, 2,8-di-tert-butyl 1,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene TBRb, Nile Red, 5,12-bis(1,1'-biphenyl-4-yl) N,N,N',N'-tetrahydro-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), ... Rakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H- Pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), and 5,10,15,20-tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene.

[0104] The light-emitting layer 113 having the above-described structure can be formed by co-evaporation using a vacuum evaporation method or by using a mixed solution. Gravure printing, offset printing, inkjet printing, spin coating and dip printing are also available. It can be produced by using a coating method or the like.

[0105] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the substrate include bis(10-hydroxybenzo[h]quinolinato)beryllium (I I) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenyl) bis(8-quinolinolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc ( II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc (I I) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc (I I) (abbreviation: ZnBTZ), and 2-(4-biphenylyl)-5-(4-t ert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4 -biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4 -triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl )-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[ 4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-ca Rubazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl) Tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-( Dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) and other heterocyclic compounds with a polyazole skeleton, such as 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 2mCzBPDBq, 4,6-bis[3-(phenanthroline) 4,6-(4,6-benzothren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2 Heterocyclic compounds with diazine skeletons such as Pm-II) and 3,5-bis[3-(9H- carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5 -tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) Among the above, heterocyclic compounds having a diazine skeleton are preferred. A heterocyclic compound having a pyridine skeleton and a heterocyclic compound having a pyridine skeleton are preferred because of their high reliability. Heterocyclic compounds with a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and are suitable for It also contributes to reducing dynamic voltage.

[0106] Furthermore, a layer for controlling the movement of electron carriers may be provided between the electron transport layer and the light emitting layer. This is achieved by adding a small amount of a substance with high electron trapping properties to a material with high electron transport properties as described above. It is a layer that adjusts the carrier balance by suppressing the movement of electron carriers. This type of structure prevents electrons from penetrating the light-emitting layer. This is highly effective in suppressing problems that arise (for example, a reduction in the device life).

[0107] In addition, an electron injection layer 115 is formed between the electron transport layer 114 and the cathode 102 and in contact with the cathode 102. The electron injection layer 115 may be formed using a material such as lithium fluoride (LiF), cesium fluoride, or the like. Alkali metals or alkaline earths such as calcium fluoride (CsF), calcium fluoride (CaF2), etc. For example, a metal or a compound thereof can be used. The layer containing alkali metals or alkaline earth metals or their compounds is used. Alternatively, the electron injection layer 115 may be made of an electride. For example, a mixed oxide of calcium and aluminum with high electron concentration is used as the oxide. The electron-injecting layer 115 may be formed of a substance having an electron-transporting property. By using a layer containing an alkali metal or alkaline earth metal, the cathode 1 This is more preferable because electron injection from O2 is carried out efficiently.

[0108] In addition, a charge generating layer 116 may be provided instead of the electron injecting layer 115 (FIG. 2B). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and cations are generated in the layer in contact with the cathode side of the layer. The charge generation layer 116 is a layer that can inject electrons into the layer that is in contact with the electrode side. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer using the composite material mentioned above as a material that can be used. 117 is a composite material comprising a film containing the above-mentioned acceptor material and a hole transporting material. By applying a potential to the P-type layer 117, Electrons are injected into the electron transport layer 114 and holes are injected into the cathode 102, which is the negative electrode, and the light-emitting element operates. At this time, the electron transport layer 114 is provided with a photoresist having a wavelength of 1000 nm or more and a charge generation layer 116 therebetween. The presence of the layer containing the material for the optical element prevents the luminance from decreasing with the accumulation of the driving time of the light emitting element. The decrease in the emission efficiency is suppressed, and a light-emitting element having a long lifetime can be obtained.

[0109] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer in addition to the P-type layer 117. It is preferable that one or both of the layers 119 be provided.

[0110] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron-relay layer 1 is between the LUMO level of the material contained in the layer adjacent to the electron-relay layer 1. Specific energy levels of the LUMO levels in electron transport materials used in 18 The potential is -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials of the formula (I) or metal complexes having a metal-oxygen bond and an aromatic ligand.

[0111] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and and their compounds (alkali metal compounds (oxides such as lithium oxide, halides, carbonates) Alkaline earth metal compounds (including carbonates such as lithium and cesium carbonate), oxides, halides compounds of rare earth metals (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates) It is possible to use a substance with high electron injection properties, such as tetrahydrofuran (Tetrahydrofuran) and tetrahydrofuran (Tetrahydrofuran).

[0112] The electron injection buffer layer 119 contains a substance having an electron transporting property and a donor substance. When formed, the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal. metals and their compounds (alkali metal compounds (oxides such as lithium oxide, halides compounds, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides , halides, carbonates) or compounds of rare earth metals (oxides, halides, In addition to carbonates), tetrathianaphthacene (abbreviated as TTN), nickelocene, decametacene, An organic compound such as thirnickelocene can also be used. The electron transport layer 114 is formed using the same material as that of the electron transport layer 114 described above. It is possible.

[0113] The material forming the cathode 102 has a small work function (specifically, 3.8 eV or less). Metals, alloys, conductive compounds, and mixtures thereof can be used. Specific examples of suitable cathode materials include alkali metals such as lithium (Li) and cesium (Cs), and surrounding elements such as magnesium (Mg), calcium (Ca), and strontium (Sr). Elements belonging to Group 1 or 2 of the periodic table, and alloys containing these elements (MgAg, AlLi ), europium (Eu), ytterbium (Yb), and other rare earth metals, including these However, when an electron injection layer is provided between the cathode 102 and the electron transport layer, By using this method, regardless of the magnitude of the work function, Al, Ag, ITO, silicon or oxide Various conductive materials such as silicon-containing indium oxide-tin oxide are used as the cathode 102. These conductive materials can be deposited by dry methods such as vacuum deposition and sputtering, It is possible to form the film by using the ink jet method, spin coating method, etc. Alternatively, the metal material may be used in a wet process to form the insulating layer. Good too.

[0114] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition and wet process methods (spin coating, casting, die coating) can be used. Coating method, blade coating method, roll coating method, inkjet method, printing method (gravure printing) printing, offset printing, screen printing, etc.), spray coating, curtain coating , Langmuir-Blodgett method, etc.) may also be used.

[0115] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0116] Here, a method for forming the EL layer 786 by droplet discharge will be described with reference to FIG. 3A to 3D are cross-sectional views illustrating a method for manufacturing the EL layer 786.

[0117] First, a conductive film 772 is formed over a planarization insulating film 770. The insulating film 730 is formed as shown in FIG. 3(A).

[0118] Next, a droplet is discharged from a droplet discharge device 783 to an exposed portion of the conductive film 772, which is an opening in the insulating film 730. Droplets 784 are ejected to form a layer 785 containing the composition. The droplets 784 contain the composition including the solvent. and is attached onto the conductive film 772 (see FIG. 3B).

[0119] The step of discharging the droplets 784 may be performed under reduced pressure.

[0120] Next, the solvent is removed from the layer 785 containing the composition, and the layer is solidified to form an EL layer 786. (See Figure 3(C)).

[0121] The solvent may be removed by a drying step or a heating step.

[0122] Next, a conductive film 788 is formed on the EL layer 786 to form a light-emitting element 782 (FIG. 3(D) )reference).

[0123] In this way, when the EL layer 786 is formed by the droplet discharge method, the composition can be selectively discharged. This reduces material waste. Since no additional steps are required, the process can be simplified and costs can be reduced.

[0124] The droplet discharge method described above is a method of discharging a composition using a nozzle having a discharge port, or one or more is a general term for anything that has a means for ejecting droplets, such as a head having multiple nozzles.

[0125] Next, a droplet discharge device used in the droplet discharge method will be described with reference to FIG. FIG. 14 is a conceptual diagram illustrating a droplet ejection device 1400.

[0126] The droplet discharge device 1400 has a droplet discharge means 1403. 3 has a head 1405, a head 1412, and a head 1416.

[0127] The head 1405 and the head 1412 are connected to a control means 1407, which controls the computer. By controlling the image forming apparatus 1410, it is possible to draw a pattern in a pre-programmed manner. can.

[0128] The timing of drawing may be, for example, the timing of the marker 1 formed on the substrate 1402. Alternatively, the reference point may be determined based on the outer edge of the substrate 1402. Here, the marker 1411 is detected by the imaging means 1404, and the image processing means 1 The signal converted into a digital signal by 409 is recognized by a computer 1410 and a control signal is generated. The generated signal is sent to the control means 1407.

[0129] The imaging means 1404 may be a charge coupled device (CCD) or a complementary metal oxide semiconductor ( An image sensor using a CMOS (Complementary Metal Oxide Semiconductor) can be used. The information of the pattern to be formed is stored in the storage medium 1408. Based on this, a control signal is sent to the control means 1407, and the individual heads 1 of the droplet discharging means 1403 are controlled. The heads 405, 1412, and 1416 can be controlled individually. The material is supplied from the material supply source 1413, the material supply source 1414, and the material supply source 1415 through piping. The heads 1405, 1412, and 1416 are supplied with the ink.

[0130] The inside of head 1405, head 1412, and head 1416 is as shown by the dotted line 1406. The structure has a space for filling the liquid material and a nozzle that is a discharge outlet. Although the head 1412 does not have the same internal structure as the head 1405, By providing nozzles of different sizes on the head 1412, different materials can be drawn at different widths simultaneously. It is possible to use one head to eject multiple types of luminescent materials and create images. When drawing on a wide area, multiple nozzles can be used to improve throughput. The same material can be ejected simultaneously to create a pattern. , head 1412 and head 1416 move on the substrate in the directions of the X, Y, and Z arrows shown in FIG. It is possible to freely scan and set the area to be drawn, and the same pattern can be printed on one board. Multiple drawings can be made.

[0131] The step of discharging the composition may be carried out under reduced pressure. After the composition is discharged, one or both of the steps of drying and baking are carried out. Both processes involve heat treatment, but the purpose, temperature and time are different. The drying and firing processes are carried out under normal or reduced pressure by laser light irradiation, instantaneous thermal annealing, or heating. The timing and number of times of this heat treatment are not particularly limited. In order to perform the drying and baking processes well, the temperature at that time should be adjusted depending on the material and composition of the substrate. It depends on the nature of the composition.

[0132] As described above, the EL layer 786 can be manufactured using a droplet discharge apparatus.

[0133] When the EL layer 786 is manufactured using a droplet discharge device, various organic materials and organic / inorganic materials are used. The compound is formed by a wet method as a composition in which a halogen perovskite is dissolved or dispersed in a solvent. In this case, various organic solvents can be used to prepare a coating composition. The organic solvents that can be used are benzene, toluene, xylene, mesitylene, tetrahydrofuran, Dioxane, ethanol, methanol, n-propanol, isopropanol ethanol, n-butanol, t-butanol, acetonitrile, dimethyl sulfoxide, dimethyl Aminoformamide, chloroform, methylene chloride, carbon tetrachloride, ethyl acetate, hexachloroform Various organic solvents such as benzene, toluene, etc. can be used. By using low polarity benzene derivatives such as xylene and mesitylene, a solution of suitable concentration can be obtained. It also prevents the materials contained in the ink from deteriorating due to oxidation. In addition, when the uniformity of the film after production and the uniformity of the film thickness are taken into consideration, A temperature of 100° C. or higher is preferred, and toluene, xylene, and mesitylene are more preferred.

[0134] The above configuration may be appropriately combined with other embodiments or other configurations in this embodiment. It is possible to do this.

[0135] Next, the embodiment of a light-emitting element (also called a stacked element) having a configuration in which a plurality of light-emitting units are stacked This light-emitting element has a plurality of electrodes between an anode and a cathode. The light-emitting element has a light-emitting unit E shown in FIG. It has the same structure as the L layer 103. That is, it is the same as the light-emitting element shown in FIG. is a light-emitting element having one light-emitting unit, and the light-emitting element shown in FIG. 2(C) has a plurality of light-emitting elements. It can be said to be a light-emitting element having a light-emitting unit.

[0136] In FIG. 2C, a first light-emitting unit 511 is disposed between the anode 501 and the cathode 502. and the second light-emitting unit 512 are stacked, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the units 512. The anode 501 and the cathode 502 correspond to the anode 101 and the cathode 102 in FIG. 2(A), respectively, as described in the explanation of FIG. 2(A). The same as that described above can be applied. The light emitting units 512 may be of the same or different construction.

[0137] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting element. The electron-injecting unit has the function of injecting electrons into the light-emitting unit and the hole into the other light-emitting unit. In FIG. 2C, when a voltage is applied, the charge generating layer 513 emits light in the first light-emitting unit 5 Any device may be used as long as it injects electrons into the second light-emitting unit 11 and holes into the second light-emitting unit 512.

[0138] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 2(B). The composite material of an organic compound and a metal oxide has the properties of carrier injection and carrier transport. Because of its excellent transmission properties, it can be driven at low voltage and low current. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 becomes a light emitting unit. Since it can also function as a hole injection layer for the unit, the light-emitting unit does not need to have a hole injection layer. It's also good.

[0139] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the layer Since it plays the role of an electron injection buffer layer in the light-emitting unit, the light-emitting unit must Furthermore, there is no need to form an electron injection layer on top of it.

[0140] Although the light emitting element having two light emitting units has been described in FIG. 2C, the light emitting element having three or more light emitting units may be The same can be applied to a light emitting device in which the light emitting units are stacked. In this way, a plurality of light-emitting units are arranged between a pair of electrodes, separated by a charge generating layer 513. This allows for high-intensity light emission while maintaining a low current density, and also allows for the realization of a device with a long life. Furthermore, a light-emitting device that can be driven at a low voltage and consumes low power can be realized.

[0141] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole For example, two light-emitting units are formed, and the first The light-emitting unit emits blue fluorescence, and the second light-emitting unit emits green and red phosphorescence. By using this technology, it is possible to obtain white light with high color rendering. The first light-emitting unit emits blue fluorescence and the second light-emitting unit emits yellow fluorescence. By obtaining blue fluorescence from the third light-emitting unit, highly efficient White light emission can be obtained.

[0142] (Embodiment 2) In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 1 will be described. .

[0143] A light-emitting device according to one embodiment of the present invention will be described with reference to FIG. 5. Note that FIG. 5(A) shows a light-emitting device. 5(B) is a cross-sectional view of FIG. 5(A) taken along lines AB and CD. This light emitting device includes a driving circuit section shown by the dotted line that controls the light emission of the light emitting elements. (source line driving circuit) 601, pixel section 602, driving circuit section (gate line driving circuit) 603 Also, 604 is a sealing substrate, and 605 is a sealing material. The inside of the hole is a space 607.

[0144] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting the input signal, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal from Lint Circuit 609 Although only the FPC is shown here, this FPC has a printed circuit board. A printed wiring board (PWB) may be attached. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0145] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601, which is a driver circuit portion, is formed in this example. , one pixel in the pixel section 602 is shown.

[0146] The source line driver circuit 601 includes an n-channel FET 623 and a p-channel FET 62 4 is combined to form a CMOS circuit. In addition, the drive circuit is a CMOS circuit Alternatively, the substrate may be formed of a PMOS circuit or an NMOS circuit. Although the driver integrated type with the drive circuit formed on the top is shown, this is not necessarily required. It may also be formed externally rather than on the substrate.

[0147] The pixel section 602 includes a switching FET 611, a current control FET 612, and The pixel is formed by a plurality of pixels including an anode 613 electrically connected to the drain. The present invention is not limited to this, and the pixel section may be a combination of three or more FETs and a capacitance element. .

[0148] There are no particular restrictions on the type and crystallinity of the semiconductor used in the FET, and amorphous semiconductors are used. Examples of semiconductors used in FETs include the first Group 3 semiconductors, Group 14 semiconductors, semiconductors, compound semiconductors, oxide semiconductors, organic semiconductor materials However, it is particularly preferable to use an oxide semiconductor. For example, In-Ga oxide, In-M-Zn oxide (M is Al, Ga, Y, Zr, La, Ce, or Nd). Preferably, an oxide semiconductor material with a conductivity of 2.5 eV or more, more preferably 3 eV or more, is used. This is a preferable structure because the off-state current of the transistor can be reduced.

[0149] An insulator 614 is formed to cover the end of the anode 613. It can be formed by using a photosensitive acrylic resin film.

[0150] In order to improve the covering property, the upper end or the lower end of the insulator 614 is provided with a curvature. For example, the material of the insulator 614 is a positive photosensitive adhesive. When using krill, the radius of curvature (0.2 μm to 3 μm) is set only at the top end of the insulator 614. It is preferable to provide a curved surface having a curved surface. Alternatively, a positive photosensitive resin can be used.

[0151] An EL layer 616 and a cathode 617 are formed on the anode 613. The anode 101, the EL layer 103, and the cathode 102 shown in FIG. 2(A) or the cathode 102 shown in FIG. 2(C) The anode 501, the EL layer (first light-emitting unit 511, charge generation layer 513 and the second light-emitting layer 514) described above are 2 light-emitting unit 512) and the cathode 502.

[0152] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealing material 605, A space 607 surrounded by an element substrate 610, a sealing substrate 604, and a sealing material 605 contains a light-emitting element. The space 607 is filled with a filler. In addition to being filled with an inert gas (nitrogen, argon, etc.), it is also possible to fill it with a sealing material 605. If a recess is formed in the sealing substrate and a desiccant is placed there, deterioration due to the influence of moisture can be prevented. This is a preferable configuration because it can suppress the degradation.

[0153] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the substrate 610 and the sealing substrate 604 include glass substrates, quartz substrates, and FRP ( Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride) A plastic substrate made of, for example, polyester or acrylic can be used.

[0154] For example, in this specification and the like, transistors and light-emitting elements are formed using various substrates. The type of substrate is not limited to a specific one. An example of the substrate is as follows: Examples include semiconductor substrates (such as single crystal substrates or silicon substrates), SOI substrates, glass substrates, Quartz substrate, plastic substrate, metal substrate, stainless steel substrate, stainless steel Substrate with foil, tungsten substrate, substrate with tungsten foil, flexible These include substrates, laminated films, papers containing fibrous materials, or base films. Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, or silicon dioxide. Examples include glass-lime glass. Flexible substrates, laminated films, and base films. Examples include: polyethylene terephthalate (PET) , polyethylene naphthalate (PEN), and polyethersulfone (PES). For example, there are plastics such as acrylic resins. Examples of such materials include polytetrafluoroethylene (PTFE), polypropylene, and polyethylene. Examples include sterol, polyvinyl fluoride, or polyvinyl chloride. Examples of the material include polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, and paper. In particular, transistors are manufactured using semiconductor substrates, single crystal substrates, SOI substrates, etc. This results in less variation in characteristics, size, or shape, a high current capacity, and a small size. It is possible to manufacture transistors with small capacitance. This configuration makes it possible to reduce the power consumption of the circuit or to increase the integration density of the circuit.

[0155] In addition, a flexible substrate is used as the substrate, and transistors and light-emitting elements are directly formed on the flexible substrate. Alternatively, a peeling layer may be formed between the substrate and the transistor or between the substrate and the light-emitting element. The release layer may be provided to separate the semiconductor device from the substrate after the semiconductor device is partially or entirely completed thereon. The transistor can be separated and transferred to another substrate. The transfer can be performed on a substrate having poor mechanical strength or a flexible substrate. The laminated structure of inorganic films such as stainless steel and silicon oxide films, and the organic film such as polyimide on the substrate A configuration in which a resin film is formed, etc., can be used.

[0156] That is, a transistor or a light-emitting element is formed on a certain substrate, and then the transistor or light-emitting element is formed on another substrate. The transistors and light-emitting elements may be transposed and arranged on the substrate. An example of a substrate onto which a transistor or a light emitting element is transferred is a substrate on which the above-mentioned transistor is formed. In addition to the substrates that can be used, paper substrates, cellophane substrates, aramid film substrates, polyimide substrates, Hard film substrate, stone substrate, wood substrate, fabric substrate (natural fiber (silk, cotton, linen), synthetic fiber (nano) Iron, polyurethane, polyester) or regenerated fiber (acetate, cupro, These include recycled polyester, leather substrates, and rubber substrates. By using a substrate, it is possible to form transistors with good characteristics and low power consumption. It is possible to form a thin film, to make a device that is durable, heat resistant, lightweight, or thin. do.

[0157] In FIG. 6, a light emitting element that emits white light is formed, and a colored layer (color filter) or the like is provided. FIG. 6(A) shows an example of a full-color light-emitting device. an insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first the first interlayer insulating film 1020, the second interlayer insulating film 1021, the peripheral portion 1042, the pixel portion 1040, Drive circuit section 1041, anodes 1024W, 1024R, 1024G, and 1024B of the light-emitting elements , partition wall 1025, EL layer 1028, cathode 1029 of the light-emitting element, sealing substrate 1031, seal Material 1032 and the like are shown.

[0158] In addition, in FIG. 6(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on the transparent substrate 1033. A transparent substrate on which a colored layer and a black layer are provided may be further provided. 1033 is aligned and fixed to the substrate 1001. The colored layer and the black layer are In FIG. 6(A), the light does not pass through the colored layer. There are light-emitting layers that emit light to the outside and light-emitting layers that transmit light through the colored layers of each color and emit light to the outside. Light that does not pass through the colored layer becomes white, and light that passes through the colored layer becomes red, blue, and green, so the image is displayed using four color pixels. The image can be expressed.

[0159] In FIG. 6(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer A color layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this way, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's fine.

[0160] In the light emitting device described above, light is taken in from the substrate 1001 side on which the FET is formed. The light emitting device has a bottom emission structure, but the light is emitted from the sealing substrate 1031 side. It may also be a light emitting device with a structure where light is extracted (top emission type). A cross-sectional view of the light-emitting device is shown in FIG. 7. In this case, a substrate 1001 that does not transmit light is used. Until the connection electrode that connects the FET and the anode of the light-emitting element is fabricated, The third interlayer insulating film 1037 is then formed in the same manner as in the case of an emission type light emitting device. The insulating film 1022 is formed to cover the insulating film 1022. This insulating film may also have a role of planarization. The insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as various other materials. It is possible.

[0161] The anodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are referred to as anodes here. However, it may be a cathode. Also, in a top-emission type light-emitting device as shown in Figure 7, In some cases, it is preferable to use the anode as a reflective electrode. EL layer 103 or the EL layer of FIG. 2(C) (first light-emitting unit 511, second light-emitting unit The structure is as described above (the layer 512 and the charge generating layer 513), and the white light is emitted. The device structure is such that the following can be obtained.

[0162] In the top emission structure shown in Figure 7, the colored layers (red colored layer 1034R, green The sealing is performed using a sealing substrate 1031 provided with a colored layer 1034G and a blue colored layer 1034B. The sealing substrate 1031 has a black layer (black A coloring layer (a red coloring layer 1034R, a green coloring layer 1035R) may be provided. The blue colored layer 1034G and the black layer 1034B are covered with an overcoat layer. Note that the sealing substrate 1031 is a light-transmitting substrate.

[0163] Although an example of full-color display using four colors, red, green, blue, and white, is shown here, the present invention is not particularly limited to this. Alternatively, a full color display may be performed using three colors of red, green, and blue, or four colors of red, green, blue, and yellow.

[0164] FIG. 8 shows a passive matrix light-emitting device according to one embodiment of the present invention. FIG. 8(A) is a perspective view showing a light emitting device, and FIG. 8(B) is a cross-sectional view taken along XY in FIG. 8(A). In FIG. 8, an EL layer 955 is disposed between an electrode 952 and an electrode 956 on a substrate 951. The end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided on the substrate 53. The sidewalls of the partition layer 954 are Accordingly, the distance between one side wall and the other side wall is inclined to become narrower. The cross section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (similar to the surface direction of the insulating layer 953) The side in contact with the insulating layer 953 is oriented in the same direction as the surface direction of the insulating layer 953. The side of the partition wall layer 954 facing in the direction of the insulating layer 953 is shorter than the side of the partition wall layer 954 that is not in contact with the insulating layer 953. This makes it possible to prevent defects in the light emitting element due to static electricity or the like.

[0165] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix, which are called pixels. Since each can be controlled by the FET formed in the This light emitting device can be suitably used as a device.

[0166] <Lighting equipment> A lighting device according to one embodiment of the present invention will be described with reference to FIG. 9. FIG. 9(B) shows a lighting device 9(A) is a cross-sectional view taken along line ef in FIG. 9(B).

[0167] The lighting device has an anode 401 formed on a light-transmitting substrate 400 serving as a support. The anode 401 corresponds to the anode 101 in FIGS. 2(A) and 2(B). When light is to be extracted, the anode 401 is made of a light-transmitting material.

[0168] A pad 412 for supplying a voltage to the cathode 404 is formed on the substrate 400 .

[0169] An EL layer 403 is formed on the anode 401. The EL layer 403 is shown in FIGS. These correspond to the EL layer 103 and the like. For details of the configuration of these layers, please refer to the relevant descriptions. .

[0170] A cathode 404 is formed to cover the EL layer 403. The cathode 404 is similar to the cathode 102 in FIG. When light is extracted from the anode 401 side, the cathode 404 contains a material with high reflectivity. The cathode 404 is connected to a pad 412 to supply a voltage.

[0171] The anode 401, the EL layer 403, and the cathode 404 form a light-emitting element. The device is sealed by fixing a sealing substrate 407 using sealing materials 405 and 406. The lighting device is completed. Either one of the seal materials 405 and 406 can be used. A desiccant may be mixed into the sealing material 406 (not shown in FIG. 9B) on the side of the substrate. This allows the material to adsorb moisture, leading to improved reliability.

[0172] In addition, a part of the pad 412 and the anode 401 is provided so as to extend outside the sealing materials 405 and 406. By doing so, it can be used as an external input terminal. An IC chip 420 or the like may be provided.

[0173] ≪Electronic equipment≫ Examples of electronic devices according to one embodiment of the present invention will be described. video equipment (also called televisions or television receivers), computers, etc. Digital cameras, digital video cameras, digital photo frames, mobile phones ( Mobile phones, also known as mobile phone devices, portable game machines, portable information terminals, sound reproducing devices, Examples include large game machines such as dick machines. Specific examples of these electronic devices are shown below. .

[0174] 10A shows an example of a television device. The television device has a housing 71 A display unit 7103 is built into the case 7101. The display unit 7103 can display images. The display portion 7103 is configured by arranging light-emitting elements in a matrix.

[0175] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0176] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0177] FIG. 10(B1) shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, It includes a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. Note that this computer uses light emitting elements arranged in a matrix for the display portion 7203. The computer in Figure 10(B1) is created by The computer in FIG. 10(B2) may have a keyboard 7204, a pointing device, and a A second display unit 7210 is provided in place of the input device 7206. The second display unit 7210 is a touch panel type, and the input screen displayed on the second display unit 7210 Input can be made by operating the display with a finger or a special pen. The display unit 7210 is not only capable of displaying input images, but also capable of displaying other images. The display unit 7203 may also be a touch panel. This prevents problems such as scratches or breakage of the screen when storing or transporting it. It can be stopped.

[0178] 10C and 10D show an example of a portable information terminal. The portable information terminal includes a housing 740 1, in addition to a display unit 7402, operation buttons 7403, an external connection port 7404, The portable information terminal includes a speaker 7405, a microphone 7406, and the like. The display portion 7402 has a matrix arrangement of the display elements.

[0179] The portable information terminals shown in FIGS. 10C and 10D have a display portion 7402 that can be touched by a finger or the like. In this case, the user can make a call or input information. Operations such as creating an email can be performed by touching the display portion 7402 with a finger or the like. can be done.

[0180] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0181] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. Desirable.

[0182] In addition, the mobile phone may have a sensor for detecting tilt such as a gyro or acceleration sensor inside. By providing a display device, the orientation of the mobile phone (portrait or landscape) can be determined and the image of the display portion 7402 can be displayed. The surface display can be switched automatically.

[0183] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0184] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0185] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0186] The electronic device can be used by appropriately combining the configurations shown in this specification. .

[0187] In addition, it is preferable to use the light-emitting element of one embodiment of the present invention in a display portion. It is possible to provide a light-emitting element with high efficiency. Therefore, an electronic device including a light-emitting element according to one embodiment of the present invention can consume less power. It can be a small electronic device.

[0188] FIG. 11 shows an example of a liquid crystal display device in which a light-emitting element is used as a backlight. The liquid crystal display device includes a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 904. 04, and the liquid crystal layer 902 is connected to a driver IC 905. A light emitting element is used in the terminal 903 , and a current is supplied to the terminal 906 .

[0189] The light-emitting element of one embodiment of the present invention is preferably used as the light-emitting element, and the light-emitting element is preferably used as the liquid crystal display element. By applying this to the backlight of a display device, it is possible to obtain a backlight with reduced power consumption. can be done.

[0190] Fig. 12 shows an example of a desk lamp according to one embodiment of the present invention. The lighting device has a housing 2001 and a light source 2002, and uses a light emitting element as the light source 2002. The position is used.

[0191] FIG. 13 shows an example of an indoor lighting device 3001. The lighting device 3001 includes one of the following features of the present invention. It is preferable to use a light-emitting element according to the embodiment.

[0192] An automobile according to one embodiment of the present invention is shown in FIG. 14. The automobile has a windshield and a dash panel. The display area 5000 to the display area 5005 are light-emitting elements. The display region is preferably formed using the light-emitting element of one embodiment of the present invention. This reduces the power consumption of the display areas 5000 to 5005, making it possible to It is suitable for.

[0193] The display area 5000 and the display area 5001 are light-emitting devices provided on the windshield of the automobile. The light-emitting element is a display device using a first electrode and a second electrode. By using electrodes that can be seen through to the other side, a so-called see-through display can be achieved. If the display is see-through, it can be installed on the windshield of a car. Even if the device is placed in a location, it can be installed without obstructing the view. When a transistor is provided, an organic transistor made of an organic semiconductor material or an oxide A light-transmitting transistor, such as a transistor using a semiconductor, is preferably used.

[0194] The display area 5002 is a display device that uses light-emitting elements provided in the pillar portion. In the area 5002, an image from an imaging means provided on the vehicle body is projected, and the pillar Similarly, it can complement the view obstructed by the The display area 5003 is a view blocked by the vehicle body, and is captured by an imaging means provided on the outside of the vehicle. By projecting images from the surrounding area, blind spots can be filled and safety can be improved. By projecting images that complement the unseen parts, safety checks can be performed more naturally and without discomfort. It is possible.

[0195] The display area 5004 and the display area 5005 display navigation information, a speedometer, RPM, and mileage. It can provide a variety of information, including distance, fuel level, gear status, and air conditioning settings. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in the display areas 5000 to 5003. The display areas 5000 to 5005 can also be used as lighting devices.

[0196] Figures 15(A) and 15(B) show an example of a foldable tablet terminal. 5(A) shows the tablet terminal in an open state, and the tablet terminal includes a housing 9630, a display unit 9631a, and a , display unit 9631b, display mode changeover switch 9034, power switch 9035, A power mode changeover switch 9036, a fastener 9033, and an operation switch 9038 are included. Note that the tablet terminal uses a light-emitting device including a light-emitting element of one embodiment of the present invention as a display unit. The display portion 9631a and / or the display portion 9631b are fabricated using the same.

[0197] A part of the display unit 9631a can be used as a touch panel area 9632a. By touching the operation keys 9637, data can be input. In 1a, for example, half of the area has a display function only, and the other half The display unit 963 has a touch panel function, but is not limited to this. The entire area of ​​the display unit 96 may have a touch panel function. The entire surface of 31a is displayed as a keyboard button to serve as a touch panel, and the display part 9631b is displayed. It can be used as a screen.

[0198] In addition, in the display unit 9631b, as in the display unit 9631a, The part can be used as a touch panel area 9632b. By touching the area where the display switch button 9639 is displayed with your finger or a stylus, Keyboard buttons can be displayed on the display portion 9631b.

[0199] In addition, when touching the touch panel area 9632a and the touch panel area 9632b at the same time, You can also input the character.

[0200] A display mode changeover switch 9034 is used to change the display orientation, such as portrait or landscape. You can switch between black and white and color display. The switch 9036 is an external switch that is detected by a light sensor built into the tablet terminal. The display brightness can be optimized according to the amount of light. In addition to sensors, other detection devices such as gyros and acceleration sensors that detect tilt are also available. may be incorporated.

[0201] FIG. 15A shows an example in which the display area of ​​the display portion 9631b is the same as that of the display portion 9631a. However, there is no particular limitation, and one size may be different from the other size. The display quality may also differ. For example, one display panel may be able to display a higher resolution image than the other. It may also be used as a rule.

[0202] FIG. 15(B) shows the tablet terminal in the closed state. Body 9630, solar cell 9633, charge / discharge control circuit 9634, battery 9635, DCD 15B shows an example in which a charge / discharge control circuit 9636 is provided. As an example of 4, a configuration having a battery 9635 and a DC-DC converter 9636 It shows.

[0203] In addition, since the tablet device can be folded in half, when not in use, the case 9630 is closed. Therefore, the display portions 9631a and 9631b can be protected. This makes it possible to provide a tablet device that is highly durable and reliable even for long-term use.

[0204] In addition, the tablet terminals shown in Figs. 15(A) and 15(B) can be used in various Functions that display information (still images, videos, text images, etc.), calendars, dates, or times The function to display information on the display unit, and the function to input or edit the information displayed on the display unit. It has input functions, functions to control processing using various software (programs), etc. It is possible.

[0205] The solar cell 9633 attached to the surface of the tablet terminal supplies power to the touch panel. The solar cell 9633 can be supplied to a display unit, a video signal processor, or the like. The battery 9635 can be efficiently charged by installing it on one or both sides of the housing 9630. This is preferable because it is possible to configure the device to perform the above.

[0206] The configuration and operation of the charge / discharge control circuit 9634 shown in FIG. 15(B) are shown in FIG. A block diagram is shown in Fig. 15(C) and will be explained. 635, DC-DC converter 9636, converter 9638, switches SW1 to SW3 , the display unit 9631, the battery 9635, the DC-DC converter 963 6. The converter 9638 and the switches SW1 to SW3 are configured to perform the charge / discharge control shown in FIG. 11(B). This corresponds to the circuit 9634.

[0207] First, an example of operation when power is generated by the solar cell 9633 using external light will be described. The power generated by the solar cell is converted to DC voltage to charge the battery 9635. The voltage is increased or decreased by the DC converter 9636. When the power charged by the solar cell 9633 is used, switch SW1 is turned on and the The inverter 9638 increases or decreases the voltage to the voltage required for the display unit 9631. When not displaying on the display unit 9631, turn SW1 off and SW2 on. The configuration may be such that the battery 9635 is charged.

[0208] Although the solar cell 9633 is shown as an example of a power generating means, the power generating means is not particularly Other power generating devices such as, but not limited to, piezoelectric elements (piezo elements) and thermoelectric conversion elements (Peltier elements) may also be used. The battery 9635 may be charged by wireless (contactless) means. It can be combined with a non-contact power transmission module that transmits and receives power to charge, or other charging methods. The power generating means may be omitted.

[0209] Furthermore, if the display unit 9631 is provided, the tablet terminal shown in FIG. Not limited.

[0210] 16(A) to 16(C) show a foldable mobile information terminal 9310. 16(A) shows the mobile information terminal 9310 in an unfolded state. The mobile information terminal 9310 is shown in a state in which it is changing from one folded state to the other. FIG. 16C shows the portable information terminal 9310 in a folded state. The foldable design offers excellent portability and a seamless, large viewing area when unfolded. This provides excellent visibility of the display.

[0211] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for a display panel 9311. A display area 931 in the display panel 9311 2 is a display area located on the side of the portable information terminal 9310 in the folded state. Area 9312 contains information icons and shortcuts to frequently used apps and programs. You can display the information and launch apps smoothly. do. [Example]

[0212] <Synthesis Example 1> In this example, a synthesis method for a light-emitting element material according to one embodiment of the present invention will be described in detail. In the examples, a first skeleton having iridium as a central metal and hole transporting properties and a second skeleton having luminescent properties are used. and an organometallic complex having a ligand having the structure [2-{(9H-calcium phosphate group} {2-(2-pyridinyl-1,2-benzol-9-yl)-2-pyridinyl-κN}phenyl-κC]bis[ ... [Ir(ppy)(C)(phenyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)(C) A specific example of the synthesis of [Ir(ppy)2(Czppy)] is given below. The structure is shown below.

[0213] [ka]

[0214] In the above [Ir(ppy)2(Czppy)], the carbazole skeleton is a hole transporting The 2-pyridylphenyl skeleton corresponds to the first skeleton having luminescence. is equivalent to

[0215] <Step 1: Synthesis of 4-chloro-2-phenylpyridine> First, 12 g of 2,4-dichloropyridine, 9.9 g of phenylboronic acid, and 34 g of potassium carbonate were mixed. g, 400 mL of DME, and 240 mL of water were placed in a three-neck flask equipped with a reflux condenser. The inside was substituted with nitrogen. Furthermore, tetrakis(triphenylphosphine)palladium(0) 0. 94g of the mixture was added and irradiated with microwaves (2.45GHz, 400W) for 2 hours. The extract was then extracted with ethyl acetate. The target product was purified by chromatography to give 12 g (yield 80%, yellow oil). The synthesis scheme of step 1 is shown below in (a-1).

[0216] [ka]

[0217] Step 2: 9-(2-phenylpyridin-4-yl)-9H-carbazole (abbreviation: Synthesis of HCzppy Next, 12 g of 4-chloro-2-phenylpyridine obtained in Step 1 above, 9H-carbazo 13g of alcohol, 11g of sodium tert-butoxide (abbreviated as tert-BuONa) The mixture was placed in a three-necked flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. 80 mL, tri-tert-butylphosphine 1.3 g, tris(dibenzylidene acetone) Add 3.0 g of palladium (0) (abbreviation: Pd2(dba)3) and heat at 120°C for 5 minutes. The reaction mixture was heated and stirred for 1 hour. The reaction mixture was filtered, and the solvent in the filtrate was evaporated. Purification was carried out by silica gel column chromatography using hexane = 1:1 as a developing solvent. As a result, 11 g of the target product was obtained (yield 53%, yellow oil). is shown in (a-2) below.

[0218] [ka]

[0219] <Step 3: Synthesis of [Ir(ppy)2(Czppy)]> Next, di-μ-chloro-tetrakis{2-[2-pyridinyl-κN]phenyl-κC}di 2.8 g of iridium(III) (abbreviation: [Ir(ppy)2Cl]2) and dichloromethane 200 mL of ethanol was placed in a three-neck flask and the atmosphere in the flask was replaced with nitrogen. A mixture of 2.0 g of the compound and 40 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 20 hours. The mixture was passed through celite and then concentrated to give a solid.

[0220] To this solid, 2.2 g of HCzppy obtained in Step 2 above, 2-ethoxyethanol (abbreviation Add 50 mL of 2-EE and 50 mL of N,N-dimethylformamide (DMF). The resulting mixture was refluxed under nitrogen for 17 hours. Gradually reduce the ratio of hexane from 1:1 to dichloromethane only. The product was purified by silica gel column chromatography using chloroform as a solvent. By silica gel column chromatography using formaldehyde:hexane=3:2 as a developing solvent, The resulting solution was concentrated and recrystallized from a mixed solvent of dichloromethane and methanol. By this, the organometallic complex, [Ir(ppy)2(Czppy) ] was obtained as an orange solid (yield: 19%).

[0221] The resulting orange solid (0.52 g) was purified by train sublimation. The purification conditions were a pressure of 2.6 Pa, an argon flow rate of 5 mL / min, and heating of the solid at 300°C. After purification by sublimation, the target orange solid was obtained in 74% yield. The synthesis scheme for Step 3 is as follows: Shown below in (a-3).

[0222] [ka]

[0223] The orange solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 17. In a specific example, an organometallic complex according to one embodiment of the present invention, represented by the above structural formula (100), It was found that [Ir(ppy)2(Czppy)] was obtained.

[0224] 1 H-NMR.δ(CDCl3):6.85-6.98(m,11H), 7.20(dd ,1H), 7.32-7.35(t,2H), 7.42-7.45(t,2H), 7.5 9-7.65(m,6H), 7.67(d,1H), 7.70-7.72(t,3H), 7.92(dd,2H), 8.13-8.16(t,3H).

[0225] Next, the UV-visible absorption spectra of the deoxygenated solution of [Ir(ppy)2(Czppy)] in dichloromethane The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were carried out at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonikko Co., Ltd.). A glove box (LABst, Bright Co., Ltd.) was used. In arM13 (1250 / 780), a deoxygenated dichloromethane solution (0. 010 mmol / L) was placed in a quartz cell, sealed, and measurements were carried out at room temperature.

[0226] The measurement results of the absorption spectrum and emission spectrum are shown in Figure 18. The horizontal axis represents wavelength, and the vertical axis represents The axes represent the absorption intensity and the emission intensity. , the thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorption spectrum shown was obtained by placing a dichloromethane solution (0.010 mmol / L) in a quartz cell. From the absorption spectrum measured with only dichloromethane in the quartz cell, The results of subtracting the spectra are shown.

[0227] As shown in FIG. 18, the organometallic complex, [Ir(ppy)2(Czpp y)] has an emission peak at 537 nm, and emits yellow-green light from a dichloromethane solution. Light was observed. [Example]

[0228] <Synthesis Example 2> In this example, a synthesis method for a light-emitting element material according to one embodiment of the present invention will be described in detail. In the examples, a first skeleton having iridium as a central metal and hole transporting properties and a second skeleton having luminescent properties are used. and a second skeleton having a ligand having the structure of bis[2-{4-(9 H-carbazol-9-yl)-2-pyridinyl-κN}phenyl-κC][2-(2- pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)( A specific example of the synthesis of [Ir(ppy)(Czppy)2] is given below. The structure is shown below.

[0229] [ka]

[0230] In the above [Ir(ppy)(Czppy)2], the carbazole skeleton is a hole transporting The 2-pyridylphenyl skeleton corresponds to the first skeleton having luminescence. is equivalent to

[0231] Step 1: Di-μ-chloro-tetrakis[4-(9H-carbazol-9-yl)- 2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(Cz Synthesis of [(ppy)2Cl]2) First, HCzppy 6.1g, iridium(III) chloride hydrate 2.9g, 2-ethoxy 90 mL of ethanol and 30 mL of water were placed in a round-bottom flask equipped with a reflux condenser, and the flask was purged with argon. The mixture was irradiated with microwaves (2.45 GHz, 200 W) for 2 hours while being heated. The mixture was filtered and washed with methanol to obtain 6.3 g of the target product (yield 76%, The synthesis scheme of step 1 is shown in (b-1) below.

[0232] [ka]

[0233] <Step 2: Synthesis of [Ir(ppy)(Czppy)2]> Next, 4.3 g of [Ir(Czppy)2Cl]2 obtained in Step 1 above was mixed with dichloromethane. 250 mL of dichloromethane (abbreviated as DCM) was placed in a three-neck flask and the atmosphere in the flask was replaced with nitrogen. A mixture of 1.9 g of silver triflate and 40 mL of isopropanol was added dropwise, and the mixture was stirred at room temperature for 20 The mixture was stirred for 1 hour, and then the resulting mixture was passed through Celite and concentrated to give a solid. 1.6 g of 2-phenylpyridine (abbreviation: Hppy), 50 mL of 2-ethoxyethanol 50 mL of N,N-dimethylformamide (DMF) was added, and the mixture was stirred for 1 hour under a nitrogen atmosphere. The mixture was refluxed for 7 hours.

[0234] The resulting mixture was concentrated and then subjected to silica gel chromatography using dichloromethane:hexane=1:1 as a developing solvent. The product was purified by column chromatography using a chloroform:hexane ratio of 3:2. The resulting solution was purified by silica gel column chromatography using a developing solvent. The resulting solution was concentrated and recrystallized from dichloromethane and methanol to give [Ir(ppy)(Cz The compound (ppy)2) was obtained as an orange solid (yield: 7%). Shown below in (b-2).

[0235] [ka]

[0236] The orange solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 19. In Example 2, an organometallic complex according to one embodiment of the present invention, represented by the structural formula (101), It was found that [Ir(ppy)(Czppy)2] was obtained.

[0237] 1 H-NMR.δ(CD2Cl2):6.82-6.96(m,9H), 7.04-7. 07(t,1H), 7.29-7.37(m,6H), 7.42-7.46(m,4H) , 7.67-7.74(m,8H), 7.80(d,1H), 7.83(d,1H), 7 .93(d,1H), 7.98(d,1H), 8.12-8.15(ms,4H), 8. 23-8.25(ms,2H).

[0238] Next, the UV-visible absorption spectra of [Ir(ppy)(Czppy)2] in a deoxygenated dichloromethane solution The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were carried out at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonikko Co., Ltd.). A glove box (LABst, Bright Co., Ltd.) was used. In arM13 (1250 / 780), a deoxygenated dichloromethane solution (0. 010 mmol / L) was placed in a quartz cell, sealed, and measurements were carried out at room temperature.

[0239] The measurement results of the absorption spectrum and emission spectrum are shown in Figure 20. The horizontal axis represents wavelength and the vertical axis represents The axes represent the absorption intensity and the emission intensity. , the thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorption spectrum shown was obtained by placing a dichloromethane solution (0.010 mmol / L) in a quartz cell. From the absorption spectrum measured with only dichloromethane in the quartz cell, The results of subtracting the spectra are shown.

[0240] As shown in FIG. 20, the organometallic complex, [Ir(ppy)(Czppy )2] has an emission peak at 530 nm, and emits yellow-green light from a dichloromethane solution. Light was observed. [Example]

[0241] In this example, the light-emitting element of one embodiment of the present invention is a light-emitting element of the [2-{(9 H-carbazol-9-yl)-2-pyridinyl-κN}phenyl-κC]bis[2-( 2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy )2(Czppy)]) (structural formula (100)) as a guest material in the light-emitting layer. [Ir(ppy)(Czppy)2] (structural formula (101)) described in Example 2 Light-emitting device 2, in which tris(2-phenylpyridinato- N,C 2’ ) Iridium (III) (abbreviation: [Ir(ppy)3]) is used as the guest material in the light-emitting layer. Regarding the comparative light-emitting element 1 used as the material, the element structure, fabrication method and characteristics The element structure of the light emitting element used in this example is shown in FIG. The composition is shown in Table 1. The chemical formulas of the materials used in this example are shown below.

[0242] [Table 1]

[0243] [ka]

[0244] <Fabrication of light-emitting device> The light emitting device shown in this example has an anode 901 formed on a substrate 1900 as shown in FIG. On top of that, a hole injection layer 1911, a hole transport layer 1912, a light emitting layer 1913, an electron transport layer 1914, An electron injection layer 1915 is laminated in this order, and a cathode 1903 is laminated on the electron injection layer 1915. It has a structure.

[0245] First, an anode 1901 was formed on a substrate 1900. The electrode area was 4 mm 2 (2mm x 2m The substrate 1900 was a glass substrate. The anode 1901 was an acid Indium tin oxide (ITO) containing silicon dioxide was deposited to a thickness of 70 nm by sputtering. The film was formed by deposition.

[0246] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV- The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition chamber and vacuum baked at 170°C for 60 minutes. After this, the substrate was allowed to cool for about 30 minutes.

[0247] Next, a hole injection layer 1911 was formed on the anode 1901. The hole injection layer 1911 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide and molybdenum chloride were mixed in a weight ratio of 4:2, and the film thickness was 60 nm. .

[0248] Next, a hole transport layer 1912 was formed on the hole injection layer 1911. The hole transport layer 1912 was 9-phenyl-9H-3-(9-phenyl-9H-carbazol-3-yl)carbazole The film was formed by vapor deposition using PCCP (abbreviation: PCCP) to a thickness of 20 nm.

[0249] Next, a light-emitting layer 1913 was formed on the hole-transporting layer 1912 .

[0250] In the case of the light-emitting element 1, the light-emitting layer 1913 is made of 9-[3-(4,6-diphenyl)-2-phenylpropanediol] as a host material. Nyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-biphenyl -9H-carbazole (abbreviation: mPCCzPTzn-02) was used as an assist material. PCCP and [Ir(ppy)2(Czppy)] are used as the guest material (phosphorescent material). The weight ratio is mPCCzPTzn-02:PCCP:[Ir(ppy)2(Czppy)]= The co-deposition was carried out so that the weight ratio was 0.5:0.5:0.10. The film thickness was 20 nm. Furthermore, the thickness of mPCCzPTzn-02:PCCP:[Ir(ppy)2(C The film was co-deposited so that the weight ratio of the film was 0.8:0.2:0.10. The thickness was set to 20 nm. Therefore, the light emitting layer 1913 has a laminated structure with a film thickness of 40 nm.

[0251] In the case of the light-emitting element 2, the light-emitting layer 1913 contains mPCCzPTzn-02 as a host material. PCCP was used as the assist material and Ir(ppy)( Czppy)2] was used, and the weight ratio was mPCCzPTzn-02:PCCP:[Ir(pp y)(Czppy)2) = 0.5:0.5:0.10 (weight ratio) The film thickness was set to 20 nm. :[Ir(ppy)(Czppy)2]=0.8:0.2:0.1 (weight ratio) The thickness of the light-emitting layer 1913 was 40 nm. It has a layered structure of m.

[0252] In the case of the comparative light-emitting element 1, the light-emitting layer 1913 was formed by using mPCCzPTzn-0 2 was used, and PCCP was used as the assist material and [Ir(ppy) )3] was used, and the weight ratio was mPCCzPTzn-02:PCCP:[Ir(ppy)3]= The co-deposition was carried out so that the weight ratio was 0.5:0.5:0.10. The film thickness was 20 nm. Furthermore, mPCCzPTzn-02:PCCP:[Ir(ppy)3]=0.8 The co-deposition was carried out so that the weight ratio was 0.2:0.1. The film thickness was 20 nm. Therefore, the light-emitting layer 1913 has a laminated structure with a film thickness of 40 nm.

[0253] Next, an electron transport layer 1914 was formed on the light emitting layer 1913. The electron transport layer 1914 was made of mP The film thickness of CCzPTzn-02 is 15 nm, and the film thickness of bathophenanthroline (abbreviation: Bphen) The layers were deposited sequentially to a thickness of 10 nm.

[0254] Next, an electron injection layer 1915 was formed on the electron transport layer 1914. The electron injection layer 1915 was Lithium fluoride (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0255] Next, a cathode 1903 was formed on the electron injection layer 1915. The cathode 1903 was made of aluminum. was formed by vapor deposition to a film thickness of 200 nm.

[0256] By the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 1900. The hole injection layer 1911, the hole transport layer 1912, and the light emitting layer 1913 described in the above steps were 13, the electron transport layer 1914, and the electron injection layer 1915 constitute the EL layer in one embodiment of the present invention. In addition, the vapor deposition process in the above-mentioned manufacturing method is all performed by the resistance heating method. The deposition method was used.

[0257] The light emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using the substrate, the sealing material was placed in a glove box with a nitrogen atmosphere. Another substrate is fixed on the substrate 1900 using a sealant. It is applied around the optical element and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 Irradiated and at 80°C This was done by heat treatment for 1 hour.

[0258] <Operating characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting elements (light-emitting element 1, light-emitting element 2, and comparative light-emitting element 1) were as follows: The measurements were carried out at room temperature, and the results are shown in Figures 22 to 25.

[0259] From these results, it is clear that the light-emitting elements according to one embodiment of the present invention (Light-emitting element 1, Light-emitting element 2, and the comparative It can be seen that comparative light emitting device 1) exhibits good current efficiency and high external quantum efficiency. , 1000cd / m 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown in Table 2 below.

[0260] [Table 2]

[0261] Furthermore, the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1 were subjected to a current of 2.5 mA / cm 2 current density of FIG. 26 shows the emission spectrum when a current was applied. The emission spectrum has a peak at around 531 nm, which is due to the organic It is suggested that this is due to the emission of the metal complex, [Ir(ppy)2(Czppy)]. The emission spectrum of the light-emitting element 2 has a peak at around 531 nm, and the emission spectrum of the light-emitting layer 1 The emission of the organometallic complex, [Ir(ppy)(Czppy)2], contained in 913 In addition, the emission spectrum of the comparative light-emitting element 1 has a peak at around 517 nm. The light-emitting layer 1913 contains an organometallic complex, [Ir(ppy)3]. It is suggested that this is due to the fact that the light-emitting element 1 and the light-emitting element 2 are made of the same material as in the present invention. In one embodiment, the organometallic complex has a carbazole skeleton at the 4-position of the 2-phenylpyridine skeleton. This makes it easier to inject and transport carriers (electrons or holes), The light emitting efficiency can be improved and the driving voltage can be reduced. It can be seen that the light-emitting element exhibits higher current efficiency and lower driving voltage than the comparative light-emitting element 1. [Example]

[0262] In this example, the light-emitting element material of the present invention, bis{2-[6-(9H-carbazole- 9-yl)-4-pyrimidinyl-κN3]phenyl-κC}-{2-[2-pyridinyl- κN]phenyl-κC}iridium(III) (abbreviation: [Ir(czppm)2(ppy )] (Structural Formula 102) alone was used to form a light-emitting layer. The structure of the light-emitting element used in this example is shown in FIG. The specific configurations are shown in Table 3. The chemical formulas of the materials used in this example are as follows: show.

[0263] [Table 3]

[0264] [ka]

[0265] <Fabrication of light-emitting device> The light emitting device shown in this example has an anode 190 formed on a substrate 1900 as shown in FIG. 1, a hole injection layer 1911, a hole transport layer 1912, a light emitting layer 1913, and an electron transport layer 1914 An electron injection layer 1915 is then laminated, and a cathode 1903 is laminated on the electron injection layer 1915. It has a structure.

[0266] First, an anode 1901 was formed on a substrate 1900. The electrode area was 4 mm 2 (2mm x 2m The substrate 1900 was a glass substrate. The anode 1901 was an acid Indium tin oxide (ITO) containing silicon dioxide was deposited to a thickness of 70 nm by sputtering. The film was formed by deposition.

[0267] Here, as a pretreatment, the surface of the substrate 1900 is washed with water and baked at 200°C for 1 hour. Then, UV ozone treatment was performed for 370 seconds. -4 The inside is decompressed to about Pa The substrate was introduced into the vacuum deposition apparatus, and the substrate was heated in the heating chamber of the vacuum deposition apparatus at 170°C for 60 minutes. After the baking, the substrate was allowed to cool for about 30 minutes.

[0268] Next, a hole injection layer 1911 was formed on the anode 1901. The hole injection layer 1911 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was co-deposited at a weight ratio of 2:1 to form a film with a thickness of 50 nm. .

[0269] Next, a hole transport layer 1912 was formed on the hole injection layer 1911. The hole transport layer 1912 was N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl [(9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine (abbreviated The film was formed by vapor deposition using PCBBiF to a thickness of 20 nm.

[0270] Next, a light-emitting layer 1913 was formed on the hole-transporting layer 1912. The light-emitting layer 1913 had the above structure. Bis{2-[6-(9H-carbazol-9-yl)-4-pyridyl]-2-(2-[6-(9H-carbazol-9-yl)-4-pyridyl]-2-(2-pyridyl) ... {2-[2-pyridinyl-κN]phenyl-κC}-{2-[2-pyridinyl-κN]phenyl-κC } Iridium (III) (abbreviation: [Ir(czppm)2(ppy)]) is used, and the film thickness is It was formed by vapor deposition to a thickness of 30 nm.

[0271] Next, an electron transport layer 1914 was formed on the light emitting layer 1913. The electron transport layer 1914 was formed by the above method. 2-[3'-(dibenzothiophen-4-yl)biphenyl-] represented by structural formula (iv) 3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) After vapor deposition to a thickness of 30 nm, bathophenanthrolinol represented by the above structural formula (vi) was added. The film was formed by vapor deposition of Bphen (abbreviation: Bphen) to a thickness of 15 nm.

[0272] Next, an electron injection layer 1915 was formed on the electron transport layer 1914. The electron injection layer 1915 was Lithium fluoride (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0273] Next, a cathode 1903 was formed on the electron injection layer 1915. The cathode 1903 was made of aluminum. was formed by vapor deposition to a film thickness of 200 nm.

[0274] By the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 1900. The hole injection layer 1911, the hole transport layer 1912, and the light emitting layer 1913 described in the above steps were 13, the electron transport layer 1914, and the electron injection layer 1915 constitute the EL layer in one embodiment of the present invention. In addition, the vapor deposition process in the above-mentioned manufacturing method is all performed by the resistance heating method. The deposition method was used.

[0275] The light emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using the substrate, the sealing material was placed in a glove box with a nitrogen atmosphere. The substrate is fixed onto the substrate 1900 using a sealant. It is applied around the optical element and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 Irradiated and at 80°C This was done by heat treatment for 1 hour.

[0276] <Operating 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 (25°C). The results are shown in Figs. 27 to 31.

[0277] These results indicate that the light-emitting element 3 of one embodiment of the present invention has a light-emitting layer formed of a single material. It can be seen that, despite the presence of a ZnO layer, the device exhibits good current efficiency and high external quantum efficiency. , 1000cd / m 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown in Table 4 below.

[0278] [Table 4]

[0279] Furthermore, the light-emitting element 3 is supplied with 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of 32. As shown in FIG. 32, the emission spectrum of the light-emitting element 3 has a peak at around 568 nm. The organic metal complex contained in the light-emitting layer 1913, [Ir(czppm)2( It is suggested that this is due to the emission of fluorine-containing ... In one embodiment, the organometallic complex has a carbazole skeleton at the 6-position of the 4-phenylpyrimidine skeleton. By having this, it is possible to easily inject and transport carriers (electrons or holes), and the device The light emitting efficiency can be improved and the driving voltage can be reduced. The carbazole skeleton (carrier transport skeleton) is located on the periphery of the light-emitting skeleton, The luminescent backbone of the molecule interacts with the luminescent backbone of other molecules, preventing concentration quenching. Therefore, high external quantum efficiency can be achieved even with a light-emitting layer made of a single material. From the above, it is possible to develop a light-emitting device having a light-emitting layer made of a single material without using co-evaporation. Even in this case, by using the light-emitting element material of one embodiment of the present invention, high current efficiency can be achieved. It has been found that it is possible to provide a light-emitting element that exhibits good characteristics at a low driving voltage. Ta. [Example]

[0280] <Synthesis Example 3> In this synthesis example, a first skeleton having iridium as the central metal and hole transporting properties and a second skeleton having luminescent properties are synthesized. and a bis{2-[6-( 9H-carbazol-9-yl)-4-pyrimidinyl-κN3]phenyl-κC}-{2 -[2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: [Ir(c We disclose a synthesis example of [Ir(czppm)2(ppy)]. The structure of y) is shown below.

[0281] [ka]

[0282] In the above [Ir(czppm)2(ppy)], the carbazole skeleton acts as a hole transporter. The 4-phenylpyrimidine skeleton corresponds to the first skeleton having light-emitting properties, and the 4-phenylpyrimidine skeleton corresponds to the second skeleton having light-emitting properties. It corresponds to the skeleton.

[0283] Step 1: 4-carbazol-9-yl-6-phenylpyrimidine (abbreviation: Hcz ppm) synthesis Sodium hydride (60% in mineral oil) 0.053g and dry N, Put 30 mL of N-dimethylformamide (abbreviated as dry DMF) into a three-neck flask. The atmosphere was replaced with nitrogen. 1.76 g of carbazole and 30 mL of dry DMF were added to the mixture, and the mixture was left at room temperature. The mixture was stirred at RT for 1 hour. Then, 1.76 g of 4-chloro-6-phenylpyrimidine and dry 30 mL of MF was added, and the mixture was stirred at room temperature for 4 hours to react. After the reaction, the resulting solution was added to water. The resulting solid was subjected to a flushing using dichloromethane as a developing solvent. The desired pyrimidine derivative Hczppm was obtained by column chromatography. (white powder, 62% yield). The synthesis scheme for Step 1 is shown below.

[0284] [ka]

[0285] Step 2: Di-μ-chloro-tetrakis{2-[2-pyridinyl-κN]phenyl Synthesis of {-κC}diiridium(III) (abbreviation: [Ir(ppy)2Cl]2) 30 mL of 2-ethoxyethanol, 10 mL of water, 2-phenylpyridine (abbreviation: Hppy ) 3.88g, iridium chloride hydrate (IrCl3·H2O) (Furuya Metal Co., Ltd.) 3.4 9 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The reaction was carried out by irradiating with microwaves (2.45 GHz, 100 W) for 2 hours. The resulting mixture was suction filtered and washed with methanol, and the binuclear complex [Ir(ppy)2Cl]2 (yellow solid, 59% yield). The synthesis scheme for Step 2 is shown below.

[0286] [ka]

[0287] Step 3: Bis{2-[6-(9H-carbazol-9-yl)-4-pyrimidinyl] {2-[2-pyridinyl-κN]phenyl-κC}yl Synthesis of Ir(czppm)2(ppy) The dinuclear complex [Ir(ppy)2Cl]2 obtained in Step 2 above (3.69 g) was mixed with dichloromethane. 390 mL of ethanol was placed in a light-shielded three-neck flask, and the atmosphere in the flask was replaced with nitrogen. A solution of 2.27 g of silver trifluoromethanesulfonate dissolved in 180 mL of methanol was added dropwise. The mixture was filtered through a filter aid and the filtrate was The mixture was concentrated to obtain a solid. Then, the obtained solid was mixed with 3.90 g of Hcz ppm and 40 g of ethanol. The mixture was placed in a three-neck flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. After heating for 1 hour, the resulting mixture was suction filtered. The resulting residue was extracted with hexane:ethyl acetate. After purification by silica gel column chromatography using ethanol = 6:1 as a developing solvent, By recrystallizing from a mixed solvent of chloromethane and methanol, the luminescence of one embodiment of the present invention can be obtained. The device material [Ir(czppm)2(ppy)] was obtained as a yellow-orange powder (yield 6 %). The synthesis scheme for Step 3 is shown below.

[0288] [ka]

[0289] Nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR charts are shown in Figures 33(A) and 33(B). B) is an enlarged view of the range from 6.50 ppm to 8.75 ppm in Figure 33(A). Thus, in Synthesis Example 3, a light-emitting element of one embodiment of the present invention represented by the above structural formula was obtained. It was found that the material [Ir(czppm)2(ppy)] was obtained.

[0290] 1 H-NMR.δ(CD2Cl2):6.82(d,1H),6.87-7.03(m, 8H),7.10(t,1H),7.37-7.40(m,4H),7.47-7.51 (m,4H),7.75-7.78(m,2H),7.88(t,2H),7.97(d ,1H),8.03(d,1H),8.12(d,4H),8.18(dd,4H),8 .23(s,2H),8.36(s,1H),8.61(s,1H).

[0291] Next, the UV-visible absorption spectrum of the dichloromethane solution of [Ir(czppm)2(ppy)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The spectra were measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). The dichloromethane solution (9.9 μmol / L) was placed in a quartz cell and measurements were carried out at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement system (Hamamatsu Photonics C1 1347-01) was used, and a glove box (Bright Co., Ltd. LABstar M13 (1250 / 780) under a nitrogen atmosphere. The resulting solution (1 / L) was placed in a quartz cell, sealed, and measured at room temperature. The optical spectrum measurement results are shown in Figure 34. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. In addition, two solid lines are shown in Figure 34, and the thin solid line represents the absorption spectrum. The absorption spectrum shown in Figure 34 is From the absorption spectrum measured by placing a fluoromethane solution (9.9 μmol / L) in a quartz cell, The absorption spectrum measured by placing only dichloromethane in a quartz cell was subtracted. are.

[0292] As shown in FIG. 34, the light-emitting element material of the present invention, [Ir(czppm)2(ppy)] The compound had an emission peak at 574 nm, and yellow emission was observed. [Example]

[0293] <Synthesis Example 4> In this synthesis example, a first skeleton having iridium as the central metal and electron transporting properties and a second skeleton having luminescent properties are synthesized. and a second framework having a ligand, [4-(4,6-difluoromethylphenyl)-2-methyl-2-propanol]. (phenyl-1,3,5-triazin-2-yl)-2-(2-pyridinyl-κN)phenyl -κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III)( A method for synthesizing Ir(ppy)2(5dptznppy) is disclosed. The structural formula of [(5dptznppy)2(5dptznppy)] is shown below.

[0294] [ka]

[0295] Step 1: 3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl Synthesis of pinacol boronic acid ester First, 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 2. 0g, bis(pinacolato)diboron 1.6g (abbreviation: (Bpin)2), potassium acetate 1 0.5g and 25mL of N,N-dimethylformamide were placed in a three-neck flask equipped with a reflux condenser. The atmosphere in the flask was replaced with nitrogen. [Pd(dppf)]palladium(II) dichloride dichloromethane adduct (abbreviation: Pd(dppf) 0.042 g of (2Cl2·CH2Cl2) was added, and the mixture was heated and stirred at 150°C for 3 hours. The solvent was distilled off from the reaction solution, and the residue was purified by silica gel column chromatography using toluene as a developing solvent. By purifying the product by HPLC, 2.0 g of the target product was obtained (yield: 88%, white solid). The synthesis scheme for step 1 is shown below.

[0296] [ka]

[0297] Step 2: 2-[3-(4,6-diphenyl-1,3,5-triazin-2-yl) Synthesis of [phenyl]pyridine (abbreviation: H5dptznppy) Next, 3-(4,6-diphenyl-1,3,5-triazine-2- 2.8 g of phenylboronic acid pinacol ester and 0.9 g of 2-bromopyridine, 1.6g of potassium carbonate, 50mL of tetrahydrofuran (abbreviation: THF), 25mL of water, The mixture was placed in a three-necked flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. Add 0.33 g of (triphenylphosphine)palladium(0), and heat and stir at 70°C for 24 hours. After the reaction, extraction was carried out with ethyl acetate. The target compound was obtained in an amount of 2.2 g ( The yield was 98%, and the product was a white solid. The synthesis scheme for Step 2 is shown below.

[0298] [ka]

[0299] Step 3: [4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2 -(2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl Iridium(III) abbreviation: [Ir(ppy)2(5dptznppy)] Synthesis of> Next, 1.9 g of [Ir(ppy)2Cl]2 and 190 mL of dichloromethane were added to a three-neck flask. The flask was placed in a flask and the atmosphere was replaced with nitrogen. 1.1 g of silver triflate and 9 g of methanol were added. The resulting mixture was passed through Celite. After that, it was concentrated to obtain a solid. To this solid, H5dptznppy obtained in Step 2 above was added. 2.0 g of the product and 70 mL of ethanol were added, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. The reaction mixture was filtered, and the residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. The product was purified by high performance liquid chromatography using chloroform as the mobile phase. The resulting solution was concentrated and reconstituted with a mixed solvent of dichloromethane and hexane. A yellow solid was obtained by crystallization (yield: 28%). The system is shown below.

[0300] [ka]

[0301] The yellow solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 35. By way of example, the organometallic complex [Ir(ppy)2(5dptznp py)] was obtained.

[0302] 1 H-NMR.δ(CDCl3):6.84-6.99(m,9H), 7.13(d,1 H), 7.53-7.64(m,11H), 7.68(d,2H), 7.74(t,1H ), 7.91(t,2H), 8.21(d,2H), 8.76(d,4H), 9.03( s, 1H). The peak at around 5.30 is derived from dichloromethane.

[0303] Next, the UV-visible spectrum of the dichloromethane solution of [Ir(ppy)2(5dptznppy)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were taken at room temperature. The emission spectrum was measured using a fluorometer (FS1000 manufactured by Hamamatsu Photonics Co., Ltd.). 920), a degassed dichloromethane solution (0.010 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 1. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Two solid lines are shown: the thin line represents the absorption spectrum and the thick line represents the emission spectrum. The absorption spectrum shown in Figure 36 is obtained from a dichloromethane solution (0.010 ml). mol / L) into a quartz cell and measured the absorption spectrum. The results are shown after subtracting the absorption spectrum measured in an English cell.

[0304] As shown in FIG. 36, the organometallic complex [Ir(ppy)2(5dptz)] according to one embodiment of the present invention nppy)] has an emission peak at 510 nm and emits yellow-green light from a dichloromethane solution. Colored light emission was observed. [Example]

[0305] <Synthesis Example 5> In this synthesis example, a first skeleton having iridium as the central metal and electron transporting properties and a light-emitting and a second skeleton having a ligand comprising bis[4-(4, 6-diphenyl-1,3,5-triazin-2-yl)-2-(2-pyridinyl-κN) phenyl-κC][2-(2-pyridinyl-κN)phenyl-κC]iridium(III ) (abbreviation: [Ir(5dptznppy)2(ppy)]) The structural formula of [r(5dptznppy)2(ppy)] is shown below.

[0306] [ka]

[0307] Step 1: 2-[3-(4,6-diphenyl-1,3,5-triazin-2-yl) Synthesis of [phenyl]pyridine (abbreviation: H5dptznppy) The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 4 in Example 6.

[0308] <Step 2: Synthesis of [Ir(5dptznppy)2(ppy)]> Place 1.9 g of [Ir(ppy)2Cl]2 and 190 mL of dichloromethane in a three-neck flask. The atmosphere in the flask was replaced with nitrogen. 1.1 g of silver triflate and 90 mL of methanol were added. The mixture was added dropwise and stirred at room temperature for 20 hours. The mixture was concentrated to give a solid. To this solid, 2.0 g of H5dptznppy and 70 mL of ethanol were added. The reaction mixture was then refluxed under a nitrogen atmosphere for 24 hours. The reaction mixture was filtered, and the residue was diluted with dichloromethane. The mixture was purified by silica gel column chromatography using fluoromethane as a developing solvent. The resulting solution was further purified by high performance liquid chromatography using chloroform as the mobile phase. The liquid was concentrated and recrystallized from a mixed solvent of dichloromethane and hexane to obtain a yellow solid. The synthesis scheme for Step 2 is shown below.

[0309] [ka]

[0310] The yellow solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The analysis results by H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in Figure 37. From this result, in this synthesis example, The organometallic complex [Ir(5dptznppy)2(ppy)] according to one embodiment of the present invention is It was found that it was obtained.

[0311] 1 H-NMR.δ(CDCl3:6.89-7.05(m,6H), 7.16(d,1H ), 7.19(d,1H), 7.52-7.65(m,16H), 7.71(d,1H) , 7.75-7.80(m,2H), 7.94(d,1H), 8.20-8.27(m, 4H), 8.74(d,4H), 8.78(d,4H), 9.07(d,2H).

[0312] Next, the UV-visible spectrum of the dichloromethane solution of [Ir(5dptznppy)2(ppy)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were taken at room temperature. The emission spectrum was measured using a fluorometer (FS1000 manufactured by Hamamatsu Photonics Co., Ltd.). 920), a degassed dichloromethane solution (0.010 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 1. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Two solid lines are shown: the thin line represents the absorption spectrum and the thick line represents the emission spectrum. The absorption spectrum shown in Figure 38 is obtained from a dichloromethane solution (0.010 ml). mol / L) into a quartz cell and measured the absorption spectrum. The results are shown after subtracting the absorption spectrum measured in an English cell.

[0313] As shown in FIG. 38, the organometallic complex [Ir(5dptznppy)2 (ppy)] has an emission peak at 501 nm and emits yellow-green light from a dichloromethane solution. Colored light emission was observed. [Example]

[0314] <Synthesis Example 6> In this synthesis example, a first skeleton having iridium as the central metal and hole transporting properties and a second skeleton having luminescent properties are synthesized. and an organometallic complex having a ligand having, [2-(4-diphenylamino) bis[2-(2-pyridinyl-κN)phenyl-κC]amino-2-pyridinyl-κN [phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(dpappy)]) The structural formula of [Ir(ppy)2(dpappy)] is shown below.

[0315] [ka]

[0316] <Step 1: Synthesis of 4-chloro-2-phenylpyridine> 4-Chloro-2-phenylpyridine was synthesized in the same manner as in Step 1 of Synthesis 1 in Example 1. Successful.

[0317] Step 2: Synthesis of 4-diphenylamino-2-phenylpyridine (abbreviated as Hdpap py) Synthesis Next, 4.5 g of 4-chloro-2-phenylpyridine obtained in Step 1 above, diphenylamine 4.9 g of amine and 4.1 g of sodium tert-butoxide were placed in a three-neck flask equipped with a reflux condenser. The flask was then filled with nitrogen. 0.57 mL of butylphosphine, tris(dibenzylideneacetone)dipalladium(0) 1.1 g of (abbreviation: Pd2(dba)3) was added, and the mixture was heated and stirred at 120°C for 5 hours. The reaction mixture was filtered, the solvent in the filtrate was evaporated, and the mixture was diluted with ethyl acetate:hexane (2:1) as a developing solvent. By purifying the mixture by silica gel column chromatography, 2.4 g of the target compound was obtained. (Yield 31%, yellow solid) was obtained. The synthesis scheme of Step 2 is shown below.

[0318] [ka]

[0319] Step 3: [2-(4-diphenylamino-2-pyridinyl-κN)phenyl-κC ]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Synthesis of [Ir(ppy)2(dpappy)]) Next, 1.8 g of [Ir(ppy)2Cl]2 and 180 mL of dichloromethane were placed in a three-neck flask. The flask was then filled with nitrogen. 1.1 g of silver triflate and 86 ml of methanol were added. The resulting mixture was passed through Celite. After that, it was concentrated to obtain a solid. To this solid, 1.5 g of Hdpappy obtained in Step 2 above was added. , 2-ethoxyethanol 35mL, N,N-dimethylformamide (abbreviation: DMF) The resulting mixture was refluxed under nitrogen for 17 hours. Silica gel column chromatography using chloromethane:hexane=1:1 as the developing solvent. It was then purified by high performance liquid chromatography using chloroform as the mobile phase. The resulting solution was concentrated and recrystallized in a mixed solvent of dichloromethane and hexane. By this, an orange solid was obtained (yield: 20%).

[0320] The resulting orange solid (0.41 g) was purified by train sublimation. The purification conditions were a pressure of 1.5 Pa, an argon flow rate of 5 mL / min, and heating of the solid at 310°C. After purification by sublimation, the target orange solid was obtained in 68% yield. The synthesis scheme for Step 3 is as follows: Shown below.

[0321] [ka]

[0322] The orange solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 39. In the synthesis example, it was found that [Ir(ppy)2(dpappy)] was obtained.

[0323] 1 H-NMR.δ(CD2Cl2):6.34(dd,1H), 6.68-6.92(m ,10H), 7.01(t,1H), 7.11(d,1H), 7.22-7.26(m, 7H), 7.29(d,1H), 7.37-7.40(m,4H), 7.53(d,1H) ), 7.59(t,1H), 7.66(t,3H), 7.74(d,1H), 7.87( d,1H), 7.91(d,1H).

[0324] Next, the UV-visible absorption spectra of [Ir(ppy)2(dpappy)] in dichloromethane were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920) ) and place a degassed dichloromethane solution (0.010 mmol / L) in a quartz cell. The measurements were carried out at room temperature. The absorption and emission spectra are shown in Figure 40. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Solid lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorption spectrum shown in Figure 40 is obtained from a dichloromethane solution (0.010 mmol / L) in a quartz cell and measured from the absorption spectrum. The results are shown by subtracting the absorption spectrum measured by inserting

[0325] As shown in FIG. 40, the organometallic complex [Ir(ppy)2(dpapp y)] has an emission peak at 531 nm, and emits yellow-green light from a dichloromethane solution. Light was observed. [Example]

[0326] <Synthesis Example 7> In this synthesis example, a first skeleton having iridium as the central metal and hole transporting properties and a light-emitting and an organometallic complex having a ligand having a second skeleton having the formula: Nylamino-2-pyridinyl-κN)phenyl-κC][2-(2-pyridinyl-κN) Phenyl-κC]iridium(III) (abbreviation: [Ir(dpappy)2(ppy)] The structural formula of [Ir(dpappy)2(ppy)] is shown below.

[0327] [ka]

[0328] <Step 1: Synthesis of 4-chloro-2-phenylpyridine> 4-Chloro-2-phenylpyridine was prepared in the same manner as in Step 1 of Synthesis Example 1 in Example 1. It was synthesized.

[0329] Step 2: Synthesis of 4-diphenylamino-2-phenylpyridine (abbreviated as Hdpap py) Synthesis Hdpappy was synthesized in the same manner as in Step 2 of Synthesis Example 6 in Example 8.

[0330] Step 3: Bis[2-(4-diphenylamino-2-pyridinyl-κN)phenyl- κC][2-(2-pyridinyl-κN)phenyl-κC]iridium(III) abbreviation: [ Synthesis of Ir(dpappy)2(ppy) First, di-μ-chloro-tetrakis{2-[2-pyridinyl-κN]phenyl-κC}di 1.8 g of iridium(III) (abbreviation: [Ir(ppy)2Cl]2) and dichloromethane 180 mL of the solution was placed in a three-neck flask and the atmosphere inside the flask was replaced with nitrogen. A mixture of 0.1 g of benzophenone and 86 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 20 hours. The mixture was passed through Celite and then concentrated to give a solid. , 2-ethoxyethanol (abbreviation: 2-EE) 35 mL, N,N-dimethylformamide 35 mL of DMF (abbreviation: DMF) was added, and the mixture was refluxed for 17 hours under a nitrogen atmosphere. The concentrate was concentrated and subjected to silica gel column chromatography using dichloromethane:hexane = 1:1 as a developing solvent. The mixture was purified by high performance liquid chromatography using chloroform as the mobile phase. The resulting solution was concentrated and purified by chromatography. Recrystallization from the solvent gave an orange solid (yield: 7.7%).

[0331] 0.22 g of the resulting orange solid was purified by train sublimation. The purification conditions were a pressure of 1.5 Pa, an argon flow rate of 5 mL / min, and heating of the solid at 330°C. After purification by sublimation, the target orange solid was obtained in a yield of 64%. The team is shown below.

[0332] [ka]

[0333] The orange solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 41. In one embodiment, the organometallic complex [Ir(dpappy)2(ppy) ] was found to be obtained.

[0334] 1 H-NMR.δ(CD2Cl2):6.29(dd,1H), 6.43(dd,1H) , 6.72-6.69(m,3H), 6.75-7.73(m,2H), 6.80-6. 79(m,2H), 6.89-6.86(m,1H), 6.95(t,1H), 7.10 (d,1H), 7.42-7.19(m,26H), 7.60(t,1H), 7.65( d,1H), 7.71(d,1H), 7.87(d,1H).

[0335] Next, the UV-visible absorption spectra of [Ir(dpappy)2(ppy)] in dichloromethane were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920) ) and place a degassed dichloromethane solution (0.010 mmol / L) in a quartz cell. The measurements were carried out at room temperature. The absorption and emission spectra are shown in Figure 42. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Solid lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorption spectrum shown in Figure 42 is obtained from a dichloromethane solution (0.010 mmol / L) in a quartz cell and measured from the absorption spectrum. The results are shown by subtracting the absorption spectrum measured by inserting

[0336] As shown in FIG. 42, the organometallic complex [Ir(dpappy)2(pp y)] has an emission peak at 534 nm, and emits yellow-green light from a dichloromethane solution. Light was observed. [Example]

[0337] <Synthesis Example 8> In this synthesis example, a first skeleton having iridium as the central metal and electron transporting properties and a light-emitting and a ligand having the structure of [4-(4,6- Diphenyl-1,3,5-triazin-2-yl)-2-(4-methyl-5-phenyl- 2-pyridinyl-κN)phenyl-κC]bis[2-(4-methyl-5-phenyl-2- [Ir(mdppy)pyridinyl-κN)phenyl-κC]iridium(III) An example of the synthesis of [Ir(mdppy)2(5dp The structural formula of (tznmdppy) is shown below.

[0338] [ka]

[0339] Step 1: 3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl Synthesis of pinacol boronic acid ester First, 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 10 g, bis(pinacolato)diboron 7.9 g (abbreviation: (Bpin)2), potassium acetate 7. 6g and 125mL of DMF were placed in a three-neck flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. Furthermore, [1,1'-bis(diphenylphosphino)ferrocene]palladium (II ) dichloride dichloromethane adduct (abbreviation: Pd(dppf)2Cl2·CH2Cl2 0.21 g of HCl was added, and the mixture was heated and stirred at 150° C. for 3 hours. The solvent of the resulting reaction solution was evaporated. The product was purified by silica gel column chromatography using toluene as a developing solvent. As a result, 7.1 g of the target product was obtained (yield: 63%, white solid). The system is shown below.

[0340] [ka]

[0341] Step 2: 5-Bromo-2-[3-(4,6-diphenyl-1,3,5-triazine] Synthesis of [(2-yl)phenyl]-4-methylpyridine> Next, 3-(4,6-diphenyl-1,3,5-triazine-2- (I)phenylboronic acid pinacol ester 6.0 g, 2,5-dibromo-4-methylpiperidinyl A solution of 4.4 g of lysine and 3.9 g of sodium carbonate dissolved in 21 mL of water, 84 mL of toluene 21 mL of ethanol was placed in a three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. Further, 0.64 g of tetrakis(triphenylphosphine)palladium(0) was added. The mixture was heated and stirred at 100°C for 13 hours. After the reaction, extraction with toluene was carried out. The product was distilled off and recrystallized with a mixed solvent of ethyl acetate and hexane to obtain 6.4 g of the target compound. (Yield: 97%, white solid) was obtained. The synthetic scheme for Step 2 is shown below.

[0342] [ka]

[0343] Step 3: 2-[3-(4,6-diphenyl-1,3,5-triazin-2-yl) Synthesis of [phenyl]-4-methyl-5-phenylpyridine (abbreviation: H5dptznmdpp Synthesis of y) Next, 5-bromo-2-[3-(4,6-diphenyl-1,3,5-diol]-2-one obtained in Step 2 above was added to the -triazin-2-yl)phenyl]-4-methylpyridine 6.4g, phenylboronic acid 1.8g of toluene, 3.4g of tripotassium phosphate, 65mL of toluene, and 6.5mL of water were added to a reflux condenser. The mixture was placed in a three-necked flask and the atmosphere in the flask was replaced with nitrogen. 0.22 g of phyno-2',6'-dimethoxybiphenyl (abbreviation: SPhos), Tris( Dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) 0.12g After the reaction, extraction with toluene was carried out. By purifying it by silica gel column chromatography using the developing solvent, the target product was obtained. 5.4 g (yield: 86%, pale yellow solid) was obtained. The synthesis scheme for Step 3 is shown below. show.

[0344] [ka]

[0345] Step 4: Di-μ-chloro-tetrakis[2-(4-methyl-5-phenyl-2-pyridinyl] [Iridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(mdppy Synthesis of )2Cl]2) Next, 3.2 g of 4-methyl-2,5-diphenylpyridine (abbreviation: Hmdppy), Iridium(III) hydrate 1.9g, 2-ethoxyethanol (abbreviation: 2-EE) 21g 7 mL of HCl and 7 mL of water were placed in a round-bottom flask equipped with a reflux condenser, and the mixture was stirred under argon bubbling. The mixture was then irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. The solid was washed with methanol to obtain 3.2 g of the target product (yield 72%, yellow solid). The synthesis scheme for step 4 is shown below.

[0346] [ka]

[0347] Step 5: [4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2 -(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-( 4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]iridium(II I) (Abbreviation: [Ir(mdppy)2(5dptznmdppy)]) Next, 3.2 g of [Ir(mdppy)2Cl]2 obtained in Step 4 above was mixed with dichloromethane. 230 mL of ethanol was placed in a three-neck flask and the atmosphere in the flask was replaced with nitrogen. A mixture of 1.5 g of the compound and 110 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 20 hours. The resulting mixture was passed through Celite and then concentrated to give a solid. 5.4 g of H5dptznmdppy and 75 mL of ethanol were added and the mixture was stirred for 1 hour under a nitrogen atmosphere. The reaction mixture was refluxed for 7 hours. The resulting reaction mixture was filtered, and the filtered product was stirred in a silica gel column using chloroform as a developing solvent. The product was purified by gel column chromatography using chloroform as the mobile phase. The resulting solution was concentrated and purified by high performance liquid chromatography. A yellow solid was obtained by recrystallization from a mixed solvent of hexane and hexane (yield: 41%). The synthetic scheme for Step 5 is shown below.

[0348] [ka]

[0349] The yellow solid obtained in step 5 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 43. It was found that [Ir(mdppy)2(5dptznmdppy)] was obtained by synthesis. It was.

[0350] 1 H-NMR.δ(CD2Cl2):2.31(s,3H), 2.34(s,3H), 2 .43(s,3H), 6.83-6.98(m,6H), 7.03-7.09(m,6H ), 7.15(d,1H), 7.30-7.39(m,9H), 7.49(d,2H), 7.54(s,1H), 7.57-7.63(m,6H), 7.70(t,2H), 7. 80(s,2H), 8.08(s,1H), 8.21(d,1H), 8.78(d,4H ), 9.03(s,1H).

[0351] Next, a dichloromethane solution of [Ir(mdppy)2(5dptznmdppy)] The ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO V55) A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and heated at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics Co., Ltd.). A degassed dichloromethane solution (0.010 mmol / L) was added to the sample. The sample was placed in an argon cell and measured at room temperature. The results are shown in Figure 44. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Two solid lines are shown in the figure; the thin line represents the absorption spectrum and the thick line represents the emission spectrum. The absorption spectrum shown in Figure 44 is a dichloromethane solution (0. From the absorption spectrum measured by placing dichloromethane (0.010mmol / L) in a quartz cell, The absorption spectrum measured by placing only the sample in a quartz cell was subtracted from the result shown.

[0352] As shown in FIG. 44, the organometallic complex [Ir(mdppy)2(5dp tznmdppy)] has an emission peak at 519 nm and is obtained from a dichloromethane solution. Yellow-green luminescence was observed. [Example]

[0353] <Synthesis Example 9> In this synthesis example, a first skeleton having iridium as the central metal and electron transporting properties and a second skeleton having luminescent properties are synthesized. and a bis[4-(4,6 -diphenyl-1,3,5-triazin-2-yl)-2-(4-methyl-5-phenyl -2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl- ... Iridium(III) (abbreviation: [Ir(5dptzn) A synthesis example of [Ir(5dptznmdppy)2(mdppy)]) is disclosed. The structural formula of (mdppy) is shown below.

[0354] [ka]

[0355] Step 1: 3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl Synthesis of pinacol boronic acid ester 3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenylboronic acid pina Cholesterol ester was synthesized in the same manner as in Step 1 of Synthesis Example 8 in Example 10.

[0356] Step 2: 5-Bromo-2-[3-(4,6-diphenyl-1,3,5-triazine] Synthesis of [(2-yl)phenyl]-4-methylpyridine> 5-Bromo-2-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl] [phenyl]-4-methylpyridine was synthesized in the same manner as in Step 2 of Synthesis Example 8 in Example 10. Successful.

[0357] Step 3: 2-[3-(4,6-diphenyl-1,3,5-triazin-2-yl) Synthesis of [phenyl]-4-methyl-5-phenylpyridine (abbreviation: H5dptznmdpp Synthesis of y) H5dptznmdppy was synthesized in the same manner as in Step 3 of Synthesis Example 8 in Example 10. Ta.

[0358] Step 4: Di-μ-chloro-tetrakis[2-(4-methyl-5-phenyl-2-pyridinyl] [Iridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(mdppy Synthesis of )2Cl]2) [Ir(mdppy)2Cl]2 was synthesized in the same manner as in Step 4 of Synthesis Example 8 in Example 10. Successful.

[0359] <Step 5: Synthesis of [Ir(5dptznmdppy)2(mdppy)]> 3.2 g of [Ir(mdppy)Cl] synthesized in Step 4 and 23 g of dichloromethane 1.0 mL of silver triflate was added to a three-neck flask and the atmosphere in the flask was replaced with nitrogen. A mixture of 110 mL of ethanol and 110 mL of ethanol was added dropwise, and the mixture was stirred at room temperature for 20 hours. The product was filtered through Celite and concentrated to give a solid. 5.4 g of dptznmdppy and 75 mL of ethanol were added and the mixture was stirred for 17 minutes under a nitrogen atmosphere. The reaction mixture was filtered, and the residue was added to silica gel using chloroform as a developing solvent. The product was purified by gel column chromatography, and then chloroform was used as the mobile phase. The resulting solution was concentrated and purified by high performance liquid chromatography. A yellow solid was obtained by recrystallization from a mixed solvent of sucrose and ethyl acetate (yield: 7.1%). The synthetic scheme for Step 5 is shown below.

[0360] [ka]

[0361] The yellow solid obtained in step 5 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 45. In one embodiment, the organometallic complex [Ir(5dptznmdppy)2 (mdppy)] was found to be obtained.

[0362] 1 H-NMR.δ(CD2Cl2):2.34(s,3H), 2.43(s,3H), 2 .45(s,3H), 6.89-7.00(m,3H), 7.05-7.12(m,6H ), 7.20(dd,2H), 7.31-7.40(m,9H), 7.51(s,1H) , 7.55-7.65(m,14H), 7.74(d,1H), 7.83(s,1H), 8.12(s,2H), 8.22(d,1H), 8.27(d,1H)8.76(d,4 H), 8.80(d,4H), 9.08(d,2H).

[0363] Next, a dichloromethane solution of [Ir(5dptznmdppy)2(mdppy)] The ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO V55) A dichloromethane solution (0.010 mmol / L) was placed in a quartz cell and heated at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics Co., Ltd.). A degassed dichloromethane solution (0.010 mmol / L) was added to the sample. The sample was placed in an argon cell and measured at room temperature. The results are shown in Figure 46. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Two solid lines are shown in the figure; the thin line represents the absorption spectrum and the thick line represents the emission spectrum. The absorption spectrum shown in Figure 46 is a dichloromethane solution (0. From the absorption spectrum measured by placing dichloromethane (0.010mmol / L) in a quartz cell, The absorption spectrum measured by placing only the sample in a quartz cell was subtracted from the result shown.

[0364] As shown in FIG. 46, the organometallic complex [Ir(5dptZnmdppy)] according to one embodiment of the present invention )2(mdppy)] has an emission peak at 510 nm and is obtained from a dichloromethane solution. Yellow-green luminescence was observed. [Example]

[0365] In this example, a light-emitting element according to one embodiment of the present invention is formed using [Ir(m dppy)2(5dptznmdppy)] (structural formula (103)) as a guest material in the emitting layer. Light-emitting device 4, in which [Ir(ppy)3] was used as a guest material in the light-emitting layer, The structure, fabrication method, and characteristics of the comparative light-emitting element 2 will be described. The element structure of the light emitting element used in this example is shown in FIG. The chemical formulas of the materials used in this example are shown in Table 5.

[0366] [Table 5]

[0367] [ka]

[0368] <Fabrication of light-emitting device> The light emitting device shown in this example has an anode 901 formed on a substrate 1900 as shown in FIG. On top of that, a hole injection layer 1911, a hole transport layer 1912, a light emitting layer 1913, an electron transport layer 1914, An electron injection layer 1915 is laminated in this order, and a cathode 1903 is laminated on the electron injection layer 1915. It has a structure.

[0369] First, an anode 1901 was formed on a substrate 1900. The electrode area was 4 mm 2 (2mm x 2m The substrate 1900 was a glass substrate. The anode 1901 was an acid Indium tin oxide (ITO) containing silicon dioxide was deposited to a thickness of 70 nm by sputtering. The film was formed by deposition.

[0370] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV- The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition chamber and vacuum baked at 170°C for 60 minutes. After this, the substrate was allowed to cool for about 30 minutes.

[0371] Next, a hole injection layer 1911 was formed on the anode 1901. The hole injection layer 1911 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was co-deposited at a weight ratio of 2:1 to form a film with a thickness of 40 nm. .

[0372] Next, a hole transport layer 1912 was formed on the hole injection layer 1911. The hole transport layer 1912 was 9-phenyl-9H-3-(9-phenyl-9H-carbazol-3-yl)carbazole The film was formed by vapor deposition using PCCP (abbreviation: PCCP) to a thickness of 20 nm.

[0373] Next, a light-emitting layer 1913 was formed on the hole-transporting layer 1912 .

[0374] In the case of the light-emitting element 4, the light-emitting layer 1913 is made of 9-[3-(4,6-diphenyl)-2-phenylpropanediol] as a host material. Nyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-biphenyl -9H-carbazole (abbreviation: mPCCzPTzn-02) was used as an assist material. PCCP, [4-(4,6-diphenyl-1,3,5-trimethylsilyl)methyl] as a guest material (phosphorescent material), niacin-2-yl)-2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl bis[2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl -κC]iridium(III) (abbreviation: [Ir(mdppy)2(5dptznmdpp y)]) was used, and the weight ratio was mPCCzPTzn-02:PCCP:[Ir(ppy)2( The co-evaporation was carried out so that the weight ratio of Czppy) was 0.6:0.4:0.10. The film thickness was set to 40 nm.

[0375] In the case of the comparative light-emitting element 2, the light-emitting layer 1913 was formed by using mPCCzPTzn-0 2 was used, and PCCP was used as the assist material and [Ir(ppy) )3] was used, and the weight ratio was mPCCzPTzn-02:PCCP:[Ir(ppy)3]= The co-deposition was carried out so that the weight ratio was 0.5:0.5:0.10. The film thickness was 20 nm. Furthermore, mPCCzPTzn-02:PCCP:[Ir(ppy)3]=0.8: The co-deposition was carried out so that the weight ratio was 0.2:0.1. The film thickness was 20 nm. Therefore, the light emitting layer 1913 has a laminated structure with a film thickness of 40 nm.

[0376] Next, an electron transport layer 1914 was formed on the light emitting layer 1913. The electron transport layer 1914 was made of mP The film thickness of CCzPTzn-02 is 15 nm, and the film thickness of bathophenanthroline (abbreviation: Bphen) The layers were deposited sequentially to a thickness of 10 nm.

[0377] Next, an electron injection layer 1915 was formed on the electron transport layer 1914. The electron injection layer 1915 was Lithium fluoride (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0378] Next, a cathode 1903 was formed on the electron injection layer 1915. The cathode 1903 was made of aluminum. was formed by vapor deposition to a film thickness of 200 nm.

[0379] By the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 1900. The hole injection layer 1911, the hole transport layer 1912, and the light emitting layer 1913 described in the above steps were 13, the electron transport layer 1914, and the electron injection layer 1915 constitute the EL layer in one embodiment of the present invention. In addition, the vapor deposition process in the above-mentioned manufacturing method is all performed by the resistance heating method. The deposition method was used.

[0380] The light emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using the substrate, the sealing material was placed in a glove box with a nitrogen atmosphere. Another substrate is fixed on the substrate 1900 using a sealant. It is applied around the optical element and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 Irradiated and at 80°C This was done by heat treatment for 1 hour.

[0381] <Operating characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting elements (light-emitting element 4, comparative light-emitting element 2) were measured. The measurements were carried out at room temperature (an atmosphere maintained at 25°C). The results are shown in Figures 47 to 51. .

[0382] These results indicate that the light-emitting elements of one embodiment of the present invention (light-emitting element 4 and comparative light-emitting element 2) It can be seen that the device exhibits good current efficiency and high external quantum efficiency. 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown in Table 6 below.

[0383] [Table 6]

[0384] Furthermore, the light-emitting element 4 and the comparative light-emitting element 2 were 2 When a current is applied at a current density of The emission spectrum is shown in FIG. 52. As shown in FIG. 52, the emission spectrum of the light-emitting element 4 is 5 The peak is at around 20 nm, which is due to the organometallic complex, [Ir( It is suggested that this is due to the emission of 5dptznmdppy). The emission spectrum of the comparative light-emitting element 2 has a peak at around 516 nm. It was shown that the emission originates from the organometallic complex, [Ir(ppy)3], contained in 1913. To be tempted.

[0385] Note that the organometallic complex used in the light-emitting element 4, which is one embodiment of the present invention, is a diphenylpyridine-based compound. By having a ligand with a diphenyltriazine skeleton bonded to the center, the carrier (electron or This makes it possible to easily inject and transport the electrons (electrons) into the device, thereby improving the luminous efficiency of the device. Furthermore, the driving voltage can be reduced. A light-emitting element having higher current efficiency and lower driving voltage than that of the conventional light-emitting element can be obtained.

[0386] Next, the current value was set to 2 mA, and the change in luminance with respect to the driving time under the condition of a constant current density was measured. 53 shows a graph of the light-emitting element which is a light-emitting element of one embodiment of the present invention. It was found that the light-emitting element No. 4 was a light-emitting element having the same favorable reliability as the comparative light-emitting element No. 2. [Example]

[0387] In this example, the light-emitting element [Ir(ppy) )2(dpappy)] (Structural formula (104)) as a guest material in the light-emitting layer. The comparative light-emitting element 5 uses [Ir(ppy)3] as a guest material in the light-emitting layer. The element structure, manufacturing method and characteristics of the comparative light emitting element 3 will be described. The element structure of the light-emitting element described above is shown in FIG. 21, and the specific configuration is shown in Table 7. The chemical formulas of the materials used in this example are shown below.

[0388] [Table 7]

[0389] [ka]

[0390] <Fabrication of light-emitting device> The light emitting device shown in this example has an anode 901 formed on a substrate 1900 as shown in FIG. On top of that, a hole injection layer 1911, a hole transport layer 1912, a light emitting layer 1913, an electron transport layer 1914, An electron injection layer 1915 is laminated in this order, and a cathode 1903 is laminated on the electron injection layer 1915. It has a structure.

[0391] First, an anode 1901 was formed on a substrate 1900. The electrode area was 4 mm 2 (2mm x 2m The substrate 1900 was a glass substrate. The anode 1901 was an acid Indium tin oxide (ITO) containing silicon dioxide was deposited to a thickness of 70 nm by sputtering. The film was formed by deposition.

[0392] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV- The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition chamber and vacuum baked at 170°C for 60 minutes. After this, the substrate was allowed to cool for about 30 minutes.

[0393] Next, a hole injection layer 1911 was formed on the anode 1901. The hole injection layer 1911 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was co-deposited at a weight ratio of 2:1 to form a film with a thickness of 40 nm. .

[0394] Next, a hole transport layer 1912 was formed on the hole injection layer 1911. The hole transport layer 1912 was 9-phenyl-9H-3-(9-phenyl-9H-carbazol-3-yl)carbazole The film was formed by vapor deposition using PCCP (abbreviation: PCCP) to a thickness of 20 nm.

[0395] Next, a light-emitting layer 1913 was formed on the hole-transporting layer 1912 .

[0396] In the case of the light-emitting element 5, the light-emitting layer 1913 is made of 9-[3-(4,6-diphenyl)-2-phenylpropanol] as a host material. (1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi 9H-carbazole (abbreviation: mPCCzPTzn-02), and N-(1 ,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]-9H-fluoren-2-amine (abbreviated as PCB BiF), and [2-(4-diphenylamino-2-pyridinyl)-2-methyl-2-pyridinyl] as a guest material (phosphorescent material). bis[2-(2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC] ] Iridium (III) (abbreviation: [Ir(ppy)2(dpappy)]) was used to CCzPTzn-02:PCBBiF:[Ir(ppy)2(Czppy)]=0.6: The co-deposition was carried out so that the weight ratio was 0.4:0.1, and the film thickness was 40 nm.

[0397] In the case of the comparative light-emitting element 3, the light-emitting layer 1913 is formed of a material selected from the group consisting of mPCCzPTzn-02 and mPCCzPTzn-02 as a host material. , PCBBiF as the assist material, and [Ir(pp mPCCzPTzn-02:PCBBiF:[Ir(ppy)3]=0 The mixture was co-deposited in a ratio of 0.6:0.4:0.1 (by weight). The film thickness was 40 nm. .

[0398] Next, an electron transport layer 1914 was formed on the light emitting layer 1913. The electron transport layer 1914 was made of mP The film thickness of CCzPTzn-02 is 20 nm, and 2,9-bis(naphthalen-2-yl)-4, 7-diphenyl-1,10-phenanthroline (NBphen) film thickness 10 nm The layers were deposited in this order.

[0399] Next, an electron injection layer 1915 was formed on the electron transport layer 1914. The electron injection layer 1915 was Lithium fluoride (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0400] Next, a cathode 1903 was formed on the electron injection layer 1915. The cathode 1903 was made of aluminum. was formed by vapor deposition to a film thickness of 200 nm.

[0401] By the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 1900. The hole injection layer 1911, the hole transport layer 1912, and the light emitting layer 1913 described in the above steps were 13, the electron transport layer 1914, and the electron injection layer 1915 constitute the EL layer in one embodiment of the present invention. In addition, the vapor deposition process in the above-mentioned manufacturing method is all performed by the resistance heating method. The deposition method was used.

[0402] The light emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using the substrate, the sealing material was placed in a glove box with a nitrogen atmosphere. Another substrate is fixed on the substrate 1900 using a sealant. It is applied around the optical element and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 Irradiated and at 80°C This was done by heat treatment for 1 hour.

[0403] <Operating characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting elements (light-emitting element 5, comparative light-emitting element 3) were measured. The measurements were carried out at room temperature (an atmosphere maintained at 25°C). The results are shown in Figures 54 to 58. .

[0404] These results indicate that the light-emitting elements of one embodiment of the present invention (light-emitting element 5 and comparative light-emitting element 3) It can be seen that the device exhibits good current efficiency and high external quantum efficiency. 2 Table 8 shows the main initial characteristics of each light-emitting element in the vicinity.

[0405] [Table 8]

[0406] Furthermore, the light-emitting element 5 and the comparative light-emitting element 3 were subjected to an electric current of 2.5 mA / cm 2 A current was passed at a current density of The resulting emission spectrum is shown in FIG. 59. As shown in FIG. 59, the emission spectrum of the light-emitting element 5 has a peak at around 523 nm, which is due to the organometallic complex, [I It is suggested that this is due to the emission of [r(ppy)2(dpappy)]. The emission spectrum of the light-emitting element 3 has a peak at about 517 nm. It is suggested that this is due to the luminescence of the organometallic complex, [Ir(ppy)3], contained therein.

[0407] Note that the organometallic complex used in the light-emitting element 5, which is one embodiment of the present invention, is a diphenylpyridine-based compound. By having a ligand with a diphenylamine skeleton attached to the backbone, carriers (electrons or holes) Therefore, the light-emitting element 5 has good luminous efficiency. It is possible.

[0408] In the light-emitting element 5 and the comparative light-emitting element 3, the assist material in the light-emitting layer was PCBBiF is used, which, as shown in the structural formula above, is a diphenylamine. It is an organic compound containing an amine skeleton. The skeleton contained in PCBBiF, which is an assist material It has been found that it is preferable that the carrier transport skeleton contained in the luminescent material is the same as that contained in the luminescent material. [Example]

[0409] In this example, a compound represented by structural formulas (C1) to (C3) having a structure according to one embodiment of the present invention was prepared. We present the results of calculations on the distribution of HOMO and LUMO for organometallic complexes. The structural formulas of the organometallic complexes represented by (C1) to (C3) are shown below.

[0410] [ka]

[0411] The Gaussian09 program was used for molecular orbital calculations. The basis set was 6-311. The singlet ground state (S0) of each molecule was determined using G, and the singlet ground state (S0) of each molecule was determined using B3PW91\6-311G. , and structural optimization was performed.

[0412] The figure showing the electron density distribution of the HOMO and LUMO in each structure calculated by the calculation is shown below. Shown in Figure 60.

[0413] As shown in Figure 60, the organometallic complex represented by structural formula (C1) has a HOMO that is mainly phenyl. The LUMO is mainly distributed between the iridium ion and the pyridine ligand, and the diphenyltriazine The results show that the organometallic complex represented by structural formula (C2) is also distributed in the HOM O is mainly distributed between the phenylpyridine derivative ligand and the iridium ion, and the LUMO is mainly The results show that the compound is distributed in diphenyltriazine. The organometallic complex has a HOMO that is mainly distributed between the phenylpyridine ligand and the iridium ion. The LUMO was also found to be distributed mainly among the phenylpyrimidine derivative ligands.

[0414] Therefore, the organometallic complex represented by the structural formula (C1) and the organometallic complex represented by the structural formula (C2) LUMO distribution in diphenyltriazine, a framework in which organometallic complexes have carrier transport properties This indicates that they are involved in carrier transport and electron injection. The organometallic complex represented by the formula (1) has a LUMO structure with a triazine skeleton that has carrier transport properties. No distribution of ions was observed, and it is thought that there is little involvement in carrier transport or electron injection.

[0415] One embodiment of the present invention is a compound semiconductor device comprising a first skeleton having a carrier transport property and a second skeleton having a light-emitting property. in one molecule and has a molecular weight of 3000 or less. Referring to the above calculation results, the organometallic complexes represented by (C1) and (C2) are difluoromethyl groups. Since the LUMO is distributed in the phenyltriazine skeleton, the skeleton is considered to be a suitable material for carrier transport and charge transport. This corresponds to the first skeleton, which has carrier transport properties responsible for the injection of electrons, and the phenylpyridine skeleton is It can be said that the organic compound corresponds to the second skeleton having optical properties. The organometallic complex represented by 3) does not show LUMO distribution in the dimethyltriazine skeleton, The LUMO is distributed in the phenylpyridine skeleton, which allows for carrier transport and electron injection. It is believed that the luminescent skeleton is responsible for both luminescence and carrier transport. [Explanation of symbols]

[0416] 101 Anode 102 Cathode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 400 boards 401 Anode 403 EL layer 404 Cathode 405 Sealing material 406 Sealing material 407 Sealing substrate 412 Pad 420 IC chip 501 Anode 502 Cathode 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 601 Driver circuit section (source line driver circuit) 602 Pixel section 603 Drive circuit section (gate line drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching FET 612 Current control FET 613 Anode 614 Insulators 616 EL layer 617 Cathode 618 Light-emitting element 730 insulating film 770 Planarization insulating film 772 Conductive film 782 Light-emitting element 783 Droplet discharge device 784 Droplet 785 layers 786 EL layer 788 Conductive Film 901 Case 902 Liquid crystal layer 903 Backlight Unit 904 Case 905 Driver IC 906 terminal 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024W anode 1024R Anode 1024G anode 1024B Anode 1025 Bulkhead 1028 EL layer 1029 Cathode 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black Matrix 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 1400 Droplet discharge device 1402 PCB 1403 Droplet discharge means 1404 Imaging means 1405 Head 1406 dotted line 1407 Control means 1408 Storage medium 1409 Image processing means 1410 Computer 1411 Marker 1412 head 1413 Material Source 1414 Material Source 1415 Material Source 1416 Head 1900 board 1901 Anode 1903 Cathode 1911 Hole injection layer 1912 Hole transport layer 1913 luminescent layer 1914 Electron transport layer 1915 Electron injection layer 2001 Case 2002 light source 3001 Lighting equipment 5000 display area 5001 Display area 5002 Display area 5003 Display area 5004 Display area 5005 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7210 Second display unit 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9033 Fasteners 9034 Switch 9035 Power Switch 9036 Switch 9038 Operation switch 9310 Mobile Information Terminal 9311 Display Panel 9312 Display area 9313 Hinge 9315 Housing 9630 chassis 9631 Display section 9631a Display section 9631b Display section 9632a Touch panel area 9632b Touch panel area 9633 Solar Cells 9634 Charge / Discharge Control Circuit 9635 Battery 9636 DC / DC Converter 9637 Operation Key 9638 Converter 9639 Button

Claims

1. An organometallic complex represented by any one of the following structural formulas: 【Chemical 1】 【Chemistry 2】 【Chemistry 3】

2. A light-emitting device comprising the organometallic complex according to claim 1 .

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