Light-emitting device

Abstract

To provide a light-emitting device of which the drive voltage is low and the light emission efficiency is high.SOLUTION: A light-emitting device includes a first organic compound, a second organic compound, and a guest material. A LUMO level of the first organic compound is lower than a LUMO level of the second organic compound and a difference therebetween is larger than 0 eV and smaller than 0.5 eV. A HOMO level of the first organic compound is lower than a HOMO level of the second organic compound. The guest material comprises a function capable of converting triplet excitation energy into light emission. The first organic compound and the second organic compound are a combination which forms an excited complex.SELECTED DRAWING: Figure 2

Description

[Technical Field]

[0001] One embodiment of the present invention is a light-emitting element using a combination of organic compounds that form an exciplex, or The present invention also relates to a display device, an electronic device, and a lighting device that have the light-emitting element.

[0002] It should be noted that one aspect of the present invention is not limited to the above-mentioned technical fields. The present invention relates to a process, a machine, a manufacture, or a manufacturing method. In particular, one aspect of the present invention relates to a composition of matter. The present invention relates to a semiconductor device, a light emitting device, a display device, a lighting device, a light emitting element, and a method for manufacturing these. [Background technology]

[0003] In recent years, electroluminescence (EL) The basic structure of these light-emitting devices is as follows: The device has a structure in which a layer containing a light-emitting material (EL layer) is sandwiched between a pair of electrodes. By applying a voltage across the material, light is emitted from the luminescent material.

[0004] Since the above-mentioned light-emitting element is a self-luminous type, a display device using it has excellent visibility and It has the advantage of not requiring a light source and consuming little power. It also has the advantage of high response speed.

[0005] A light-emitting element in which an organic material is used as the light-emitting material and an EL layer containing the light-emitting material is provided between a pair of electrodes. In the case of a device (for example, an organic EL device), applying a voltage between a pair of electrodes causes light to flow from the cathode Electrons are injected from the cathode and holes are injected from the anode into the luminescent EL layer, causing a current to flow. The injected electrons and holes are then recombined to excite the light-emitting organic material. The excited light-emitting organic material is then in a luminescent state, and light can be emitted from the excited light-emitting organic material.

[0006] The types of excited states that organic materials can form include singlet excited states (S * ) and triplet excited states state(T * ) emission from the singlet excited state is fluorescence, and emission from the triplet excited state is phosphorescence. The statistical generation ratio of these in a light-emitting element is called S * :T * =1 :3. Therefore, it is more effective to use a light-emitting element that emits phosphorescence than a light-emitting element that uses a material that emits fluorescence (fluorescent material). Therefore, a light-emitting element using a material that emits light (phosphorescent material) can have higher luminous efficiency. Therefore, phosphorescent materials capable of converting triplet excited state energy into luminescence are used. In recent years, development of light-emitting devices has been actively pursued (see, for example, Patent Document 1).

[0007] The energy required to excite an organic material is determined by the highest occupied molecular orbital (HMO) of the organic material. st Occupied Molecular Orbital (HOMO) Position and Lowest Unoccupied Molecular Orbit It depends on the energy difference between the electron and the LUMO level, which is roughly It corresponds to the energy of the singlet excited state. In this case, triplet excitation energy is converted into light-emitting energy. When the energy difference between the singlet and triplet excited states is large, the organic material is excited. The energy required to cause this is the energy difference. The energy required to excite the organic material and the energy required to emit light are The difference in energy between the two materials affects the device characteristics as an increase in the driving voltage of the light-emitting device. There is a need for a method to suppress the increase in drive voltage. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-182699 Summary of the Invention [Problem to be solved by the invention]

[0009] To reduce the driving voltage, organic materials with good carrier (electron and / or hole) transport properties are used. When using organic materials, it is necessary to adjust the carrier balance. It may be difficult to adjust the light emitting element or make the light emitting element emit light efficiently. It is not easy to achieve both high and low drive voltages.

[0010] Therefore, in one embodiment of the present invention, a novel light-emitting element having a phosphorescent material is In particular, it is an object of the present invention to provide a light-emitting element having high luminous efficiency. In particular, an object of one embodiment of the present invention is to provide a light-emitting element with reduced voltage. Another object of one embodiment of the present invention is to provide a light-emitting element with excellent reliability.

[0011] Another object of the present invention is to provide a light-emitting element with reduced power consumption. An object of one embodiment of the present invention is to provide a novel light-emitting device. The present invention aims to provide a novel display device.

[0012] Note that the above description of the object does not preclude the existence of other objects. It is not necessary to solve all of these problems. Problems other than those mentioned above can be solved by the description of the specification, etc. It is obvious from the description of the specification, etc. that other problems can be extracted. do. [Means for solving the problem]

[0013] One embodiment of the present invention is to form an exciplex that can efficiently excite a phosphorescent material. It is a light-emitting element that can

[0014] Therefore, one embodiment of the present invention is a light-emitting device having a light-emitting layer between a pair of electrodes, the light-emitting layer including a first active a first organic compound, a second organic compound, and a guest material, The LUMO level is lower than the LUMO level of the second organic compound and is higher than the LUMO level of the first organic compound. The difference in LUMO levels of the second organic compound is greater than 0 eV and less than or equal to 0.5 eV, and The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound, and the guest material has a function of converting triplet excitation energy into luminescence, and a first organic compound and a second organic compound form an exciplex.

[0015] In the above structure, the first organic compound has a first electron transporting skeleton and a first hole transporting skeleton. the second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton; It is preferable to have

[0016] In each of the above structures, the LUMO level of the first organic compound and the LUMO level of the second organic compound are The difference in MO level is preferably greater than 0 eV and equal to or less than 0.3 eV.

[0017] In the above structure, the first electron transporting skeleton and the second electron transporting skeleton are π electron It is either a deficient heteroaromatic ring, an arylborane skeleton, or a phosphine oxide skeleton, The first hole transporting skeleton and the second hole transporting skeleton are each a π-electron rich heteroaromatic ring, an aromatic aromatic ring, or a π-electron rich heteroaromatic ring. Preferably, the amine skeleton is either one of the amine skeletons.

[0018] In the above structure, the first electron transporting skeleton is a nitrogen-containing heteroaromatic ring having 8 to 18 carbon atoms. The second electron transporting skeleton is preferably a nitrogen-containing heteroaromatic ring having 3 to 8 carbon atoms.

[0019] In each of the above structures, the first hole transporting skeleton has a π-electron-rich heteroaromatic ring, The second hole transporting skeleton preferably has an aromatic amine skeleton, particularly a triarylamine skeleton. It's nice.

[0020] In each of the above structures, the second organic compound is represented by the following structural formulas (100) to (109): Preferably, the organic compound is represented by the formula:

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] In each of the above structures, the exciplex has a function of donating excitation energy to the guest material. It is preferable that the

[0025] In each of the above structures, the guest material preferably contains iridium.

[0026] Another embodiment of the present invention is an organic compound represented by any one of the structural formulas (100) to (109). is.

[0027] Another embodiment of the present invention is an organic compound represented by any one of the structural formulas (100) to (109). The light emitting element has one or more of the above.

[0028] Another embodiment of the present invention is a light-emitting element having any of the above structures, a color filter, a seal, or a light-emitting device. Another embodiment of the present invention is a display device including the display device. The present invention also provides an electronic device having a touch sensor and a housing. The present invention is a lighting device having a light-emitting element having any of the above configurations and a housing or a touch sensor. Furthermore, one embodiment of the present invention is not only a light-emitting device having a light-emitting element, but also an electronic device having a light-emitting device. Therefore, the light-emitting device in this specification includes image display devices, It also refers to a light source (including lighting equipment). exible Printed Circuit), TCP (Tape Carrier) The TCP is attached to a module with a printed wiring board. The module is mounted with a COG (Chip On Glass) method. A light emitting device may also include a module in which an integrated circuit (C) is directly mounted. [Effects of the Invention]

[0029] According to one embodiment of the present invention, a novel light-emitting element having a phosphorescent material is provided. In particular, according to one embodiment of the present invention, a light-emitting element with high emission efficiency can be provided. In particular, according to one embodiment of the present invention, a light-emitting element requiring reduced voltage can be provided. According to one embodiment of the present invention, a light-emitting element with excellent reliability can be provided.

[0030] According to one embodiment of the present invention, a light-emitting element with reduced power consumption can be provided. According to one embodiment of the present invention, a novel light-emitting device can be provided. According to one embodiment of the present invention, a novel display device can be provided.

[0031] The description of these effects does not preclude the existence of other effects. It is not necessary to have all of these effects. Effects other than these may be included in the description. It is obvious from the description of the specification, drawings, claims, etc. From this, it is possible to extract other effects. [Brief explanation of the drawings]

[0032] [Figure 1] 1A and 1B are schematic cross-sectional views of a light-emitting element of one embodiment of the present invention and a diagram illustrating the correlation between energy levels; [Figure 2] 1A and 1B are diagrams illustrating the correlation of energy levels in a light-emitting layer of a light-emitting element according to one embodiment of the present invention. [Figure 3] 1A and 1B are schematic cross-sectional views of a light-emitting element according to one embodiment of the present invention. [Figure 4] FIG. 1 is a conceptual diagram of an active matrix light-emitting device according to one embodiment of the present invention. [Figure 5] FIG. 1 is a conceptual diagram of an active matrix light-emitting device according to one embodiment of the present invention. [Figure 6] FIG. 1 is a conceptual diagram of an active matrix light-emitting device according to one embodiment of the present invention. [Figure 7] 1 is a schematic diagram of a display device according to one embodiment of the present invention. [Figure 8] FIG. 1 is a circuit diagram of a display device according to one embodiment of the present invention. [Figure 9] FIG. 1 is a circuit diagram of a display device according to one embodiment of the present invention. [Figure 10] 1 is a schematic diagram of a display device according to one embodiment of the present invention. [Figure 11] 1 is a schematic diagram of a display device according to one embodiment of the present invention. [Figure 12] 1 is a schematic diagram of a display device according to one embodiment of the present invention. [Figure 13] 1 is a schematic diagram of an electronic device according to one embodiment of the present invention. [Figure 14] 1 is a schematic diagram of an electronic device according to one embodiment of the present invention. [Figure 15] 1 is a schematic diagram of an electronic device according to one embodiment of the present invention. [Figure 16] 1 is a schematic diagram of an electronic device according to one embodiment of the present invention. [Figure 17] FIG. 1 illustrates a lighting device according to one embodiment of the present invention. [Figure 18] FIG. 1 illustrates a lighting device according to one embodiment of the present invention. [Figure 19] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 20] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 21] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 22] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 23] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 24] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 25] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 26] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 27] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 28] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 29] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 30] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 31] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 32] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 33] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 34] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 35] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 36] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 37] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 38] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 39] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 40] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 41] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 42] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 43] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 44] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 45] FIG. 2 is a diagram illustrating an NMR chart according to an embodiment. [Figure 46] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 47] 1A and 1B are diagrams illustrating absorption spectra and emission spectra of compounds according to an example. [Figure 48] 1 is a schematic diagram of a light-emitting element according to an embodiment. [Figure 49] FIG. 10 is a graph showing current efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 50] FIG. 10 is a graph showing luminance-voltage characteristics of a light-emitting element according to an example. [Figure 51] FIG. 10 is a graph showing current density-voltage characteristics of a light-emitting element according to an example. [Figure 52] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 53] 10A and 10B are graphs illustrating emission spectra of light-emitting elements according to Examples. [Figure 54] FIG. 10 is a diagram illustrating the relationship between the driving voltage and the difference in LUMO level between host materials according to an example. [Figure 55] FIG. 10 is a graph showing current efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 56] FIG. 10 is a graph showing luminance-voltage characteristics of a light-emitting element according to an example. [Figure 57] FIG. 10 is a graph showing current density-voltage characteristics of a light-emitting element according to an example. [Figure 58] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 59] 10A and 10B are graphs illustrating emission spectra of light-emitting elements according to Examples. [Figure 60] FIG. 10 is a diagram illustrating the relationship between the driving voltage and the difference in LUMO level between host materials according to an example. [Figure 61] 10A to 10C are diagrams illustrating the results of a reliability test on a light-emitting element according to an example. [Figure 62] FIG. 10 is a graph showing current efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 63] FIG. 10 is a graph showing luminance-voltage characteristics of a light-emitting element according to an example. [Figure 64] FIG. 10 is a graph showing current density-voltage characteristics of a light-emitting element according to an example. [Figure 65] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 66] 10A and 10B are graphs illustrating emission spectra of light-emitting elements according to Examples. [Figure 67] FIG. 10 is a graph showing current efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 68] FIG. 10 is a graph showing luminance-voltage characteristics of a light-emitting element according to an example. [Figure 69] FIG. 10 is a graph showing current density-voltage characteristics of a light-emitting element according to an example. [Figure 70] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 71] 10A and 10B are graphs illustrating emission spectra of light-emitting elements according to Examples. [Figure 72] 10A to 10C are diagrams illustrating the results of a reliability test on a light-emitting element according to an example. [Figure 73] FIG. 10 is a graph showing current efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 74] FIG. 10 is a graph showing luminance-voltage characteristics of a light-emitting element according to an example. [Figure 75] FIG. 10 is a graph showing current density-voltage characteristics of a light-emitting element according to an example. [Figure 76] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of a light-emitting element according to an example. [Figure 77] 10A and 10B are graphs illustrating emission spectra of light-emitting elements according to Examples. DETAILED DESCRIPTION OF THE INVENTION

[0033] 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. Therefore, the present invention is not limited to the embodiments described below. The terms and conditions of the present invention are not to be construed as being limited to the content.

[0034] In addition, the position, size, range, etc. of each component shown in the drawings etc. are not necessarily shown in order to facilitate understanding. It may not represent the actual position, size, range, etc. Therefore, the disclosed invention The position, size, range, etc. are not necessarily limited to those disclosed in the drawings, etc.

[0035] In addition, in this specification, ordinal numbers such as 1st, 2nd, etc. are used for convenience, In some cases, the order of processes or layers may not be indicated. For example, "first" may be replaced with "second" or " can be appropriately replaced with "third" etc. The ordinal numbers used to identify an aspect of the present invention may not match. be.

[0036] In addition, in this specification and the like, when explaining the configuration of the invention using drawings, the same The reference numerals may be commonly used even among different drawings.

[0037] In addition, in this specification and the like, the terms "film" and "layer" are interchangeable. For example, the term "conductive layer" can be changed to the term "conductive film." Alternatively, for example, the term "insulating film" may be changed to "insulating layer" It may be possible to change the term to

[0038] In this specification and the like, the singlet excited state (S * ) is a single atom with excitation energy The S1 level is the lowest singlet excited energy level. The lowest excited energy level is the singlet excited state. (T *) is a triplet state with excitation energy. Also, the T1 level is a triplet The lowest excited energy level of the triplet excited state is In this specification and the like, the term "singlet excited state" or "singlet excited energy" is used simply. Even when written as an energy level, it refers to the lowest singlet excited state or S1 level. In addition, when it is written as triplet excited state or triplet excited energy level, However, it may refer to the lowest triplet excited state or T1 level.

[0039] In this specification and the like, the fluorescent material refers to a material that emits light when it relaxes from a singlet excited state to a ground state. On the other hand, phosphorescent materials are materials that emit light in the visible light region from the triplet excited state to the ground state. When the material relaxes to the phosphorus state, it emits light in the visible light region at room temperature. An optical material is one of materials that can convert triplet excitation energy into visible light.

[0040] The phosphorescence energy or triplet excitation energy is the shortest wavelength side of the phosphorescence emission. It can be derived from the wavelength of the emission peak (including the shoulder). , and performing time-resolved photoluminescence in a low-temperature (e.g., 10 K) environment. The emission energy of thermally activated delayed fluorescence can be observed by It can be derived from the wavelength of the emission peak (including the shoulder) on the shortest wavelength side of the light.

[0041] In this specification and the like, room temperature refers to a temperature between 0°C and 40°C.

[0042] In this specification, the blue wavelength region refers to wavelengths of 400 nm or more and less than 500 nm. blue emission has at least one emission spectrum peak in this region. The green wavelength range is the wavelength range of 500 nm or more and less than 580 nm. Green emission is emission having at least one emission spectrum peak in this region. The red wavelength range is the wavelength range between 580 nm and 680 nm. The emission is an emission having at least one emission spectrum peak in the region.

[0043] In this specification, a bipolar material is a material that has both hole transport and electron transport functions. It is an organic compound that has both an electron transport skeleton and a hole transport skeleton in one molecule. The electron transporting skeleton is a π-electron deficient heteroaromatic ring, and the hole transporting skeleton is an amine skeleton or a π An example is an electron-rich heteroaromatic ring.

[0044] (Embodiment 1) In this embodiment, a light-emitting element of one embodiment of the present invention will be described below with reference to FIGS. 1 and 2. Reveal.

[0045] <Configuration example 1 of light-emitting element> First, the structure of a light-emitting element of one embodiment of the present invention will be described with reference to FIGS. The following is an explanation.

[0046] FIG. 1A is a schematic cross-sectional view of a light-emitting element 150 of one embodiment of the present invention.

[0047] The light emitting element 150 has a pair of electrodes (electrode 101 and electrode 102), and The EL layer 100 has at least a light-emitting layer 140. .

[0048] The EL layer 100 shown in FIG. 1A includes a hole injection layer 111, a cathode layer 112, a cathode layer 113, a cathode layer 114, a cathode layer 115, a cathode layer 116, a cathode layer 117, a cathode layer 118, a cathode layer 119 ... It has functional layers such as a hole transport layer 112, an electron transport layer 118, and an electron injection layer 119.

[0049] In this embodiment, of the pair of electrodes, electrode 101 is an anode, and electrode 1 Although the description will be given assuming that O2 is a cathode, the configuration of the light emitting element 150 is not limited to this. The electrode 101 is the cathode, the electrode 102 is the anode, and the layers between the electrodes are stacked in the reverse order. That is, from the anode side, the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113 may be arranged in this order. The light-transmitting layer 140, the electron transporting layer 118, and the electron injection layer 119 may be stacked in this order. .

[0050] The configuration of the EL layer 100 is not limited to the configuration shown in FIG. 1(A). , a hole transport layer 112, an electron transport layer 118, and an electron injection layer 119. Alternatively, the EL layer 100 may be configured to have either a hole or electron injection layer. Reduce the barrier, improve the transportability of holes or electrons, or inhibit the transportability of holes or electrons or suppressing the quenching phenomenon caused by the electrode. The functional layers may each be a single layer or may be a laminate of multiple layers. It may be composed of

[0051] FIG. 1(B) is a cross-sectional view showing an example of the light-emitting layer 140 shown in FIG. 1(A). The light-emitting layer 140 shown in FIG. 1B includes a host material 141 and a guest material 142. The host material 141 includes an organic compound 141_1 and an organic compound 141_2.

[0052] Furthermore, a light-emitting organic material may be used as the guest material 142. The materials include materials that can emit fluorescence (hereinafter referred to as fluorescent materials) and materials that emit phosphorescence. In the following description, the following materials are also referred to as phosphorescent materials. A configuration using a phosphorescent material as the guest material 142 will be described. 42 may be read as a phosphorescent material.

[0053] As shown in FIG. 1B, the light-emitting layer is formed of an organic compound 141_1 and an organic compound 141_2. In the case of using two host materials (co-host system), the two host materials are generally The materials used are one electron transport material and one hole transport material. The structure includes a hole injection barrier between the hole transport layer 112 and the light emitting layer 140 and a barrier between the electron transport layer 118 and the light emitting layer 140. This is preferable because the electron injection barrier between the layers 140 is reduced, and the driving voltage can be reduced. This is a desirable configuration.

[0054] <Light-emitting mechanism of light-emitting elements> Next, the light emitting mechanism of the light emitting layer 140 will be described below.

[0055] The organic compound 141_1 and the organic compound 141_2 contained in the host material 141 in the light-emitting layer 140 The substance 141_2 is an exciplex (exciplex or Excitl Forms a nucleus (also called ex).

[0056] The organic compound 141_1, the organic compound 141_2, and the guest material in the light-emitting layer 140 The correlation of the energy levels with 142 is shown in Figure 1(C). The symbols and symbols are as follows: ·Host(141_1): Organic compound 141_1 (host material) ·Host(141_2): Organic compound 141_2 (host material) Guest (142): Guest material 142 (phosphorescent compound) ·S PH1 : S1 level of organic compound 141_1 (host material) T PH1 :T1 level of organic compound 141_1 (host material) ·S PH2 : S1 level of organic compound 141_2 (host material) T PH2 :T1 level of organic compound 141_2 (host material) ·S PG : S1 level of guest material 142 (phosphorescent compound) T PG : T1 level of guest material 142 (phosphorescent compound) ·S PE : S1 level of the exciplex T PE :T1 level of exciplex

[0057] The organic compound 141_1 and the organic compound 141_2 form an exciplex, and the S 1 level (S PE ) and T1 level (T PE ) are adjacent energies (Fig. 1(C) See Route E1).

[0058] Organic compound 141_1 and organic compound 141_2 accept holes and electrons, respectively. Alternatively, when one of the two is excited, it quickly forms an exciplex. Therefore, the exciplex in the light-emitting layer 140 Most of the excited molecules exist as exciplexes. The excited energy levels of exciplexes (S PE Also is T PE ) is a host material (organic compound 141_1 and organic compound 1) that forms an exciplex. 41_2) S1 level (S PH1 and S PH2 ) and therefore has a lower excitation energy This allows the host material 141 to form an excited state. The driving voltage of the element can be reduced.

[0059] And the (S PE ) and (T PE ) and the energy of the guest material 142 (phosphorescent compound) to the T1 level to obtain light emission (Figure 1(C) Route E2, E See 3).

[0060] In addition, the T1 level of the exciplex (T PE ) is the T1 level (T PG )twist By doing so, the singlet excitation energy and and triplet excitation energy to the S1 level (S PE ) and T1 level (T PE )mosquito The T1 level (T PG ) can transfer energy to

[0061] In addition, in order to efficiently transfer excitation energy from the exciplex to the guest material 142, , the T1 level of the exciplex (T PE ) are each organic compound that forms an exciplex (organic compound 14 T1 levels (T PH1 and T PH2 ) or It is preferable that the organic compound (organic compound 141_1 and organic Compound 141_2) is less likely to quench the triplet excitation energy of the exciplex. Energy transfer from the exciplex to the guest material 142 occurs efficiently.

[0062] In addition, the combination of organic compound 141_1 and organic compound 141_2 has hole transport properties. When a compound having electron transport properties is used in combination with a compound having electron transport properties, the mixing ratio Specifically, the carrier balance can be easily controlled by using a material having hole transport properties. The compound having electron transport properties:compound having electron transport properties is preferably in the range of 1:9 to 9:1 (weight ratio). In addition, by having this configuration, the carrier balance can be easily controlled. In addition, the carrier recombination region can be easily controlled.

[0063] The above-described processes of routes E2 and E3 are referred to as ExTET (Exc It is sometimes called a triplex-triplet energy transfer In other words, the light-emitting layer 140 functions to transfer excitation energy from the exciplex to the guest material 142. In this case, it is not necessarily T PE From S PE The reverse intersystem crossing efficiency to No, S PE The quantum yield of light emission from the material does not need to be high, so a wide range of materials can be selected. It becomes Noh.

[0064] The combination of organic compound 141_1 and organic compound 141_2 forms an exciplex Any combination that allows this is acceptable, but one of them is in the highest occupied molecular orbital of the other. Occupied Molecular Orbital (HOMO) level It has a low HOMO level and the other lowest unoccupied molecular orbital (Lowest Unoccupied Orbital) d LUMO level lower than the LUMO level It is preferred that the aryl group has a position.

[0065] As mentioned above, ExTET contributes greatly to improving the efficiency and reliability of phosphorescent light-emitting devices and reducing their driving voltage. Since ExTET requires the formation of exciplexes, The selection of 141_1 and organic compound 141_2 is important.

[0066] Here, the difference in LUMO levels between organic compound 141_1 and organic compound 141_2 is less than 0 eV. By using a combination of organic compounds with a luminescence energy of 0.5 eV or less, The present inventors have found that this can contribute to reducing the driving voltage of the molecule. The difference in LUMO level between 141_1 and organic compound 141_2 is greater than 0 eV, 0.3 eV The following is the result.

[0067] The HOMO and LUMO levels of organic materials are generally determined by CV (cyclic voltammetry). ), photoelectron spectroscopy, optical absorption spectroscopy, inverse photoelectron spectroscopy, etc. When comparing values, it is preferable to use values ​​estimated by the same measurement.

[0068] As described above, the organic compound 141_1 and the organic compound 141_2 are such that one of them traps holes, The other accepts an electron and quickly forms an exciplex. In this study, both organic compound 141_1 and organic compound 141_2 are bipolar materials. A bipolar material has both a hole transporting skeleton and an electron transporting skeleton in one molecule. Therefore, the carrier transport property in the light-emitting layer can be improved, which contributes to a reduction in the driving voltage. This can be done.

[0069] When bipolar materials are used for organic compound 141_1 and organic compound 141_2, respectively , to form an exciplex with organic compound 141_1 and organic compound 141_2 In the light-emitting layer 140, one needs to accept holes and the other needs to accept electrons. Therefore, bipolar materials that accept holes have a higher HOMO level than bipolar materials that accept electrons. The bipolar material that accepts electrons has a lower L than the bipolar material that accepts holes. It is preferable that it has a UMO level.

[0070] Here, for example, the organic compound 141_1 is an electron transport material, and the organic compound 141_2 is a hole transport material. When a conductive material is used, electron or hole carriers may be generated in the light-emitting layer depending on the mixing ratio. In other words, in general, the exciplex is formed, and the rear transport property is reduced. In order to achieve this, a certain amount of electron transport material and hole transport material are required in the layer. The hole transporting material inhibits the electron transporting property, and the hole transporting material inhibits the hole transporting property, so the driving voltage increases. On the other hand, there are cases where both organic compound 141_1 and organic compound 141_2 are affected. When a bipolar material is used, the bipolar material has both electron transport and hole transport functions. Therefore, the driving voltage can be reduced regardless of the mixture ratio.

[0071] <Configuration example 2 of light-emitting element> FIG. 2 shows the organic compound 141_1 and the organic compound 141_2 in the light-emitting layer 140 of the light-emitting element according to one embodiment of the present invention. The energy relationship between the HOMO level and the LUMO level of Compound 141_2 is shown in Figure 2. Organic compound 141_1 is a bipolar material that accepts electrons, and organic compound 141_2 accepts holes. The bipolar material to be received is described below.

[0072] Bipolar materials have both electron-transporting and hole-transporting skeletons in the same molecule. Therefore, it has excellent properties in both hole transport and electron transport. The UMO levels are often associated with electron-transporting backbones, and the HOMO levels are often positive Pore ​​transporting skeletons are related to transporting skeletons. Therefore, by selecting an appropriate skeleton, The difference in LUMO and HOMO levels between two bipolar materials can be adjusted. Therefore, by selecting a material with an appropriate skeleton, it is possible to improve the electron transfer between the two materials. The injection barrier and hole injection barrier can be reduced. C) The energy relationship of the bipolar material that forms exciplexes is as follows: There is a combination.

[0073] Figure 2(A) shows the difference in LUMO levels between two organic materials when ExTET is used. This is an example of a combination where the difference in LUMO levels is smaller than 0 eV, 0.5 e 0 eV or less, and more preferably, it is greater than 0 eV and less than 0.3 eV. Since the difference in level is small, the electron injection barrier is reduced, and the driving voltage can be reduced. In this case, there is no particular limitation on the hole transport skeleton that constitutes the bipolar material. This is a preferable configuration because the material can be selected. Therefore, even if a guest material with a high HOMO level is used in the light-emitting layer, the guest material does not undergo hole transport. Therefore, the increase in driving voltage can be suppressed.

[0074] To utilize ExTET, as mentioned above, the bipolar material that accepts holes must accept electrons. The bipolar material that accepts electrons has a higher HOMO level than the bipolar material that accepts holes. Preferably, the bipolar material has a lower LUMO level than the material that receives the

[0075] The electron transporting skeleton in the first organic compound and the second organic compound is π-electron deficient. Examples of such heteroaromatic rings include arylborane skeletons and phosphine oxide skeletons. The π-electron deficient heteroaromatic ring is preferably a 6-membered nitrogen-containing heterocyclic ring, specifically a π- It is a lysine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring. On the other hand, the hole transporting skeleton in the first organic compound and the second organic compound is a π electron Examples of the π-electron-rich heteroaromatic ring include an aromatic amine skeleton. Of these, a five-membered nitrogen-containing heterocycle is preferred, specifically a pyrrole ring, a furan ring, or a thiamine ring. In particular, the aromatic amine skeleton is preferably a triarylamine skeleton. In the first organic compound and the second organic compound, the heteroaromatic ring In contrast, an aromatic ring such as a benzene ring or a heteroaromatic ring may be further condensed.

[0076] In one aspect of the present invention, the above skeleton can be appropriately selected and ExTET can be used. The combination of the first organic compound and the second organic compound can be appropriately selected. The following explains how to combine them, listing specific frameworks.

[0077] Bipolar materials can be used to combine these materials (ExTET). When realizing the combination of electron-transporting skeletal materials, the bipolar material that receives electrons is and a hole transporting skeleton having a π-electron-rich heteroaromatic ring. The electron transporting skeleton is preferably a material having a nitrogen-containing heteroaromatic ring having 8 to 18 carbon atoms. This is preferable because the LUMO level tends to be low, but the present invention is not limited to this. As the electron transporting skeleton, a quinoline skeleton, a quinazoline skeleton, or a quinoxaline skeleton is more preferred. The benzoquinoxaline skeleton is more preferable. Further, as the hole transporting skeleton, a carbazole skeleton, a di Examples of the hole-transporting skeleton include a benzothiophene skeleton and a dibenzofuran skeleton. This is preferable because the HOMO level tends to be relatively low. To maintain this, the bipolar material that accepts electrons must not have a triarylamine skeleton. It is preferable that:

[0078] When using ExTET, the bipolar material that accepts holes is an electron transport material. As the hole transporting skeleton, a nitrogen-containing heteroaromatic ring is used, and as the hole transporting skeleton, an aromatic amine skeleton, particularly a thiazolinone, is used. A material having a triarylamine skeleton is preferred. The electron transporting skeleton may have a π-electron-rich heteroaromatic ring. It is preferable that the compound has a nitrogen-containing heteroaromatic ring having 3 to 8 atoms because the LUMO level tends to be high. However, the present invention is not limited to this. More specifically, the triazine skeleton or the diazine skeleton The diazine skeleton is preferably a pyrimidine skeleton, a pyrazine skeleton, or a quinoxaline skeleton. , dibenzoquinoxaline skeleton, quinazoline skeleton, benzofuropyrimidine skeleton, etc. The electron transporting skeleton is more preferably a pyrimidine skeleton. The material having a bipolar material transporting skeleton (having 8 to 10 carbon atoms) that accepts electrons is The LUMO level tends to be higher than that of materials with nitrogen-containing heteroaromatic rings (18). Materials with aromatic amine skeletons are bipolar materials that accept electrons and have a transporting skeleton (π electron passing The HOMO level tends to be higher than that of materials with heteroaromatic rings. The formation of an exciplex between a bipolar material that receives electrons and a bipolar material that receives holes This can be done.

[0079] When using ExTET, the bipolar material that receives holes has the following structure: Compounds represented by formulas (100) to (109) are examples of bipolar materials that accept holes. The fees are not limited to the following:

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] Figure 2(B) shows the difference in HOMO levels between two organic materials when using ExTET. This is an example of a combination of bipolar materials with small HOMO level differences. is preferably greater than 0 eV and not greater than 0.5 eV, and more preferably greater than 0 eV and not greater than 0 The difference in the HOMO levels is small, so the hole injection barrier is reduced. The driving voltage can be reduced. When a bipolar material is used in such a configuration, Therefore, there is no particular limitation on the electron transporting skeleton that constitutes the bipolar material. In addition, a material with a low LUMO level can be selected. Therefore, even if a guest material with a low LUMO level is used in the light-emitting layer, the guest material is not an electron trapping material. Therefore, the increase in driving voltage can be suppressed.

[0084] Figure 2(C) shows the difference between the HOMO and LUMO levels when ExTET is used. This is an example using a small combination between two organic materials, preferably bipolar materials. The small difference in LUMO levels and HOMO levels reduces the electron and hole injection barriers. Therefore, the driving voltage can be reduced.

[0085] <Material> Next, components of a light-emitting element according to one embodiment of the present invention will be described in detail below.

[0086] <Light-emitting layer> In the light-emitting layer 140, the host material 141 is present in the largest amount by weight, and the guest material 142 The phosphorescent material is dispersed in the host material 141. The T1 level of the organic compound 141_1 and the organic compound 141_2 is It is preferable that the T1 level is higher than the T1 level of the material (guest material 142).

[0087] As the organic compound 141_1, a material with high electron transport properties can be used. 0 -6 cm 2 It is preferable that the material has an electron mobility of .beta. / Vs or more. As materials that are easily transported (materials with electron transport properties), π-type compounds such as nitrogen-containing heteroaromatic compounds are Compounds with electron-deficient heteroaromatic ring skeletons and zinc or aluminum metal complexes are used. Nitrogen-containing heterocyclic condensed rings are particularly preferred. Specifically, quinoline ligands, Metal complexes containing benzoquinoline, oxazole, or thiazole ligands oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxadiazole derivatives, Sarin derivatives, dibenzoquinoxaline derivatives, phenanthroline derivatives, pyridine derivatives , bipyridine derivatives, pyrimidine derivatives, triazine derivatives, and the like.

[0088] Specifically, for example, tris(8-quinolinolato)aluminum(III) (abbreviation: A lq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Al mq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation :BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)a Aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as Znq, In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II)( Abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) ( Metal complexes with oxazole or thiazole ligands, such as ZnBTZ In addition to metal complexes, 2-(4-biphenylyl)-5 -(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazo OXD-7), 9-[4-(5-phenyl-1,3, 4-Oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11) , 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)- 1,2,4-Triazole (abbreviation: TAZ), 9-[4-(4,5-diphenyl-4H- 1,2,4-triazol-3-yl)phenyl]-9H-carbazole (abbreviation: CzT AZ1), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl -1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene- 4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBI m-II), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: B Heterocyclic compounds such as 2-[3-(dibenzothiophen-4-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-( Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxalate (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl) 2mCzBPDB q), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]di Benzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzo[f,h]quinoxaline] [4-( ... TPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl]di Benzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 2-[3-(3, 9'-bi-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (Abbreviation: 2mCzCzPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl] phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diphenyl)pyrimidine 4,6-zothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mC Heterocyclic compounds with diazine skeletons such as 2-{4-[3-(N-phenyl)-2-(4 ... (9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}- Triazines such as 4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) Heterocyclic compounds with an amine skeleton and 3,5-bis[3-(9H-carbazol-9-yl] )phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridinyl) Heterocyclization of pyridine skeletons such as [(phenyl)phenyl]benzene (abbreviation: TmPyPB) Compound, 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: Heteroaromatic compounds such as BzOs can also be used. The triazine skeleton, diazine (pyrimidine, pyrazine, pyridazine) skeleton, and pyridine skeleton are also Heterocyclic compounds having an azine skeleton are preferred because they are stable and highly reliable. Heterocyclic compounds having the above structure have high electron transport properties and contribute to reducing the driving voltage. 2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene- 2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine Polymer compounds such as PF-BPy (PF-6,6'-diyl) can also be used. The substances mentioned here are mainly 1×10 -6 cm 2 / Vs or higher electron mobility Note that any substance other than those mentioned above may be used as long as it has a high electron transporting property. .

[0089] The organic compound 141_2 is a compound that can form an exciplex with the organic compound 141_1. Specifically, a π-electron-rich heteroaromatic ring skeleton or an aromatic amine skeleton is preferred. It is preferable that the compound has a highly donor skeleton. Examples include dibenzothiophene derivatives, dibenzofuran derivatives, and carbazole derivatives. In this case, organic compound 141_1 and organic compound 141_ The emission peak of the exciplex formed with 2 is the triplet ML of the guest material 142 (phosphorescent material). Absorption of CT (Metal to Ligand Charge Transfer) transition The organic compound 141_1, the organic compound 142_2, and the organic compound 143_3 were used to overlap the absorption band of the longest wavelength. It is preferable to select an organic compound 141_2 and a guest material 142 (phosphorescent material). This allows the light-emitting element to have a dramatically improved luminous efficiency. When a thermally activated delayed fluorescent material is used instead of the conventional material, the absorption band at the longest wavelength side is a single band. It is preferable that the absorption band is

[0090] As the organic compound 141_2, the following material having a high hole transporting property can be used: Cut.

[0091] As a material with high hole transport properties, 1×10 -6 cm 2 / Vs or higher hole mobility Specifically, aromatic amines, carbazole derivatives, aromatic carbons, etc. The hole transport material may be a polymer. It may also be a compound.

[0092] As the material having high hole transporting properties, specifically, aromatic amine compounds such as N, N'-Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as DT DPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyla N,N'-bis[4-[bis(3-methylphenyl) {N,N'-diphenyl-(1,1'-biphenyl)-4,4' -diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylamino) [phenyl]-N-phenylamino]benzene (abbreviation: DPA3B), etc. .

[0093] Specific examples of carbazole derivatives include 3-[N-(4-diphenylamino phenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1 ), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9 -phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenyl [N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation PCzTPN2), 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl 3,6-bis[N- (9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol PCzPCA2, 3-[N-(1-naphthyl)-N-(9-phenylcarbazone] [carbazol-3-yl]amino]-9-phenylcarbazole (abbreviation: PCzPCN1) The following can be mentioned:

[0094] Other carbazole derivatives include 4,4'-di(N-carbazolyl)biphene. 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] nyl]-2,3,5,6-tetraphenylbenzene, etc. can be used.

[0095] Furthermore, examples of aromatic hydrocarbons include 2-tert-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 thracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl) phenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene Helical anthracene (abbreviated as DNA), 9,10-diphenylanthracene (abbreviated as DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 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(2-naphthyl)anthracene thyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'- Bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl , 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9' -Bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11- tetra(tert-butyl)perylene, etc. In addition, pentacene, Years etc. can also be used. In this way, 1 × 10 -6 cm 2 Hole mobility above / Vs It is more preferable to use an aromatic hydrocarbon having 14 to 42 carbon atoms.

[0096] The aromatic hydrocarbon may have a vinyl skeleton. Examples of aromatic hydrocarbons include 4,4'-bis(2,2-diphenylvinyl)biphenyl. (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl] anthracene (abbreviation: DPVPA), etc.

[0097] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl ether) Nylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. can.

[0098] Furthermore, examples of materials with high hole transport properties include 4,4'-bis[N-(1-naphthyl)-2-methyl-2-propanol]. N,N'-(phenyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD) Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4, 4'-diamine (abbreviation: TPD), 4,4',4''-tris(carbazol-9-yl) ) triphenylamine (abbreviation: TCTA), 4,4',4''-tris[N-(1-naphthyl) 4,4-Triphenylamine (abbreviation: 1'-TNATA) ',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDAT A), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino] Triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9' -bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4 -phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenyl Nylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluorene-2 -yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl -9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamino N-(9,9-dimethyl-2-diphenylamino-9H- Fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenyl) N-phenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl) Triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1B) P), 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 (abbreviated as PCBN BB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)a amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazol-3-yl) -N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N', N''-triphenyl-N,N',N''-tris(9-phenylcarbazole-3-yl) N-(4-biphenyl)benzene-1,3,5-triamine (abbreviation: PCA3B) -N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-chlor PCBiF, N-(1,1'-biphenyl-4-yl) -N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-di Methyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 9,9-dimethyl-N -phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] Fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl -9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-a PCBASF, 2-[N-(9-phenylcarbazol-3-yl)-N -phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bi Spiro-9,9'-[N-(4-diphenylaminophenyl)-N-phenylamino] -bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl) Phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N' -Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9- Aromatic amine compounds such as dimethylfluorene-2,7-diamine (abbreviation: YGA2F) Also, 3-[4-(1-naphthyl)-phenyl]-9-phenyl 3-[4-(9-phenanthryl)-phenyl]-9H-carbazole (abbreviation: PCPN), 3,3'-bis(9-phenyl-9H-carbazole) -phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis(N-carbazole) mCP, 3,6-bis(3,5-diphenylphenyl)-9-fluorobenzene Phenylcarbazole (abbreviation: CzTP), 3,6-di(9H-carbazol-9-yl) -9-phenyl-9H-carbazole (abbreviation: PhCzGI), 2,8-di(9H-carbazole) 4-{3-[3- (9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran ( Abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-trimethyl 1,3,5-tri(dibenzofuran) (abbreviation: DBF3P-II), 2,8-diphenylthiophen-4-yl)-benzene (abbreviation: DBT3P-II) -4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiof fluorene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene- 9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) , 4-[3-(triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mD Amine compounds such as BTP-II, carbazole compounds, thiophene compounds, furan compounds, fluorene compounds, triphenylene compounds, phenanthrene compounds, etc. Among the compounds mentioned above, those having a pyrrole skeleton, a furan skeleton, a thiophene skeleton, an aromatic Compounds having an aromatic amine skeleton are preferred because they are stable and highly reliable. The compound having the formula (I) has high hole transporting properties and contributes to reducing the driving voltage.

[0099] The guest material 142 (phosphorescent material) is an iridium, rhodium, or platinum-based organic material. Metal complexes, or metal complexes, among which organic iridium complexes, e.g., iridium The orthometalated complex is preferably a 4H-triazole. Ligand, 1H-triazole ligand, imidazole ligand, pyridine ligand, pyrimidine The metal complexes include a pyrazine ligand, an isoquinoline ligand, and the like. Examples include platinum complexes having porphyrin ligands.

[0100] In addition, as the guest material 142 (phosphorescent material), the LUMO level of the organic compound 141_1 It has a lower LUMO level and a lower HOMO level than the HOMO level of organic compound 141_2. The organic compound 141_1, the organic compound 141_2, and the guest material 14 It is preferable to select 2 (phosphorescent material). This allows for high luminous efficiency and low driving voltage. The light emitting element may be a light emitting element that moves.

[0101] Examples of substances having a blue or green emission peak include tris{2-[5-(2 -methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazo {3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: Ir(mpp tz-dmp)3), tris(5-methyl-3,4-diphenyl-4H-1,2,4-trimethyl- Triazolato)iridium(III) (abbreviation: Ir(Mptz)3), tris[4-(3- Biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]i Iridium(III) (abbreviation: Ir(iPrptz-3b)3), tris[3-(5-biphenyl] (phenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]irid Ir(III) (abbreviated as Ir(iPr5btz)3), a 4H-triazole skeleton and organometallic iridium complexes with tris[3-methyl-1-(2-methylphenyl) -5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: Ir (Mptz1-mp)3), tris(1-methyl-5-phenyl-3-propyl-1H- 1,2,4-Triazolate)iridium(III) (abbreviation: Ir(Prtz1-Me) 3) and fac-triazole-based organometallic iridium complexes. S[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]isopropyl Iridium(III) (abbreviation: Ir(iPrpmi)3), tris[3-(2,6-dimethyl phenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(I II) Imidazole skeleton-containing compounds such as Ir(dmpimpt-Me) Organic metal iridium complexes and bis[2-(4',6'-difluorophenyl)pyridinato- N,C 2’]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FI r6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]Ili Dium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis (Trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) pico Ir(CF3ppy)2(pic) (fluorophenyl)pyridinato-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIr(acac)) Among the above, 4H-triazole is an organometallic iridium complex. a nitrogen-containing five-membered heterocyclic skeleton such as a 1H-triazole skeleton and an imidazole skeleton; The organometallic iridium complexes have high triplet excitation energy and are highly reliable and highly efficient. It is particularly preferred because it is also excellent in

[0102] Furthermore, examples of substances having a green or yellow emission peak include tris(4-methylphenyl) Ir(mppm)3, Tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: I r(tBuppm)3), (acetylacetonato)bis(6-methyl-4-phenylpyridine) Iridium(III) (abbreviation: Ir(mppm)2(acac)), (acetylacetonate ruacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium( III) (Abbreviation: Ir(tBuppm)2(acac)), (acetylacetonato)bis [4-(2-norbornyl)-6-phenylpyrimidinato]iridium(III) (abbreviation : Ir(nbppm)2(acac)), (acetylacetonato)bis[5-methyl-6 -(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: Ir(mpmppm)2(acac)), (acetylacetonato)bis{4,6-dimethyl 2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl- κC}iridium(III) (abbreviation: Ir(dmppm-dmp)2(acac)), ( acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III)( Organometallic iridium compounds with pyrimidine skeletons, such as Ir(dppm)2(acac) complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazine Iridium(III) (abbreviation: Ir(mppr-Me)2(acac)), (acetyl arylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridide Pyrazine skeletons such as Ir(III) (abbreviation: Ir(mppr-iPr)2(acac)) Organometallic iridium complexes and tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N ,C 2’ ) Iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(ac ac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), tris(benzo[h]quinolinato)iridium Ir(III) (abbreviation: Ir(bzq)3), tris(2-phenylquinolinato-N,C 2 ’) Iridium(III) (abbreviation: Ir(pq)3), bis(2-phenylquinolinato- N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: Ir(pq)2(ac Organometallic iridium complexes with pyridine skeletons such as bis(2,4-difluorophenyl)- ... Phenyl-1,3-oxazolato-N,C 2’ ) Iridium(III) acetylacetoner Ir(dpo)2(acac)), bis{2-[4'-(perfluorophenyl) (phenyl)pyridinato-N,C 2’}Iridium(III) acetylacetonate( Abbreviation: Ir(p-PF-ph)2(acac)), bis(2-phenylbenzothiazol- -N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: Ir(bt)2(a In addition to organometallic iridium complexes such as tris(acetylacetonato)(monophenyl) Anthroline) terbium(III) (abbreviation: Tb(acac)3(Phen)) Among the above, organometallic iridium complexes having a pyrimidine skeleton are Dium complexes are particularly preferred because they are remarkably excellent in reliability and luminous efficiency.

[0103] Furthermore, examples of substances having a yellow or red emission peak include (diisobutyryl) Methanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(II I) (abbreviation: Ir(5mdppm)2(dibm)), bis[4,6-bis(3-methyl [phenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: Ir (5mdppm)2(dpm)), bis[4,6-di(naphthalen-1-yl)pyrimidinyl] Nato](dipivaloylmethanato)iridium(III) (abbreviation: Ir(d1npm)2( Organometallic iridium complexes with pyrimidine skeletons, such as (acetylacetonyl acetone) Iridium(III) (abbreviation: I r(tppr)2(acac)), bis(2,3,5-triphenylpyrazinate)(dipyr Valoylmethanato)iridium(III) (abbreviation: Ir(tppr)2(dpm)), ( Acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]i Ir(Fdpq)2(acac) and other pyrazine-based compounds Organometallic iridium complexes and 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( In addition to organometallic iridium complexes with pyridine skeletons such as acac), 2,3,7, 8,12,13,17,18-Octaethyl-21H,23H-porphyrin platinum(II) ) (abbreviation: PtOEP) and tris(1,3-diphenyl-1,3-propanediol). Eu(DB)(propanedionato)(monophenanthroline)europium(III) M)3(Phen)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetate [Tonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3( Among the above, rare earth metal complexes such as pyrimidine skeletons are Organometallic iridium complexes having the above structure are particularly preferred because they are remarkably excellent in reliability and luminous efficiency. In addition, organometallic iridium complexes with a pyrazine skeleton can emit red light with good chromaticity. can be done.

[0104] Among the above-mentioned iridium complexes, organic gold complexes having a pyrimidine skeleton or a pyrazine skeleton are also suitable. In iridium complexes, the ligands have high electron-accepting properties and tend to have low LUMO levels. This is suitable for one aspect of the present invention. Compounds with electron-withdrawing substituents such as iridium complexes also have LUMO levels This is preferable because the

[0105] The light-emitting material contained in the light-emitting layer 140 is a material capable of converting triplet excitation energy into light. The material capable of converting triplet excitation energy into luminescence is a phosphorescent material. In addition to this, thermally activated delayed fluorescence Therefore, phosphorescent materials are also known as The above-mentioned part may be read as a thermally activated delayed fluorescent material. Delayed fluorescent materials are materials with a small difference between the triplet excitation energy level and the singlet excitation energy level. The function of converting energy from a triplet excited state to a singlet excited state by reverse intersystem crossing. Therefore, the triplet excited state can be converted to the singlet state by a small amount of thermal energy. It is possible to upconvert to an excited state (reverse intersystem crossing) and emit light (fluorescence) from the singlet excited state. ) can be efficiently exhibited. In addition, the conditions for efficiently obtaining thermally activated delayed fluorescence are In this case, the energy difference between the triplet excitation energy level and the singlet excitation energy level is preferably is greater than 0 eV and less than or equal to 0.2 eV, more preferably greater than 0 eV and less than or equal to 0.1 eV The following points can be mentioned.

[0106] When the thermally activated delayed fluorescent material is composed of one kind of material, for example, the following material is used: It is possible.

[0107] First, fullerene and its derivatives, acridine derivatives such as proflavine, and eosin are listed. In addition, magnesium (Mg), zinc (Zn), cadmium (Cd), tin (S n), platinum (Pt), indium (In), or palladium (Pd) Examples of the metal-containing porphyrin include protoporphyrin. Porphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-fluoride Tin complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (Sn F2 (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride Complex (SnF2(Copro III-4Me)), Octaethylporphyrin-Fluoride Tin complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(E tio I)), octaethylporphyrin-platinum chloride complex (PtCl2OEP), etc. It can be obtained.

[0108] In addition, as a thermally activated delayed fluorescent material composed of one kind of material, π-electron-rich heteroaromatic Heterocyclic compounds having an aromatic ring and a π-electron-deficient heteroaromatic ring can also be used. is 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3- a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol {4,6-diphenyl-1,3,5-triazine (PC CzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4, 6-Diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5- Phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl 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-DPS), 10-phenyl-10H,10'H-spiro[acridine -9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. The heterocyclic compounds have a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, Among them, a skeleton having a π-electron-deficient heteroaromatic ring is preferred. Among them, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton) and triazine skeleton The azine skeleton is preferred because it is stable and reliable. Among the skeletons that have such structures, acridine skeleton, phenoxazine skeleton, thiophene skeleton, and furan skeleton are Since the pyrrole skeleton and the pyrrole skeleton are stable and reliable, any of the skeletons can be used. It is preferable that the pyrrole skeleton has one or more of the following. skeleton, a carbazole skeleton, and 3-(9-phenyl-9H-carbazol-3-yl)- A 9H-carbazole skeleton is particularly preferred. The substance in which the π-electron-rich heteroaromatic ring is directly bonded to the π-electron-deficient heteroaromatic ring exhibits the donor property of the π-electron-rich heteroaromatic ring. The acceptor properties of both heteroaromatic rings are strong, and the levels of the singlet excited state and the triplet excited state are high. This is particularly preferable because the difference in the level is small.

[0109] The light-emitting layer 140 may be composed of two or more layers. When the light-emitting layer 140 is formed by laminating the first light-emitting layer and the second light-emitting layer in this order from the hole transport layer side, a substance having hole transporting properties is used as a host material for the first light-emitting layer, and a substance having hole transporting properties is used as a host material for the second light-emitting layer In addition, a structure in which a substance having an electron transporting property is used as the first light-emitting layer and the second light-emitting layer is also available. The light-emitting materials in the optical layer and the optical layer may be the same or different materials, and they may emit light of the same color. Even if the material has a function of emitting light, it may have a function of emitting light of different colors. The two light-emitting layers may contain light-emitting materials that emit light of different colors. By using each of these layers, multiple light emissions can be obtained simultaneously. It is preferable to select a light-emitting material for each light-emitting layer so that the resulting light emitted will be white.

[0110] In addition, in the light-emitting layer 140, materials other than the host material 141 and the guest material 142 are It may have.

[0111] The light-emitting layer 140 can be formed by a deposition method (including a vacuum deposition method), an ink-jet method, a coating method, a grating method, or the like. It can be formed by a method such as rabbet printing. In addition to the above-mentioned materials, quantum dots and the like can also be used. Even if the inorganic compound or polymer compound (oligomer, dendrimer, polymer, etc.) good.

[0112] <Hole injection layer> The hole injection layer 111 is formed by injecting holes from one of the pair of electrodes (electrode 101 or electrode 102). It has the function of promoting hole injection by reducing the injection barrier, and is used in materials such as transition metal oxides and fluorine. It is formed by phthalocyanine derivatives or aromatic amines. Examples include molybdenum oxide, vanadium oxide, ruthenium oxide, and tungsten oxide. , manganese oxide, etc. Phthalocyanine derivatives include phthalocyanine, Examples of aromatic amines include benzidine derivatives and phenyl Diamine derivatives, etc. Polymer compounds such as polythiophene and polyaniline Materials such as self-doped polythiophenes, poly(ethylenediamines), can also be used. Typical examples include poly(oxythiophene) / poly(styrenesulfonic acid).

[0113] The hole injection layer 111 is made of a compound material including a hole transporting material and a material that exhibits electron accepting properties. Alternatively, a layer containing a material exhibiting electron accepting properties and a layer containing a material exhibiting electron accepting properties may be used. A stack of layers containing hole transport materials may also be used. It is possible to exchange charges in the presence of a magnetic field. Materials that exhibit electron-accepting properties include quinodimethane. Organic acceptors such as benzophenone derivatives, chloranil derivatives, and hexaazatriphenylene derivatives Specifically, 7,7,8,8-tetracyano-2,3,5,6- Tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7, 10,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation These compounds have electron-withdrawing groups (halogen groups or cyano groups), such as hydroxybenzoates (HAT-CN). In addition, transition metal oxides, for example, oxides of metals from Groups 4 to 8, can be used. In general, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, These include tungsten oxide, manganese oxide, and rhenium oxide. Among these, it is preferred because it is stable, has low hygroscopicity, and is easy to handle.

[0114] As the hole transporting material, a material having a higher hole transporting property than an electron transporting property can be used. x10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. The aromatic amines and carboxylic acids listed as examples of hole transport materials that can be used in the light-emitting layer 140 are Also usable are benzol derivatives, aromatic hydrocarbons, stilbene derivatives, etc. The hole transporting material may be a polymer compound.

[0115] <Hole transport layer> The hole transport layer 112 is a layer containing a hole transport material. The hole transporting layer 112 can be formed by the hole injection layer 111. Since the hole injection layer 111 has a function of transporting the injected holes to the light emitting layer 140, the highest coverage of the hole injection layer 111 is Highest Occupied Molecular Orbital (H It is preferable that the HOMO level be the same as or close to the OMO level.

[0116] Also, 1×10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. However, other substances may be used as long as they have a higher hole transporting property than electron transporting property. The layer containing a substance with a high hole transporting property may be a single layer or a double layer of the above substance. More than one layer may be laminated.

[0117] ≪Electron transport layer≫ The electron transport layer 118 is connected to the other of the pair of electrodes (electrode 101 or electrode 102) via the electron injection layer 119. The electron transport material has a function of transporting electrons injected from the electrode 102 to the light-emitting layer 140. As the material, a material with higher electron transportability than holes can be used, and the -6 cm 2 It is preferable that the material has an electron mobility of 1 / Vs or more. As materials (materials with electron transport properties), π-electron deficient materials such as nitrogen-containing heteroaromatic compounds are Heteroaromatic compounds and metal complexes can be used. Specifically, quinoline ligands, benzo Metal complexes with quinoline, oxazole, or thiazole ligands, Quinoxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline Derivatives, dibenzoquinoxaline derivatives, phenanthroline derivatives, pyridine derivatives, bipyridin derivatives Examples include lysine derivatives, pyrimidine derivatives, and triazine derivatives. -6 cm 2 It is preferable that the material has an electron mobility of 1 / Vs or more. Any substance other than those mentioned above may be used for the electron transport layer as long as it has a high electron transporting property. The electron transport layer 118 may be formed not only as a single layer, but also as a laminate of two or more layers made of the above-mentioned materials. That's fine.

[0118] In addition, a layer for controlling the movement of electron carriers is provided between the electron transport layer 118 and the light emitting layer 140. The layer for controlling the movement of electron carriers may be made of a material having high electron transport properties as described above. A layer in which a small amount of a substance with high electron trapping properties is added to the By doing so, it becomes possible to adjust the carrier balance. Suppression of problems caused by electrons penetrating the optical layer (such as reduced device lifespan) has a great effect on.

[0119] ≪Electron injection layer≫ The electron injection layer 119 promotes electron injection by reducing the electron injection barrier from the electrode 102. For example, Group 1 metals, Group 2 metals, or their oxides and halides In addition, the electron transport material and the corresponding electron transport material can be used. A composite material of a material exhibiting electron donating properties can also be used. Examples include Group 1 metals, Group 2 metals, and oxides thereof. are lithium fluoride (LiF), sodium fluoride (NaF), and cesium fluoride (CsF ), calcium fluoride (CaF2), lithium oxide (LiO x ) and other alkaline gold Metals, alkaline earth metals, or compounds thereof can be used. A rare earth metal compound such as erbium (ErF3) can be used. An electride may be used for 119. The electride may be, for example, calcium. Examples include a material in which electrons are highly concentrated in a mixed oxide of aluminum and silicon. The injection layer 119 may be made of a material that can be used in the electron transport layer 118 .

[0120] The electron injection layer 119 may contain a composite material formed by mixing an organic compound and an electron donor (donor). Such composite materials may be formed by electron donors giving electrons to organic compounds. In this case, the organic compound is It is preferable that the material is excellent in transporting the generated electrons. Specifically, for example, the above-mentioned The material constituting the electron transport layer 118 (metal complex, heteroaromatic compound, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to organic compounds. For the metal, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, sodium , cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of oxides include sodium oxide and barium oxide. Lewis oxides such as magnesium oxide are also included. A base can also be used. In addition, organic compounds such as tetrathiafulvalene (TTF) can be used. You can also use objects.

[0121] The above-mentioned light-emitting layer, hole-injection layer, hole-transport layer, electron-transport layer, and electron-injection layer are These methods include vapor deposition (including vacuum deposition), inkjet printing, coating, and gravure printing. The light-emitting layer, the hole-injecting layer, the hole-transporting layer, the electron In addition to the materials mentioned above, inorganic compounds such as quantum dots and high molecular weight compounds can be used for the transport layer and electron injection layer. A polymer compound (oligomer, dendrimer, polymer, etc.) may also be used.

[0122] Quantum dots include colloidal quantum dots, alloy quantum dots, and core-shell quantum dots. It is also possible to use quantum dots of the 2nd group and the 16th group, quantum dots of the 13th group, and the like. Contains element groups from group 15, 13 and 17, 11 and 17, or 14 and 15 Quantum dots may also be used. Alternatively, cadmium (Cd), selenium (Se), zinc (Zn ), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium Quantum dots containing elements such as Ga, As, and Al are used. It's fine.

[0123] <Pair of electrodes> The electrode 101 and the electrode 102 function as an anode or a cathode of the light-emitting element. The electrode 101 and the electrode 102 may be made of a metal, an alloy, a conductive compound, or a mixture or laminate thereof. It can be formed using the following.

[0124] One of the electrodes 101 and 102 is made of a conductive material that has a function of reflecting light. The conductive material is preferably aluminum (Al) or a compound containing Al. Examples of alloys containing Al include Al and L (L is titanium (Ti), neodymium (Ne), etc. (representing one or more of Nd, Ni, and La) Examples of suitable alloys include alloys containing Al and Ti, or alloys containing Al, Ni and La. Aluminum has low resistance and high light reflectivity. Since aluminum is abundant and inexpensive, the cost of manufacturing a light-emitting element using aluminum is reduced. In addition, silver (Ag) or Ag and N (N) can be used in combination with yttrium ( Y), Nd, magnesium (Mg), ytterbium (Yb), Al, Ti, gallium ( Ga), zinc (Zn), indium (In), tungsten (W), manganese (Mn), Tin (Sn), iron (Fe), Ni, copper (Cu), palladium (Pd), iridium (Ir ), or an alloy containing gold (Au), etc. Examples of alloys containing silver include alloys containing silver, palladium, and copper, alloys containing silver and copper, and alloys containing silver and magnesium. Alloys containing nesium, alloys containing silver and nickel, alloys containing silver and gold, silver and ytterbium Other examples include alloys containing tungsten, chromium (Cr), molybdenum (Mo ), copper, titanium, and other transition metals can be used.

[0125] The light emitted from the light-emitting layer is emitted through one or both of the electrodes 101 and 102. Therefore, at least one of the electrodes 101 and 102 is transparent to light. It is preferable that the conductive material is made of a conductive material having a function of transmitting visible light. The light transmittance is 40% or more and 100% or less, preferably 60% or more and 100% or less, and Its resistivity is 1×10 -2 Examples include conductive materials with a resistance of Ω·cm or less.

[0126] The electrodes 101 and 102 have a function of transmitting light and a function of reflecting light. The conductive material may be formed of a conductive material having a visible light reflectance of 20 or less. % or more and 80% or less, preferably 40% or more and 70% or less, and the resistivity is 1×10 -2 Conductive materials with a resistance of Ω·cm or less include metals, alloys, and conductive materials. The layer can be formed by using one or more of the following compounds. Indium Tin Oxide (ITO), silicon or silicon oxide Indium tin oxide (ITSO), indium oxide-zinc oxide (Indi Indium tin oxide containing titanium, indium tin oxide, Metals such as indium oxide containing titanium oxide, tungsten oxide, and zinc oxide Oxides can be used. In addition, the thickness of the oxide is preferably within a range of 1 nm to 30 nm. A metal thin film having a thickness of 1 μm or less can be used. Examples of metals include Ag, Alloys such as Ag and Al, Ag and Mg, Ag and Au, and Ag and Yb can be used.

[0127] In this specification and the like, a material having a function of transmitting light refers to a material having a function of transmitting visible light. Any material having the above and having electrical conductivity may be used, and examples thereof include ITO. In addition to oxide conductors, oxide semiconductors or organic conductors containing organic materials are also included. The organic conductor may be, for example, a mixture of an organic compound and an electron donor. Examples of such materials include composite materials, and composite materials made by mixing organic compounds and electron acceptors. Alternatively, inorganic carbon materials such as graphene may be used. The ratio is preferably 1×10 5 Ω·cm or less, more preferably 1×10 4 Ω cm The following is the result.

[0128] In addition, by laminating a plurality of the above materials, one or both of the electrodes 101 and 102 can be formed. may form both.

[0129] In order to improve the light extraction efficiency, the electrode is in contact with the light-transmitting electrode. A material having a higher refractive index than the electrode may be used. Any material that has the function of providing the desired electrical conductivity may be used. For example, in addition to the oxide conductors described above, oxide semiconductors and organic materials can be used. The organic material may be, for example, a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, or an electron transport layer. The materials exemplified for the electron injection layer are also usable. Inorganic carbon materials and thin films that are light-transmitting are also usable. These high refractive index materials can be used to form thin films with a size of several nanometers to several tens of nanometers. A plurality of layers may be laminated.

[0130] When the electrode 101 or the electrode 102 functions as a cathode, the work function is small. (3.8 eV or less) materials. For example, materials in Group 1 or 2 of the Periodic Table of Elements. Elements belonging to the group (alkali metals such as lithium, sodium, and cesium, calcium, strontium, etc.) Alkaline earth metals such as rontium, magnesium, etc.), alloys containing these elements (e.g., Rare earth metals such as Ag and Mg, Al and Li), europium (Eu), Yb, etc. An alloy containing a metal, such as an alloy containing aluminum or silver, can be used.

[0131] Furthermore, when the electrode 101 or the electrode 102 is used as an anode, a material having a large work function (4. It is preferable to use a material having a refractive index of 0 eV or more.

[0132] The electrodes 101 and 102 are made of a conductive material that reflects light and a light-transmitting material. In this case, the electrode 101 and the electrode 102 may be laminated with a conductive material having a permeability function. 02 resonates the desired light from each light-emitting layer, allowing the light of that wavelength to be intensified. This is preferable because it can have the function of adjusting the optical distance.

[0133] The electrode 101 and the electrode 102 can be formed by a sputtering method, a vapor deposition method, a printing method, or a coating method. , MBE (Molecular Beam Epitaxy) method, CVD method, pulse laser The deposition method, ALD (Atomic Layer Deposition) method, etc. are used appropriately. It is possible.

[0134] <Substrate> Furthermore, the light-emitting element according to one embodiment of the present invention may be formed on a substrate made of glass, plastic, or the like. As for the order of fabrication on the substrate, the layers may be stacked in order from the electrode 101 side. They may be stacked in order from the pole 102 side.

[0135] The substrate on which the light-emitting element according to one embodiment of the present invention can be formed is, for example, glass or quartz. Alternatively, a flexible substrate may be used. The substrate is a flexible substrate, such as polycarbonate. Examples of suitable substrates include plastic substrates made of vinyl acetate and polyarylate. Inorganic vapor deposition films can also be used. Any other material may be used as long as it functions as a support in the development. Anything that has the function of protecting the optical element and the optical device may be used.

[0136] As described above, the structure shown in this embodiment mode can be used in appropriate combination with other embodiment modes. Cut.

[0137] (Embodiment 2) In this embodiment, a light emitting element (hereinafter also referred to as a stacked element) having a structure in which a plurality of light emitting units are stacked is The embodiment of the light-emitting element (hereinafter referred to as "light-emitting element") will be described with reference to FIG. It is a light-emitting element having a plurality of light-emitting units between electrodes. It has the same structure as the EL layer 103 shown in the first embodiment. The light-emitting element is a light-emitting element having one light-emitting unit, and in this embodiment, It can be said to be a light emitting element having an optical unit.

[0138] <Configuration example 3 of light-emitting element> FIG. 3 is a schematic cross-sectional view of the light emitting element 250. As shown in FIG.

[0139] The light-emitting element 250 shown in FIG. 3 has a plurality of electrodes between a pair of electrodes (electrode 101 and electrode 102). 3, the light-emitting unit 106 and the light-emitting unit 108. Any one of the plurality of light-emitting units is shown in FIG. 1(A) and FIG. 1(B). ) is preferably configured similarly to the EL layer 100 shown in FIG. The light emitting element 150 shown in B) has one light emitting unit, and the light emitting element 250 has multiple light emitting units. It is preferable that the light emitting element 250 has a light emitting unit. The following description will be given assuming that the electrode 101 functions as a cathode and the electrode 102 functions as a cathode. The configuration may be reversed.

[0140] In addition, in the light-emitting element 250 shown in FIG. 3, the light-emitting unit 106 and the light-emitting unit 108 The light-emitting unit 106 and the light-emitting unit 108 are laminated together, and a charge generating layer 1 is provided between the light-emitting unit 106 and the light-emitting unit 108. The light-emitting units 106 and 108 have the same configuration but are different. For example, the light-emitting unit 108 may have a configuration as shown in FIG. It is preferable to use an L layer 100 .

[0141] The light emitting element 250 has a light emitting layer 120 and a light emitting layer 170. In addition to the light-emitting layer 120, the knit 106 includes a hole injection layer 111, a hole transport layer 112, an electron transport layer The light-emitting unit 108 also includes a light-emitting layer 170. In addition to the above, a hole injection layer 116, a hole transport layer 117, an electron transport layer 118, and an electron injection layer 11 It has 9.

[0142] The charge generation layer 115 is made of a material having a hole transporting property to which an acceptor material, which is an electron acceptor, is added. Even if the structure is such that a donor substance, which is an electron donor, is added to the electron transporting material, Alternatively, both of these structures may be laminated.

[0143] When the charge generation layer 115 contains a composite material of an organic compound and an acceptor substance, the composite material The composite material that can be used for the hole-injection layer 111 shown in Embodiment 1 is used as the composite material. The organic compound may be an aromatic amine compound, a carbazole compound, an aromatic Various compounds such as hydrocarbons and polymeric compounds (oligomers, dendrimers, polymers, etc.) As the organic compound, a compound having a hole mobility of 1×10 -6 cm 2 / It is preferable to use a substance with a Vs or higher. However, Other materials may be used as long as they are materials. The material has excellent carrier injection and transport properties, allowing low voltage and low current operation. It should be noted that the anode side surface of the light-emitting unit is in contact with the charge generating layer 115. In this case, the charge generating layer 115 also serves as a hole injection layer or a hole transport layer for the light emitting unit. Therefore, the light-emitting unit does not need to have a hole injection layer or a hole transport layer. Alternatively, when the cathode side surface of the light-emitting unit is in contact with the charge generating layer 115, In this case, the charge generation layer 115 also serves as an electron injection layer or an electron transport layer of the light-emitting unit. Therefore, the light-emitting unit does not have an electron injection layer or an electron transport layer. That's fine.

[0144] The charge generating layer 115 may be a layer containing a composite material of an organic compound and an acceptor substance, or another layer containing a compound of an organic compound and an acceptor substance. It may be formed as a laminated structure combining layers made of materials. A layer containing a composite material of a compound and an acceptor material, and a layer containing a compound selected from electron donor materials. Alternatively, a layer containing an organic compound and a layer containing a compound having high electron transporting properties may be combined. A layer containing a composite material of a compound and an acceptor substance and a layer containing a transparent conductive film are combined. It may be formed.

[0145] The charge generating layer 115 sandwiched between the light emitting unit 106 and the light emitting unit 108 When a voltage is applied between the electrode 101 and the electrode 102, electrons are injected into one of the light-emitting units, It is sufficient if it injects holes into the other light-emitting unit. For example, in FIG. When a voltage is applied so that the potential of electrode 101 is higher than the potential of electrode 102, charge generation Layer 115 injects electrons into light-emitting unit 106 and holes into light-emitting unit 108. .

[0146] From the viewpoint of light extraction efficiency, the charge generation layer 115 is transparent to visible light (specifically, It is preferable that the charge generating layer 115 has a visible light transmittance of 40% or more. The charge generating layer 115 has a lower conductivity than the pair of electrodes (electrodes 101 and 102). It still works.

[0147] By forming the charge generating layer 115 using the above-mentioned materials, when a light emitting layer is laminated, In this case, the increase in the driving voltage can be suppressed.

[0148] In addition, as shown in the first embodiment, the light-emitting layer 140 or the light-emitting layer 170 may be formed of a material selected from the group consisting of fluorine, methyl methacrylate ... Two bipolar materials are used for each of the two host materials, and the LUMO level between the bipolar materials is By adjusting the HOMO level, the driving voltage can be further reduced.

[0149] The charge generation layer 115 is made up of a layer containing a composite material of an organic compound and a metal oxide and a layer containing other materials. For example, a layer structure including an organic compound and a metal compound may be used. a layer containing a composite material of a metal oxide, a compound selected from electron donating materials, and an electron transporting material; Alternatively, a layer containing an organic compound and a metal oxide may be formed in combination. Alternatively, a layer containing a composite material of a fluorine-containing compound and a transparent conductive film may be combined.

[0150] In either case, the charge generating layer 11 sandwiched between the light emitting unit 106 and the light emitting unit 108 5, when a voltage is applied between the first electrode 101 and the second electrode 102, one of the light-emitting units It is sufficient if electrons are injected into one light-emitting unit and holes are injected into the other light-emitting unit. 3, the voltage is set so that the potential of the first electrode 101 is higher than the potential of the second electrode. When a voltage is applied, the charge generating layer 115 injects electrons into the light emitting unit 106, Any device that can inject holes into the gate 108 may be used.

[0151] In this embodiment, the light emitting element having two light emitting units has been described. However, the light emitting element having three or more light emitting units may be The present invention can be similarly applied to a light-emitting device in which the light-emitting units are stacked. As in the light-emitting device according to the embodiment, a plurality of light-emitting units are separated by a charge generating layer between a pair of electrodes. By cutting and arranging the LEDs, high brightness light emission is possible while keeping the current density low, and furthermore, long life is achieved. Furthermore, it is possible to realize a light-emitting device that can be driven at a low voltage and consumes little power. This can be done.

[0152] In each of the above configurations, the gates used in the light-emitting units 106 and 108 The light emitting colors of the light emitting materials may be the same or different. The guest unit 106 and the light-emitting unit 108 have the function of emitting light of the same color. When the material is included, the light emitting element 250 becomes a light emitting element that exhibits high light emitting luminance with a small current value. It is more preferable that the light emitting units 106 and 108 emit light of different colors. When the light-emitting element 250 includes a guest material having a light-emitting function, the light-emitting element 250 can emit multicolor light. In this case, either one of the light-emitting layer 120 and the light-emitting layer 170 or In both cases, the light emitting element 250 is formed by using a plurality of light emitting materials with different emission wavelengths. The emission spectrum is a composite of light with different emission peaks, so Both result in an emission spectrum with two maxima.

[0153] The above-mentioned structure is also suitable for obtaining white light emission. By making the lights complementary to each other, white light can be emitted. The resulting white light is highly luminescent, or at least has red, green, and blue components. It is preferable to select a suitable material.

[0154] In addition, at least one of the light-emitting layer 120 and the light-emitting layer 170 is further divided into layers, Each divided layer may contain a different light-emitting material. Alternatively, at least one of the light-emitting layers 170 may be composed of two or more layers. For example, the first light-emitting layer and the second light-emitting layer can be laminated in this order from the hole transport layer side to form the light-emitting layer. In this case, a material having hole transport properties is used as the host material of the first light-emitting layer, and a material having hole transport properties is used as the host material of the second light-emitting layer. In this case, a material having an electron transporting property is used as the host material. The light-emitting materials in the light-emitting layer and the second light-emitting layer may be the same or different. Even if a material has the function of emitting light of the same color, it may have the function of emitting light of different colors. The material may be a material having the following characteristics: By using a material with a structure that includes three primary colors or four or more colors, it is possible to obtain white light with high color rendering. It is also possible to do so.

[0155] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0156] (Embodiment 3) In this embodiment mode, a light-emitting device using the light-emitting element described in Embodiment Mode 1 and Embodiment Mode 2 is This will be explained with reference to FIG. 4(A) and FIG. 4(B).

[0157] FIG. 4(A) is a top view showing a light-emitting device, and FIG. 4(B) is a cross-sectional view of FIG. 4(A) along lines AB and CD. This light emitting device is a cross-sectional view of a light emitting element. The illustrated drive circuit section (source side drive circuit) 601, pixel section 602, drive circuit section (gate side The driving circuit 603 is also included. 604 is a sealing substrate, 625 is a desiccant, and 605 is a shielding material. The inside surrounded by the sealing material 605 is a space 607 .

[0158] The lead wiring 608 is connected to the source side driver circuit 601 and the gate side driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. Even if a printed wiring board (PWB) is installed The light emitting device in this specification includes not only the light emitting device itself but also an FPC or This includes the state where the PWB is installed.

[0159] Next, a cross-sectional structure of the light emitting device will be described with reference to FIG. The driving circuit section and the pixel section are formed in the pixel section. A circuit 601 and one pixel in a pixel portion 602 are shown.

[0160] The source side driver circuit 601 includes an n-channel TFT 623 and a p-channel TFT 624. The drive circuit is a CMOS circuit that combines various CMOS circuits, P It may be formed of a MOS circuit or an NMOS circuit. Although this shows a driver integrated type in which the driver circuit is formed on the board, this is not necessarily required. It can also be formed externally.

[0161] The pixel section 602 includes a switching TFT 611, a current control TFT 612, and its drain. The pixel includes a first electrode 613 electrically connected to the first An insulator 614 is formed to cover the end of the electrode 613. It can be formed by using a photosensitive resin film of a mold.

[0162] In addition, in order to improve the coverage of the film formed on the insulator 614, The upper end or the lower end of the insulator 614 is formed to have a curved surface. When photosensitive acrylic is used as the material, it is possible to make only the upper end of the insulator 614 curved. The radius of curvature of the curved surface is preferably 0.2 μm or more and 0.3 μm or less. The border 614 may be either a negative or positive photosensitive material.

[0163] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a large material, for example, an ITO film or an indium-silicon-containing film. Indium tin oxide film, indium oxide film containing 2wt% to 20wt% zinc oxide, nitride In addition to single layer films such as titanium film, chromium film, tungsten film, Zn film, and Pt film, titanium nitride film and Lamination with a film mainly composed of aluminum, titanium nitride film and a film mainly composed of aluminum A three-layer structure of a titanium nitride film and a silicon dioxide film can be used. The resistance is low, good ohmic contact can be achieved, and it can also function as an anode. This can be done.

[0164] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 can be formed by various methods such as the above. The polymer may be a polymer or a polymer compound (including an oligomer or a dendrimer).

[0165] Furthermore, a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode As the material, materials with a small work function (Al, Mg, Li, Ca, or their alloys or compounds) It is preferable to use a material such as MgAg, MgIn, or AlLi. When the generated light is transmitted through the second electrode 617, the second electrode 617 is formed with a thin film. Thin metal films and transparent conductive films (ITO, containing 2 wt% to 20 wt% zinc oxide) Indium oxide, silicon-containing indium tin oxide, zinc oxide (ZnO), etc. It is better to use layers.

[0166] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting element 618. The light emitting element 618 is a light emitting element having the configurations of the first and second embodiments. It is preferable that the pixel portion is formed with a plurality of light emitting elements. In the light emitting device of the present embodiment, a light emitting device having the configuration described in the first and second embodiments is used. The light-emitting element may include both a light-emitting element and a light-emitting element having other configurations.

[0167] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light emitting element is disposed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. 618 is provided. The space 607 is filled with a filler. In addition to cases where inert gas (nitrogen, argon, etc.) is filled, resin or desiccant or its Sometimes it is filled with both.

[0168] 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 sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic can be used.

[0169] As described above, the light-emitting device using the light-emitting elements described in the first and second embodiments can be obtained.

[0170] <Configuration example 1 of light-emitting device> FIG. 5 shows an example of a display device in which a light emitting element that emits white light is formed, and a coloring layer (color filter) is formed. An example of a light emitting device in which a light emitting diode (LED) filter is formed is shown.

[0171] FIG. 5A shows a substrate 1001, an underlying insulating film 1002, a gate insulating film 1003, and a gate electrode. 1006, 1007, 1008, a first interlayer insulating film 1020, and a second interlayer insulating film 1021 , a peripheral portion 1042, a pixel portion 1040, a driving circuit portion 1041, and a first electrode 102 of the light-emitting element. 4W, 1024R, 1024G, 1024B, partition 1026, EL layer 1028, light-emitting element 10, a second electrode 1029, a sealing substrate 1031, a sealing material 1032, and the like are shown.

[0172] 5(A) and 5(B) show colored layers (red colored layer 1034R, green colored layer 10 34G, blue colored layer 1034B) is provided on the transparent substrate 1033. A black matrix 1035 may be further provided. The transparent substrate 1033 is aligned and fixed to the substrate 1001. The color layer is covered with an overcoat layer 1036. In FIG. 5(A), the light The light-emitting layer emits light to the outside without passing through the colored layer, and the light-emitting layer emits light to the outside by passing through the colored layer of each color. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, blue, or green. This allows images to be expressed using four color pixels.

[0173] In FIG. 5B, a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 103 4B is formed between the gate insulating film 1003 and the first interlayer insulating film 1020. As shown in FIG. 5(B), the colored layer may be provided between the substrate 1001 and the sealing substrate 1031. stomach.

[0174] In the light emitting device described above, light is taken in toward the substrate 1001 on which the TFT is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure.

[0175] <Configuration Example 2 of Light-Emitting Device> A cross-sectional view of a top-emission type light-emitting device is shown in FIG. A connecting electrode that connects the TFT and the anode of the light-emitting element can be formed. The process is the same as that for the bottom emission type light emitting device until the third interlayer is formed. An insulating film 1037 is formed to cover the electrode 1022. This insulating film plays a role of planarization. The third interlayer insulating film 1037 may be made of the same material as the second interlayer insulating film 1021, or other materials. The substrate can be formed using a variety of materials.

[0176] The lower electrodes 1025W, 1025R, 1025G, and 1025B of the light-emitting element are used as anodes. However, it may be a cathode. Also, a top-emission type light-emitting device as shown in FIG. In this case, the lower electrodes 1025W, 1025R, 1025G, and 1025B are reflective electrodes. It is preferable that the second electrode 1029 has a function of reflecting light and a function of transmitting light. It is preferable that the second electrode 1029 and the lower electrodes 1025W, 1025R, and A microcavity structure is applied between 025G and 1025B to amplify light of a specific wavelength. The EL layer 1028 has the same structure as that described in the second embodiment. The device structure is designed to obtain white light emission.

[0177] In Figures 5(A), 5(B), and 6, the EL layer configuration that can obtain white light emission is as follows: This can be achieved by using multiple light-emitting layers or multiple light-emitting units. However, the configuration for obtaining white light emission is not limited to these.

[0178] In the top emission structure shown in Figure 6, the colored layers (red colored layer 1034R, green colored layer The sealing can be performed by a sealing substrate 1031 provided with a blue colored layer 1034G and a blue colored layer 1034B. The sealing substrate 1031 has a black layer (black matrix) positioned between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1035) may be provided. 034G, blue colored layer 1034B) and black layer (black matrix) are overcoated The sealing substrate 1031 may be covered with a transparent layer. .

[0179] Although an example of full-color display using four colors, red, green, blue, and white, is shown here, there is no particular limitation. Alternatively, full color display may be performed using three colors: red, green, and blue. Alternatively, full color display may be performed using four colors: red, green, blue, and yellow. A full color display may be performed.

[0180] As described above, the light-emitting device using the light-emitting elements described in the first and second embodiments can be obtained.

[0181] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0182] (Fourth embodiment) In this embodiment mode, a display device using the light-emitting element described in Embodiment Mode 1 and Embodiment Mode 2 is A specific example of the display device will be described below. The display device illustrated below is a display device that uses a reflective liquid crystal element and a light-emitting A display device having both a transmissive element and a reflective element and capable of displaying in both a transmissive mode and a reflective mode. It is preferable to apply the light emitting devices described in the first and second embodiments to the light emitting device. It's nice.

[0183] <Display device configuration example 1> 7A is a block diagram showing an example of the configuration of the display device 400. The display device 4 has a plurality of pixels 410 arranged in a matrix on the display unit 362. 00 includes a circuit GD and a circuit SD. Also, a plurality of pixels 410 arranged in a direction R, A plurality of wirings G1, a plurality of wirings G2, and a plurality of wirings ANO electrically connected to the circuit GD, and It also has a plurality of wirings CSCOM, a plurality of pixels 410 arranged in a direction C, and a circuit SD The semiconductor device has a plurality of wirings S1 and a plurality of wirings S2 electrically connected to the semiconductor device.

[0184] The pixel 410 has a reflective liquid crystal element and a light emitting element. The substrate and the light-emitting element have overlapping portions.

[0185] 7B1 shows a structural example of the electrode 311b included in the pixel 410. The electrode 311b has: It functions as a reflective electrode for the liquid crystal element in the pixel 410. The electrode 311b also has an opening 4 51 is provided.

[0186] In FIG. 7(B1), the light emitting element 360 located in the area overlapping with the electrode 311b is shown by a broken line. The light emitting element 360 is disposed so as to overlap with an opening 451 of the electrode 311b. As a result, the light emitted by the light emitting element 360 is emitted through the opening 451 to the display surface side.

[0187] In FIG. 7(B1), pixels 410 adjacent in the direction R correspond to different colors. At this time, as shown in FIG. 7B1, the openings 451 are formed in two pixels adjacent to each other in the direction R. It is preferable that the electrodes 311b are provided at different positions so that they are not arranged in a line. This allows the two light emitting elements 360 to be spaced apart, and the light emitted by the light emitting elements 360 The phenomenon (also called crosstalk) that the light from the adjacent pixel 410 is incident on the colored layer of the adjacent pixel 410 is prevented. In addition, two adjacent light emitting elements 360 can be arranged apart from each other. Therefore, even when the EL layer of the light emitting element 360 is separately produced using a shadow mask or the like, This makes it possible to realize a high-definition display device.

[0188] Alternatively, an arrangement such as that shown in FIG. 7(B2) may be used.

[0189] If the ratio of the total area of ​​the openings 451 to the total area of ​​the non-openings is too large, the liquid crystal element may not be used. In addition, the ratio of the total area of ​​the openings 451 to the total area of ​​the non-openings If the value is too small, the display using the light emitting element 360 will be too dark.

[0190] Furthermore, if the area of ​​the opening 451 provided in the electrode 311b that functions as a reflective electrode is too small, Therefore, the efficiency of light extraction from the light emitted by the light emitting element 360 decreases.

[0191] The shape of the opening 451 may be, for example, a polygon, a rectangle, an ellipse, a circle, a cross, or the like. It may also be in the form of thin stripes, slits, or a checkered pattern. The apertures 451 may be arranged close to adjacent pixels. Preferably, the apertures 451 are arranged so that the same color is It is placed close to other pixels to be displayed, which helps to suppress crosstalk.

[0192] [Circuit configuration example] 8 is a circuit diagram showing a configuration example of a pixel 410. In FIG. 8, two adjacent pixels 41 It shows 0.

[0193] The pixel 410 includes a switch SW1, a capacitance element C1, a liquid crystal element 340, a switch SW2, and a transistor. The pixel 410 includes a transistor M, a capacitor C2, and a light-emitting element 360. Wire G1, wire G2, wire ANO, wire CSCOM, wire S1, and wire S2 are electrically 8, the wiring VCOM1 electrically connected to the liquid crystal element 340, and a wiring VCOM2 electrically connected to the light emitting element 360.

[0194] FIG. 8 shows an example in which transistors are used for the switches SW1 and SW2. is doing.

[0195] The switch SW1 has a gate connected to the wiring G1 and a source or drain connected to the wiring S 1, and the other of the source or drain is connected to one electrode of the capacitance element C1 and the liquid crystal element 3 The other electrode of the capacitance element C1 is connected to the wiring CSCOM. The other electrode of the liquid crystal element 340 is connected to the wiring VCOM1.

[0196] The switch SW2 has a gate connected to the wiring G2 and a source or drain connected to the wiring G3. The other of the source and drain is connected to one electrode of the capacitance element C2, The other electrode of the capacitance element C2 is connected to the source of the transistor M. The transistor M is connected to either the source or drain of the transistor M and the wiring ANO. The other of the drains is connected to one electrode of the light emitting element 360. The other electrode is connected to the wiring VCOM2.

[0197] In FIG. 8, transistor M has two gates that sandwich a semiconductor, and these are connected. This increases the current that the transistor M can pass. This can be done.

[0198] A signal that controls the switch SW1 to be in a conductive state or a non-conductive state is applied to the wiring G1. A predetermined potential can be applied to the wiring VCOM1. A signal for controlling the alignment state of the liquid crystal of the liquid crystal element 340 can be applied. A predetermined potential can be applied to the OM.

[0199] A signal that controls the switch SW2 to be in a conductive state or a non-conductive state is applied to the wiring G2. A potential difference that causes the light emitting element 360 to emit light is generated between the wiring VCOM2 and the wiring ANO. The wiring S2 can be connected to a potential that controls the conduction state of the transistor M. A signal to control the

[0200] In the pixel 410 shown in FIG. 8, when a reflective mode display is performed, for example, the wiring G1 and the wiring S1 and displays the image using optical modulation by the liquid crystal element 340. In addition, when displaying in the transmissive mode, the signal given to the wiring G2 and the wiring S2 is The light emitting element 360 can be driven by the When driving, signals given to the wiring G1, the wiring G2, the wiring S1, and the wiring S2 are It can be driven by

[0201] In FIG. 8, one pixel 410 includes one liquid crystal element 340 and one light emitting element 360. 9A shows an example in which one pixel 410 has one liquid crystal display element. The crystal element 340 and four light-emitting elements 360 (light-emitting elements 360r, 360g, 360b, 360 9(A) shows an example in which the pixel 410 shown in FIG. 9(A) has one These pixels are capable of displaying full color.

[0202] In FIG. 9A, in addition to the example of FIG. 8, a line G3 and a line S3 are connected to the pixel 410. do.

[0203] In the example shown in FIG. 9A, for example, four light emitting elements 360 are arranged to emit red (R), green (G), and blue light. Light-emitting elements that emit green (G), blue (B), and white (W) colors can be used. A reflective liquid crystal element that exhibits white color can be used as the element 340. When displaying in reflective mode, it is possible to display white with high reflectivity. When display is performed in the transmission mode, display with high color rendering can be performed with low power consumption.

[0204] 9B shows an example of the configuration of a pixel 410. The pixel 410 has an electrode 311 The light emitting element 360w overlaps with the opening of the electrode 311, and the light emitting element 360w is disposed around the electrode 311. The light emitting element 360r, the light emitting element 360g, and the light emitting element 360b. It is preferable that the light emitting areas of the element 360g and the light emitting element 360b are approximately equal.

[0205] <Display device configuration example 2> 10 is a perspective schematic diagram of a display device 300 according to one embodiment of the present invention. The substrate 351 and the substrate 361 are bonded together. It is indicated by a line.

[0206] The display device 300 includes a display unit 362, a circuit unit 364, wiring 365, a circuit unit 366, and wiring 367. The substrate 351 includes, for example, a circuit portion 364, wiring 365, a circuit portion 366, wiring 367, etc. The wiring 367 and the electrode 311b functioning as a pixel electrode are provided. Example of IC373, FPC372, IC375 and FPC374 mounted on 351 Therefore, the configuration shown in FIG. 10 is a display device 300, an IC 373, an FPC 3 72, IC375 and FPC374.

[0207] The circuit portion 364 can be, for example, a circuit that functions as a scanning line driver circuit.

[0208] The wiring 365 has a function of supplying signals and power to the display portion and the circuit portion 364. Power is input to wiring 365 from the outside via FPC 372 or from IC 373.

[0209] In addition, in FIG. 10, a substrate 351 is formed by a COG (Chip On Glass) method or the like. The IC 373 is, for example, a scanning line driving circuit, Alternatively, an IC having a function as a signal line driver circuit or the like can be applied. In some cases, the circuit functions as a scanning line driver circuit and a signal line driver circuit. A circuit that functions as a signal line driver circuit is provided externally, and the display device 3 is connected to the FPC 372. When inputting a signal to drive 00, it is also possible to configure without IC373. In addition, IC373 can be mounted on FPC using the COF (Chip On Film) method. It may be implemented in 372.

[0210] 10 shows an enlarged view of a part of the display unit 362. The display unit 362 has a plurality of displays. The electrodes 311b of the display element are arranged in a matrix. and functions as a reflective electrode for the liquid crystal element 340, which will be described later.

[0211] 10, the electrode 311b has an opening. The light emitting element 360 is provided on the substrate 351 side. The light from the light emitting element 360 is incident on the electrode 311b. The light is emitted to the substrate 361 side through the opening.

[0212] FIG. 11 shows a part of the area including the FPC 372, the circuit section 36, and the like of the display device shown in FIG. 4, a part of the area including the display unit 362, a part of the area including the circuit unit 366, 1 shows an example of a cross section when a part of the region including FPC374 is cut.

[0213] The display device shown in FIG. 11 has a structure in which a display panel 700 and a display panel 800 are stacked. The display panel 700 includes a resin layer 701 and a resin layer 702. 700 has a resin layer 201 and a resin layer 202. The resin layer 702 and the resin layer 201 are an adhesive layer. The resin layer 701 is bonded to the substrate 351 by an adhesive layer 51. The resin layer 202 is bonded to the substrate 361 by an adhesive layer 52.

[0214] [Display panel 700] The display panel 700 includes a resin layer 701, an insulating layer 478, a plurality of transistors, and a capacitance element 4 05, insulating layer 411, insulating layer 412, insulating layer 413, insulating layer 414, insulating layer 415, light emitting element 360, spacer 416, adhesive layer 417, colored layer 425, light-shielding layer 426, insulating layer 47 6 and a resin layer 702.

[0215] The circuit section 364 has a transistor 401. The display section 362 has a transistor 402 and and a transistor 403.

[0216] Each transistor has a gate, an insulating layer 411, a semiconductor layer, a source, and a drain. The gate and the semiconductor layer overlap with an insulating layer 411 interposed therebetween. A part of the insulating layer 411 is a gate insulating layer. One part functions as an edge layer, and the other part functions as a dielectric of the capacitor element 405 . The conductive layer serving as the source or the drain of the transistor 402 is a part of the capacitor 405. It also serves as the other electrode.

[0217] 11 shows a bottom gate transistor. The circuit section 364 and the display section 362 may have different transistor structures. Each of them may have multiple types of transistors.

[0218] For example, as shown in FIG. 12, a modification of FIG. 11 is provided, in which transistors 205 and 206 and connections The elements constituting the light-emitting element 36 can be formed of a light-transmitting conductor. The light emitted from the transistors 205 and 206 and the connection 207 is partially or entirely Furthermore, the light that is incident from the substrate 361 side and passes through the liquid crystal 312 can be transmitted. The reliability of the transistors 205 and 206 can be improved by using the conductive layer 193b. To improve the conductivity of the semiconductor layer, a conductive layer is provided to act as a gate electrode and a conductive layer is provided to act as a back gate electrode. One or both of the conductive layers may be formed of a material that does not transmit light, such as a metal.

[0219] 11, the capacitor 405 has a pair of electrodes and a dielectric therebetween. The element 405 is made of the same material as the gate of the transistor and a conductive layer formed in the same process. a conductive layer formed of the same material and in the same process as the source and drain of the transistor; , has.

[0220] The insulating layer 412, the insulating layer 413, and the insulating layer 414 each cover a transistor and the like. The number of insulating layers covering the transistors and the like is not particularly limited. The insulating layer 412, the insulating layer 413, and the insulating layer 414 function as a planarization layer. At least one layer is preferably made of a material that is difficult for impurities such as water or hydrogen to diffuse into. It is possible to effectively prevent external impurities from diffusing into the transistor. This can improve the reliability of the display device.

[0221] When an organic material is used for the insulating layer 414, the insulating layer 414 exposed at the edge of the display device is There is a risk that impurities such as moisture may enter the light emitting element 360 from the outside of the display device through the insulating film. If the light emitting element 360 is deteriorated due to the intrusion of impurities, it will lead to deterioration of the display device. Preferably, the insulating layer 414 is not located at the edge of the display device, as shown in FIG. In the configuration of FIG. 11, the insulating layer using an organic material is located at the edge of the display device, so that the light-emitting element This can prevent impurities from entering the element 360.

[0222] The light-emitting element 360 includes an electrode 421, an EL layer 422, and an electrode 423. The light emitting element 360 may have an optical adjustment layer 424. The light emitting element 360 has a colored layer 425 side. It is a top emission structure that injects

[0223] The transistor, the capacitor, the wiring, etc. are arranged so as to overlap the light-emitting region of the light-emitting element 360. This allows the aperture ratio of the display section 362 to be increased.

[0224] One of the electrodes 421 and 423 functions as an anode, and the other functions as a cathode. A voltage higher than the threshold voltage of the light emitting element 360 is applied between the electrode 421 and the electrode 423. When a voltage is applied, holes are injected into the EL layer 422 from the anode side and electrons are injected from the cathode side. The injected electrons and holes recombine in the EL layer 422, and the luminescent material contained in the EL layer 422 will light up.

[0225] The electrode 421 is electrically connected to the source or drain of the transistor 403. They may be connected directly or via another conductive layer. It functions as a pixel electrode and is provided for each light emitting element 360. Two adjacent electrodes 42 1 is electrically isolated by an insulating layer 415.

[0226] The electrode 423 functions as a common electrode and is provided across the plurality of light-emitting elements 360. A constant potential is supplied to the electrode 423.

[0227] The light emitting element 360 overlaps the colored layer 425 via an adhesive layer 417. The spacer 416 is The electrode 423 overlaps the light-shielding layer 426 via the adhesive layer 417. In FIG. Although the figure shows a case where there is a gap between the two, they may be in contact. Although the configuration in which the light blocking layer 416 is provided on the substrate 351 side is shown, it is also possible to provide the light blocking layer 426 on the substrate 361 side (for example, Alternatively, it may be provided on the substrate 361 side.

[0228] A color filter (colored layer 425) and a microcavity structure (optical adjustment layer 424) This combination allows the display device to emit light with high color purity. The thickness of layer 424 varies depending on the color of each pixel.

[0229] The colored layer 425 is a colored layer that transmits light in a specific wavelength range, for example, red, green, or blue. Alternatively, a color filter that transmits light in the yellow wavelength range can be used.

[0230] Note that one embodiment of the present invention is not limited to the color filter type, but may also be a color-coded type or a color conversion type. Alternatively, a quantum dot method or the like may be applied.

[0231] The light-shielding layer 426 is provided between the adjacent colored layers 425. The light from the adjacent light emitting element 360 is blocked, and color mixing between the adjacent light emitting elements 360 is suppressed. Here, by providing the end of the colored layer 425 so as to overlap the light-shielding layer 426, light leakage can be reduced. The light-shielding layer 426 is made of a material that blocks the light emitted by the light-emitting element 360. The light-shielding layer 426 is made of a material other than the display unit 362 such as the circuit unit 364. It is preferable to provide the light emitting element in the region (a) because unintended light leakage due to guided light or the like can be suppressed.

[0232] An insulating layer 478 is formed on one surface of the resin layer 701. An insulating layer 476 is formed on one surface. The insulating layer 476 and the insulating layer 478 are moisture-proof. It is preferable to use a film having high moisture resistance. By arranging transistors, etc., it is possible to prevent impurities such as water from entering these elements. This is preferable because it increases the reliability of the display device.

[0233] Highly moisture-proof insulating films include silicon nitride films and silicon nitride oxide films. and films containing nitrogen and aluminum, such as aluminum nitride films. Alternatively, a silicon oxide film, a silicon oxynitride film, an aluminum oxide film, or the like may be used.

[0234] For example, the water vapor permeability of a highly moisture-proof insulating film is 1×10 -5 [g / (m 2 ·day) ] or less, preferably 1 × 10 -6 [g / (m 2 ·day)] or less, preferably 1 × 1 0 -7 [g / (m 2 ·day)] or less, more preferably 1 × 10 -8 [g / (m 2 ·d ay)] below.

[0235] The connection portion 406 includes a wiring 365. The wiring 365 is connected to the source and drain of the transistor. The connection portion 406 can be formed from the same material and in the same process as the circuit portion 3. 64 is electrically connected to an external input terminal that transmits signals and potentials from the outside. 4 shows an example in which an FPC 372 is provided as an input terminal. 72 and the connection portion 406 are electrically connected.

[0236] The connection layer 419 may be made of various anisotropic conductive films (ACFs). Conductive Film) and Anisotropic Conductive Paste (ACP) opic conductive paste) can be used.

[0237] This concludes the description of the display panel 700.

[0238] [Display panel 800] The display panel 800 is a reflective liquid crystal display device that employs a vertical electric field method.

[0239] The display panel 800 includes a resin layer 201, an insulating layer 578, a plurality of transistors, and a capacitance element 5 05, wiring 367, insulating layer 511, insulating layer 512, insulating layer 513, insulating layer 514, liquid crystal element The substrate 529, the alignment film 564a, the alignment film 564b, the adhesive layer 517, the insulating layer 576, and the resin layer It has 202.

[0240] The resin layer 201 and the resin layer 202 are bonded together by an adhesive layer 517. A liquid crystal 563 is sealed in the area surrounded by the resin layer 201, the resin layer 202, and the adhesive layer 517. A polarizing plate 599 is located on the outer surface of the substrate 361.

[0241] The liquid crystal element 529 includes an electrode 311b, an electrode 562, and a liquid crystal 563. b functions as a pixel electrode. Electrode 562 functions as a common electrode. The orientation of the liquid crystal 563 can be controlled by the electric field generated between the electrode 562 and the liquid crystal 563. An alignment film 564a is provided between the liquid crystal 563 and the electrode 311b. An alignment film 564b is provided between them.

[0242] The resin layer 202 is provided with an insulating layer 576, an electrode 562, an alignment film 564b, and the like. do.

[0243] The resin layer 201 is provided with an electrode 311b, an alignment film 564a, a transistor 501, a transistor A capacitor 503, a capacitor element 505, a connection portion 506, a wiring 367, and the like are provided.

[0244] On the resin layer 201, an insulating layer 511, an insulating layer 512, an insulating layer 513, an insulating layer 514, etc. are formed. An insulating layer is provided.

[0245] Here, the source or the drain of the transistor 503 is electrically connected to the electrode 311b. The conductive layer that is not connected may function as a part of the signal line. The conductive layer 503 that functions as the gate may also function as a part of the scan line.

[0246] FIG. 11 shows an example in which a transistor 501 is provided as an example of the circuit portion 366. There are.

[0247] At least one of the insulating layers 512 and 513 covering each transistor is resistant to water and hydrogen. It is preferable to use a material in which impurities are less likely to diffuse, such as the above.

[0248] An electrode 311b is provided on the insulating layer 514. The electrode 311b is The source of the transistor 503 is connected through openings formed in the insulating layers 513 and 512. The electrode 311b is electrically connected to either the source or the drain of the capacitor 505. The electrode is electrically connected to one of the electrodes.

[0249] Since the display panel 800 is a reflective liquid crystal display device, visible light is reflected to the electrode 311b. A conductive material that transmits visible light is used for the electrode 561, and a conductive material that transmits visible light is used for the electrode 562.

[0250] Examples of conductive materials that transmit visible light include indium (In), zinc (Zn), It is preferable to use a material containing one selected from tin (Sn). Indium tin oxide (ITO), indium zinc Lead oxide, indium oxide with tungsten oxide, indium oxide with tungsten oxide Indium zinc oxide, indium oxide with titanium oxide, indium tin oxide with titanium oxide materials, indium tin oxide containing silicon oxide (ITSO), zinc oxide, and gallium oxide ZnO, etc. A film containing graphene can also be used. Graphene The film containing graphene oxide can be formed, for example, by reducing a film containing graphene oxide.

[0251] Examples of conductive materials that reflect visible light include aluminum, silver, and their alloys. Other examples include alloys containing metal materials such as gold, platinum, nickel, tungsten, and chromium. Metallic materials such as aluminum, molybdenum, iron, cobalt, copper, or palladium, or In addition, the above metal materials or alloys may contain lanthanum, Neodymium, germanium, etc. may be added. Aluminum and titanium alloy , aluminum and nickel alloy, aluminum and neodymium alloy, aluminum, nickel Aluminum-containing alloys such as lanthanum alloys (Al-Ni-La) alloys), silver and copper alloys, silver, palladium and copper alloys (Ag-Pd-Cu, also known as APC) Alternatively, an alloy containing silver, such as an alloy of silver and magnesium, may be used.

[0252] Here, a linear polarizing plate may be used as the polarizing plate 599, but a circular polarizing plate may also be used. As the circular polarizer, for example, a laminate of a linear polarizer and a quarter-wave retardation plate is used. This makes it possible to suppress reflection of external light. Depending on the type, the cell gap, orientation, driving voltage, etc. of the liquid crystal element used in the liquid crystal element 529 are adjusted. By adjusting the contrast, a desired contrast can be achieved.

[0253] The electrode 562 is provided on the resin layer 201 side in a portion close to the end of the resin layer 202. The conductive layer is electrically connected to the connector 543. As a result, the conductive layer is A potential or a signal can be supplied to the electrode 562 from an FPC 374, an IC, or the like placed thereon.

[0254] The connector 543 may be, for example, a conductive particle. For this purpose, particles of organic resin or silica coated with a metal material may be used. It is preferable to use nickel or gold as the metal material, as this reduces the contact resistance. Particles coated with layers of two or more metal materials, such as nickel coated with gold, are used. It is preferable to use a material that can be elastically or plastically deformed as the connector 543. In this case, the connectors 543, which are conductive particles, are preferably used as shown in FIG. In this way, the connecting body 543 and the connecting body 543 may be crushed in the vertical direction. The contact area with the electrically conductive layer is increased, reducing contact resistance and preventing connection failures. The occurrence of the above defects can be suppressed.

[0255] The connector 543 is preferably disposed so as to be covered with the adhesive layer 517. For example, The connectors 543 may be dispersed in the previous adhesive layer 517 .

[0256] A connecting portion 506 is provided in an area near the end of the resin layer 201. The connecting portion 506 is , and is electrically connected to the FPC 374 via a connection layer 519 .

[0257] This concludes the description of the display panel 800.

[0258] [Display element] The display element of the first pixel located on the display surface side is an element that reflects external light and displays the image. Such devices do not have a light source, so they consume very little power when displaying. The display element of the first pixel is typically a reflective type. Alternatively, a liquid crystal element having a shutter can be used as the display element of the first pixel. MEMS (Micro Electro Mechanical Systems) m) elements, optical interference type MEMS elements, microcapsule type, electrophoresis type, electro Uses elements that use the electrowetting method, electronic liquid powder method, etc. It is possible.

[0259] The display element of the second pixel located on the opposite side to the display surface side has a light source. It is possible to use an element that displays using light from a light source. The brightness and chromaticity of light are not affected by external light, so color reproducibility is high (the color gamut is wide). ) and high contrast, i.e., vivid display. The display element is, for example, an OLED (Organic Light Emitting Diode), LED(Light Emitting Diode), QLED(Qu Self-luminous light emitters such as an ant-dot Light Emitting Diode Alternatively, a light source may be used as the display element of the second pixel. A backlight and a transmissive liquid crystal element that controls the amount of transmitted light from the backlight. Combinations may also be used.

[0260] [Liquid Crystal Element] As a liquid crystal element, for example, a vertical alignment (VA) A liquid crystal element to which a vertical alignment mode is applied can be used. Multi-Domain Vertical Alignment) mode, PVA( Patterned Vertical Alignment) mode, ASV (Adv Advanced Super View mode can be used.

[0261] In addition, the liquid crystal element may be a liquid crystal element to which various modes are applied. In addition to VA mode, there are also TN (Twisted Nematic) and IPS (In-Vention) modes. -Plane-Switching) mode, FFS (Fringe Field Switching) itching) mode, ASM(Axially Symmetric aligne) d Micro-cell mode, OCB (Optically Compensated ed Birefringence mode, FLC (Ferroelectric L Liquid Crystal mode, AFLC (AntiFerroelectric) Liquid crystal elements that use a liquid crystal mode or the like can be used. .

[0262] The liquid crystal element is a device that controls the transmission or non-transmission of light by the optical modulation action of the liquid crystal. The optical modulation effect of the liquid crystal is due to the electric field applied to the liquid crystal (horizontal electric field, vertical electric field). The liquid crystal used in the liquid crystal element is controlled by a bias current (including an electric field or an oblique electric field). Thermotropic liquid crystal, low molecular weight liquid crystal, high molecular weight liquid crystal, polymer dispersed liquid crystal (PDLC) Polymer Dispersed Liquid Crystal, Ferroelectric Liquid Crystal , antiferroelectric liquid crystal, guest-host liquid crystal, etc. can be used. Depending on the conditions, cholesteric phase, smectic phase, cubic phase, chiral nematic phase, etc. It shows the crystalline phase, isotropic phase, etc.

[0263] The liquid crystal material may be either a positive type liquid crystal or a negative type liquid crystal. The optimum liquid crystal material may be selected depending on the mode and design to be applied.

[0264] In addition, an alignment film can be provided to control the alignment of the liquid crystal. When employed, a liquid crystal that exhibits a blue phase without using an alignment film may be used. When the temperature of cholesteric liquid crystal is increased, the phase changes from the cholesteric phase to the isotropic phase. The blue phase appears only in a narrow temperature range, so it is difficult to distinguish between the two. In order to improve the range, a liquid crystal composition containing a chiral agent of several weight percent or more is used in the liquid crystal layer. A liquid crystal composition containing a liquid crystal exhibiting a blue phase and a chiral agent has a short response time and exhibits optically isotropic Furthermore, a liquid crystal composition containing a liquid crystal exhibiting a blue phase and a chiral agent does not require alignment treatment. Furthermore, since no alignment film is required, rubbing treatment is not required. This prevents electrostatic damage caused by rubbing, and This can reduce defects and damage to the liquid crystal display device during the manufacturing process.

[0265] When a reflective liquid crystal element is used, a polarizing plate is provided on the display surface side. It is preferable to place a light diffusion plate on the display surface side, as this improves visibility.

[0266] [Light-emitting element] The light emitting element can be a self-luminous element, which can be illuminated by current or voltage. This category includes devices with controlled brightness, such as LEDs, QLEDs, and organic EL devices. Although inorganic EL elements or the like can be used, the light emitting elements described in the first and second embodiments can also be used. It is preferable to use an optical element.

[0267] In this embodiment mode, a top-emission type light-emitting element can be used as the light-emitting element. It is preferable to use a conductive film that transmits visible light for the electrode on the light extraction side. It is preferable to use a conductive film that reflects visible light for the electrode on the side that is not exposed. The device may be a single device having one EL layer, or multiple EL layers may be combined into a charge generating layer. The elements may be tandem elements stacked with one another via a gap.

[0268] The EL layer has at least a light-emitting layer. The EL layer has a hole-injecting layer as a layer other than the light-emitting layer. high hole-transporting material, hole-blocking material, high electron-transporting material, electron injection materials with high electron transporting and hole transporting properties, or bipolar materials (materials with high electron transporting and hole transporting properties), etc. The film may further include a layer containing a metal oxide.

[0269] The EL layer may contain the low molecular weight compounds, high molecular weight compounds, and inorganic compounds listed in the first embodiment. The layers constituting the EL layer can be formed by deposition (including vacuum deposition), The layer can be formed by a transfer method, a printing method, an ink jet method, a coating method, or the like.

[0270] [Adhesive layer] The adhesive layer can be a photo-curable adhesive such as an ultraviolet curable adhesive, a reaction-curable adhesive, or a heat-curable adhesive. Various curing adhesives such as adhesives and anaerobic adhesives can be used. Epoxy resin, acrylic resin, silicone resin, phenolic resin, polyimide resin, imide resin, PVC (polyvinyl chloride) resin, PVB (polyvinyl butyral) resin, E VA (ethylene vinyl acetate) resin, etc. In particular, the moisture permeability of epoxy resin, etc. A material with low viscosity is preferable. Two-component resin may also be used. It may be used.

[0271] The resin may also contain a desiccant. For example, an oxide of an alkaline earth metal (an acid The material used is one that absorbs moisture by chemical adsorption, such as calcium oxide or barium oxide. Alternatively, materials such as zeolite and silica gel can absorb water by physical adsorption. If a desiccant is included, impurities such as moisture will not penetrate into the element. This is preferable because it can suppress the occurrence of light leakage and improve the reliability of the display panel.

[0272] In addition, by mixing a filler with a high refractive index or a light scattering material into the resin, it is possible to improve the light extraction efficiency. For example, titanium oxide, barium oxide, zeolite, Ruthenium and the like can be used.

[0273] [Connection layer] Anisotropic Conductive Film (ACF) is used as the connection layer. conductive film) and anisotropic conductive paste (ACP) Conductive Paste) can be used.

[0274] [Colored layer] Materials that can be used for the coloring layer include metal materials, resin materials, pigments, and dyes. Examples include resin materials.

[0275] [Light blocking layer] Materials that can be used for the light-shielding layer include carbon black, titanium black, Examples of the light-shielding layer include metals, metal oxides, and composite oxides including solid solutions of multiple metal oxides. The film may be a film containing a resin material, or may be a thin film made of an inorganic material such as a metal. In addition, the light-shielding layer may be a laminated film of films containing the material of the colored layer. A film containing a material used for a colored layer that transmits light and a material used for a colored layer that transmits light of another color. By using the same material for the colored layer and the light-shielding layer, a laminated structure with a film containing This is preferable because it allows the use of common equipment and simplifies the process.

[0276] The structure shown in this embodiment mode can be appropriately combined with the structure shown in other embodiment modes. can be done.

[0277] (Embodiment 5) In this embodiment mode, an electron device including the light-emitting element described in Embodiments 1 and 2 as a part thereof is The light-emitting device described in the first and second embodiments is one of the light-emitting devices of the present invention. Since the light-emitting element according to the embodiment is included, the driving voltage is low, the light-emitting efficiency is high, and the reliability is good. As a result, the electronic device described in this embodiment has reduced power consumption. It is possible to provide an electronic device having a highly reliable display section.

[0278] <Electronic device instructions> 13(A) to 13(G) are diagrams showing electronic devices. These electronic devices are 9000, a display unit 9001, a speaker 9003, an operation key 9005 (power switch or including operation switches), connection terminal 9006, sensor 9007 (force, displacement, position, speed, acceleration Speed, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field , current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared measurement equipment 9008, etc. Also, the sensor 90 07 may have a function to measure biometric information such as a pulse sensor or a fingerprint sensor.

[0279] The electronic devices shown in FIGS. 13A to 13G can have various functions. For example, functions to display various information (still images, videos, text images, etc.) on the display, Sensor function, calendar, date or time display function, various software ( It has the function of controlling processing by using a program, wireless communication function, and various functions using wireless communication function. Functions for connecting to computer networks, transmitting various data using wireless communication functions, or receiving the program or data recorded on the recording medium, and It should be noted that the functions shown in FIGS. 13(A) to 13(G) can be implemented. The functions that the electronic device shown in the figure can have are not limited to these, and it may have various functions. Although not shown in FIGS. 13A to 13G, the electronic device may include: The electronic device may be provided with a camera or the like to take still images. The function to take pictures, take videos, and save the images to a recording medium (external or built-in to the camera) ) and a function to display the captured image on the display unit.

[0280] The electronic devices shown in FIGS. 13A to 13G will be described in detail below.

[0281] FIG. 13A is a perspective view showing a mobile information terminal 9100. The display portion 9001 is flexible. The display unit 9001 can be incorporated along the screen. It is equipped with a touch panel, and can be operated by touching the screen with a finger or a stylus. By touching the icon displayed on the display 9001, the application can be started. can.

[0282] 13B is a perspective view showing a portable information terminal 9101. For example, the device has one or more functions selected from a telephone, a notebook, an information viewing device, etc. Specifically, it can be used as a smartphone. Although the speaker 9003, the connection terminal 9006, the sensor 9007, etc. are omitted in the illustration, It can be installed in the same position as the mobile information terminal 9100 shown in FIG. The information terminal 9101 can display text and image information on multiple surfaces. For example, Three operation buttons 9050 (also called operation icons or simply icons) are displayed on the display unit 900. 9051 shown in a dashed rectangle can be displayed on one side of the display unit 90. 01. An example of the information 9051 is an e-mail A display that notifies you of incoming calls, SNS (social networking services), etc. , subject of email or SNS, sender name of email or SNS, date and time, time, There are also displays showing the remaining battery level, the strength of the received signal, etc. Even if you display operation buttons 9050 instead of information 9051 at the displayed position, good.

[0283] The housing 9000 is made of a material such as alloy, plastic, or ceramic. Reinforced plastic can also be used as the plastic. Carbon Fiber Reinforced Resin Composite (CFRP), a type of carbon fiber composite Carbon fiber reinforced plastics (CFRP) have the advantage of being lightweight and corrosion-resistant. Other reinforced plastics include glass fiber reinforced plastics and aramid fiber reinforced plastics. Examples of alloys include aluminum alloys and Magnesium alloys include non-metallic alloys containing zirconium, copper, nickel, and titanium. Amorphous alloys (also called metallic glasses) have excellent elastic strength. It is an amorphous alloy that has a glass transition region at room temperature and is also called a bulk-solidifying amorphous alloy. It is an alloy having a substantially amorphous atomic structure. The alloy material is poured into the housing mold and solidified to form a part of the housing with bulk solidified amorphous alloy. Amorphous alloys include zirconium, copper, nickel, titanium, as well as beryllium and silicon. Cobalt, niobium, boron, gallium, molybdenum, tungsten, manganese, iron, cobalt The amorphous alloy may contain yttrium, vanadium, phosphorus, carbon, etc. Not limited to solid casting, but also vacuum deposition, sputtering, electrolytic plating, electroless plating, etc. The amorphous alloy may be formed by the above method. As long as the alloy maintains a state free of crystallites, it may contain microcrystals or nanocrystals. , both complete solid solution alloys with a single solid phase structure and partial solutions with two or more phases. The housing 9000 is made of an amorphous alloy, which gives it high elasticity. Therefore, even if the portable information terminal 9101 is dropped, the housing 9000 is made of an amorphous alloy. If the impact is applied, the mobile information terminal 910 will return to its original shape even if it is temporarily deformed at the moment of impact. 1 can improve the impact resistance.

[0284] 13C is a perspective view showing a portable information terminal 9102. The portable information terminal 9102 is , and has the function of displaying information on three or more surfaces of the display unit 9001. An example is shown in which information 9053 and information 9054 are displayed on different sides. The user of the portable information terminal 9102 stores the portable information terminal 9102 in the breast pocket of his / her clothes. In this state, the display (information 9053 in this case) can be confirmed. The telephone number or name of the caller is displayed in a position that can be observed from above the mobile information terminal 9102. The user can view the display without taking the mobile information terminal 9102 out of his pocket. You can check the call and decide whether to accept it or not.

[0285] 13(D) is a perspective view showing a wristwatch-type portable information terminal 9200. The 9200 is suitable for mobile phone calls, e-mail, document browsing and writing, music playback, and internet communications. It is possible to run various applications such as computer games. The display surface of the display unit 9001 is curved, and the display is performed along the curved display surface. In addition, the portable information terminal 9200 can perform short-distance wireless communication according to a communication standard. For example, by communicating with a wireless headset, handset The mobile information terminal 9200 also has a connection terminal 9006. It has a connector and can directly exchange data with other information terminals. Charging can also be performed via the connection terminal 9006. It may also be possible to supply power wirelessly without going through 6.

[0286] 13(E), (F), and (G) are perspective views showing a foldable portable information terminal 9201. FIG. 13(E) is a perspective view of the portable information terminal 9201 in an unfolded state, and FIG. (F) shows the mobile information terminal 9201 being changed from one of the unfolded state and the folded state to the other. 13(G) is a perspective view of the portable information terminal 9201 in a folded state. The portable information terminal 9201 is highly portable when folded, and is easily portable when unfolded. When the display is turned on, the seamless, wide display area provides excellent visibility of the display. The display unit 9001 of the display device 01 is made up of three housings 9000 connected by hinges 9055. The two housings 9000 are supported by the hinge 9055. This allows the portable information terminal 9201 to be reversibly transformed from an unfolded state to a folded state. For example, the portable information terminal 9201 can be bent with a radius of curvature of 1 mm or more and 150 mm or less. It can be done.

[0287] Furthermore, examples of electronic devices include television sets (televisions or television receivers) (also called "computer"), computer monitors, digital cameras, digital video cameras, Digital photo frames, mobile phones (also called mobile phones or mobile phone devices), goggle-type Displays (head-mounted displays), portable game consoles, portable information terminals, audio playback Examples include live video equipment, large gaming machines such as pachinko machines, etc.

[0288] Furthermore, the electronic device of one embodiment of the present invention may include a secondary battery and may perform contactless power transmission. It is preferable that the secondary battery can be charged using the power supply.

[0289] As the secondary battery, for example, a lithium polymer battery (lithium ion battery) using a gel electrolyte is used. Lithium-ion secondary batteries such as lithium-ion polymer batteries, lithium-ion batteries, nickel-metal hydride batteries batteries, nickel-cadmium batteries, organic radical batteries, lead-acid batteries, secondary air batteries, nickel-zinc batteries, silver-zinc batteries Examples include lead batteries.

[0290] The electronic device according to one embodiment of the present invention may include an antenna. By using the battery, it is possible to display images, information, etc. on the display unit. , the antenna may be used for contactless power transfer.

[0291] FIG. 14A shows a video camera, which includes a housing 7701, a housing 7702, a display portion 7703, It has operation keys 7704, a lens 7705, a connection part 7706, etc. The lens 7705 is provided in a housing 7701, and the display portion 7703 is provided in a housing 7702. The housing 7701 and the housing 7702 are connected by a connection portion 7706. The angle between the housing 7701 and the housing 7702 can be changed by the connecting part 7706. The image on the display portion 7703 is transmitted between the housing 7701 and the housing 7702 at the connection portion 7706. 702.

[0292] FIG. 14B shows a notebook personal computer, which includes a housing 7121 and a display unit 712. 2, a keyboard 7123, a pointing device 7124, etc. The 122 has a very high pixel density and can be made highly detailed, so it can be used in 8-inch displays despite being small to medium-sized. k display, and very clear images can be obtained.

[0293] FIG. 14C shows the appearance of the head mounted display 7200.

[0294] The head-mounted display 7200 includes a mounting part 7201, a lens 7202, and a main body 72 7203, a display unit 7204, a cable 7205, etc. It has a built-in 7206 battery.

[0295] A cable 7205 supplies power from a battery 7206 to the main body 7203. 03 is equipped with a wireless receiver and the like, and receives image data and other video information and displays it on a display unit 7204. In addition, a camera installed in the main body 7203 can record the movements of the user's eyeballs and eyelids. By capturing the user's viewpoint and calculating the coordinates of the user's viewpoint based on that information, It can be used as an input means.

[0296] Furthermore, the wearing unit 7201 may be provided with a plurality of electrodes at positions that come into contact with the user. The main body 7203 detects the current flowing through the electrodes in accordance with the movement of the user's eyeballs, The device may have a function to recognize the user's point of view. By doing so, the attachment unit 720 may have a function of monitoring the pulse of the user. The sensor 1 may have various sensors such as a temperature sensor, a pressure sensor, an acceleration sensor, etc. The device may have a function to display the user's biological information on the display unit 7204. The image displayed on the display unit 7204 is changed according to the movement of the device. Good too.

[0297] 14(D) shows the appearance of a camera 7300. The camera 7300 includes a housing 7301, a front It has a display unit 7302, operation buttons 7303, a shutter button 7304, a connecting unit 7305, etc. A lens 7306 can also be attached to the camera 7300.

[0298] The coupling section 7305 has electrodes and is connected to the finder 7400 (to be described later) as well as the strobe device. etc. can be connected.

[0299] Here, the camera 7300 is a camera in which the lens 7306 is removed from the housing 7301 and replaced. However, the lens 7306 and the housing 7301 may be integrated. .

[0300] An image can be captured by pressing the shutter button 7304. The display unit 302 has a touch sensor, and can capture images by operating the display unit 7302. is.

[0301] The display device or the touch sensor of one embodiment of the present invention can be applied to the display portion 7302. can.

[0302] FIG. 14(E) shows an example in which a finder 7400 is attached to a camera 7300. is doing.

[0303] The finder 7400 includes a housing 7401, a display portion 7402, buttons 7403, and the like. .

[0304] The housing 7401 has a coupling portion that engages with the coupling portion 7305 of the camera 7300. A viewfinder 7400 can be attached to the camera 7300. The device has electrodes, and displays images received from a camera 7300 via the electrodes on a display unit 7402. It can be shown.

[0305] The button 7403 functions as a power button. The 7402 display can be toggled on and off.

[0306] In addition, in FIGS. 14(D) and (E), the camera 7300 and the finder 7400 are separate electronic devices. The camera 7300 is a device, and these are configured to be detachable. The display device of the embodiment of the present invention may have a built-in finder equipped with a touch sensor. .

[0307] 15(A) to 15(E) show the external appearance of the head mounted displays 7500 and 7510. FIG.

[0308] The head-mounted display 7500 includes a housing 7501, two display units 7502, and an operation unit. It has a button 7503 and a band-like fastener 7504 .

[0309] The head mounted display 7500 is the same as the head mounted display 7200. In addition to the functions it has, it also has two displays.

[0310] By having two displays 7502, the user can see one display per eye. This allows for high-resolution images to be displayed even when using parallax for 3D display. The display portion 7502 is configured to display an image in an arc shape with the user's eye as its approximate center. This keeps the distance from the user's eyes to the display surface constant. This allows users to see more natural images. Even if the image changes depending on the viewing angle, the image is displayed in the normal direction to the display surface. Since the user's eyes are positioned, the effect can be virtually ignored, resulting in a more realistic look. It is possible to display images with

[0311] The operation button 7503 has functions such as a power button. The display may have a button.

[0312] The head-mounted display 7510 includes a housing 7501, a display unit 7502, a band It has a blade-shaped fixture 7504 and a pair of lenses 7505.

[0313] A user can view the display on the display portion 7502 through the lens 7505 . It is preferable to arrange the display portion 7502 in a curved manner. By placing the device in this way, users can feel a high level of realism.

[0314] The display device of one embodiment of the present invention can be applied to the display portion 7502. Since such a display device can increase the resolution, a lens 75 is used as shown in FIG. Even when enlarged using 05, the pixels are not visible to the user, providing a more realistic image. The video can be displayed.

[0315] FIG. 16A shows an example of a television device. The television device 9300 includes a housing 9 9001 is built into the housing 9000. 000 is supported.

[0316] The television device 9300 shown in FIG. 16A is operated by an operation switch provided in the housing 9000. This can be done by a separate remote control 9311 or a switch. The display unit 9001 may be provided with a touch sensor, and the operation can be performed by touching the display unit 9001 with a finger or the like. The remote control operator 9311 may display information to be output from the remote control operator 9311. The remote control 9311 may have a display unit that displays the operation keys or touch panel. The panel allows you to operate the channel and volume, and the display unit 9001 You can manipulate the video.

[0317] The television device 9300 includes a receiver, a modem, and the like. It is possible to receive general television broadcasts by using a modem. By connecting to a communication network, it can be one-way (sender to receiver) or two-way. It is also possible to communicate information (between a sender and a receiver, or between receivers).

[0318] Furthermore, since the electronic device or lighting device of one embodiment of the present invention is flexible, it can be easily installed inside a house or a building. It can also be incorporated into walls or exterior walls, or along the curved surfaces of the interior or exterior of a vehicle. be.

[0319] FIG. 16(B) shows the exterior of the automobile 9700. FIG. 16(C) shows the driver's seat of the automobile 9700. The automobile 9700 includes a body 9701, wheels 9702, a dashboard 9703, a The display device or the light-emitting device of one embodiment of the present invention includes a light emitting element 9704 and the like. For example, the display portion 9710 to the display portion 9720 shown in FIG. The display device, the light-emitting device, or the like according to one embodiment of the present invention can be provided in the display portion 9715.

[0320] The display portion 9710 and the display portion 9711 are display devices provided on a windshield of an automobile. In a display device or a light-emitting device according to one embodiment of the present invention, electrodes and wirings are formed using a light-transmitting conductive material. By making it from a transparent material, the other side can be seen through, creating a so-called see-through state. If the display unit 9710 or the display unit 9711 is in a see-through state, the car 97 Therefore, the display device or the like according to one embodiment of the present invention does not obstruct the view even when the vehicle is driving. The light emitting device or the like can be installed on the windshield of the automobile 9700. When a transistor for driving a light-emitting device is provided, an organic semiconductor material is used. Transistors that have light-transmitting properties, such as organic transistors using a semiconductor or transistors using an oxide semiconductor, A transistor may be used.

[0321] The display unit 9712 is a display device provided in a pillar portion. By displaying the image from the imaging means on the display unit 9712, the view blocked by the pillars can be cleared. The display unit 9713 is a display device provided in the dashboard. For example, an image captured by an imaging means provided on the vehicle body is displayed on the display unit 9713. This allows the driver to supplement the view obstructed by the dashboard. By projecting images from the imaging means installed in the In addition, by projecting images that complement the invisible parts, it is possible to create a more natural and natural appearance. Safety can be checked without any sense of discomfort.

[0322] FIG. 16(D) shows the interior of a car with bench seats for the driver and passenger. The display unit 9721 is a display device provided in the door. By displaying an image from the imaging means on the display unit 9721, it is possible to The display portion 9722 is a display device provided on the handle. The display unit 9723 is a display device provided in the center of the seat surface of the bench seat. The display device is installed on the seat or backrest, and the heat generated by the display device is It can also be used as a seat heater using this as a heat source.

[0323] The display unit 9714, the display unit 9715, or the display unit 9722 displays navigation information, speech such as the odometer, tachometer, mileage, fuel level, gear status, and air conditioning settings. It is also possible to provide various other information. The above information can be changed as needed to suit the user's preferences. The images can also be displayed on the display units 9710 to 9713, the display unit 9721, and the display unit 9723. In addition, the display units 9710 to 9715 and the display units 9721 to 9723 are illuminated. The display units 9710 to 9715 can also be used as a lighting device. The portion 9721 to the display portion 9723 can also be used as a heating device.

[0324] The electronic device described in this embodiment has a display unit for displaying some information. However, the light-emitting element of one embodiment of the present invention can also be applied to electronic devices that do not have a display portion. In addition, the display unit of the electronic device described in this embodiment has flexibility. and a configuration in which the display can be performed along a curved display surface, or a foldable display unit. However, the present invention is not limited to this, and any structure that does not have flexibility and displays on a flat surface may be used. It may also be composed.

[0325] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. can be done.

[0326] (Embodiment 6) In this embodiment, a light-emitting element of one embodiment of the present invention is applied to various electronic devices and lighting devices. An example of this will be described with reference to FIGS. 17 and 18. FIG.

[0327] By fabricating the light-emitting element of one embodiment of the present invention over a flexible substrate, it is possible to fabricate a light-emitting element having a curved surface. It is possible to realize electronic devices and lighting devices having light-emitting regions.

[0328] Furthermore, a light-emitting device using a light-emitting element according to one embodiment of the present invention can be used for automobile lighting. For example, lighting can be installed on the windshield, ceiling, etc.

[0329] FIG. 17(A) shows a perspective view of one side of the multifunction terminal 3500, and FIG. 17(B) shows a perspective view of the multifunction terminal 3500. 3 shows a perspective view of the other side of the multifunction terminal 3500. The multifunction terminal 3500 has a housing 350 2 incorporates a display unit 3504, a camera 3506, a light 3508, etc. The light emitting element of the embodiment can be used for lighting 3508.

[0330] The light source 3508 functions as a surface light source by using the light-emitting element of one embodiment of the present invention. Therefore, unlike point light sources such as LEDs, light emission with little directionality can be obtained. For example, when the lighting 3508 and the camera 3506 are used in combination, the lighting 3508 is turned on or off. The light 3508 can be illuminated or blinked, and captured by the camera 3506. It functions as a surface light source, allowing you to take photos that look like they were taken under natural light. Cut.

[0331] The multifunction terminal 3500 shown in FIGS. 17(A) and 17(B) is the same as that shown in FIGS. 13(A) to 13(G). ) can have a variety of functions.

[0332] In addition, inside the housing 3502, a speaker, a sensor (force, displacement, position, velocity, acceleration, angle Speed, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, Includes functions to measure voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays The multifunction terminal 3500 may include a speaker, a microphone, etc. By providing a detection device having a sensor that detects tilt, such as a gyro or acceleration sensor, The screen display of the display unit 3504 is automatically adjusted by determining the orientation (portrait or landscape) of the functional terminal 3500. You can make it so that it switches.

[0333] The display unit 3504 can also function as an image sensor. By touching the palm or fingers to the sensor 504 and capturing an image of the palm print, fingerprint, etc., personal authentication can be performed. In addition, the display unit 3504 may be provided with a backlight that emits near-infrared light or a sensor that emits near-infrared light. If a light source for imaging is used, it is also possible to image finger veins, palm veins, etc. The light-emitting element of one embodiment of the present invention may be applied to 04.

[0334] FIG. 17(C) shows a perspective view of a security light 3600. The light 3600 is The housing 3602 has a light 3608 on the outside, and the housing 3602 is equipped with a speaker 3610 and the like. The light-emitting element of one embodiment of the present invention can be used for the lighting 3608.

[0335] Light 3600 may include, for example, a device for grasping, holding, or holding light 3608. The inside of the housing 3602 is provided with a light 3600. The light emitting device may be provided with an electronic circuit that can control the light emitting method. Alternatively, a circuit that can emit light intermittently multiple times may be used, or the current value of the light emission may be controlled. The circuit may be configured so that the amount of light emitted can be adjusted by adjusting the amount of light emitted. At the same time, a circuit may be incorporated to output a loud alarm sound from the speaker 3610. stomach.

[0336] The Light 3600 can emit light in any direction, so it can be used to target, for example, thugs. It can be used to scare off predators with light or light and sound. It may also be equipped with a camera such as a still camera, or a function having a photography function.

[0337] FIG. 18 shows an example in which the light-emitting element is used as an indoor lighting device 8501. Since the surface area can be increased, a large-area lighting device can be formed. By using a housing having the above structure, a lighting device 8502 having a curved light-emitting area can be formed. The light-emitting element shown in this embodiment mode has a thin film shape, and the housing can be designed with a high degree of freedom. Therefore, it is possible to create lighting devices with various elaborate designs. A large lighting device 8503 may be provided on the wall. A touch sensor may be provided in 503 to turn the power on or off.

[0338] In addition, by using light-emitting elements on the surface of the table, it has the function of a table. The lighting device 8504 can be used as a lighting device. This allows the lighting device to function as furniture.

[0339] In this manner, a lighting device and an electronic device can be obtained by applying a light-emitting element of one embodiment of the present invention. Note that the lighting devices and electronic devices to which the present invention can be applied are the same as those described in this embodiment. The present invention can be applied to electronic devices in a wide range of fields.

[0340] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. You can be there. [Example]

[0341] In this example, N-(biphenyl-4- yl)-N-{4-[6-(biphenyl-4-yl)pyrimidin-4-yl]phenyl} -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: 6BP-4FBiPPm) The synthesis method of (structural formula (100)) and the physical properties of the compound will be explained.

[0342] <Synthesis Example 1> Step 1: N-(biphenyl-4-yl)-N-{4-[6-(biphenyl-4-yl) )pyrimidin-4-yl]phenyl}-9,9-dimethyl-9H-fluorene-2-amine Synthesis of 6BP-4FBiPPm

[0343] In a 200 mL three-neck flask, add 1.2 g (4.5 mmol) of 4-(4-biphenyl)-6- Chloropyrimidine and 2.2 g (4.5 mmol) of 4-[N-(biphenyl-4-yl) )-N-(9,9-dimethyl-9H-fluoren-2-yl)amino]phenylboronic acid , 1.9 g (13.5 mmol) potassium carbonate, 55 mg (0.18 mmol) trichloride To this mixture was added 25 mL of toluene and 1 mL of bis(2-methylphenyl)phosphine. 0 mL of ethanol and 7 mL of water were added. The mixture was stirred under reduced pressure to remove To this mixture was added 20 mg (0.090 mmol) of palladium(II) acetate. The mixture was stirred at 90°C for 6 hours under a nitrogen stream. After stirring, the aqueous layer was extracted with toluene. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, and This mixture was separated by gravity filtration, and the filtrate was concentrated to obtain a solid. Column chromatography (developing solvent: toluene, then toluene:ethyl acetate 4:1) The solid was obtained by purifying the solid using silica gel (Kanto Chemical Co., Ltd., catalog number: The obtained solid was recrystallized from toluene / ethanol to give a yellow solid. The compound was obtained in an amount of 2.7 g in a yield of 89%. The synthetic scheme of Step 1 is shown in formula (A-1) below.

[0344] [ka]

[0345] The resulting solid (2.7 g) was purified by train sublimation at a pressure of 2.8 P. a) The purification was carried out by heating at 305°C under the condition of an argon flow rate of 15 mL / min. 2.3 g of a yellow solid was obtained with a recovery of 88%.

[0346] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(DMSO-d6,300MHz):δ=1.43(s,6H),7.12 -7.18(m,3H),7.26(d,J1=8.7Hz,2H),7.30-7.3 8(m,3H),7.40-7.56(m,7H),7.68-7.73(m,4H), 7.80(dd,J1=7.2Hz,J2=1.5Hz,3H),7.85(d,J1= 8.1Hz,1H),8.89(d,J1=8.4Hz,2H),8.34(d,J1= 8.7Hz,2H),8.46(d,J1=8.1Hz,2H),8.58(d,J1= 1.5Hz,1H), 9.24(d,J1=1.5Hz,1H)

[0347] In addition, the obtained solid 1The 1 H NMR charts are shown in Figures 19(A) and 19(B). Figure 19(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 19(A). The measurement results showed that the target product, 6BP-4FBiPPm, was obtained.

[0348] <Characteristics of 6BP-4FBiPPm> The absorption and emission spectra of the toluene solution of 6BP-4FBiPPm are shown in Figure 20. The absorption and emission spectra of the thin film are shown in Figure 21. The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer. A spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. Only toluene was placed in a quartz cell and measured. The absorption spectrum of toluene measured was compared with that of a toluene solution of 6BP-4FBiPPm. By subtracting the absorption spectra of the 6BP-4FBiPPm toluene solution shown in Figure 20, The absorption spectrum of the thin film was measured using a spectrophotometer (Hitachi High A spectrophotometer (U4100 manufactured by Technologies) was used. A fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used.

[0349] As shown in Figure 20, the toluene solution of 6BP-4FBiPPm exhibits the following wavelengths: 395 nm, 356 nm, and 310 nm. Similarly, from Figure 20, the peak of the emission wavelength is 468 nm (excitation wavelength). In addition, from Figure 21, the 6BP-4FBiPPm thin film Absorption peaks are observed around 2 nm, 362 nm, 313 nm, 265 nm, and 204 nm. Similarly, from Figure 21, the emission wavelength peak is seen around 497 nm (excitation wavelength 402 nm). It was confirmed that 6BP-4FBiPPm emits blue light. can also be used as a host for luminescent materials and fluorescent materials that emit light in the visible range.

[0350] In addition, thin films of 6BP-4FBiPPm are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the film was small and of good quality.

[0351] The HOMO and LUMO levels of 6BP-4FBiPPm were measured by cyclic voltammetry. The calculation method is shown below.

[0352] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 05-6) was used, and the supporting electrolyte was tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. The working electrode was a platinum electrode (PT, manufactured by BAS Co., Ltd.). E platinum electrode), and as an auxiliary electrode, a platinum electrode (B.A.S. Co., Ltd., VC-3 P The counter electrode (5 cm) was used as the reference electrode, and Ag / Ag + Electrode (B.A.E. The measurements were carried out at room temperature (20 The scan speed during CV measurement was standardized to 0.1 V / sec. The oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. The potential Ec is the midpoint potential of the oxidation-reduction wave, and the potential Ec is the midpoint potential of the reduction-oxidation wave. The potential energy of the reference electrode relative to the vacuum level is -4.94 eV. Since it is known that there is a HOMO level [eV] = -4.94-Ea, the LUMO level From the formula [eV]=-4.94-Ec, the HOMO level and LUMO level are can be requested.

[0353] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was The electrical stability of the compounds was investigated by comparing the oxidation-reduction waves in the first cycle.

[0354] As a result, in the measurement of the oxidation potential Ea [V] of 6BP-4FBiPPm, the HOMO level The LUMO level was found to be -5.48 eV, while the LUMO level was found to be -2.79 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveforms after the measurement, the peaks were 92% for Ea measurement and 87% for Ec measurement. The coating strength of 6BP-4FBiPPm was maintained, indicating that it is resistant to oxidation and reduction. was confirmed to be very good. [Example]

[0355] In this example, 4-[6-(biphenyl)-2-(4-(2-methyl-2-phenyl)-1,3-diol]-2,4-diol, which is one of the organic compounds according to one embodiment of the present invention, was synthesized. -4-yl)pyrimidin-4-yl]-4'-phenyl-4"-(9-phenyl-9H- Carbazol-3-yl)triphenylamine (abbreviation: 6BP-4PCBBiPPm) ( The synthesis method of the compound represented by structural formula (101) and the physical properties of the compound will be explained.

[0356] <Synthesis Example 2> Step 1: 4-[6-(biphenyl-4-yl)pyrimidin-4-yl]-4'-phenyl Nyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation Synthesis of 6BP-4PCBBiPPm

[0357] In a 200 mL three-neck flask, add 1.7 g (5.0 mmol) of 4-(4-biphenyl)-6- (4-chlorophenyl)pyrimidine and 2.7 g (5.5 mmol) of N-biphenyl- [4-(9-phenyl-9H-carbazol-3-yl)phenyl]amine, 1.5 g (15 mmol) of sodium tert-butoxide and 90 mg (0.25 mmol ) di(1-adamantyl)-n-butylphosphine was added to the mixture. 25 mL of bis(dibenzyl)propanol was added and the mixture was degassed by stirring under reduced pressure. Add 29 mg (0.050 mmol) of palladium(0) and evaporate under a nitrogen atmosphere. The mixture was heated and stirred at 110°C for 23.5 hours. After stirring, toluene was added to the mixture, and the mixture was Zeal (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135), Celite (Wako Junyaku Kogyo Co., Ltd., Catalog No.: 531-16855), and filtered through alumina. The filtrate was concentrated to give a solid. The solid was recrystallized from toluene to give a pale yellow solid. 3.3 g of a yellow solid was obtained in a yield of 82%. The synthesis scheme of Step 1 is shown in formula (A-2) below. show.

[0358] [ka]

[0359] The resulting pale yellow solid (3.2 g) was purified by train sublimation. The sublimation was carried out at 380°C under the conditions of 0.9 Pa and an argon flow rate of 15 mL / min. After purification, 2.8 g of a yellow solid was obtained with a recovery rate of 88%.

[0360] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(1,1,2,2-Tetrachloroethane-d2,300M Hz):δ=7.31-7.41(m,8H),7.43-7.54(m,9H),7. 61-7.75(m,13H),7.81(d,J1=8.4Hz,1H),8.11- 8.14(m,3H),8.21-8.28(m,3H),8.39(d,J1=0.9 Hz,2H),9.30(s,1H)

[0361] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 22(A) and 22(B). Figure 22(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 22(A). The measurement results show that the target substance, 6BP-4PCBBiPPm, was obtained. Ta.

[0362] <Characteristics of 6BP-4PCBBiPPm> Next, the absorption and emission spectra of the toluene solution of 6BP-4PCBBiPPm were measured. The absorption spectrum and emission spectrum of the thin film are shown in Figure 23. Measurement method was carried out in the same manner as in Example 1 described above.

[0363] As shown in Figure 23, the toluene solution of 6BP-4PCBBiPPm exhibited peaks at 394 nm, 347 nm, and 3 Absorption peaks are observed around 24 nm, 302 nm, and 282 nm. The wavelength peak was 468 nm (excitation wavelength 396 nm). -4PCBBiPPm thin films are available in 400nm, 355nm, 332nm, 304nm, and 28nm. Absorption peaks are observed around 2 nm and 244 nm. Similarly, from Figure 24, the emission wavelength peaks are The compound of one embodiment of the present invention is a luminescent material. It can also be used as a host for fluorescent materials that emit light in the visible range.

[0364] In addition, the thin film of 6BP-4PCBBiPPm is resistant to aggregation even in the atmosphere and does not change in shape. It was found that the film had good quality with little degradation.

[0365] Next, the HOMO and LUMO levels of 6BP-4PCBBiPPm were calculated by cyclic boron spectroscopy. The calculation was performed in the same manner as in Example 1.

[0366] As a result, in the measurement of the oxidation potential Ea [V] of 6BP-4PCBBiPPm, the HOMO The energy level was found to be -5.48 eV, while the LUMO level was -2.82 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the test, the Ea measurement was 79% and the Ec measurement was 94%. The peak intensity of 6BP-4PCBBiPPm was maintained, indicating that it is resistant to oxidation and reduction. It was confirmed that the resistance to [Example]

[0367] In this example, N-(biphenyl-4-yl)-2-methyl-2-phenylpropanol, which is one of the organic compounds according to one embodiment of the present invention, was used. -N-{3-[6-(biphenyl-4-yl)pyrimidin-4-yl]phenyl}- 9,9-Dimethyl-9H-fluoren-2-amine (abbreviation: 6BP-4mFBiPPm) The synthesis method of (structural formula (102)) and the physical properties of the compound will be explained.

[0368] <Synthesis Example 3> Step 1: N-(biphenyl-4-yl)-N-{3-[6-(biphenyl-4-yl) )pyrimidin-4-yl]phenyl}-9,9-dimethyl-9H-fluorene-2-amine Synthesis of 6BP-4mFBiPPm

[0369] In a 200 mL three-neck flask, add 2.1 g (6.0 mmol) of 4-(4-biphenyl)-6- (3-chlorophenyl)pyrimidine and 2.4 g (6.6 mmol) of N-(biphenyl -4-yl)-9,9-dimethyl-9H-fluoren-2-amine, 1.73 g (18. 0 mmol) of sodium tert-butoxide and 107 mg (0.30 mmol) of Di(1-adamantyl)-n-butylphosphine was added to the mixture. The mixture was degassed by adding bis(dibenzylidene Add 34 mg (0.060 mmol) of palladium(0) in acetone and heat under a nitrogen stream for 1 The mixture was heated and stirred at 10°C for 35 hours. After stirring, toluene was added to the mixture, and Florisil, The mixture was filtered through celite and alumina under suction to obtain a filtrate, which was then concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: toluene, then The resulting solid was purified with toluene / ethanol (100:3). The solid was recrystallized from methanol to give a pale yellow solid (3.9 g, 97% yield). is shown in the following formula (A-3).

[0370] [ka]

[0371] The resulting pale yellow solid (3.8 g) was purified by train sublimation. The sublimation was carried out at 300°C under the conditions of 0.7 Pa and an argon flow rate of 15 mL / min. After purification, 3.2 g of a pale yellow solid was obtained with a recovery rate of 84%.

[0372] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(DMSO-d6,300MHz):δ=1.40(s,6H),7.09 (dd,J1=7.8Hz,J2=2.1Hz,1H),7.19(d,J1=8.7H z,2H),7.26-7.58(m,12H),7.66-7.70(m,4H),7 .76-7.82(m,4H),7.87(d,J1=8.7Hz,2H),8.12( d,J1=7.8Hz,1H),8.18(t,J1=2.1Hz,1H),8.45( d,J1=8.4Hz,2H),8.64(d,J1=0.9Hz,1H),9.22( d, J1 = 0.9 Hz, 1 H)

[0373] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 25(A) and 25(B). Figure 25(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 25(A). The measurement results showed that the target product, 6BP-4mFBiPPm, was obtained. .

[0374] <Characteristics of 6BP-4mFBiPPm> The absorption and emission spectra of 6BP-4mFBiPPm in toluene are shown in Figure 26. The absorption spectrum and emission spectrum of the thin film are shown in Figure 27. The measurement methods for the absorption spectrum of the thin film and the emission spectrum were the same as those in Example 1. The emission spectrum of the thin film was measured using a micro PL microscope (Horiba Ltd., LabR AM HR-PL) was used.

[0375] As shown in Figure 26, the toluene solution of 6BP-4mFBiPPm has peaks at around 352 nm and 327 nm. Similarly, from Figure 26, the emission wavelength peak is 496 nm (excitation wavelength 35 4 nm). Also, from Figure 27, the thickness of the 6BP-4mFBiPPm thin film was 365 nm, Absorption peaks are observed around 327 nm, 264 nm, and 204 nm. The peak of the light wavelength was observed around 496 nm (excitation wavelength 410 nm). The compounds can also be used as hosts for luminescent materials and fluorescent materials that emit light in the visible range.

[0376] In addition, thin films of 6BP-4mFBiPPm are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the film had good quality with small values.

[0377] Next, the HOMO and LUMO levels of 6BP-4mFBiPPm were investigated by cyclic boron spectroscopy. The calculation was based on volatility (CV) measurements and was performed in the same manner as in Example 1.

[0378] As a result, in the measurement of the oxidation potential Ea [V] of 6BP-4mFBiPPm, The LUMO level was found to be -5.46 eV, while the LUMO level was found to be -2.83 eV. In addition, in repeated measurements of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the test, the Ea measurement showed 91% and the Ec measurement showed 90%. Since the peak intensity was maintained, 6BP-4mFBiPPm was found to be resistant to oxidation and reduction. It was found to be very well tolerated. [Example]

[0379] In this example, 3-[6-(biphenyl- 4-yl)pyrimidin-4-yl]-4'-phenyl-4"-(9-phenyl-9H-ca 6BP-4mPCBBiPPm) The synthesis method of the compound represented by structural formula (103) and the physical properties of the compound will be explained below.

[0380] <Synthesis Example 4> Step 1: 3-[6-(biphenyl-4-yl)pyrimidin-4-yl]-4'-phenyl Nyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation Synthesis of 6BP-4mPCBBiPPm

[0381] In a 200 mL three-neck flask, add 1.7 g (5.0 mmol) of 4-(4-biphenyl)-6- (3-chlorophenyl)pyrimidine and 2.7 g (5.5 mmol) of N-biphenyl- [4-(9-phenyl-9H-carbazol-3-yl)phenyl]amine, 1.45g (15.1 mmol) of sodium tert-butoxide and 90 mg (0.25 mmol) of sodium tert-butoxide. l) Di(1-adamantyl)-n-butylphosphine was added to the mixture. 25 mL of ethanol was added, and the mixture was degassed by stirring under reduced pressure. Add 29 mg (0.050 mmol) of bis(dibenzylideneacetone)palladium(0) The mixture was heated and stirred at 110°C for 35 hours under a nitrogen stream. After stirring, toluene was added to the mixture. The mixture was filtered through Florisil, Celite, and alumina with suction to obtain a filtrate. The mixture was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: toluene). The resulting solid was purified with toluene, then toluene:ethyl acetate=100:1. The solid was reprecipitated with ethyl acetate / ethanol to give 3.3 g of a yellow solid in 83% yield. The synthesis scheme of AP-1 is shown in formula (A-4) below.

[0382] [ka]

[0383] The resulting yellow solid (3.3 g) was purified by train sublimation at a pressure of 3. The purification was carried out by heating at 370°C under conditions of 0 Pa and an argon flow rate of 15 mL / min. After that, 2.7 g of a yellow solid was obtained with a recovery rate of 83%.

[0384] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(DMSO-d6,300MHz):δ=7.24(dd,J1=8.7H z,J2=14.7Hz,4H),7.29-7.62(m,13H),7.65-7. 82(m,13H),7.88(d,J1=8.4Hz,2H),8.15(d,J1= 7.8Hz,1H),8.19(s,1H),8.35(d,J1=7.2Hz,1H) ,8.47(d,J1=8.4Hz,2H),8.60(d,J1=1.5Hz,1H) ,8.66(s,1H),9.25(s,1H)

[0385] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 28(A) and 28(B). Figure 28(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 28(A). The measurement results show that the target substance, 6BP-4mPCBBiPPm, was obtained. It was.

[0386] <Characteristics of 6BP-4mPCBBiPPm> Figure 2 shows the absorption and emission spectra of 6BP-4mPCBBiPPm in toluene. The absorption spectrum and emission spectrum of the thin film are shown in Figure 9. The absorption spectrum of the solution is The methods for measuring the absorption spectrum of the thin film were the same as those in Example 1. The emission spectra of the thin films were measured using a micro PL microscope (Horiba Ltd., La bram HR-PL) was used.

[0387] As shown in Figure 29, the toluene solution of 6BP-4mPCBBiPPm exhibited a 392 nm and 282 nm Similarly, from Figure 29, the emission wavelength peak is 498 nm (excitation wavelength 332 nm). Also, from Figure 30, the thin film of 6BP-4mPCBBiPPm was 36 Absorption peaks are observed around 3 nm, 330 nm, 285 nm, and 251 nm. As a result, the peak of the emission wavelength was observed around 494 nm (excitation wavelength 410 nm). The compound of one embodiment can also be used as a host for a luminescent material or a fluorescent material that emits light in the visible region.

[0388] In addition, the thin film of 6BP-4mPCBBiPPm is resistant to aggregation even in the atmosphere, and the morphology It was found that the film quality was good with little change.

[0389] Next, the HOMO and LUMO levels of 6BP-4mPCBBiPPm were cyclically The calculation was based on voltammetry (CV) measurements, and the calculation method was the same as in Example 1.

[0390] As a result, in the measurement of the oxidation potential Ea [V] of 6BP-4mPCBBiPPm, HOM The O level was found to be -5.45 eV, while the LUMO level was -2.84 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the cycle, the Ea measurement was 89% and the Ec measurement was 90%. % peak intensity, it was found that 6BP-4mPCBBiPPm was oxidized and reduced. It was confirmed that the resistance to [Example]

[0391] In this example, 4,6-bis{4-[N- (biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)] Synthesis of {aminophenyl}pyrimidine (abbreviation: 4,6FBiP2Pm) (structural formula (104)) The synthesis method and physical properties of the compound will be explained.

[0392] <Synthesis Example 5> Step 1: 4,6-bis{4-[N-(biphenyl-4-yl)-N-(9,9-dimethyl) 4,6-trimethyl-9H-fluoren-2-yl)]aminophenyl}pyrimidine (abbreviation: 4,6FB Synthesis of iP2Pm

[0393] In a 200 mL three-neck flask, add 1.3 g (4.2 mmol) of 4,6-bis(4-chlorophenoxy) N-(biphenyl-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine, 0.15 g (0.42 mmol) of di( 1-Adamantyl)-n-butylphosphine, 2.43g (25mmol) sodium To this mixture was added 40 mL of toluene. The mixture was degassed by stirring under reduced pressure. l) bis(dibenzylideneacetone)palladium(0) was added, and the mixture was heated at 110°C under a nitrogen stream. After stirring, toluene was added to the mixture, and Florisil and Celite were added. The resulting filtrate was concentrated to obtain a solid. The solid was purified by silica gel column chromatography (developing solvent: toluene, then toluene:acetic acid This solid was purified with ethyl acetate (50:1) to give a solid. The mixture was purified with toluene (developing solvent: toluene, then toluene:ethyl acetate=500:1) to obtain a solid. The obtained solid was recrystallized from toluene / ethanol to obtain a yellow solid. The solid was recrystallized twice more from toluene / ethanol to give 2.9 g of a yellow solid in 71% yield. The synthetic scheme of step 1 is shown in formula (A-5) below.

[0394] [ka]

[0395] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(DMSO-d6,300MHz):δ=1.42(s,12H),7.1 0-7.16(m,6H),7.23(d,J1=8.7Hz,4H),7.27-7. 37(m,8H),7.41-7.50(m,6H),7.64-7.67(m,8H) ,7.74(d,J1=7.8Hz,2H),7.79(d,J1=8.4Hz,2H) ,8.22(d,J1=8.1Hz,4H),8.31(s,1H),9.12(s,1 H)

[0396] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 31(A) and 31(B). Figure 31(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 31(A). The measurement results showed that the target compound, 4,6FBiP2Pm, was obtained.

[0397] <4,6FBiP2Pm characteristics> Next, the absorption spectrum and emission spectrum of the toluene solution of 4,6FBiP2Pm are shown in Figure 32. The absorption spectrum and emission spectrum of the thin film are shown in Figure 33. The measurement method was explained above. The same procedure as in Example 1 was carried out.

[0398] From Figure 32, the toluene solution of 4,6FBiP2Pm exhibits 403nm, 356nm, and 282nm. Similarly, from Figure 32, the peak of the emission wavelength is 457 nm (excitation Also, from Figure 33, the 4,6FBiP2Pm thin film had a wavelength of 407nm. m, absorption peaks around 360nm, 335nm, 290nm, 261nm, and 208nm Similarly, from Figure 33, the peak of the emission wavelength is around 488 nm (excitation wavelength 400 nm). The compound according to one embodiment of the present invention can be used as a host for a luminescent material or a fluorescent material emitting light in the visible region. is also available.

[0399] In addition, thin films of 4,6FBiP2Pm are less likely to aggregate even in the atmosphere, and their morphology changes little. It was found that the film quality was very good.

[0400] Next, the HOMO and LUMO levels of 4,6FBiP2Pm were measured by cyclic voltammetry. The calculation was performed in the same manner as in Example 1.

[0401] As a result, in the measurement of the oxidation potential Ea [V] of 4,6FBiP2Pm, the HOMO level is The LUMO level was found to be -5.49 eV, while the LUMO level was found to be -2.72 eV. In addition, in repeated measurements of the oxidation-reduction wave, the When compared with the waveforms shown in Fig. 1, the peaks were 93% for Ea measurement and 70% for Ec measurement. Since the hardness of 4,6FBiP2Pm was maintained, it is considered that the resistance to oxidation and reduction is very high. It was always found to be good. [Example]

[0402] In this example, 4,6-bis{3-[N- (biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)] {aminophenyl}pyrimidine (abbreviation: 4,6mFBiP2Pm) (structural formula (105)) The synthesis method and physical properties of the compound will be explained.

[0403] <Synthesis Example 6> Step 1: 4,6-bis{3-[N-(biphenyl-4-yl)-N-(9,9-dimethyl) 4,6mF Synthesis of BiP2Pm

[0404] In a 200 mL three-neck flask, add 1.3 g (4.2 mmol) of 4,6-bis(3-chlorophenoxy) N-(biphenyl-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine, 151 mg (0.42 mmol) of di( 1-Adamantyl)-n-butylphosphine, 2.4g (25mmol) sodium tert-butoxide was added to the mixture. 40 mL of toluene was added to the mixture. The mixture was degassed by stirring under reduced pressure. ) bis(dibenzylideneacetone)palladium(0) was added and the mixture was heated at 110°C under a nitrogen stream. After stirring for 34.5 hours, toluene was added to the mixture, and the mixture was filtered through Florisil and Celite. The mixture was filtered through alumina under suction to obtain a filtrate. The filtrate was concentrated to obtain a solid. The product was purified by silica gel column chromatography (eluent: hexane:toluene = 2:1, This solid was purified with toluene (in the absence of toluene) to obtain a solid. High-performance liquid column chromatography was performed using chloroform as the developing solvent. The obtained fraction was concentrated to obtain a solid. After adding the solution and irradiating with ultrasound, the mixture was filtered to obtain 1.6 g of a yellow solid in a yield of 41%. The synthesis scheme is shown in formula (A-6) below.

[0405] [ka]

[0406] The obtained solid (1.4 g) was purified by train sublimation at a pressure of 2.9 P. a) The purification was carried out by heating at 355°C under the condition of an argon flow rate of 15 mL / min. A yellow solid was obtained in an amount of 1.3 g, with a recovery of 91%.

[0407] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(DMSO-d6,300MHz):δ=1.38(s,12H),7.0 5(dd,J1=8.1Hz,J2=1.8Hz,2H),7.16(d,J1=8.7 Hz,4H),7.24-7.36(m,10H),7.42-7.54(m,8H), 7.64-7.68(m,8H),7.77(t,J1=8.1Hz,4H),8.03 (d,J1=7.8Hz,2H),8.10(s,2H),8.51(s,1H),9. 11(s,1H)

[0408] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 34(A) and 34(B). Figure 34(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 34(A). The measurement results showed that the target product, 4,6mFBiP2Pm, was obtained.

[0409] <Characteristics of 4.6mFBiP2Pm> Next, the absorption and emission spectra of the toluene solution of 4,6mFBiP2Pm are shown in Figure 3. The absorption spectrum and emission spectrum of the thin film are shown in Figure 36. The experiment was carried out in the same manner as in Example 1 shown in .

[0410] As shown in Figure 35, the toluene solution of 4,6mFBiP2Pm exhibits an absorption peak around 364 nm. Similarly, from Figure 35, the peak of the emission wavelength was 498 nm (excitation wavelength 348 nm). Also, from Figure 36, the thin film of 4,6mFBiP2Pm has Absorption peaks are observed around 5 nm, 275 nm, 249 nm, and 207 nm. As a result, the peak of the emission wavelength was observed around 512 nm (excitation wavelength 400 nm). The compound of one embodiment can also be used as a host for a luminescent material or a fluorescent material that emits light in the visible region.

[0411] In addition, the thin film of 4,6mFBiP2Pm is resistant to aggregation even in the atmosphere and its morphology remains unchanged. It was found that the film was small and of good quality.

[0412] Next, the HOMO and LUMO levels of 4,6mFBiP2Pm were measured by cyclic voltammograms. The calculation was performed in the same manner as in Example 1.

[0413] As a result, in the measurement of the oxidation potential Ea [V] of 4,6mFBiP2Pm, the HOMO level The LUMO level was found to be -5.46 eV, while the LUMO level was found to be -2.80 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveforms after the measurement, the peaks were 97% for Ea measurement and 70% for Ec measurement. The coating strength of 4,6mFBiP2Pm was maintained, indicating that it is resistant to oxidation and reduction. was confirmed to be very good. [Example]

[0414] In this example, N-(4-biphenyl), which is one of the organic compounds according to one embodiment of the present invention, was synthesized. -N-(9,9-dimethyl-9H-fluoren-2-yl)-4-[3-(dibenzo[f ,h]quinoxalin-2-yl)phenyl]phenylamine (abbreviation: 2mpFBiBPD The synthesis method of Bq) (structural formula (106)) and the physical properties of this compound will be explained.

[0415] <Synthesis Example 7> Step 1: N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2 -yl)-4-[3-(dibenzo[f,h]quinoxalin-2-yl)phenyl]phenyl Synthesis of 2mpFBiBPDBq

[0416] In a 200 mL three-neck flask, add 2.0 g (3.9 mmol) of N-(4-bromophenyl) -N-(4-biphenylyl)-9,9-dimethyl-9H-fluoren-2-amine, 1 0.7g (3.9mmol) of 4,4,5,5-tetramethyl-2-[3-(dibenzo[f ,h]quinoxalin-2-yl)phenyl]-1,3,2-dioxaborolane and 24m g (0.078 mmol) of tri(o-tolyl)phosphine and 1.1 g (7.8 mmol) of 1) Potassium carbonate was added to the flask, and the atmosphere in the flask was replaced with nitrogen. Add 4.5 mL of ethanol and 4.0 mL of water, and stir under reduced pressure. After degassing, 8.8 mg (0.078 mmol) of palladium acetate ( II) was added and stirred at about 80° C. for 7 hours. After stirring, the mixture was suction filtered to obtain a solid. The obtained solid was dissolved in about 30 mL of hot toluene, and the solution was applied to a silica gel column. When purified by chromatography (developing solvent: hexane:toluene=9:1), The solid was purified by high performance liquid chromatography (HPLC). The solid was recrystallized from toluene / hexane to give the target pale yellow solid. 1.7 g of a solid was obtained in a yield of 59%. The synthesis scheme of Step 1 is shown in Formula (A-7) below. .

[0417] [ka]

[0418] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1H NMR(CDCl3,500MHz):δ=1.47(s,6H),7.17(d d,J1=8.5Hz,J2=2.0Hz,1H),7.27-7.35(m,8H), 7.41-7.46(m,3H),7.56(d,J=9.0Hz,2H),7.61- 7.69(m,7H),7.76-7.84(m,5H),8.28,(d,J=8.0 Hz,1H),8.60(s,1H),8.66(d,J=8.0Hz,2H),9.2 5(dd,J1=8.0Hz,J2=2.0Hz,1H),9.44(dd,J1=8. 0Hz,J2=2.0Hz,1H),9.46(s,1H)

[0419] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 37(A) and 37(B). Figure 37(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 37(A). The measurement results showed that the target substance, 2mpFBiBPDBq, was obtained.

[0420] <2mpFBiBPDBq characteristics> Next, the absorption and emission spectra of the toluene solution of 2mpFBiBPDBq are shown in Figure 3. The absorption spectrum and emission spectrum of the thin film are shown in Figure 39. The experiment was carried out in the same manner as in Example 1 shown in .

[0421] From Figure 38, the toluene solution of 2mpFBiBPDBq shows an absorption peak around 361 nm. Similarly, from Figure 38, the peak of the emission wavelength was 466 nm (excitation wavelength 366 nm). Also, from Figure 39, the 2mpFBiBPDBq thin film has 366nm, 311nm, and 26 Similarly, from Figure 39, the peak of the emission wavelength is The compound according to one embodiment of the present invention is a luminescent material. It can also be used as a host for fluorescent materials that emit light in the visible range.

[0422] In addition, the thin film of 2mpFBiBPDBq is resistant to aggregation even in the atmosphere and its morphology remains unchanged. It was found that the film was small and of good quality.

[0423] Next, the HOMO and LUMO levels of 2mpFBiBPDBq were measured by cyclic voltammograms. The calculation was performed in the same manner as in Example 1.

[0424] As a result, in the measurement of the oxidation potential Ea [V] of 2mpFBiBPDBq, the HOMO level The LUMO level was found to be -5.42 eV, while the LUMO level was found to be -2.93 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveforms after Ea measurement, the peaks were 91% and 86% for Ec measurement. The peak strength of 2mpFBiBPDBq was maintained, indicating that it is resistant to oxidation and reduction. was confirmed to be very good.

[0425] In addition, thermogravimetry-differential thermal analysis (TG-DTA) of 2mpFBiBPDBq gravimetry-Differential Thermal Analysis The measurements were carried out using a high vacuum differential thermobalance (manufactured by Bruker AXS Co., Ltd.). , TG-DTA2410SA) was used. At normal pressure, the temperature rise rate was 10 °C / min, and under a nitrogen gas flow ( When measured under the condition of flow rate: 200 mL / min, the relationship between weight and temperature (thermogravimetry) Therefore, the 5% weight loss temperature of 2mpFBiBPDBq was 500°C or higher. , it was shown that 2mpFBiBPDBq has good heat resistance. [Example]

[0426] In this example, N-(4-biphenylyl), which is one of the organic compounds of one embodiment of the present invention, was used. -N-(9,9-dimethyl-9H-fluoren-2-yl)-(4-{3-[6-(9, 9-Dimethyl-9H-fluoren-2-yl)pyrimidin-4-yl]phenyl}phenyl Synthesis method of 6FL-4mpFBiBPPm (structural formula (107)) The physical properties of this compound will be explained.

[0427] <Synthesis Example 8> Step 1: 4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)pyridine Synthesis of myidine

[0428] In a 200 mL three-neck flask, add 13 g (87 mmol) of 4,6-dichloropyrimidine and 1 3 g (40 mmol) of 4,4,5,5-tetramethyl-2-(9,9-dimethyl-9H -fluoren-2-yl)-1,3,2-dioxaborolane and 13 g (120 mmol ) of sodium carbonate was added to the flask, and the atmosphere in the flask was replaced with nitrogen. 4-Dioxane and 60 mL of water were added, and the mixture was degassed by stirring under reduced pressure. To this mixture, 0.28 g (0.40 mmol) of bis(triphenylphosphine) para Dithium(II) dichloride was added, and the mixture was irradiated with microwaves at 400 W for 8 hours. After irradiation for a certain period of time, the mixture was filtered by suction, and the aqueous layer of the obtained filtrate was extracted with toluene. The combined layer was washed with saturated saline. The solution was dried over magnesium sulfate. The mixture was gravity filtered to obtain a filtrate. The filtrate was concentrated to obtain an oily substance, and 20 mL of Aqueous toluene was added and the solution was suction filtered through Celite-alumina-Florisil. The filtrate was concentrated to give an oily substance, which was then purified by high performance liquid chromatography (HPLC). The obtained fraction was concentrated to give an oily product. The oily product was dried under reduced pressure. This gave 7.3 g of the desired pale brown oil in 60% yield. This series of operations was repeated twice. This resulted in the production of the target compound, 4-chloro-6-(9,9-dimethyl-9H-fluorene-2-yl). The synthesis scheme of Step 1 is shown in the following formula (A-8). ) shown.

[0429] [ka]

[0430] Step 2: 4-(3-chlorophenyl)-6-(9,9-dimethyl-9H-fluorene Synthesis of (2-yl)pyrimidine

[0431] In a 200 mL three-neck flask, add 10 g (32 mmol) of 4-chloro-6-(9,9-dimethylamino)methyl (9H-fluoren-2-yl)pyrimidine and 5.0 g (32 mmol) of 3-chloro- phenylboronic acid and 0.19 g (0.64 mmol) of tri(o-tolyl)phosphite. The flask was charged with 8.8 g (64 mmol) of potassium carbonate and the atmosphere in the flask was replaced with nitrogen. To this mixture, 140 mL of toluene, 20 mL of ethanol, and 32 mL of water were added. The mixture was degassed by stirring under reduced pressure. After degassing, 72 mg (0.32 mmol) of 1) Palladium (II) acetate was added and stirred at about 80°C for 27 hours. The aqueous layer of the product was extracted with toluene, and the combined organic layer was washed with saturated saline. The mixture was dried over magnesium, and gravity filtered to obtain a filtrate. The obtained filtrate was concentrated. To the oily substance obtained by this procedure, 20 mL of toluene was added, and the solution was diluted with Celite-alumina-fluoride. The filtrate was concentrated and the oily substance was filtered through Lorisil. The resulting fraction was concentrated to give an oily product. The oily substance obtained was dried under reduced pressure to obtain the target compound, 4-(3-chlorophenyl)-6-( 6.0 g of pale brown oil of 9,9-dimethyl-9H-fluoren-2-ylpyrimidine The synthesis scheme of Step 2 is shown in formula (A-9) below.

[0432] [ka]

[0433] Step 3: 4,4,5,5-tetramethyl-2-{3-[6-(9,9-dimethyl-9 H-fluoren-2-yl)pyrimidin-4-yl]phenyl}-1,3,2-dioxa Synthesis of borolane

[0434] In a 200 mL three-neck flask, add 6.0 g (15 mmol) of 4-(3-chlorophenyl)-6 -(9,9-dimethyl-9H-fluoren-2-yl)pyrimidine and 5.0 g (20 m mol) of bis(pinacolato)diboron and 0.14 g (0.40 mmol) of di(1- Adamantyl-n-butylphosphine and 3.9 g (40 mmol) of potassium acetate The flask was then purged with nitrogen. 80 mL of xylene was added to the mixture, and the mixture was stirred without reducing the pressure. The mixture was heated to 40°C and 0.16 g (0.20 mm ol) [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) di Chloride dichloromethane adduct was added, and the mixture was stirred at 140°C for 17 hours under a nitrogen stream. After stirring, the mixture was suction filtered, and the obtained filtrate was concentrated to give an oily substance. The product was purified by silica gel column chromatography (developing solvent: hexane:toluene = 2:1). The oily substance was dried under reduced pressure to obtain the target product. 4,4,5,5-tetramethyl-2-{3-[6-(9,9-dimethyl-9H-fluorene (2-phenyl-4-yl)phenyl}-1,3,2-dioxaborolane 2.9 g of a yellow oil was obtained in a yield of 41%. The synthesis scheme of Step 3 is shown in the following formula (A-10) ) shown.

[0435] [ka]

[0436] Step 4: N-(4-biphenylyl)-N-(9,9-dimethyl-9H-fluorene- 2-yl)-4-{3-[6-(9,9-dimethyl-9H-fluoren-2-yl)pyridine 6FL-4mpFBiBPPm Synthesis of

[0437] In a 100 mL three-neck flask, add 1.5 g (3.0 mmol) of N-(4-bromophenyl) -N-(4-biphenylyl)-9,9-dimethyl-9H-fluoren-2-amine, 1 0.4g (3.0mmol) of 4,4,5,5-tetramethyl-2-{3-[6-(9,9 -dimethyl-9H-fluoren-2-yl)pyrimidin-4-yl]phenyl}-1,3 ,2-dioxaborolane and 18 mg (0.060 mmol) of tri(o-tolyl)phos Put the fin and 0.83g (6.0mmol) of potassium carbonate into the flask and replace the air in the flask with nitrogen. To this mixture, 12 mL of toluene, 3.0 mL of ethanol, and 3.0 mL of water were added. The mixture was degassed by stirring under reduced pressure. After degassing, 6.7 mg (0. 039 mmol) of palladium(II) acetate was added, and the mixture was stirred at about 80°C for 8 hours. The aqueous layer of this mixture was extracted with toluene, and the combined organic layer was washed with saturated saline. The solution was dried over magnesium sulfate, and the mixture was gravity filtered to obtain a filtrate. The filtrate was concentrated and the oily substance was purified by silica gel column chromatography (eluent: toluene). The oily substance was purified by high performance liquid chromatography. The solid was purified by HPLC and washed with hexane. The target pale yellow solid was obtained in 0.89 g and a yield of 37%. This is shown in equation (A-11).

[0438] [ka]

[0439] The resulting pale yellow solid (0.82 g) was purified by train sublimation. The purification conditions were a pressure of 10 Pa, argon gas flow rate of 5.0 mL / min, and 32 The pale yellow solid was heated at 0°C. After purification by sublimation, the yellow solid of 6FL-4mpFBiBPPm was obtained. 0.65g was obtained with a recovery rate of 79%.

[0440] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1H NMR(CDCl3,500MHz):δ=1.46(s,6H),1.59(s ,6H),7.14(dd,J1=8.5Hz,J2=2.0Hz,1H),7.25- 7.53(m,14H),7.54(d,J=9.0Hz,2H),7.61-7.68 (m,7H),7.77-7.81(m,2H),7.87(d,J=8.0Hz,1H ),8.10,(d,J=8.0Hz,1H),8.14(dd,J1=8.0Hz,J 2=2.0Hz,1H),8.22(d,J=1.5Hz,1H),8.29(d,J= 1.5Hz,1H),8.41(t,J=1.5Hz,1H),9.36(d,J=1. 5Hz, 1H)

[0441] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 40(A) and 40(B). Figure 40(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 40(A). The measurement results show that the target substance, 6FL-4mpFBiBPPm, was obtained. It was.

[0442] <6FL-4mpFBiBPPm characteristics> Next, the absorption and emission spectra of 6FL-4mpFBiBPPm in toluene The absorption spectrum and emission spectrum of the thin film are shown in Figure 41. The method was the same as in Example 1 above.

[0443] As shown in Figure 41, the toluene solution of 6FL-4mpFBiBPPm has an absorption peak at around 346 nm. Similarly, from Figure 41, the peak of the emission wavelength is 445 nm (excitation wavelength 346 nm). Also, from Figure 42, the thin film of 6FL-4mpFBiBPPm was 380 nm and 34 Absorption peaks are observed around 8 nm, 277 nm, 215 nm, and 207 nm. As a result, the peak of the emission wavelength was observed around 490 nm (excitation wavelength 376 nm). The compound of one embodiment can also be used as a host for a luminescent material or a fluorescent material that emits light in the visible region.

[0444] In addition, thin films of 6FL-4mpFBiBPPm are resistant to aggregation even in the atmosphere, and have good morphology. It was found that the film quality was good with little change.

[0445] Next, the HOMO and LUMO levels of 6FL-4mpFBiBPPm were cyclically The calculation was based on voltammetry (CV) measurements, and the calculation method was the same as in Example 1.

[0446] As a result, in the measurement of the oxidation potential Ea [V] of 6FL-4mpFBiBPPm, HOM The O level was found to be -5.42 eV, while the LUMO level was -2.80 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the cycle, the Ea measurement was 93% and the Ec measurement was 83%. % peak intensity, it was found that 6FL-4mpFBiBPPm was oxidized and reduced. It was confirmed that the resistance to [Example]

[0447] In this example, N-[4-(9-phenyl)-2-methyl-2-propanol], which is one of the organic compounds according to one embodiment of the present invention, was used. -N-(9,9-dimethyl-9H-fluoro-3-yl-9H-carbazol-3-yl)phenyl] Fluoren-2-yl)-4-{3-[6-(9,9-dimethyl-9H-fluoren-2-yl)- 6FL-4mpPCBF The synthesis method of BPPm (structural formula (108)) and the physical properties of this compound will be explained.

[0448] <Synthesis Example 9> (N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-(9, 9-dimethyl-9H-fluoren-2-yl)-4-{3-[6-(9,9-dimethyl- 9H-fluoren-2-yl)pyrimidin-4-yl]phenyl}phenylamine (abbreviation Synthesis of 6FL-4mpPCBFBPPm)

[0449] In a 100 mL three-neck flask, add 1.7 g (2.7 mmol) of N-(4-chlorophenyl) -N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-di Methyl-9H-fluoren-2-amine and 1.3 g (2.7 mmol) of 4,4,5, 5-tetramethyl-2-{3-[6-(9,9-dimethyl-9H-fluoren-2-yl )pyrimidin-4-yl]phenyl}-1,3,2-dioxaborolane and 1.9 g (9 0.0mmol) of tripotassium phosphate and 22mg (0.060mmol) of di(1-adipate Mantyl-n-butylphosphine was added and the atmosphere in the flask was replaced with nitrogen. 5 mL of 1,4-dioxane and 0.67 g (9.0 mmol) of tert-butyl alcohol Coal was added. The mixture was degassed by stirring under reduced pressure. After degassing, the mixture 6.7 mg (0.030 mmol) of palladium(II) acetate was added to the mixture and heated at approximately 80°C for 1 After stirring for 4 hours, the mixture was filtered by suction, and the filtrate was concentrated to give an oily substance. was purified by silica gel column chromatography (developing solvent: toluene), The oily substance was washed with hexane to give 1.4 g of the desired yellow solid. The yield was 54%. The synthesis scheme of Step 1 is shown in formula (A-12) below.

[0450] [ka]

[0451] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(CDCl3,300MHz):δ=1.47(s,6H),1.59(s ,6H),7.17(dd,J1=8.4Hz,J2=1.8Hz,1H),7.28- 7.51(m,15H),7.60-7.69(m,13H),7.77-7.82(m ,2H),7.87(d,J=8.4Hz,1H),8.11(d,J=7.8Hz,1 H),8.15(dd,J1=7.8Hz,J2=1.5Hz,1H),8.20(d, J=7.5Hz,1H),8.22,(d,J=1.5Hz,1H),8.29(d,J =1.5Hz,1H),8.37(d,J=1.5Hz,1H),8.42(t,J=1 .5Hz,1H), 9.37(d,J=0.9Hz,1H)

[0452] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 43(A) and 43(B). Figure 43(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 43(A). The measurement results show that the target substance, 6FL-4mpPCBFBPPm, was obtained. It was.

[0453] <6FL-4mpPCBFBPPm Characteristics> Next, the absorption and emission spectra of 6FL-4mpPCBFBPPm in toluene were measured. The rule is shown in Figure 44.

[0454] As can be seen from Figure 44, the toluene solution of 6FL-4mpPCBFBPPm has an absorption peak at around 346 nm. Similarly, from Figure 44, the emission wavelength peak is 448 nm (excitation wavelength 346 nm). The compound of one embodiment of the present invention can be used as a host for a light-emitting substance or a fluorescent substance emitting light in the visible region. is also available.

[0455] Next, the HOMO and LUMO levels of 6FL-4mpPCBFBPPm were cycled. The calculation was based on the CV measurement. The calculation method was the same as in Example 1.

[0456] As a result, in the measurement of the oxidation potential Ea [V] of 6FL-4mpPCBFBPPm, HO The MO level was found to be -5.37 eV, while the LUMO level was -2.81 eV. I discovered something. [Example]

[0457] In this example, N-[4-(9-phenylphenyl)-2-(2-methyl-2-propanol]-2,3-diol, which is one of the organic compounds according to one embodiment of the present invention, was used. -9H-carbazol-3-yl)phenyl]-N-{4-[6-(9,9-dimethyl- 9H-fluoren-2-yl)pyrimidin-4-yl]phenyl}-1,1'-biphenyl Synthesis of 6FL-4-PcbbiPPm (Structural Formula (109)) The physical properties of the compound will be explained.

[0458] <Synthesis Example 10> Step 1: N-(4-chlorophenyl)-N-[4-(9-phenyl-9H-carbazo] Synthesis of [(3-yl)phenyl]-1,1'-biphenyl-4-amine

[0459] In a reaction vessel, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]- 2.92 g (6.0 mmol) of 1,1'-biphenyl-4-amine and sodium tert-butyl amine 1.73 g (18 mmol) of t-butoxide and 1.50 g ( 6.3 mmol) and 30 mL of toluene were added. The mixture was stirred under reduced pressure. The reaction vessel was degassed with HCl and the atmosphere inside was replaced with nitrogen. 34.5 mg (0.06 mmol) of dithionite (0) and tri(tert-butyl)phosphine 0.36 mL (0.12 mmol) of ethanol (10 wt% hexane solution) was added to this mixture. The mixture was stirred at 85°C for 5 hours under a nitrogen atmosphere. After that, the mixture was cooled to room temperature and then heated in a 350 mL of ene was added and stirred, and then the solid was separated by suction filtration. After concentration, about 100 mL of brown liquid was obtained. This brown liquid was then separated by filtration through Celite, alumina, and Florisy silica gel. The obtained filtrate was concentrated, and then recrystallized by adding ethanol to obtain a pale yellow solid. 3.60 g of a yellow solid was obtained. This pale yellow solid was heated and stirred in ethanol, and then filtered. The target product, a pale yellow powder, was obtained in 2.29 g with a yield of 64%. The synthesis scheme for Step 1 is shown below. Shown in (A-13).

[0460] [ka]

[0461] Step 2: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborola N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]- Synthesis of )phenyl]-1,1'-biphenyl-4-amine

[0462] In a reaction vessel, N-(4-chlorophenyl)-N-[4-(9-phenyl-9H-carbazo] [(3-yl)phenyl]-1,1'-biphenyl-4-amine 1.49g (2.5m mol), bis(pinacolato)diboron 0.95g (3.75mmol), and potassium acetate 0.74 g (7.5 mmol) of ethanol and 30 mL of ethylene glycol dimethyl ether This mixture was degassed by stirring under reduced pressure, and the atmosphere inside the reaction vessel was replaced with nitrogen. After that, the contents of the container were heated to about 60°C and stirred, and then [1,1'-bis(diphenylphosphine Ferrocene palladium (II) dichloride dichloromethane adduct 20.4 mg ( 0.025mmol) and 2-dichlorohexylphosphino-2',6'-dimethoxybiphenyl 20.5 mg (0.050 mmol) of phenyl was added, and the mixture was heated under a nitrogen atmosphere. The mixture was stirred under reflux for 19 hours, then cooled to room temperature and toluene was added. After that, it was concentrated to obtain about 50 mL of a brown liquid. This brown liquid was purified using Celite and silica gel. The resulting filtrate was concentrated and recrystallized by adding ethanol to obtain the desired yellow product. The synthesis scheme for step 2 is shown below in formula (A-14). Shown below.

[0463] [ka]

[0464] Step 3: N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]- N-{4-[6-(9,9-dimethyl-9H-fluoren-2-yl)pyrimidine-4- yl]phenyl}-1,1'-biphenyl-4-amine (abbreviation: 6FL-4PCBBiP Synthesis of Pm

[0465] Add N-(4-chlorophenyl)-N-[4-(9-phenyl-9H-carbazole] [(3-yl)phenyl]-1,1'-biphenyl-4-amine 1.38g (2.0mm ol) and 4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)pyrimidin 0.61g (2.0mmol) of gin and 1.27g (6.0mmol) of potassium phosphate tripotassium 20 mL of diethylene glycol dimethyl ether (diglyme) was added. The mixture was degassed by stirring under reduced pressure, and the atmosphere in the reaction vessel was replaced with nitrogen. The contents were heated to approximately 60°C and stirred, and then 4.5 mg (0.02 mmol) of palladium (II) acetate was added. l) and 14.3 mg (0.04 mmol) of di(1-adamantyl)-n-butylphosphine l) was added, and the mixture was stirred for 24 hours while being heated at 120°C under a nitrogen stream. After that, the mixture was cooled to room temperature, and then extracted and washed with toluene and water to obtain a black solution. Magnesium sulfate was added to this solution, and the solution was filtered to remove water. A black solution was obtained by distillation. The resulting solution was concentrated and then purified with ethanol. The product was recrystallized by adding alcohol, and 1.10 g of a yellow powder was obtained in a yield of 66%. The synthesis scheme of Group 3 is shown in formula (A-15) below.

[0466] [ka]

[0467] 1.10 g of the resulting yellow powder was purified by train sublimation. The production was carried out by heating the yellow powder at 370°C under the conditions of a pressure of 3.23 Pa and an argon flow rate of 15 mL / min. After sublimation purification, the target pale yellow solid was obtained in a yield of 0.48 g, with a recovery rate of 43%. Got it.

[0468] Nuclear magnetic resonance spectroscopy of the obtained solid ( 1 The analytical data by 1 H NMR are shown below. 1 H NMR(CDCl3,500MHz):δ=1.58(s,6H),7.31-7 .40(m,10H),7.44-7.50(m,7H),7.57-7.71(m,1 1H),7.80(dd,J1=8.7Hz,J2=2.4Hz,1H),7.87(d ,J=8.1Hz,1H),8.10-8.13(m,4H),8.20(d,J=8. 4Hz,1H),8.26(d,J=1.2Hz,1H),8.37(s,1H),9. 29(d,J=1.2Hz,1H)

[0469] In addition, the obtained solid 1 The 1 H NMR charts are shown in Figures 45(A) and 45(B). Figure 45(B) is an enlarged view of the range from 7.0 ppm to 9.5 ppm in Figure 45(A). The measurement results show that the target substance, 6FL-4PCBBiPPm, was obtained. Ta.

[0470] <Characteristics of 6FL-4PCBBiPPm> Next, the absorption and emission spectra of the toluene solution of 6FL-4PCBBiPPm were measured. The absorption spectrum and emission spectrum of the thin film are shown in Figure 46 and Figure 47, respectively. was carried out in the same manner as in Example 1 described above.

[0471] As shown in Figure 46, the toluene solution of 6FL-4PCBBiPPm has wavelengths around 394 nm and 338 nm. Similarly, from Figure 46, the emission wavelength peak is 467 nm (excitation wavelength 3 94nm). Also, from Figure 47, the thin film of 6FL-4PCBBiPPm was 400nm m, absorption peaks around 335nm, 309nm, 287nm, 242nm, and 207nm Similarly, from Figure 47, the peak of the emission wavelength is around 505 nm (excitation wavelength 410 nm). The compound according to one embodiment of the present invention can be used as a host for a luminescent material or a fluorescent material emitting light in the visible region. is also available.

[0472] In addition, the thin film of 6FL-4PCBBiPPm is resistant to aggregation even in the atmosphere and does not change shape. It was found that the film had good quality with little degradation.

[0473] Next, the HOMO and LUMO levels of 6FL-4PCBBiPPm were calculated by cyclic boron spectroscopy. The calculation was performed in the same manner as in Example 1.

[0474] As a result, in the measurement of the oxidation potential Ea [V] of 6FL-4PCBBiPPm, the HOMO The energy level was found to be -5.48 eV, while the LUMO level was -2.80 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the test, the Ea measurement was 81% and the Ec measurement was 86%. The peak intensity of 6FL-4PCBBiPPm was maintained, indicating that it is resistant to oxidation and reduction. It was confirmed that the resistance to [Example]

[0475] In this example, a light-emitting element according to one embodiment of the present invention, light-emitting elements 2 to 5, and a comparative light-emitting element In Comparative Light-Emitting Element 1 and Light-Emitting Elements 2 to 5, the light-emitting layer contained two types of The host material was a bipolar material and one guest material. The bipolar material (with a lower LUMO level) that accepts electrons in the light-emitting layer is 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzoyl 2mDBTBPDBq-II was used to accept holes. The bipolar material (the one with the higher HOMO level) used was changed for each device, and the device characteristics were compared. A cross-sectional view of the light-emitting device fabricated in this example is shown in FIG. 48, and the details of the device structure are shown in Table 1. In addition, the CV measurement between the two bipolar materials used in the light-emitting layer of each device was performed. The difference in LUMO levels is shown in Table 2. The structures and abbreviations of the compounds used are shown below. For the structures and abbreviations of other compounds, please refer to the previous examples.

[0476] [ka]

[0477] [Table 1]

[0478] [Table 2]

[0479] <Fabrication of light-emitting element> <Fabrication of Comparative Light-Emitting Device 1> An ITSO film was formed as an electrode 101 on a substrate 200 to a thickness of 70 nm. The electrode area of ​​the electrode 101 is 4 mm 2 (2mm x 2mm).

[0480] Next, 4,4',4''-(benzene-1, 3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and oxidized moiety DBT3P-II:MoO3 is 1:0.5 by weight. The co-evaporation was carried out so that the thickness of the layer was 60 nm.

[0481] Next, on the hole injection layer 111, 4-phenyl-4'-(9-phenyl-4'-phenyl)- (phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) The deposition was carried out so that the thickness was nm.

[0482] Next, a light-emitting layer 160 was formed on the hole-transporting layer 112 by the addition of 2mDBTBPDBq-II and N -(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-2-yl)] 9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF) and bis[2-(6-tert-butyl-4-pyrimidinyl-κN 3 )centre phenyl-κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) (abbreviation Name: Ir(tBuppm)2(acac)) and a weight ratio of (2mDBTBPDBq-II :PCBBiF:Ir(tBuppm)2(acac)) to 0.6:0.4:0.05 The co-deposition was carried out so that the thickness of the light-emitting layer 160 was 40 nm. , 2mDBTBPDBq-II is a bipolar material that accepts electrons, and PCBBiF is It is a bipolar material that accepts holes, and Ir(tBuppm)2(acac) is the guest material. It is a phosphorescent material.

[0483] Next, on the light-emitting layer 160, 2mDBTBPDBq-I was deposited as the electron transport layer 118(1). I was then deposited to a thickness of 20 nm as the electron transport layer 118(2). Then, benzophenone (abbreviated as BPhen) was deposited to a thickness of 10 nm. On the electron transport layer 118, lithium fluoride (LiF) was deposited to a thickness of 1000 nm as the electron injection layer 119. The deposition was carried out to a thickness of 1 nm.

[0484] Next, on the electron injection layer 119, aluminum (Al) was deposited to a thickness of 20 It was formed so that the thickness was 0 nm.

[0485] Next, the device is sealed using a sealant for organic EL in a glove box with a nitrogen atmosphere. The substrate 220 for forming the comparative light-emitting element is fixed to the substrate 200 on which the organic material is formed. Specifically, a sealant was applied to the periphery of the substrate 220, and the substrate 220 and the organic The substrate 200 on which the material was formed was bonded together, and ultraviolet light with a wavelength of 365 nm was applied at 6 J / cm 2 light The light-emitting element was irradiated with light and then heat-treated at 80° C. for 1 hour. Through the above steps, comparative light-emitting element 1 was obtained.

[0486] <Fabrication of light-emitting element 2> The light-emitting element 2 differs from the comparative light-emitting element 1 in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0487] That is, the light-emitting layer 160 of the light-emitting element 2 was made of 2mDBTBPDBq-II and 6BP -4FBiPPm and Ir(tBuppm)2(acac) were mixed in a weight ratio of (2mDBTB PDBq-II:6BP-4FBiPPm:Ir(tBuppm)2(acac)) They were co-evaporated to a thickness of 40 nm in a ratio of 0.6:0.4:0.05.

[0488] <Fabrication of Light-Emitting Element 3> The light-emitting element 3 differs from the comparative light-emitting element 1 in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0489] That is, the light-emitting layer 160 of the light-emitting element 3 was made of 2mDBTBPDBq-II and 6BP -4PCBBiPPm and Ir(tBuppm)2(acac) were mixed in a weight ratio of 2mDB TBPDBq-II:6BP-4PCBBiPPm:Ir(tBuppm)2(acac )) were co-evaporated to a thickness of 40 nm in a ratio of 0.6:0.4:0.05. did.

[0490] <Fabrication of Light-Emitting Element 4> The light-emitting layer 160 of the light-emitting element 4 was made of 2mDBTBPDBq-II and 6BP-4mFB iPPm and Ir(tBuppm)2(acac) were mixed in a weight ratio of 2mDBTBPDBq -II:6BP-4mFBiPPm:Ir(tBuppm)2(acac)) is 0.6: They were co-deposited at a ratio of 0.4:0.05 to a thickness of 40 nm.

[0491] <Fabrication of Light-Emitting Element 5> The light-emitting layer 160 of the light-emitting element 5 is made of 2mDBTBPDBq-II and 6BP-4mPCB BiPPm and Ir(tBuppm)2(acac) were mixed in a weight ratio of (2mDBTBPDB q-II:6BP-4mPCBBiPPm:Ir(tBuppm)2(acac)) is 0 They were co-evaporated to a thickness of 40 nm in a ratio of 0.6:0.4:0.05.

[0492] <Light-emitting element characteristics> Next, the characteristics of the comparative light-emitting element 1 and the light-emitting elements 2 to 5 prepared above were measured. A color luminance meter (Topcon, BM-5A) was used to measure the CIE chromaticity. A multichannel spectrometer (Hamamatsu Photonics, PMA-11) was used to measure the spectrum. Used.

[0493] FIG. 49 shows the current efficiency-luminance characteristics of the comparative light-emitting element 1 and the light-emitting elements 2 to 5. The voltage characteristics are shown in Figure 50, the current density-voltage characteristics are shown in Figure 51, and the external quantum efficiency-luminance characteristics are shown in Figure 52. The comparative light-emitting element 1 and the light-emitting elements 2 to 5 were each 2.5 mA / cm 2 Electricity The emission spectrum when a current was applied at a current density is shown in FIG.

[0494] Also, 1000 cd / m 2 The comparative light-emitting element 1 and the light-emitting elements 2 to 5 in the vicinity The device characteristics are shown in Table 3.

[0495] [Table 3]

[0496] As shown in FIG. 53, the electroluminescence spectra of the comparative light-emitting element 1 and the light-emitting elements 2 to 5 The peak wavelength is around 546 nm, and the full width at half maximum is 57 nm to 65 nm. Each showed a light.

[0497] As shown in FIG. 52 and Table 3, the maximum external quantum efficiency of the comparative light-emitting element 1 is 26%. On the other hand, the maximum external quantum efficiency of each of the light-emitting elements 2 to 5 is 28% or more. , and showed very high external quantum efficiency.

[0498] In addition, Figure 54 shows the difference in LUMO level between the host materials of each device and the 10 mA / cm 2 In time 54 shows the relationship between the driving voltage and the comparative light-emitting element 1. showed a low driving voltage, which is attributed to the difference in LUMO levels between the two host materials used in the emissive layer. is smaller than 0.5 eV, and two types of host materials are used as bipolar materials. Because there are. [Example]

[0499] In this example, a light-emitting element according to one embodiment of the present invention, a light-emitting element 7, a light-emitting element 8, and a comparative light-emitting element An example of fabricating the light-emitting element 6 will be described. In the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8, the light-emitting layer contained two Two types of bipolar materials were used as the host material and one type of guest material. The bipolar material (with a low LUMO level) that accepts electrons is used in the light-emitting layer. As a method for obtaining holes, 2mDBTBPDBq-II is used. The bipolar material (the one with the higher HOMO level) was changed for each device, and the device characteristics were compared. A cross-sectional view of the light-emitting device fabricated in this example is shown in FIG. 48, and the details of the device structure are shown in Table 4. In addition, the CV measurement between the two bipolar materials used in the light-emitting layer of each device was used to estimate the The difference in LUMO levels obtained is shown in Table 5. The structures and abbreviations of the compounds used are shown below. For the structures and abbreviations of other compounds, please refer to the previous examples.

[0500] [ka]

[0501] [Table 4]

[0502] [Table 5]

[0503] <Fabrication of light-emitting element> <Fabrication of Comparative Light-Emitting Device 6> The comparative light-emitting element 6 was fabricated in a manner different from that of the comparative light-emitting element 1 described above, except for the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0504] That is, the light-emitting layer 160 of the comparative light-emitting element 6 was formed by mixing 2mDBTBPDBq-II and PC BBiF and bis[2-(6-phenyl-4-pyrimidinyl-κN] 3 ) Phenyl-κC ](2,4-pentanedionato-κ 2 O,O')iridium(III) (abbreviation: Ir(d ppm)2(acac)) and a weight ratio of (2mDBTBPDBq-II:PCBBiF: Ir(dppm)2(acac)) is 0.6:0.4:0.05, and the thickness The thickness was co-evaporated to 40 nm.

[0505] <Fabrication of Light-Emitting Element 7> The light-emitting element 7 differs from the comparative light-emitting element 1 in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0506] That is, the light-emitting layer 160 of the light-emitting element 7 was made of 2mDBTBPDBq-II and 6BP-4 FBiPPm and Ir(dppm)2(acac) were mixed in a weight ratio of (2mDBTBPDBq- II:6BP-4FBiPPm:Ir(dppm)2(acac)) is 0.6:0.4: The co-evaporation was carried out so that the SiO 2 content was 0.05 and the thickness was 40 nm.

[0507] <Fabrication of Light-Emitting Element 8> The light-emitting element 8 differs from the comparative light-emitting element 1 described above in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0508] That is, the light-emitting layer 160 of the light-emitting element 8 was made of 2mDBTBPDBq-II and 6BP-4 PCBBiPPm and Ir(dppm)2(acac) were mixed in a weight ratio of 2mDBTBPDB q-II:6BP-4PCBBiPPm:Ir(dppm)2(acac)) is 0.6: They were co-deposited at a ratio of 0.4:0.05 to a thickness of 40 nm.

[0509] <Light-emitting element characteristics> Next, the characteristics of the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8 prepared above were measured. The method was the same as in Example 11.

[0510] FIG. 55 shows the current efficiency vs. luminance characteristics of the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8. The voltage characteristics are shown in Figure 56, the current density-voltage characteristics are shown in Figure 57, and the external quantum efficiency-luminance characteristics are shown in Figure 58. , respectively. In addition, the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8 were 2 The emission spectrum when a current was passed at a current density of 1000 kJ / s is shown in FIG.

[0511] Also, 1000 cd / m 2 The comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8 The device characteristics are shown in Table 6.

[0512] [Table 6]

[0513] As shown in FIG. 59, the electroluminescence spectra of the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8 The peak wavelength is around 586 nm, and the full width at half maximum is 69 nm to 73 nm. Each showed a light.

[0514] As shown in FIG. 58 and Table 6, the maximum external quantum efficiency of the comparative light-emitting element 6 was 30%. The maximum external quantum efficiency of the light-emitting devices 7 and 8 was 31% or more, respectively. 58, the light-emitting elements 7 and 8 exhibited high external quantum efficiency. The external quantum efficiency was higher than that of the light-emitting element 6. The difference in LUMO levels between the two host materials is less than 0.5 eV, and the two host materials This is because bipolar materials are used for each material. In comparison, it can be said that the carrier balance of the light-emitting elements 7 and 8 is good.

[0515] In addition, Figure 60 shows the difference in LUMO level between the host materials of each device and the 10 mA / cm 2 In time 60 shows the relationship between the driving voltage and the light-emitting element 7 and the light-emitting element 8 compared to the comparative light-emitting element 6. showed a low driving voltage. This is due to the difference in the LUMO levels between the two host materials used in the emitting layer. The difference is less than 0.5 eV, and a bipolar material is used for each of the two host materials. This is because

[0516] <Reliability of light-emitting elements> Next, the initial luminance of the comparative light-emitting element 6, the light-emitting element 7, and the light-emitting element 8 was 5000 cd / m 2 in A constant current drive test was carried out, and the results are shown in Figure 61. As can be seen from Figure 61, the comparative light-emitting element Compared with Light-emitting Device 6, Light-emitting Devices 7 and 8 exhibited good reliability. The light-emitting element 8 has a higher LU between the two host materials used in the light-emitting layer than the comparative light-emitting element 6. This is because the difference in MO levels is small, and therefore the electron injection barrier is small. [Example]

[0517] In this example, examples of fabricating light-emitting elements, light-emitting element 9, and light-emitting element 10, which are embodiments of the present invention, are described. In the light-emitting elements 9 and 10, the light-emitting layer contains two types of host materials and one type of gate electrode. Two types of bipolar materials were used as the host material, and As a bipolar material (with a lower LUMO level) that accepts electrons, 2mDBTBPD Using Bq-II, a bipolar material (HOMO level: The light-emitting device fabricated in this example has a cross section, and the device characteristics are compared. The schematic diagram is shown in Figure 48, and the details of the device structure are shown in Table 7. The difference in LUMO levels between the two bipolar materials estimated by CV measurements is shown in Table 8. The structures and abbreviations of the compounds used in this example are shown in the previous examples. good.

[0518] <Fabrication of light-emitting element> <Fabrication of Light-Emitting Element 9> The light-emitting element 9 differs from the comparative light-emitting element 1 in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0519] [Table 7]

[0520] [Table 8]

[0521] That is, the light-emitting layer 160 of the light-emitting element 9 was made of 2mDBTBPDBq-II and 4,6m FBiP2Pm and Ir(dppm)2(acac) were mixed in a weight ratio of (2mDBTBPDB q-II:4,6mFBiP2Pm:Ir(dppm)2(acac)) is 0.6:0. The mixture was co-deposited to a ratio of 4:0.05 and to a thickness of 40 nm.

[0522] <Fabrication of Light-Emitting Element 10> The light-emitting element 10 differs from the comparative light-emitting element 1 described above in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0523] That is, the light-emitting layer 160 of the light-emitting element 10 is made of 2mDBTBPDBq-II and 4,6F BiP2Pm and Ir(dppm)2(acac) were mixed in a weight ratio of (2mDBTBPDBq -II:4,6FBiP2Pm:Ir(dppm)2(acac)) is 0.6:0.4: The co-evaporation was carried out so that the SiO 2 content was 0.05 and the thickness was 40 nm.

[0524] <Light-emitting element characteristics> Next, the characteristics of the light-emitting elements 9 and 10 fabricated as described above were measured. Same as 1.

[0525] The current efficiency-luminance characteristics of the light-emitting elements 9 and 10 are shown in FIG. 62, and the luminance-voltage characteristics are shown in FIG. 63. The current density-voltage characteristics are shown in Figure 64, and the external quantum efficiency-luminance characteristics are shown in Figure 65. In addition, the light emitting element 9 and the light emitting element 10 were supplied with 2.5 mA / cm 2 When a current is applied at a current density of The emission spectrum is shown in Figure 66.

[0526] Also, 1000 cd / m2 The device characteristics of the light-emitting elements 9 and 10 in the vicinity are shown in Table 9. Shown below.

[0527] [Table 9]

[0528] As shown in FIG. 66, the peak wavelengths of the electroluminescence spectra of the light-emitting elements 9 and 10 are , and 579 nm, and orange light emission with a full width at half maximum of about 67 nm was observed.

[0529] As shown in FIG. 65 and Table 9, the maximum external quantum efficiency of the light-emitting elements 9 and 10 was The external quantum efficiency was over 25%, respectively, demonstrating extremely high external quantum efficiency.

[0530] Furthermore, from FIG. 63 and Table 9, the light emitting elements 9 and 10 have a luminance of approximately 1000 cd / m 2 Driving voltage at The values ​​of the two host materials used in the emitting layer were very low, at 2.7 V. The difference in LUMO levels between the two host materials is less than 0.5 eV. This is because polar materials are used. [Example]

[0531] Example 1 In this example, a light-emitting element 11 and a light-emitting element 12, which are embodiments of the present invention, are fabricated. In the light-emitting elements 11 and 12, the light-emitting layer contains two types of host materials and one type of Two types of bipolar materials were used as host materials, and the light-emitting layer The bipolar material (with a lower LUMO level) that accepts electrons is 2mDBT. Using BPDBq-II, a bipolar material (HOMO) that accepts holes was formed in the light-emitting layer. The element with the higher level was replaced with each other, and the element characteristics were compared. The cross-sectional view of each element is shown in Figure 48, and the details of the element structure are shown in Table 10. LUMO level difference estimated by CV measurements between two bipolar materials used in optical layers. The structures and abbreviations of the compounds used in this example are shown in Table 11. Just take it into consideration.

[0532] [Table 10]

[0533] [Table 11]

[0534] <Fabrication of light-emitting element> <Fabrication of Light-Emitting Element 11> The light-emitting element 11 differs from the comparative light-emitting element 1 described above in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0535] That is, the light-emitting layer 160 of the light-emitting element 11 was made of 2mDBTBPDBq-II and 2mp FBiBPDBq and Ir(dppm)2(acac) were mixed in a weight ratio of (2mDBTBPD Bq-II:2mpFBiBPDBq:Ir(dppm)2(acac)) is 0.6:0 Co-evaporation was carried out to a ratio of 0.4:0.05 and a thickness of 20 nm, followed by deposition by weight. Ratio(2mDBTBPDBq-II:2mpFBiBPDBq:Ir(dppm)2(ac a)) was set to 0.8:0.2:0.05 and the thickness was set to 20 nm. It was evaporated.

[0536] <Fabrication of Light-Emitting Element 12> The light-emitting element 12 differs from the comparative light-emitting element 1 described above in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0537] That is, the light-emitting layer 160 of the light-emitting element 12 was formed by mixing 2mDBTBPDBq-II and 6FL -4mpFBiBPPm and Ir(dppm)2(acac) were mixed in a weight ratio of (2mDBT BPDBq-II:6FL-4mpFBiBPPm:Ir(dppm)2(acac)) The ratios were 0.6:0.4:0.05 and the thickness was 20 nm. Next, the weight ratio (2mDBTBPDBq-II:6FL-4mpFBiBPPm:Ir( dppm)2(acac)) to be 0.8:0.2:0.05, and the thickness was 20 The deposition was carried out by co-evaporation so that the thickness became nm.

[0538] Next, the characteristics of the light-emitting elements 11 and 12 fabricated as described above were measured. Same as 11.

[0539] The current efficiency-luminance characteristics of the light-emitting elements 11 and 12 are shown in FIG. 67, and the luminance-voltage characteristics are shown in FIG. 8, the current density-voltage characteristics are shown in Figure 69, and the external quantum efficiency-luminance characteristics are shown in Figure 70. In addition, light-emitting element 11 and light-emitting element 12 are irradiated with 2.5 mA / cm 2 A current was passed at a current density of The resulting emission spectrum is shown in Figure 71.

[0540] Also, 1000 cd / m 2 The element characteristics of the light emitting element 11 and the light emitting element 12 are shown in the vicinity of Shown in 12.

[0541] [Table 12]

[0542] As shown in FIG. 71, the peak wavelengths of the electroluminescence spectra of the light-emitting elements 11 and 12 are The wavelength of the light emitted was approximately 588 nm, and the full width at half maximum was approximately 75 nm. .

[0543] As shown in FIG. 70 and Table 12, the maximum external quantum efficiency of the light-emitting elements 11 and 12 were over 31%, respectively, demonstrating very high external quantum efficiencies.

[0544] Furthermore, from FIG. 68 and Table 12, the light emitting element 11 and the light emitting element 12 have a luminance of approximately 1000 cd / m 2 Time Drive The voltages were very low, 3.0 V and 2.9 V, respectively. The difference in LUMO levels between two host materials is less than 0.5 eV, and two host materials This is because bipolar materials are used for each material.

[0545] <Reliability of light-emitting elements> Next, the initial luminance of the light-emitting element 11 and the light-emitting element 12 is 5000 cd / m 2 Constant current drive test The results are shown in Fig. 72. As can be seen from Fig. 72, the luminance of the light-emitting elements 11 and 12 was 10% reduction time (LT 90 ) showed good reliability of 740 hours or more. 2 is LT 90 The reliability was excellent, exceeding 1100 hours. [Example]

[0546] In this example, a manufacturing example of a light-emitting element 13, which is one embodiment of the present invention, will be described. In the light-emitting layer of the device 13, two types of host materials and one type of guest material were used. Two types of bipolar materials are used as the light-emitting layer. 2mDBTBPDBq-II was used as the polar material (lower LUMO level). In the layer, the bipolar material that accepts holes (the one with the higher HOMO level) is 6FL-4P A light-emitting device was fabricated using CBBiPPm. Schematic cross-sectional view of the light-emitting device fabricated in this example. The details of the device structure are shown in Figure 48 and Table 13. The difference in LUMO levels between the two bipolar materials estimated by CV measurements is shown in Table 14. For the structures and abbreviations of the compounds used in this example, please refer to the previous examples. stomach.

[0547] [Table 13]

[0548] [Table 14]

[0549] <Fabrication of light-emitting element> <Fabrication of Light-Emitting Element 13> The light-emitting element 13 differs from the comparative light-emitting element 1 described above in the fabrication process only in the material of the light-emitting layer 160. The other steps were the same as those for the comparative light-emitting element 1.

[0550] That is, the light-emitting layer 160 of the light-emitting element 13 was made of 2mDBTBPDBq-II and 6FL -4PCBBiPPm and Ir(dppm)2(acac) were mixed in a weight ratio of 2mDBTB PDBq-II:6FL-4PCBBiPPm:Ir(dppm)2(acac)) is 0 Co-evaporation was carried out to a thickness of 20 nm in a ratio of 0.7:0.3:0.05, followed by The weight ratio (2mDBTBPDBq-II:6FL-4PCBBiPPm:Ir(dpp m)2(acac)) to 0.8:0.2:0.05 and a thickness of 20 nm Co-evaporation was carried out so that

[0551] Next, the characteristics of the light-emitting device 13 fabricated as described above were measured. The measurement method was the same as in Example 11. do.

[0552] FIG. 73 shows the current efficiency-luminance characteristics of the light-emitting element 13, FIG. 74 shows the luminance-voltage characteristics, and The external quantum efficiency vs. luminance characteristics are shown in Figure 75 and Figure 76, respectively. 2.5 mA / cm to element 13 2 Figure 77 shows the emission spectrum when a current is applied at a current density of show.

[0553] Also, 1000 cd / m 2 Table 15 shows the device characteristics of the light-emitting element 13 in the vicinity.

[0554] [Table 15]

[0555] As shown in FIG. 77, the peak wavelength of the electroluminescence spectrum of the light-emitting element 13 is 581 nm. The compound emitted orange light with a full width at half maximum of 69 nm.

[0556] As shown in Figure 76 and Table 15, the maximum external quantum efficiency of Light-emitting Device 13 was 29% or more. and showed very high external quantum efficiency.

[0557] Also, from Figure 74 and Table 15, the light emitting element 13 has a luminance of approximately 1000 cd / m 2 The drive voltage is 2.8V This is due to the difference in LUMO levels between the two host materials used in the emitting layer. is smaller than 0.5 eV, and two types of host materials are used as bipolar materials. Because there are.

[0558] Therefore, the difference in LUMO levels between the two host materials used in the light-emitting layer is less than 0.5 eV. Furthermore, the use of bipolar materials for each of the two host materials contributes to the low driving voltage. It has been shown that this is suitable for reducing the emission, improving the luminous efficiency, and increasing reliability. [Explanation of symbols]

[0559] 50 Adhesive layer 51 Adhesive layer 52 Adhesive layer 100 EL layer 101 Electrode 102 electrode 103 EL layer 106 Lighting Unit 108 Lighting Unit 111 Hole injection layer 112 Hole transport layer 113 Electron transport layer 114 Electron injection layer 115 Charge generation layer 116 Hole injection layer 117 Hole transport layer 118 Electron transport layer 119 Electron injection layer 120 luminescent layer 140 Light-emitting layer 141 Host Materials 141_1 Organic compounds 141_2 Organic compounds 142 Guest Materials 150 light-emitting elements 160 luminescent layer 170 Light-emitting layer 200 boards 201 Resin layer 202 Resin layer 205 Transistor 206 Transistor 207 Connection 220 board 250 light-emitting elements 300 display device 311 Electrode 311b electrode 312 LCD 340 Liquid Crystal Devices 351 Circuit Board 360 Light-emitting element 360b Light-emitting element 360g light emitting element 360r light emitting element 360w light emitting element 361 PCB 362 Display section 364 Circuit section 365 Wiring 366 Circuit section 367 Wiring 372 FPC 373 IC 374 FPC 375 IC 400 display device 401 Transistor 402 transistor 403 Transistor 405 Capacitor 406 Connection 410 pixels 411 Insulating layer 412 Insulating layer 413 Insulating Layer 414 Insulating Layer 415 Insulating Layer 416 Spacer 417 Adhesive layer 419 Connection Layer 421 Electrode 422 EL layer 423 Electrode 424 Optical adjustment layer 425 Colored layer 426 Light blocking layer 451 Aperture 476 Insulating Layer 478 Insulating Layer 501 Transistor 503 Transistor 505 Capacitor 506 Connection 511 Insulating layer 512 Insulation layer 513 Insulating Layer 514 Insulating layer 517 Adhesive layer 519 Connection Layer 529 Liquid crystal element 543 Connectors 562 Electrode 563 LCD 564a Alignment film 564b Alignment film 576 Insulating Layer 578 Insulating Layer 599 Polarizing Plate 600A ALS model 601 Source side drive circuit 602 Pixel section 603 Gate side drive circuit 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 610 Element substrate 611 Switching TFT 612 Current Control TFT 613 Electrode 614 Insulators 616 EL layer 617 Electrode 618 Light-emitting element 623 n-channel TFT 624 p-channel TFT 700 display panel 701 Resin layer 702 Resin layer 800 display panel 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 Interlayer insulating film 1021 Interlayer insulating film 1022 Electrode 1024B Electrode 1024G electrode 1024R electrode 1025B Lower electrode 1025G bottom electrode 1025R lower electrode 1026 Bulkhead 1028 EL layer 1029 Electrode 1031 Sealing substrate 1032 Sealing material 1033 Base material 1034B Colored layer 1034G colored layer 1034R colored layer 1036 Overcoat layer 1035 Black layer 1037 Interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 3500 Multifunction Terminal 3502 Case 3504 Display section 3506 Camera 3508 Lighting 3600 Light 3602 Housing 3608 Lighting 3610 Speaker 7121 Housing 7122 Display section 7123 Keyboard 7124 Pointing Device 7200 Head Mounted Display 7201 Mounting part 7202 Lens 7203 Main unit 7204 Display section 7205 Cable 7206 Battery 7300 Camera 7301 Housing 7302 Display section 7303 Operation button 7304 Shutter button 7305 Joint 7306 Lens 7400 Finder 7401 Housing 7402 Display section 7403 Button 7500 Head Mounted Display 7501 Case 7502 Display section 7503 Operation button 7504 Fixtures 7505 Lens 7510 Head Mounted Display 7701 Housing 7702 Case 7703 Display section 7704 Operation key 7705 Lens 7706 Connection 8501 Lighting equipment 8502 Lighting equipment 8503 Lighting equipment 8504 Lighting equipment 9000 chassis 9001 Display section 9003 Speaker 9005 Operation key 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Operation button 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9100 Mobile Information Terminal 9101 Mobile Information Terminal 9102 Mobile Information Terminal 9200 Mobile Information Terminal 9201 Mobile Information Terminal 9300 Television equipment 9301 Stand 9311 Remote control operation machine 9700 Automobiles 9701 Body 9702 wheels 9703 Dashboard 9704 Light 9710 Display section 9711 Display section 9712 Display section 9713 Display section 9714 Display section 9715 Display section 9721 Display section 9722 Display section 9723 Display section

Claims

1. A device comprising a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.10 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

2. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.11 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

3. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.13 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

4. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.14 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

5. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.15 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

6. A device comprising a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.16 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

7. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.22 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

8. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.10 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

9. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.11 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

10. A device comprising a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.13 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

11. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.14 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

12. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.15 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

13. A device comprising a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.16 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

14. Having a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex. The first organic compound has a first electron-transporting skeleton and a first hole-transporting skeleton, The second organic compound has a second electron-transporting skeleton and a second hole-transporting skeleton, The second hole-transporting skeleton has an aromatic amine skeleton, The LUMO level of the first organic compound is lower than the LUMO level of the second organic compound. The difference between the LUMO level of the first organic compound and the LUMO level of the second organic compound is 0.22 eV or more and 0.5 eV or less. The HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. A light-emitting element, wherein the first organic compound and the second organic compound form an excited complex in a given combination.

15. In any one of claims 8 to 14, The organometallic complex is a light-emitting element containing iridium.

16. In any one of claims 1 to 15, The first hole-transporting skeleton is a light-emitting element having at least one of a carbazole skeleton, a dibenzothiophene skeleton, and a dibenzofuran skeleton.

Images