Light emitting device

Abstract

A light-emitting substance used for a light-emitting layer and a novel organic compound that can be used as a host material in which the light-emitting substance is dispersed are provided. A light-emitting element including the organic compound is provided. A light-emitting device, an electronic device, and a lighting device each including the light-emitting element are provided.SOLUTION: The light-emitting device includes an EL layer between a pair of electrodes. The EL layer includes a first compound and a second compound. The first compound is a phosphorescent iridium complex having a LUMO level higher than or equal to - 3. 5eV and lower than or equal to - 2. 5eV. The light-emitting element includes an EL layer between a pair of electrodes, the EL layer includes a first compound and a second compound, the first compound is a phosphorescent iridium metal complex including a diazine skeleton, and the second compound is an organic compound including a pyrimidine skeleton.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a light-emitting element, a light-emitting device, an electronic device, a lighting device, and a novel organic compound. [Background technology]

[0002] In recent years, electroluminescence (EL) The basic structure of these light-emitting devices is as follows: The device has a layer containing a light-emitting substance sandwiched between a pair of electrodes. This allows light emission from the luminescent substance.

[0003] These light-emitting elements are self-luminous, so the pixels are more visible than those of LCDs. It has the advantage of being simple and does not require a backlight, making it suitable for use as a flat panel display element. Furthermore, such a light-emitting element can be manufactured to be thin and lightweight. Another major advantage is that it has an extremely fast response time.

[0004] These light emitting elements can be formed in a film shape, so that light can be emitted in a planar manner. Therefore, a large-area element can be easily formed. This is a feature that is difficult to obtain with point light sources such as light bulbs and LEDs, or linear light sources such as fluorescent lights. Therefore, it is highly useful as a surface light source that can be applied to lighting, etc.

[0005] The light-emitting element that utilizes electroluminescence is either an organic compound or They can be broadly classified according to whether they are organic or inorganic compounds. In the case of an organic EL element having a layer containing the organic compound, applying a voltage to the light emitting element By this, electrons flow from the cathode and holes flow from the anode. The injected electrons and holes excite the organic compound. The excited organic compound emits light.

[0006] The types of excited states that organic compounds can form are singlet excited states and triplet excited states. It is possible to obtain a singlet excited state (S * ) is emitted from the triplet excited state (T * ) from The light emitted is called phosphorescence. The statistical generation rate of phosphorescence in a light-emitting device is S * :T * It is believed that the ratio is 1:3.

[0007] In compounds that convert the singlet excited state into luminescence (hereinafter referred to as fluorescent compounds), Therefore, no emission from the triplet excited state (phosphorescence) was observed, but emission from the singlet excited state (fluorescence) ) is observed. Therefore, the internal quantum efficiency of the light-emitting device using the fluorescent compound is The theoretical limit of the photon density (the ratio of photons generated to injected carriers) is S * :T * =1 :3, it is said to be 25%.

[0008] On the other hand, compounds that convert the triplet excited state into luminescence (hereinafter referred to as phosphorescent compounds) are used. In some cases, light emission from the triplet excited state (phosphorescence) is observed. Since the transition from the singlet excited state to the triplet excited state occurs easily, the internal quantum efficiency is 1 In theory, this means that a luminous efficiency of up to 0.00% is possible, meaning that a luminous efficiency higher than that of fluorescent compounds is possible. For this reason, in order to realize a highly efficient light-emitting element, a light-emitting element using a phosphorescent compound is required. Child development has been booming in recent years.

[0009] When the light-emitting layer of the light-emitting element is formed using the above-mentioned phosphorescent compound, the concentration of the phosphorescent compound To suppress quenching by quenching or triplet-triplet annihilation, a matrix of other compounds is used. In many cases, the phosphorescent compound is dispersed in the matrix. The compound that becomes the host material is used, and the compound dispersed in the matrix, such as a phosphorescent compound, is used as the guest material. These materials are called dopants.

[0010] When a phosphorescent compound is used as a guest material, the properties required for the host material are The triplet excitation energy (energy difference between the ground state and the triplet excited state) is larger than that of the compound The goal is to have this.

[0011] In addition, the singlet excitation energy (energy difference between the ground state and the singlet excited state) is triplet Since it is larger than the triplet excitation energy, a material with a large triplet excitation energy has a large single Therefore, the large triplet excitation energy as described above is A substance having such a structure is also useful in a light-emitting element that uses a fluorescent compound as a light-emitting substance. .

[0012] When a phosphorescent compound is used as a guest material, pyridine is used as a host material or an electron transport material. Compounds having methylamine or the like as a partial structure have been studied (for example, Patent Document 1).

[0013] In addition, when a phosphorescent compound is used as a guest material, a carbazole skeleton and Compounds combining nitrogen-containing heteroaromatic rings have been disclosed (for example, Patent Document 2). [Prior art documents] [Patent documents]

[0014] [Patent Document 1] Japanese Patent Application Laid-Open No. 2003-45662 [Patent Document 2] International Publication No. 2011-046182 Summary of the Invention [Problem to be solved by the invention]

[0015] As reported in Patent Document 1 or Patent Document 2, a host material for a phosphorescent compound However, the development of fluorescent materials and guest materials for phosphorescent compounds is still in progress. When viewed as an element, it is important to consider aspects such as luminous efficiency, reliability, luminous characteristics, synthesis efficiency, and cost. There is still room for improvement, and the development of better light-emitting devices is desired.

[0016] In view of the above problems, one embodiment of the present invention is to provide a light-emitting substance used in a light-emitting layer and a light-emitting layer in which the light-emitting substance is dispersed. and a light-emitting element having a new organic compound that can be used as a host material for In particular, when a phosphorescent iridium metal complex is used as a light-emitting substance, One of the objects of the present invention is to provide a new organic compound that can be suitably used as a conductive material. do.

[0017] Another embodiment of the present invention is a light-emitting device, an electronic device, or a lighting device including the light-emitting element. One of the purposes is to provide [Means for solving the problem]

[0018] One embodiment of the present invention has an EL layer between a pair of electrodes, and the EL layer contains a first compound and a second compound. and a compound, wherein the first compound has a LUMO level of −3.5 eV or more and −2.5 eV or more. The second compound is an organic compound containing a pyrimidine skeleton. The light-emitting element is characterized by being an object.

[0019] Another embodiment of the present invention is a light-emitting diode (ELD) device including an EL layer between a pair of electrodes, the EL layer including a first compound and a second compound, wherein the first compound is a phosphorescent iridium gold compound having a diazine skeleton. The second compound is an organic compound containing a pyrimidine skeleton. It is a light emitting element.

[0020] Another embodiment of the present invention is a light-emitting diode (ELD) device including an EL layer between a pair of electrodes, the EL layer including a first compound and a second compound, wherein the first compound has a LUMO level of -3.5 eV or more and -2 a phosphorescent iridium metal complex containing a diazine skeleton with an IR of 0.5 eV or less, and the second compound is The light-emitting element is characterized by being an organic compound containing a pyrimidine skeleton.

[0021] Another embodiment of the present invention is a display device having a plurality of EL layers between a pair of electrodes, At least one of the layers has a first compound and a second compound, and the first compound is LU. Phosphorescent iridium containing a diazine skeleton with an MO level of -3.5 eV or more and -2.5 eV or less the first compound is a metal complex, and the second compound is an organic compound containing a pyrimidine skeleton. It is a light-emitting element.

[0022] In each of the above structures, the diazine skeleton is preferably coordinately bonded to iridium. The diazine skeleton is preferably a pyrimidine skeleton.

[0023] A light-emitting element having a guest material that is a first compound and a host material that is a second compound. The guest material and the host material have the same pyrimidine skeleton, so that the host This improves the transfer of carriers from the material to the guest material.

[0024] Note that the second compound of one embodiment of the present invention is a heterocyclic compound and has a high electron-transport property; In addition to the EL layer of the light-emitting element, the compound can also be used as an electron transport layer or an electron injection layer.

[0025] In addition, when a plurality of EL layers are provided between a pair of electrodes, a charge generating layer is provided between the EL layers. By arranging the current density, it is possible to emit light in a high brightness range while keeping the current density low. Since the temperature can be kept low, a long-life element can be realized.

[0026] In each of the above structures, the first compound has a HOMO level of -6.0 eV or more and -5.0 eV or more. It is preferable that the phosphorescent iridium metal complex has a phosphorescent emission intensity of 0.0 eV or less. This makes it easier for the phosphorescent iridium metal complex to trap holes, improving hole mobility in the light-emitting element. This suppresses the change in the temperature over time, which is expected to result in a longer life for the device.

[0027] In each of the above configurations, the second compound preferably has a molecular weight of 2000 or less. For example, when the second compound is vapor-deposited using a vapor deposition device, the molecular weight of the second compound is 2000 or less (or less). More preferably, the molecular weight is 1000 or less, which can improve the vapor deposition efficiency. In order to stabilize the quality of the formed film, a polymer with a high glass transition temperature (Tg) and a molecular weight of 5 00 or higher is preferred.

[0028] In each of the above structures, the second compound may have a benzene skeleton, a biphenyl skeleton, a naphtha skeleton, or phenanthrene skeleton, carbazole skeleton, phenanthrene skeleton, triphenylene skeleton, dibenzothiophene skeleton It is preferable that the benzofuran skeleton contains at least one of a phenanthroline skeleton and a dibenzofuran skeleton as a substituent. By including the above-mentioned substituent in the second compound, a high phosphorescence level (also called triplet level) can be obtained. ) can be included.

[0029] In each of the above structures, the second compound can be represented by general formula (G1).

[0030] [ka]

[0031] In general formula (G1), R 1 , and R 2 are each independently hydrogen, alkyl having 1 to 4 carbon atoms represents a group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group; , Ar 1 The structure is at least one of a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton. The substituents include any one of the following. 2 is hydrogen, naphthalene skeleton, phenanthrene The alkylene group includes at least one of a phenylene skeleton and a triphenylene skeleton as a substituent.

[0032] In each of the above structures, the second compound can be represented by general formula (G2). The compound represented by the following general formula (G2) is a novel compound useful as the second compound. This is one aspect of the present invention.

[0033] [ka]

[0034] In general formula (G2), R 1 ~R 5 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms. , a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group , or a substituted or unsubstituted triphenylyl group. 4 is hydrogen, substitution or an unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylyl group, Also, Ar 5 is hydrogen, alkyl group having 1 to 4 carbon atoms, substituted or unsubstituted represents either a phenyl group or a substituted or unsubstituted biphenyl group. 3 , and α 4 each independently represents a substituted or unsubstituted phenylene group, and j and k each independently represent a substituted or unsubstituted phenylene group. , each independently represents 0 or 1.

[0035] In each of the above structures, the second compound can be represented by general formula (G2-1): The compound represented by the following general formula (G2-1) is a novel compound useful as the second compound. This is a compound and is one aspect of the present invention.

[0036] [ka]

[0037] In general formula (G2-1), R 1 ~R 8 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, represents a substituted or unsubstituted triphenylyl group, and Ar 4 , Ar 6 , and Ar 7 are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenyl ... or an unsubstituted triphenylyl group. 3 , α 4 , α 6 , and α 7 teeth , each independently represent a substituted or unsubstituted phenylene group; each independently represents 0 or 1.

[0038] In each of the above structures, the second compound can be represented by general formula (G3). The compound represented by the following general formula (G3) is a novel compound useful as the second compound. This is one aspect of the present invention.

[0039] [ka]

[0040] In general formula (G3), R 1 ~R 10 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, represents either a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group represents a substituted or unsubstituted triphenylyl group; 7 is hydrogen, substituted or unsubstituted a substituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, Either a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted triphenylyl group Also, α 3 , and α 7 each independently represents a substituted or unsubstituted phenylene group. In addition, j and n each independently represent 0 or 1.

[0041] In each of the above structures, the second compound can be represented by structural formula (300).

[0042] [ka]

[0043] In each of the above configurations, the weight ratio of the second compound is greater than that of the first compound. That is, the second compound is a host material in the light-emitting device, and the first compound is a The object is the guest material.

[0044] Another embodiment of the present invention is an organic compound represented by general formula (G4).

[0045] [ka]

[0046] In general formula (G4), Ar 11 , Ar 12 , R 11 ~R 13 , and R 21 ~R 23 teeth, each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted represents either a substituted or unsubstituted biphenyl group. 13 and Ar 14 Ha, so each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophen-4-yl group, It represents either a substituted or unsubstituted dibenzofuran-4-yl group. 1 , α 2 , α 8 , and α 9 each independently represents a substituted or unsubstituted phenylene group; i, x, and y each independently represent 0 or 1. 1 and E 2 Yes, respectively independently represent sulfur or oxygen.

[0047] Another embodiment of the present invention is an organic compound represented by general formula (G5).

[0048] [ka]

[0049] In general formula (G5), Ar 11 , Ar 12 , R 11 ~R 13 , and R 21 ~R 23 teeth, each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted represents either a substituted or unsubstituted biphenyl group. 13 and Ar 14 Ha, so each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophen-4-yl group, It represents either a substituted or unsubstituted dibenzofuran-4-yl group. 1 and E 2 each independently represents sulfur or oxygen.

[0050] Another embodiment of the present invention is an organic compound represented by general formula (G6).

[0051] [ka]

[0052] In general formula (G6), R 11 ~R 13 and R 21 ~R 23 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, It represents either an aryl group or an aryl group. 1 and E 2 each independently represents sulfur or oxygen represent.

[0053] Another embodiment of the present invention is an organic compound represented by general formula (G7).

[0054] [ka]

[0055] In general formula (G7), R 11 ~R 13 and R 21 ~R 23 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, It represents either an aryl group or an aryl group. 1 and E 2 each independently represents sulfur or oxygen represent.

[0056] Another embodiment of the present invention is an organic compound represented by structural formula (400).

[0057] [ka]

[0058] Another embodiment of the present invention is a light-emitting element including any of the above organic compounds between a pair of electrodes. In particular, it is preferable that the light-emitting layer contains the organic compound.

[0059] Furthermore, a light-emitting device, an electronic device, and a lighting device using the light-emitting element are also included in the scope of the present invention. In this specification, the term "light emitting device" refers to an image display device, a light emitting device, etc. The panel also includes a connector, such as an FPC (Flexible Printed Circuit). TAB (Tape Automated Bond) ing) tape or TCP (Tape Carrier Package) is attached modules with printed wiring boards at the end of TAB tape or TCP or a COG (Chip On Glass) method is used to mount an IC (Integrated Circuit) on the light emitting element. The light emitting device also includes all modules in which the above is directly mounted. [Effects of the Invention]

[0060] One embodiment of the present invention is a method for manufacturing a light-emitting layer comprising: a light-emitting substance to be used in a light-emitting layer; In particular, a light-emitting element having a novel organic compound that can be used as a phosphorescent light-emitting element can be provided. It can be suitably used as a host material when an iridium metal complex is used as a light-emitting substance. Furthermore, one embodiment of the present invention can provide a novel organic compound having low driving voltage and high current efficiency. One embodiment of the present invention is to provide a light-emitting element having high extinction coefficient by using the light-emitting element. It is possible to provide a light-emitting device, an electronic device, and a lighting device with reduced power consumption. [Brief explanation of the drawings]

[0061] [Figure 1] A diagram for explaining a light-emitting element according to an aspect of the present invention. [Figure 2] A diagram for explaining a light-emitting element according to an aspect of the present invention. [Figure 3] A diagram for explaining a light-emitting element according to an aspect of the present invention. [Figure 4] A diagram for explaining a light-emitting element according to an aspect of the present invention. [Figure 5] A diagram for explaining a light-emitting element according to an aspect of the present invention. [Figure 6] A diagram for explaining a light-emitting device according to an aspect of the present invention. [Figure 7] A diagram for explaining a light-emitting device according to an aspect of the present invention. [Figure 8] A diagram for explaining an electronic device according to an aspect of the present invention. [Figure 9] A diagram for explaining a lighting device according to an aspect of the present invention. [Figure 10] A diagram showing the 1H NMR chart of 4,6mPnP2Pm. [Figure 11] A diagram showing the absorption spectrum and emission spectrum of a toluene solution of 4,6mPnP2Pm. [Figure 12] A diagram showing the absorption spectrum and emission spectrum of a thin film of 4,6mPnP2Pm. [Figure 13] A diagram showing the 1H NMR chart of 2Ph-4,6mNP2Pm. [Figure 14] A diagram showing the absorption spectrum and emission spectrum of a toluene solution of 2Ph-4,6mNP2Pm. [Figure 15] A diagram showing the absorption spectrum and emission spectrum of a thin film of 2Ph-4,6mNP2Pm. [Figure 16] A diagram showing the 1H NMR chart of 4,6mTpP2Pm. [Figure 17] A diagram showing the absorption spectrum and emission spectrum of a toluene solution of 4,6mTpP2Pm. [Figure 18] A diagram showing the absorption spectrum and emission spectrum of a thin film of 4,6mTpP2Pm. [Figure 19] A diagram showing the 1H NMR chart of 4,6mDBTP2Pm-II. [Figure 20] FIG. 4 shows the absorption spectrum and emission spectrum of a toluene solution of 4,6mDBTP2Pm-II. [Figure 21] 4,6mDBTP2Pm-II thin film absorption spectrum and emission spectrum. [Figure 22] 1H NMR chart of 2,4DBTP2Pm-II. [Figure 23] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 2,4DBTP2Pm-II. [Figure 24] FIG. 1 shows the absorption spectrum and emission spectrum of a thin film of 2,4DBTP2Pm-II. [Figure 25] 1H NMR chart of 2,5DBTP2Pm-II. [Figure 26] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 2,5DBTP2Pm-II. [Figure 27] FIG. 1 shows the absorption spectrum and emission spectrum of a thin film of 2,5DBTP2Pm-II. [Figure 28] 1H NMR chart of 4,6mDBTP2Pm-III. [Figure 29] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 4,6mDBTP2Pm-III. [Figure 30] 4,6mDBTP2Pm-III thin film absorption spectrum and emission spectrum. [Figure 31] 1H NMR chart of 4,6mDBFP2Pm-II. [Figure 32] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 4,6mDBFP2Pm-II. [Figure 33] FIG. 1 shows the absorption spectrum and emission spectrum of a thin film of 4,6mDBFP2Pm-II. [Figure 34] 1H NMR chart of 2,4DBFP2Pm-II. [Figure 35] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 2,4DBFP2Pm-II. [Figure 36] FIG. 1 shows the absorption spectrum and emission spectrum of a thin film of 2,4DBFP2Pm-II. [Figure 37] 1H NMR chart of 2,5DBFP2Pm-II. [Figure 38] FIG. 1 shows the absorption spectrum and emission spectrum of a toluene solution of 2,5DBFP2Pm-II. [Figure 39] FIG. 1 shows the absorption spectrum and emission spectrum of a thin film of 2,5DBFP2Pm-II. [Figure 40] 1A and 1B are diagrams illustrating a light-emitting element 1 according to an embodiment of the present invention. [Figure 41] FIG. 10 is a graph showing current density-luminance characteristics of the light-emitting element 1. [Figure 42] FIG. 10 shows voltage-luminance characteristics of the light-emitting element 1. [Figure 43] FIG. 10 shows luminance vs. current efficiency characteristics of Light-Emitting Element 1. [Figure 44] FIG. 2 shows voltage-current characteristics of the light-emitting element 1. [Figure 45] FIG. 10 is a graph showing luminance-chromaticity coordinate characteristics of the light-emitting element 1. [Figure 46] FIG. 10 shows luminance vs. power efficiency characteristics of the light-emitting element 1. [Figure 47] FIG. 2 shows an emission spectrum of the light-emitting element 1. [Figure 48] FIG. 10 is a graph showing time-normalized luminance characteristics of the light-emitting element 1. [Figure 49] FIG. 2 is a graph showing time-voltage characteristics of the light-emitting element 1. [Figure 50] 1A to 1C are diagrams illustrating light-emitting elements 2 to 7 of an embodiment. [Figure 51] FIG. 10 shows current density-luminance characteristics of Light-emitting element 2. [Figure 52] FIG. 10 shows voltage-luminance characteristics of Light-emitting element 2. [Figure 53] FIG. 10 shows luminance-current efficiency characteristics of Light-emitting Element 2. [Figure 54] FIG. 10 is a graph showing voltage-current characteristics of the light-emitting element 2. [Figure 55] FIG. 10 is a graph showing luminance-chromaticity coordinate characteristics of the light-emitting element 2. [Figure 56]FIG. 10 shows luminance vs. power efficiency characteristics of the light-emitting element 2. [Figure 57] FIG. 10 shows an emission spectrum of the light-emitting element 2. [Figure 58] FIG. 10 is a graph showing current density-luminance characteristics of Light-emitting element 3. [Figure 59] FIG. 10 shows voltage-luminance characteristics of the light-emitting element 3. [Figure 60] FIG. 10 shows luminance-current efficiency characteristics of Light-emitting Element 3. [Figure 61] FIG. 10 is a graph showing voltage-current characteristics of the light-emitting element 3. [Figure 62] FIG. 10 is a graph showing luminance-chromaticity coordinate characteristics of the light-emitting element 3. [Figure 63] FIG. 10 is a graph showing luminance vs. power efficiency characteristics of the light-emitting element 3. [Figure 64] FIG. 10 shows an emission spectrum of the light-emitting element 3. [Figure 65] FIG. 10 is a graph showing current density-luminance characteristics of Light-emitting element 4. [Figure 66] FIG. 10 shows voltage-luminance characteristics of the light-emitting element 4. [Figure 67] FIG. 10 shows luminance-current efficiency characteristics of Light-emitting Element 4. [Figure 68] FIG. 10 is a graph showing voltage-current characteristics of the light-emitting element 4. [Figure 69] FIG. 10 is a graph showing luminance-chromaticity coordinate characteristics of the light-emitting element 4. [Figure 70] FIG. 10 shows luminance vs. power efficiency characteristics of the light-emitting element 4. [Figure 71] FIG. 10 shows an emission spectrum of the light-emitting element 4. [Figure 72] FIG. 10 is a graph showing current density-luminance characteristics of the light-emitting element 5. [Figure 73] FIG. 10 is a graph showing voltage-luminance characteristics of the light-emitting element 5. [Figure 74] FIG. 10 shows luminance-current efficiency characteristics of the light-emitting element 5. [Figure 75] FIG. 10 is a graph showing voltage-current characteristics of the light-emitting element 5. [Figure 76] FIG. 10 is a graph showing the luminance-chromaticity coordinate characteristics of the light-emitting element 5. [Figure 77] FIG. 10 is a graph showing luminance vs. power efficiency characteristics of the light-emitting element 5. [Figure 78]Figure showing the emission spectrum of the light-emitting element 5. [Figure 79] Figure showing the current density - luminance characteristics of the light-emitting element 6. [Figure 80] Figure showing the voltage - luminance characteristics of the light-emitting element 6. [Figure 81] Figure showing the luminance - current efficiency characteristics of the light-emitting element 6. [Figure 82] Figure showing the voltage - current characteristics of the light-emitting element 6. [Figure 83] Figure showing the luminance - chromaticity coordinate characteristics of the light-emitting element 6. [Figure 84] Figure showing the luminance - power efficiency characteristics of the light-emitting element 6. [Figure 85] Figure showing the emission spectrum of the light-emitting element 6. [Figure 86] Figure showing the current density - luminance characteristics of the light-emitting element 7. [Figure 87] Figure showing the voltage - luminance characteristics of the light-emitting element 7. [Figure 88] Figure showing the luminance - current efficiency characteristics of the light-emitting element 7. [Figure 89] Figure showing the voltage - current characteristics of the light-emitting element 7. [Figure 90] Figure showing the luminance - chromaticity coordinate characteristics of the light-emitting element 7. [Figure 91] Figure showing the luminance - power efficiency characteristics of the light-emitting element 7. [Figure 92] Figure showing the emission spectrum of the light-emitting element 7. [Figure 93] Figure showing the time - normalized luminance characteristics of the light-emitting element 4. [Figure 94] Figure showing the time - voltage characteristics of the light-emitting element 4. [Figure 95] Figure showing the time - normalized luminance characteristics of the light-emitting element 5. [Figure 96] Figure showing the time - voltage characteristics of the light-emitting element 5. [Figure 97] Figure showing the LC-MS measurement results of 4,6mPnP2Pm. [Figure 98] Figure showing the ToF-SIMS measurement results of 4,6mPnP2Pm. [Figure 99] Figure showing the LC-MS measurement results of 2Ph-4,6mNP2Pm. [Figure 100] 4,6mTpP2Pm LC-MS measurement results. [Figure 101] 4,6mDBTP2Pm-II LC-MS measurement results. [Figure 102] 4,6mFigure showing the ToF-SIMS measurement results of DBTP2Pm-II. [Figure 103] 2,5mDBTP2Pm-II LC-MS measurement results. [Figure 104] 4,6mDBTP2Pm-III LC-MS measurement results. [Figure 105] FIG. 1 shows the results of LC-MS measurement of 4,6mDBFP2Pm-II. [Figure 106] FIG. 1 shows the results of LC-MS measurement of 2,4mDBFP2Pm-II. [Figure 107] FIG. 1 shows the results of LC-MS measurement of 2,5mDBFP2Pm-II. DETAILED DESCRIPTION OF THE INVENTION

[0062] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the embodiments and details thereof may be modified without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications can be made to the above. The present invention should not be construed as being limited to the description of the embodiments.

[0063] (Embodiment 1) In this embodiment, a phosphorescent iridium metal complex is used as the first compound, and a phosphorescent iridium metal complex is used as the second compound. A light-emitting element having an organic compound containing a pyrimidine skeleton will be explained using FIG. do.

[0064] The light-emitting element shown in this embodiment has a pair of electrodes (a first electrode 101 and a second electrode 102) as shown in FIG. The EL layer 102 including the light-emitting layer 113 is sandwiched between the two electrodes 103. In addition to the light-emitting layer 113, a hole injection layer 111, a hole injection layer 112, a hole injection layer 113, a hole injection layer 114, a hole injection layer 115, a hole injection layer 116, a hole injection layer 117, a hole injection layer 118, a hole injection layer 119 ... The electron transport layer 112, the electron transport layer 114, the electron injection layer 115, the charge generation layer 116, etc. In this embodiment, the first electrode 101 is used as an anode, and the second electrode The electrode 103 is used as a cathode. The first electrode 101 is formed on the substrate 100. The substrate 100 may be a glass substrate or the like.

[0065] By applying a voltage to such a light emitting element, light is injected from the first electrode 101 side. The holes injected from the second electrode 103 side and the electrons injected from the second electrode 103 side are recombined in the light-emitting layer 113. The first compound, a phosphorescent iridium metal complex, is excited. The first compound, a phosphorescent iridium metal complex, emits light when it returns to the ground state. In one embodiment of the present invention, the first compound, a phosphorescent iridium metal complex, is a luminescent element. It functions as a luminescent substance in the cells.

[0066] The hole injection layer 111 in the EL layer 102 is made of a material having a high hole transporting property and an acceptor. The layer contains an acceptor material, and electrons are transferred from a material with high hole transporting properties to the acceptor material. Therefore, holes are generated from the hole injection layer 111. Holes are injected into the light-emitting layer 113 through the transport layer 112 .

[0067] The charge generation layer 116 is a layer containing a substance with a high hole transporting property and an acceptor substance. The acceptor substance extracts electrons from the substance with high hole transport properties, The extracted electrons are transported from the electron injection layer 115 having electron injection properties to the electron transport layer 114. It is injected into the light-emitting layer 113 .

[0068] A specific example of manufacturing the light-emitting element described in this embodiment mode will be described below.

[0069] The first electrode 101 and the second electrode 103 may be made of a metal, an alloy, an electrically conductive compound, or In particular, indium oxide-tin oxide ( ITO: Indium Tin Oxide, an oxide containing silicon or silicon oxide Contains indium-tin oxide, indium-zinc oxide, tungsten oxide and zinc oxide Indium oxide, gold (Au), platinum (Pt), nickel (Ni), tungsten (W ), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu) , palladium (Pd), titanium (Ti), and other elements belonging to Groups 1 or 2 of the periodic table The elements are alkali metals such as lithium (Li) and cesium (Cs), and calcium Alkaline earth metals such as calcium (Ca), strontium (Sr), magnesium (Mg), and and alloys containing these (MgAg, AlLi), europium (Eu), ytterbium Rare earth metals such as Yb and alloys containing these, as well as graphene, etc. can be used. The first electrode 101 and the second electrode 103 can be formed by, for example, sputtering or The film can be formed by vapor deposition (including vacuum deposition) or the like.

[0070] The hole-transporting layer 111, the hole-transporting layer 112, and the charge-generating layer 116 are made of a material having a hole-transporting property. Examples of high-value substances include 4,4'-bis[N-(1-naphthyl)-N-phenylamine]. N,N'-bis(3-methylphenyl) (amino)-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,N-diphenylamino)triphenyl 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 Aromatic amine compounds such as 3-[N-(9-phenylcarbazole) [N-3-yl]-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC A1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyla 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzPCA2), -N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol Other examples include 4,4'-di(N-carbazolyl) )biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl] 4-(10-phenyl-9-anthracenyl)benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl) phenyl]-9H-carbazole (abbreviation: CzPA) and other carbazole compounds, 1,3, 5-tri(dibenzothiophen-4-yl)-benzene (abbreviation: DBT3P-II) Dibenzothiophene compounds, 1,3,5-tri(dibenzofuran-4-yl)-benzene (abbreviation: DBF3P-II) and other dibenzofuran compounds, fused ring compounds such as [phenanthrene-9-yl]-phenyl-phenanthrene (abbreviation: Pn3P) The substances mentioned here are mainly 10 -6 cm 2 / Vs or more However, if a material has a higher hole transporting property than an electron transporting property, Other materials may also be used.

[0071] Furthermore, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriflate) Phenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl (N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide (abbreviation: PTPDMA) Poly[N,N'-bis(4-butylphenyl)-N,N'-bis (phenyl)benzidine (abbreviated as Poly-TPD) It is also possible.

[0072] The hole injection layer 111 and the charge generation layer 116 are made of the above-mentioned material having high hole transport properties and A mixed layer with a substance having acceptor properties may be used. In this case, the carrier injection property is good. The acceptor material to be used is preferably a transition metal oxide or a metal in the periodic table. Examples of the oxides include oxides of metals belonging to groups 4 to 8 of the metal oxides. Ribidene is particularly preferred.

[0073] The light-emitting layer 113 is formed by dissolving a phosphorescent iridium metal complex, which is a first compound, in a guest compound that serves as a light-emitting material. The first compound, a phosphorescent iridium metal complex, is used as a catalyst material, and the triplet excited state is This layer is formed using a substance with high energy as a host material.

[0074] Here, the guest material is a first compound having a LUMO level of −3.5 eV or higher. A phosphorescent iridium metal complex with an emission energy of -2.5 eV or less is used. The second compound is an organic compound containing a pyrimidine skeleton.

[0075] The LUMO level of organic compounds containing pyrimidine skeletons is affected by the pyrimidine skeleton ( The LUMO orbital is located near the pyrimidine skeleton, which is why the Therefore, when the first organic compound and the second organic compound are combined as described above, This improves the transfer of carriers (electrons) from the host material to the guest material, This allows the guest material to emit light more efficiently and improves its lifespan. Since the compound does not become a molecule trap, it has high electron transport properties derived from the pyrimidine skeleton of the host material. From this viewpoint, the host material The LUMO level of the material is also preferably −3.5 eV or more and −2.5 eV or less.

[0076] The second compound, an organic compound containing a pyrimidine skeleton, is a compound containing a benzene skeleton, a biphenyl skeleton, and a phenyl group. Nyl skeleton, naphthalene skeleton, carbazole skeleton, phenanthrene skeleton, triphenylene skeleton At least one of the following skeletons is a substituent: By using such a structure, the LUMO level of the second compound is Since the pyrimidine skeleton is strongly influenced by the LUMO orbital (the LUMO orbital exists near the pyrimidine skeleton), effect becomes more pronounced.

[0077] In particular, the second compound, an organic compound containing a pyrimidine skeleton, is a compound containing a carbazole skeleton. In this case, the structure becomes one in which holes can easily flow, resulting in bipolar properties, which is preferable. When it contains condensed rings such as the phenanthrene skeleton, triphenylene skeleton, etc., carrier transport properties When a dibenzothiophene skeleton or a dibenzofuran skeleton is contained, it is preferable. This structure is preferred because it stabilizes the film quality (especially the dibenzothiophene skeleton and dibenzothiophene skeleton). The 4-substituted furan skeleton is electrochemically stable and is therefore preferred.

[0078] That is, the second compound is an organic compound represented by general formula (G1).

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[0080] In general formula (G1), R 1 , and R 2 are each independently hydrogen, alkyl having 1 to 4 carbon atoms represents a group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group; , Ar 1 The structure is at least one of a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton. The substituents include any one of the following. 2 is hydrogen, naphthalene skeleton, phenanthrene The alkylene group includes at least one of a phenylene skeleton and a triphenylene skeleton as a substituent.

[0081] In this case, the substituent Ar 1 and Ar 2 The same substituent is preferable because synthesis is simpler. On the other hand, the substituent Ar 1 and Ar 2 The different substituents result in a more steric structure. This is desirable.

[0082] The second compound represented by the general formula (G1) specifically includes compounds represented by the general formula (G The compound represented by general formula (G2) is more preferably a compound represented by general formula (G3). The compound is a novel compound useful as a compound of formula (I), and is one aspect of the present invention.

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[0084] In general formula (G2), R 1 ~R 5 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms. , a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group , or a substituted or unsubstituted triphenylyl group. 4 is hydrogen, substitution or an unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylyl group, Also, Ar 5 is hydrogen, alkyl group having 1 to 4 carbon atoms, substituted or unsubstituted represents either a phenyl group or a substituted or unsubstituted biphenyl group. 3 , and α 4 each independently represents a substituted or unsubstituted phenylene group, and j and k each independently represent a substituted or unsubstituted phenylene group. , each independently represents 0 or 1.

[0085] The second compounds represented by the above general formulas (G1) and (G2) are specifically The structure represented by general formula (G2-1) is more preferred. The compound represented is a novel compound useful as a second compound, and is an embodiment of the present invention. .

[0086] [ka]

[0087] In general formula (G2-1), R 1 ~R 8 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, represents a substituted or unsubstituted triphenylyl group, and Ar 4 , Ar 6 , and Ar 7 are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenyl ... or an unsubstituted triphenylyl group. 3 , α 4 , α 6 , and α 7 teeth , each independently represent a substituted or unsubstituted phenylene group; each independently represents 0 or 1.

[0088] The second compounds represented by the above general formulas (G1), (G2), and (G2-1) Specifically, the structure represented by the general formula (G3) is more preferable. The compound represented by 3) is a novel compound useful as the second compound, and is one aspect of the present invention. is.

[0089] [ka]

[0090] In general formula (G3), R 1 ~R 10 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, represents either a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, Also, Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group represents a substituted or unsubstituted triphenylyl group; 7 is hydrogen, substituted or unsubstituted a substituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, Either a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted triphenylyl group Also, α 3 , and α 7 each independently represents a substituted or unsubstituted phenylene group. In addition, j and n each independently represent 0 or 1.

[0091] Ar in the above general formulae (G2), (G2-1), and (G3) 1 ~Ar 7 has a substituent When the alkyl group is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted In the case of an alkyl group, the solubility in organic solvents increases, This is preferable because it is easy to synthesize and form a film by a wet method. In the case of a substituted or unsubstituted biphenyl group, the carrier transport property is good, which is preferable. The presence of these substituents is preferable because it results in a more three-dimensional structure and stabilizes the film quality. However, if the presence of these substituents requires more synthesis steps, it is better not to have any substituents. preferable.

[0092] In addition, R in the general formulae (G1), (G2-1), and (G3) 1 , R 2 , general formula (G2 ) in R 1 , R 2 , Ar 5 It is preferable that any two of these are hydrogen, since synthesis is simpler. In addition, hydrogen is preferable because it improves carrier (electron) injection properties and is expected to reduce voltage. In addition, R in general formulas (G1), (G2-1), and (G3) is preferably 1 , R 2 , general R in formula (G2) 1 , R 2 , Ar 5 Any two of the following are independently selected from the group consisting of 1 to 10 carbon atoms: 4 alkyl group, substituted or unsubstituted phenyl group, or substituted or unsubstituted biphenyl group This is preferable because the amorphous property is improved and the film quality is stabilized.

[0093] In the above general formulae (G2), (G2-1), and (G3), the 4th and 6th positions of the pyrimidine are An aryl group (Ar 3 ~Ar 7 ) is bonded to the pyrimidine This is to make it difficult for the conjugation to extend from the skeleton to these aryl groups. Since these aryl groups are bonded at the meta position to the alkylene skeleton, further conjugation is difficult to extend. Therefore, the band between the HOMO level and the LUMO level is The gap (Bg) tends to be wider, and the S1 level and T1 level tend to be higher. It can be used as a host material for a dopant that emits light at a shorter wavelength. More specifically, phosphorescent materials in the visible range (blue to red) are preferred. It is suitable as a host material for fluorescent materials and organic EL devices. It is also suitable as a host material for light-emitting materials with deep HOMO levels.

[0094] Ar in general formulae (G1), (G2), (G2-1), and (G3) 1 ~Ar 7 of Specific structures include, for example, substituents shown in structural formulas (Ar-1) to (Ar-5). Examples include:

[0095] [ka]

[0096] In addition, α in general formulas (G2), (G2-1), and (G3) 3 , α 4 , α 6 , and and α 7 Specific examples of the structure include the structures shown in structural formulas (α-1) to (α-3). Examples include substitution bases.

[0097] [ka]

[0098] When the bond is at the para position as in structural formula (α-1), the carrier transport property is better. As shown in structural formula (α-2) and structural formula (α-3), the bond is at the meta position or the ortho position. It is preferable that the T1 level and S1 level are high.

[0099] In addition, the second compounds represented by the above general formulae (G1), (G2), (G2-1), and (G3) Specific examples of the compounds include those represented by the structural formulas (100) to (107) and those represented by the structural formulas (110) to (117). Structural formula (123), Structural formula (130) ~ Structural formula (135), Structural formula (140) ~ Structural formula ( 145), structural formula (150) to structural formula (161), and structural formula (300) to structural formula (32) 1) can be mentioned. Among these, the organic compounds represented by the general formula (G2) Specific examples of the second compound include those represented by structural formula (306) to structural formula (309), structural formula (3 18), and organic compounds represented by structural formula (320). Specific examples of the second compounds represented by structural formulas (300) to (2-1) and (G3) include compounds represented by structural formulas (301) to (302). Structural formula (305), structural formula (310) to structural formula (317), structural formula (319), and structure Examples of the organic compounds are those represented by the formula (321). However, the present invention is not limited to these. It will not be done.

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[0112] In addition, various reactions can be applied to synthesize the second compound. For example, The second compound represented by general formula (G1) is synthesized by carrying out the synthesis reaction shown below. The method for synthesizing the second compound is not limited to the following synthesis method.

[0113] <Method for synthesizing second compound represented by general formula (G1)> First, the synthesis scheme (A-1) is shown below. , a dihalogenated pyrimidine organic compound (a1), an arylboron organic compound (a2), and By coupling the above, a halogenated pyrimidine organic compound (a3) ​​can be synthesized. can be done.

[0114] [ka]

[0115] In the synthesis scheme (A-1), X 1 , and X 2 represents hydrogen or halogen. However, X 1 , and X 2 When represents a halogen, it is preferably bromine because of its high reactivity. More preferably, it represents iodine. 1 represents boronic acid or dialkoxyboron. R 1 , and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted represents a phenyl group or a substituted or unsubstituted biphenyl group. 1 is a substitution or is an unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, and at least one of a phenylyl group and a phenylyl group as a substituent.

[0116] The coupling reaction in the synthetic scheme (A-1) can be carried out under various reaction conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be applied.

[0117] In the synthetic scheme (A-1), the Suzuki-Miyaura reaction is used. A palladium catalyst can be used as the catalyst, and the palladium catalyst can be a palladium complex. A mixture of palladium acetate and its ligands can be used. Diazolidinium(II), tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(II), (phenylphosphine)palladium(II) dichloride. tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexyl Examples of substances that can be used as bases include natrium phosphine and the like. organic bases such as sodium tert-butoxide and inorganic bases such as sodium carbonate and potassium carbonate In addition, the reaction is preferably carried out in a solution. As the solvent, a mixture of acetonitrile and water, a mixture of thinners such as toluene or xylene and water, Mixed solvents: toluene, xylene, alcohols such as ethanol, and water. 3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) and water mixed solvents, and mixed solvents of ethers such as ethylene glycol dimethyl ether and water However, the catalysts, bases, and solvents that can be used are not limited to these. In addition, in the synthesis scheme (A-1), instead of the arylboron compound (a2), aryl aluminum, aryl zirconium, aryl zinc, or aryl tin The reaction is preferably carried out in an inert atmosphere such as nitrogen or argon. Heating may also be performed using electromagnetic waves.

[0118] Next, as shown in the following synthesis scheme (A-2), a halogenated pyrimidine organic compound was synthesized. The compound (a3) ​​is coupled with an arylboron organic compound (a4) to form the above compound (a3). A second compound represented by general formula (G1) can be synthesized.

[0119] [ka]

[0120] In addition, X 2 represents hydrogen or halogen. 2 represents a halogen, In view of high reactivity, it preferably represents bromine, and more preferably iodine. 2 is a boronic acid or represents dialkoxyboron. Also, R 1 , and R 2 are independently hydrogen, carbon number 1 ~4 alkyl group, substituted or unsubstituted phenyl group, or substituted or unsubstituted biphenyl Also, Ar 1 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, and at least one of a substituted or unsubstituted triphenylyl group and a substituted or unsubstituted triphenylyl group. Includes.

[0121] The coupling reaction in the synthetic scheme (A-2) can be carried out under various reaction conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be applied.

[0122] In the synthetic scheme (A-2), the Suzuki-Miyaura reaction can be used. The compound can be synthesized by taking into consideration the above synthesis scheme (A-1).

[0123] In addition, Ar 1 and Ar 2 are the same, the above synthesis schemes (A-1) and (A-2) can be carried out simultaneously. In other words, the organic compound (a1) can be reacted with (a2) and (a4) at the same time. In addition, since the reaction can be carried out, the synthesis becomes simple and convenient, which is preferable.

[0124] In this manner, the second compound of one embodiment of the present invention can be synthesized.

[0125] In the light-emitting layer 113, the second compound (host material) and the first compound By forming the light-emitting layer 113 containing the guest material, the light-emitting layer 113 emits light with high luminous efficiency. Phosphorescence can be obtained.

[0126] Specific examples of the first compound include the compounds represented by the structural formulas (200) to (206) and the compounds represented by the structural formulas (201) to (205). (210) ~ Structural formula (213), Structural formula (220) ~ Structural formula (222), Structural formula (230) ), structural formula (231), and structural formula (240). However, the present invention is not limited to these.

[0127] Structural formula (200) to structural formula (206) have a pyrimidine skeleton, and structural formula (210) to structural formula (216) have a pyrimidine skeleton. The structural formula (213) has a pyrazine skeleton, and the structural formulas (220) to (222) have pyrazine skeletons. It has a lysine skeleton or a quinoline skeleton, and the structural formula (230) and the structural formula (231) are quinoxaline. The structural formula (240) is a phosphorescent iridium metal having a sarin skeleton and a triazine skeleton. It is a complex.

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[0132] The phosphorescent iridium metal complex is not limited to the above structure. Organic compounds containing the lysine skeleton have a high T1 level, so they are more sensitive to blue-green light than those containing the blue-green light. It can be used as a host material for a phosphorescent material emitting light at a longer wavelength. The LUMO level of the phosphorescent iridium metal complex is between -3.5 eV and -2.5 eV. It is preferable that

[0133] The HOMO level of the phosphorescent iridium metal complex is between -6.0 eV and -5.0 eV. By adopting such a configuration, the phosphorescent iridium metal complex can be This makes it easier to trap holes, and the change over time in the hole mobility of the light-emitting device is suppressed. As a result, the device is expected to have a longer life. The compound has a benzene skeleton, a biphenyl skeleton, a naphthalene skeleton, a phenanthrene skeleton, a triphenyl skeleton, At least one of a phenylene skeleton, a dibenzothiophene skeleton, and a dibenzofuran skeleton When the second compound contains one as a substituent, the second compound is an organic compound containing a pyrimidine skeleton, HO. Since the MO level is below -6.0 eV, the hole trap effect described above becomes more pronounced. become.

[0134] In another embodiment of the present invention, the host material has a pyrimidine skeleton, and the guest material Preferably, both the host material and the guest material have a diazine skeleton. It is more preferable that the polymer has an inorganic skeleton. As a result, the LUMO levels of the guest molecules can be selected from the host material. This allows for good carrier (electron) movement to the guest material, making it easier for the guest material to emit light efficiently. Furthermore, if the LUMO levels are close, the guest material becomes an extreme electron trap. Therefore, the high electron transport property derived from the pyrimidine skeleton of the host material is not hindered. This allows for a low voltage element. This allows for the production of a light emitting device with high efficiency, long life, and low driving voltage. When both the host material and the guest material have a pyrimidine skeleton, It is believed that the interaction between guest molecules becomes stronger, making these effects more pronounced.

[0135] In addition, the LUMO levels of the host and guest materials can be selected to be close to each other. The reasons for this are as follows: First, the LUMO level of the host material is In particular, the pyrimidine skeleton, which is a type of amine skeleton, is affected by the general formula (G1) and (G2) The LUMO orbitals of the host materials represented by (G2-1) and (G3) are located around the pyrimidine skeleton. On the other hand, the guest material also has a diazine skeleton that is easily reduced, so its LU The MO level is affected by the diazine skeleton. In particular, when the diazine skeleton is coordinated to iridium, In this case, the LUMO orbital resides around the diazine skeleton rather than the central metal. Both the host and guest materials have LUMO orbitals derived from the diazine skeleton. Therefore, the LUMO levels are close to each other.

[0136] In this way, the phosphorescent iridium metal complex (first compound) has a diazine skeleton, particularly a pyridine skeleton. Even when the phosphorescent iridium metal complex has an iridium skeleton, the LUMO level is −3.5 The HOMO level is preferably -6.0 eV or more and -2.5 eV or less. It is preferable that the upper limit is −5.0 eV or less. In this case, the host material (second compound Preferred examples of ) are as described above.

[0137] As described above, the second compound (host material) in one embodiment of the present invention is reduced. The LUMO orbital is located around the pyrimidine skeleton, which is easily absorbed and has excellent electron transport properties. The electron transport property is high, and the driving voltage of the device is reduced.

[0138] In addition, in the first embodiment, a phosphorescent iridium metal complex is used as the first compound. Although the optical element has been described above, the present invention is not limited to the above structure. Organic compounds containing valence atoms have high T1 levels, and therefore high S1 levels. Therefore, the second compound, an organic compound containing a pyrimidine skeleton, is a fluorescent material in the visible range. It can be used as a host material.

[0139] In addition, multiple types of materials (host materials) are used to disperse the light-emitting materials (guest materials). Therefore, the light-emitting layer can be formed by using the organic compound containing the pyrimidine skeleton as the second compound. In addition, a second host material may be included.

[0140] The second host material may be, for example, the material used in the hole transport layer 112.

[0141] The electron transport layer 114 is a layer containing a substance with a high electron transport property. Alq3, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3) , bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Zn(BOX)2, bis[2-(2-hydroxyphenyl)benzothiazol- ] zinc (abbreviation: Zn(BTZ)2) and other metal complexes can be used. 4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazol-1,3,4-diol PBD, 1,3-bis[5-(p-tert-butylphenyl)-1, 3,4-Oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-te rt-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-trimethyl Azole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethyl phenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtT AZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP) ), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: B Heteroaromatic compounds such as poly(2,5-pyridine) can also be used. -diyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl )-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-di Octylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-di Polymer compounds such as PF-BPy (abbreviated as PF-BPy) can also be used. The solid material is mainly 10 -6 cm 2 It is a substance with an electron mobility of 1 / Vs or more. Any substance other than those mentioned above may be used as the electron transport layer as long as it has a higher electron transporting property than hole transporting property. good.

[0142] The second compound used in the present invention, an organic compound containing a pyrimidine skeleton, also has electron transport properties. Since it is a material with good properties, it is suitable for the electron transport layer.

[0143] The electron transport layer 114 may be a single layer or may be a laminate of two or more layers made of the above-mentioned materials. It may also be layered.

[0144] The electron injection layer 115 is a layer containing a substance with high electron injection properties. Lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2) alkali metals, alkaline earth metals, such as lithium oxide (LiOx), or the like; Also, rare earth compounds such as erbium fluoride (ErF3) can be used. Metal compounds can be used. In addition, the above-mentioned materials constituting the electron transport layer 114 can be used. You can also be there.

[0145] Alternatively, the electron injection layer 115 may be formed by mixing an organic compound and an electron donor. Composite materials may also be used. Such composite materials are made by adding electrons to organic compounds via electron donors. In this case, the organic compound is In this case, it is preferable that the material is excellent in transporting the generated electrons. The electron transport layer 114 may be made of a material (metal complex, heteroaromatic compound, etc.). The electron donor may be any substance that exhibits electron donating properties to organic compounds. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, Examples of the elements include aluminum, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of suitable cations include barium oxide and barium nitrate. It is also possible to use organic compounds such as tetrathiafulvalene (TTF). It is also possible to do so.

[0146] The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 11 4. The electron injection layer 115 and the charge generation layer 116 are formed by deposition (including vacuum deposition), The layer can be formed by an ink jet method, a coating method, or the like.

[0147] In the light-emitting element described above, a potential difference generated between the first electrode 101 and the second electrode 103 Current flows due to this, and holes and electrons recombine in the EL layer 102, causing light to be emitted. This light emission is emitted from either the first electrode 101 or the second electrode 103. Therefore, the first electrode 101 and the second electrode 103 are connected to each other. Either one or both of the electrodes is a light-transmitting electrode.

[0148] The light-emitting device described above is based on the first compound, a phosphorescent iridium metal complex. Since phosphorescence can be obtained, it is possible to achieve highly efficient light emission compared to light-emitting devices that use fluorescent compounds. The device can be realized.

[0149] Note that the light-emitting element shown in this embodiment mode is an example of the structure of a light-emitting element, but A light-emitting element having a different structure shown in another embodiment can also be applied to the light-emitting device according to this embodiment. In addition, the light emitting device including the light emitting element may be a passive matrix light emitting device. In addition to the optical device and the active matrix type light emitting device, other devices different from those described in other embodiments may be used. A light emitting device having a microcavity structure including a light emitting element having the structure described above can be manufactured. and all of these are included in the present invention.

[0150] In the case of an active matrix type light emitting device, the structure of the TFT is not particularly limited. For example, a staggered or inverted staggered TFT can be used as appropriate. The driver circuit formed on the FT substrate can be made up of N-type and P-type TFTs. Alternatively, it may be composed of only one of N-type TFTs or P-type TFTs. Furthermore, there is no particular limitation on the crystallinity of the semiconductor film used in the TFT. An amorphous semiconductor film, a crystalline semiconductor film, an oxide semiconductor film, or the like can be used.

[0151] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0152] (Embodiment 2) In this embodiment, an organic compound including a pyrimidine skeleton will be described.

[0153] One embodiment of the present invention is an organic compound represented by general formula (G4).

[0154] [ka]

[0155] In general formula (G4), Ar 11 , Ar 12 , R 11 ~R 13 , and R 21 ~R 23 teeth, each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted represents either a substituted or unsubstituted biphenyl group. 13 and Ar 14 Ha, so each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophen-4-yl group, It represents either a substituted or unsubstituted dibenzofuran-4-yl group. 1 , α2 , α 8 , and α 9 , each independently represents a substituted or unsubstituted phenylene group. , i, x, and y each independently represent 0 or 1. 1 and E 2 Is that Each independently represents sulfur or oxygen.

[0156] Another embodiment of the present invention is an organic compound represented by general formula (G5).

[0157] [ka]

[0158] In general formula (G5), Ar 11 , Ar 12 , R 11 ~R 13 , and R 21 ~R 23 teeth, each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted represents either a substituted or unsubstituted biphenyl group. 13 and Ar 14 Ha, so each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophen-4-yl group, It represents either a substituted or unsubstituted dibenzofuran-4-yl group. 1 and E 2 each independently represents sulfur or oxygen.

[0159] Another embodiment of the present invention is an organic compound represented by general formula (G6).

[0160] [ka]

[0161] In general formula (G6), R 11 ~R 13 and R 21 ~R 23 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, It represents either an aryl group or an aryl group. 1 and E 2 each independently represents sulfur or oxygen represent.

[0162] Another embodiment of the present invention is an organic compound represented by general formula (G7).

[0163] [ka]

[0164] In general formula (G7), R 11 ~R 13 and R 21 ~R 23 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, It represents either an aryl group or an aryl group. 1 and E 2 each independently represents sulfur or oxygen represent.

[0165] Another embodiment of the present invention is an organic compound represented by structural formula (400).

[0166] [ka]

[0167] In addition, Ar in general formula (G4) and general formula (G5) 13 , and Ar 14 Specific Examples of suitable structures include the substituents shown in structural formulas (Ar-6) to (Ar-11). It can be obtained.

[0168] [ka]

[0169] In addition, α in general formula (G4) 1 , α 2 , α 8 , and α 9 The specific structure of Examples of the substituents include those shown in structural formulae (α-4) to (α-6).

[0170] [ka]

[0171] When the bond is at the para position as in structural formula (α-4), the carrier transport property is better. As shown in structural formula (α-5) and structural formula (α-6), the bond is at the meta position or the ortho position. It is preferable that the T1 level and S1 level are high.

[0172] In addition, Ar 13 , Ar 14 When has substituents, the substituents each independently represent a carbon atom. alkyl groups with 1 to 4 prime numbers, substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups Also, α represents either one of the aryl groups. 1 , α 2 , α 8 , and α 9 When has a substituent, The substituents are each independently an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. , substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophen-4-yl It represents either a group or a substituted or unsubstituted dibenzofuran-4-yl group. In (G4) to (G6), the phenylene group bonded to the pyrimidine ring is It represents one or two of the 2-, 4-, 5-, or 6-positions of the ring. ~(G7) is a substituent selected from an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group is attached to the 2-, 4-, 5-, or 6-position of the pyrimidine ring. It is preferable that the alkyl group has one or more of these substituents. The film is three-dimensional and stable, which is preferable. In addition, in the case of alkyl groups, the solubility in solvents is This is preferable because it improves the properties of the film and makes it easier to handle during synthesis and wet film formation. In some cases, the absence of these substituents is preferred due to environmental considerations.

[0173] In addition, Ar in general formulas (G4) and (G5) 11 , Ar 12 is hydrogen, Furthermore, hydrogen improves carrier (electron) injection properties and is therefore preferred for low voltage applications. This is desirable as it is expected to increase the pressure. 11 , Ar 12 Each independently has 1 to 4 carbon atoms an alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group The presence of such a film is preferable because it improves the amorphous property and stabilizes the film quality.

[0174] Specific examples of the organic compound represented by the general formula (G4) include the compounds represented by the structural formulas (400) to ( 415), and organic compounds represented by structural formulas (430) to (440). However, the present invention is not limited to these.

[0175] [ka]

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] Various reactions can be applied to synthesize the organic compound of one embodiment of the present invention. For example, by carrying out the synthesis reaction shown below, one of the compounds of the present invention represented by general formula (G4) can be obtained. The organic compound according to one embodiment of the present invention can be synthesized. The synthesis method is not limited to the following synthesis method.

[0181] <Method for synthesizing organic compound represented by general formula (G4)> First, the synthesis scheme (B-1) is shown below.

[0182] [ka]

[0183] As shown in the synthesis scheme (B-1), the dihalogenated pyrimidine compound (b1) and the aryl group By coupling with a halogenated boron compound (b2), a halogenated pyrimidine compound (b3) can be synthesized.

[0184] In the synthetic scheme (B-1), R 11 ~R 13 are independently hydrogen, carbon number 1 to 4 alkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups Also, Ar 13 is hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group, Substituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothio represents either a benzophen-4-yl group or a substituted or unsubstituted dibenzofuran-4-yl group Also, α 1 and α 8 each independently represents a substituted or unsubstituted phenylene group. Furthermore, h and x each independently represent 0 or 1. 1 is sulfur or oxygen Also, X 3 and X 4 each independently represents hydrogen, chlorine, bromine, or iodine. However, Ar 13 If is hydrogen, then X 4 represents hydrogen. X 3 and X 4 is highly reactive Therefore, it preferably represents bromine, more preferably iodine. 3 is a boronic acid or diamine represents Glucoxiborone.

[0185] The coupling reaction in the synthetic scheme (B-1) can be carried out under various reaction conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be applied.

[0186] In the synthetic scheme (B-1), the Suzuki-Miyaura reaction is used. A palladium catalyst can be used as the catalyst, and the palladium catalyst can be a palladium complex. A mixture of palladium acetate and its ligands can be used. Diazolidinium(II), tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(II), (phenylphosphine)palladium(II) dichloride. tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexyl Examples of substances that can be used as bases include natrium phosphine and the like. organic bases such as sodium tert-butoxide and inorganic bases such as sodium carbonate and potassium carbonate In addition, the reaction is preferably carried out in a solution. As the solvent, a mixture of acetonitrile and water, a mixture of thinners such as toluene or xylene and water, Mixed solvents: toluene, xylene, alcohols such as ethanol, and water. 3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) and water mixed solvents, and mixed solvents of ethers such as ethylene glycol dimethyl ether and water However, the catalysts, bases, and solvents that can be used are not limited to these. There is none.

[0187] In the synthesis scheme (B-1), instead of the arylboron compound (b2), aryl aluminum, aryl zirconium, aryl zinc, or aryl tin compounds The reaction is preferably carried out in an inert atmosphere such as nitrogen or argon. Alternatively, heating may be performed using electromagnetic waves.

[0188] Subsequently, as shown in the synthesis scheme (B-2), a halogenated pyrimidine compound (b3) By coupling with an aryl boron compound (b4), one of the compounds shown in this embodiment can be obtained. An organic compound represented by general formula (G4) can be synthesized.

[0189] [ka]

[0190] In the synthetic scheme (B-2), Ar 11 , Ar 12 , R 11 ~R 13 , and R 2 1 ~R 23 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted It represents either a phenyl group or a substituted or unsubstituted biphenyl group. 13 and Ar 14 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted fluorocarbon phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzothiophene 4-yl group, or a substituted or unsubstituted dibenzofuran-4-yl group. α 1 , α 2 , α 8 , and α 9 each independently represents a substituted or unsubstituted phenylene group. Furthermore, h, i, x, and y each independently represent 0 or 1. 1 and E 2 Each independently represents sulfur or oxygen. 3 are hydrogen, chlorine, bromine, or or iodine, except Ar 13 If is hydrogen, then X 3 represents hydrogen. X 3 is reactive From the viewpoint of the height, it preferably represents bromine, more preferably iodine. 4 is a boronic acid or represents dialkoxyboron.

[0191] The coupling reaction in the synthetic scheme (B-2) can be carried out under various reaction conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be applied.

[0192] In the synthetic scheme (B-2), the Suzuki-Miyaura reaction can be used. For details, please refer to the above synthesis scheme (B-1), and therefore further explanation is omitted.

[0193] When the aryl group moieties of the compound (b2) and the compound (b4) are the same, the above synthetic scheme Compounds (B-1) and (B-2) can be reacted simultaneously (i.e., converted to compound (b1)). Compound (b2) and compound (b4) can be added simultaneously to react with each other, making the synthesis simple. More preferable.

[0194] In this manner, the organic compound of this embodiment can be synthesized.

[0195] The organic compound of this embodiment has a high S1 level, a high T1 level, a high HOMO level, and a high LUMO level. Because it has a wide energy gap (Eg) between levels, it is possible to By using it as a host material to disperse the optical substance, high current efficiency can be achieved. The organic compound of the present embodiment is suitable as a host material for dispersing a phosphorescent compound. The compound has a high electron transporting property and is therefore suitable as a material for an electron transporting layer in a light-emitting element. By using the organic compound of this embodiment, a low driving voltage, Furthermore, a light-emitting element having high current efficiency can be realized. Thus, a light-emitting device, an electronic device, and a lighting device with reduced power consumption can be obtained.

[0196] (Embodiment 3) In this embodiment mode, a light-emitting element in which the organic compound shown in Embodiment Mode 2 is used for a light-emitting layer will be described. This will be explained using Figure 2.

[0197] In this embodiment, a compound represented by the structural formula (400), which is an example of the organic compound shown in Embodiment 2, is 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation) A light-emitting device including 4,6mDBTP2Pm-II will be described with reference to FIG.

[0198] The light-emitting element of this embodiment mode has an EL layer having at least a light-emitting layer sandwiched between a pair of electrodes. The EL layer may have a plurality of layers in addition to the light-emitting layer. In other words, the carriers are distributed at a distance from the electrode so that the light-emitting region is formed at a distance from the electrode. To allow recombination to occur, the material must be made of a material with high carrier injection properties and high carrier transport properties. In this specification, a material having a high carrier injection property and a layer having a high carrier injection property are used. A layer made of a material with high carrier transport properties is called a functional layer, which has functions such as carrier injection and transport. The functional layers include a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. It can be used.

[0199] In the light-emitting element of this embodiment shown in FIG. 2A, the first electrode 1010 and the second electrode The EL layer 1020 having the light-emitting layer 1130 is provided between a pair of electrodes 1030 . The EL layer 1020 includes a hole injection layer 1110, a hole transport layer 1120, an emitting layer 1130, and an electron transport layer. The light-emitting element in FIG. On the substrate 1000, a first electrode 1010 and a positive electrode 1011 are stacked in this order on the first electrode 1010. Hole injection layer 1110, hole transport layer 1120, light emitting layer 1130, electron transport layer 1140, electron injection It is composed of an insulating layer 1150 and a second electrode 1030 provided on top of it. In the light-emitting element shown in this embodiment, the first electrode 1010 functions as an anode, and the second electrode 1011 functions as an anode. The second electrode 1030 functions as a cathode.

[0200] The substrate 1000 is used as a support for the light emitting device. Glass, quartz, plastic, etc. may be used. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), for example, Plastic substrate made of polycarbonate, polyarylate, and polyethersulfone In addition, films (polypropylene, polyester, polyvinyl fluoride, It is also possible to use an inorganic vapor deposition film, etc. Any other material may be used as long as it functions as a support in the element manufacturing process. .

[0201] The first electrode 1010 is made of a metal having a large work function (specifically, 4.0 eV or more), It is preferable to use alloys, conductive compounds, and mixtures thereof. For example, indium tin oxide (ITO), silicon Or silicon oxide-containing indium oxide-tin oxide, indium oxide-zinc oxide, acid Examples include tungsten oxide and indium oxide containing zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they can also be formed by the sol-gel method. For example, indium oxide-zinc oxide can be produced using indium oxide. It is formed by sputtering using a target containing 1 to 20 wt% zinc oxide. In addition, indium oxide containing tungsten oxide and zinc oxide (IW ZO) is a mixture of indium oxide with 0.5 to 5 wt% tungsten oxide and 0. It can be formed by sputtering using a target containing 1 to 1 wt% Other metals include gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, and copper. , palladium, or nitrides of metal materials (for example, titanium nitride).

[0202] However, the layer of the EL layer 1020 formed in contact with the first electrode 1010 is It is formed using a composite material made by mixing an organic compound and an electron acceptor. In this case, the material used for the first electrode 1010 may be any of various metals regardless of the magnitude of the work function. , alloys, conductive compounds, and mixtures thereof can be used. For example, aluminum It is also possible to use alloys containing tungsten, silver, and aluminum (for example, Al-Si).

[0203] The EL layer 1020 formed on the first electrode 1010 has at least a light-emitting layer 1130. In addition, a part of the EL layer 1020 contains an organic compound according to one embodiment of the present invention. A known substance can be used for a part of the EL layer 1020, and low molecular weight compounds and The EL layer 1020 can be formed from a material selected from the group consisting of organic compounds, organic polymers, and polymer compounds. This includes not only those consisting of organic compounds but also those containing inorganic compounds as part of the composition. Let's say.

[0204] In addition to the light-emitting layer 1130, the EL layer 1020 also includes a hole injection layer 1131 as shown in FIG. 110, a hole transport layer 1120, an electron transport layer 1140, an electron injection layer 1150, etc. are appropriately combined. The laminate is formed by laminating the layers together.

[0205] The hole injection layer 1110 is a layer containing a substance with high hole injection properties. Examples of the oxides include molybdenum oxide, titanium oxide, vanadium oxide, and rhenium oxide. Ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum metal oxides such as zinc oxide, silver oxide, tungsten oxide, and manganese oxide. In addition, phthalocyanine (abbreviated as HPc) and copper (II) phthalocyanine (abbreviated as Phthalocyanine compounds such as CuPc can be used.

[0206] In addition, the low molecular weight organic compound 4,4',4''-tris(N,N-diphenylamine) N-(3-)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3- Methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl Nyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl) -N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNT PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyla 3-[N-(9-phenylcarbazole-3-ylamino]benzene (abbreviation: DPA3B), [N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3 ,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9 -phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N- (9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: Aromatic amine compounds such as PCzPCN1) can be used.

[0207] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriazole) phenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl N-(Nylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide ] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'- Examples of polymer compounds include bis(phenyl)benzidine (abbreviated as Poly-TPD). In addition, poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid ) (PEDOT / PSS), polyaniline / poly(styrene sulfonate) (PAni / P A polymer compound to which an acid such as SS has been added can be used.

[0208] The hole injection layer 1110 is formed by mixing an organic compound and an electron acceptor. Such a composite material may be formed by bonding an organic compound with an electron acceptor. In this case, the organic compound has excellent hole injection and hole transport properties. The material is preferably a material that is excellent in transporting the generated holes (a material with high hole transport properties). .

[0209] The organic compounds used in the composite materials include aromatic amine compounds, carbazole compounds, aromatic Aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), and various chemical compounds As the organic compound used for the composite material, a hole transporting compound having It is preferable that the organic compound has a high molecular weight. -6 cm 2 / Vs or more However, it is preferable that the material has a higher hole transporting property than an electron transporting property. Other organic materials that can be used in the composite material are listed below. The compounds are specifically listed below.

[0210] Examples of organic compounds that can be used in composite materials include TDATA and MTDAT. A, DPAB, DNTPD, DPA3B, PCzPCA1, PCzPCA2, PCzPC N1,4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl Nyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl -4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFL Aromatic amine compounds such as 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carba CzPA, 9-phenyl-3-[4-(10-phenyl-9-anthraquinone) phenyl]-9H-carbazole (abbreviation: PCzPA), 1,4-bis[4-(N- Carbazoles such as [carbazolyl]phenyl-2,3,5,6-tetraphenylbenzene Compounds can be used.

[0211] In addition, 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 (abbreviation: DPPA), 2- tert-Butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t- BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10 -Diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene DMNA, 9,10-bis[2-(1-naphthyl)phenyl]-2-tert-butyl ether t-Butylanthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene aromatic compounds such as 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene Aromatic hydrocarbon compounds can be used.

[0212] Furthermore, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene , 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10 ,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bi bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert- butyl)perylene, pentacene, coronene, 4,4'-bis(2,2-diphenylvinyl ) biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl )phenyl]anthracene (abbreviation: DPVPA) and other aromatic hydrocarbon compounds. can be done.

[0213] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetramethyl ... Organic compounds such as fluoroquinodimethane (abbreviated as F4-TCNQ) and chloranil, and transition metals In addition, metal oxides belonging to Groups 4 to 8 of the periodic table can be used. Specifically, vanadium oxide, niobium oxide, titanium oxide, talc, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide Molybdenum oxide is particularly preferred because it has high electron-accepting properties. It is preferred because it has low moisture absorption and is easy to handle.

[0214] In addition, the polymer compounds such as PVK, PVTPA, PTPDMA, and Poly-TPD mentioned above A composite material may be formed using the material and the above-mentioned electron acceptor and used in the hole injection layer 1110. stomach.

[0215] The hole transport layer 1120 is a layer containing a substance with a high hole transport property. Examples of suitable bis[N-(9,9-diphenyl ether]-phosphate dehydrogenase (NPB), TPD, BPAFLP, 4,4'-bis[N-(9,9-diphenyl ether]-phosphate dehydrogenase (BPAFLP), Methylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPB i), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl An aromatic amine compound such as bis(2-amino)biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 / Vs or more. However, other materials may be used as long as they have a higher hole transporting property than electron transporting property. Note that the layer containing a substance with a high hole transporting property is not limited to a single layer, and may be a layer containing the above-mentioned substance. Two or more layers may be laminated.

[0216] The hole transport layer 1120 may also contain carbazoles such as CBP, CzPA, and PCzPA. derivatives, and anthracene derivatives such as t-BuDNA, DNA, and DPAnth Good too.

[0217] The hole transport layer 1120 is made of PVK, PVTPA, PTPDMA, Poly-TP Polymer compounds such as D can also be used.

[0218] The light-emitting layer 1130 is a layer containing a light-emitting substance. 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine, (abbreviation: 4,6mDBTP2Pm-II) is used in the light-emitting layer. 6mDBTP2Pm-II (abbreviation) is a method for converting a light-emitting material (guest material) into another material (host material). ) in the light-emitting layer, it can be used as a host material. The structure is such that a guest material, which is a light-emitting substance, is dispersed in DBTP2Pm-II (abbreviation). Thus, light emission from the guest material can be obtained. The compounds are useful as host materials in the light-emitting layer.

[0219] In addition, multiple types of materials (host materials) are used to disperse the light-emitting materials (guest materials). Therefore, the light-emitting layer can be made of 4,6mDBTP2Pm-II (abbreviation) or the second The host material may include the following.

[0220] The second host material may be, for example, the material used in the hole transport layer 1120 .

[0221] Examples of the luminescent substance include a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence. Examples of fluorescent materials that can be used in the light-emitting layer 1130 include: For example, N,N'-bis[4-(9H-carbazol-9-yl]-2,4-di ... )phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2 S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthraquinone) 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), )-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation :PCBAPA). Green light-emitting materials include N-(9,10- Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)- 2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2P CABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-trimethyl Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-biphenyl [(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl Nyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(2DPABPhA)] (1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl) Phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N, N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA) In addition, rubrene and 5,12-bis(1,1'-biphenyl) are used as yellow emitting materials. (4-yl)-6,11-diphenyltetracene (abbreviation: BPT). In addition, N,N,N',N'-tetrakis(4-methylphenyl) ) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl- N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoro Examples include oranthen-3,10-diamine (abbreviation: p-mPhAFD).

[0222] Furthermore, examples of phosphorescent compounds that can be used in the light-emitting layer 1130 include blue-based Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2 ’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)methyl] (fluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluoro (triphenyl)pyridinato-N,C 2’ ] Iridium (III) acetylacetonate (abbreviation Also, as a green emitting material, tris( 2-Phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: Ir(ppy)3 ), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzyl) Iridium(III) acetylacetonate (abbreviation: Ir(pbi) 2(acac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate Tonanate (abbreviation: Ir(bzq)2(acac)), tris(benzo[h]quinolinato) Iridium(III) (abbreviation: Ir(bzq)3) is one of the most common ions. Bis(2,4-diphenyl-1,3-oxazolato-N,C) 2’ ) Iriji Ir(III) acetylacetonate (abbreviation: Ir(dpo)2(acac)), bis[ 2-(4'-perfluorophenylphenyl)pyridinato]iridium(III) acetyl Ir(p-PF-ph)2(acac)), bis(2-phenyl Benzothiazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: I r(bt)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluoro Iridium(III) (abbreviation: Ir(Fdppr)-5-methylpyrazinato) -Me)2(acac)), (acetylacetonato)bis{2-(4-methoxyphenyl )-3,5-dimethylpyrazinato}iridium(III) (abbreviation: Ir(dmmoppr )2(acac)) and the like. In addition, tris(2-fluorophenyl) Phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: Ir(pq)3), bis (2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetonate ( Abbreviation: Ir(pq)2(acac)), (acetylacetonato)bis(3,5-dimethyl -2-phenylpyrazinato)iridium(III) (abbreviation: Ir(mppr-Me)2( acac)), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenyl) Nilpyrazinato)iridium(III) (abbreviation: Ir(mppr-iPr)2(acac )) and the like. Red light-emitting materials include bis[2-(2'-benzo[4 ,5-α]thienyl)pyridinato-N,C 3’ ]Iridium(III) acetylacetonate Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N ,C 2’ ) Iridium(III) acetylacetonate (abbreviation: Ir(piq)2(ac ac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxazone Salinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), (acetyl Iridium(III) Name: Ir(tppr)2(acac)), (dipivaloylmethanato)bis(2,3,5- Triphenylpyrazinate)iridium(III) (abbreviation: Ir(tppr)2(dpm) ), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porph Examples of organometallic complexes include tris(triphosphate) platinum(II) (abbreviation: PtOEP). (Acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb( acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionate )(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phe n)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](mono Phenanthroline) europium(III) (abbreviation: Eu(TTA)3(Phen)), etc. The rare earth metal complexes are luminescence from rare earth metal ions (electron transition between different multiplicities) Therefore, it can be used as a phosphorescent compound.

[0223] Furthermore, a polymer compound can be used as the light-emitting substance. The material used was poly(9,9-dioctylfluorene-2,7-diyl) (abbreviation: PFO). , poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,5-dimethacrylate] dimethylaminobenzoate-1,4-diyl)] (abbreviation: PF-DMOP), poly{(9,9-dioxo- N,N'-di-(p-butylphenyl)- 1,4-diaminobenzene]} (abbreviation: TAB-PFH) and others. As the light-emitting material of the system, poly(p-phenylene vinylene) (abbreviation: PPV), poly[(9, 9-Dihexylfluorene-2,7-diyl)-alt-co-(benzo[2,1,3] thiadiazole-4,7-diyl)] (abbreviation: PFBT), poly[(9,9-dioctyl -2,7-divinylenefluorenylene)-alt-co-(2-methoxy-5-(2-ethoxy- In addition, orange to red As the light-emitting material, poly[2-methoxy-5-(2'-ethylhexoxy)-1,4-phenylene] Poly(3-butylthiophene-2,5-diphenylenevinylene) (abbreviation: MEH-PPV), yl) (abbreviation: R4-PAT), poly{[9,9-dihexyl-2,7-bis(1-thiocyanyl) Novinylene)fluorenylene]-alt-co-[2,5-bis(N,N'-diphenyl amino)-1,4-phenylene]}, poly{[2-methoxy-5-(2-ethylhexyl oxy)-1,4-bis(1-cyanovinylenephenylene)]-alt-co-[2,5- Bis(N,N'-diphenylamino)-1,4-phenylene]}(abbreviation: CN-PPV- DPD) etc.

[0224] In addition, the organic compound shown in the second embodiment and the second compound shown in the first embodiment also emit fluorescent light. Since it exhibits such properties, it can be used as a light-emitting material.

[0225] The electron-transporting layer 1140 is a layer containing a substance with a high electron-transporting property. Examples of the aluminum compounds include tris(8-quinolinolato)aluminum (abbreviation: Alq), tris (4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzoate) hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl -8-quinolinolato)(4-phenylphenolato)aluminum (abbreviation: BAlq), etc. Metal complexes having a quinoline skeleton or a benzoquinoline skeleton are also included. Bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbreviation: Zn(BOX )2), bis[2-(2-hydroxyphenyl)benzothiazolato]zinc (abbreviation: Zn( Metal complexes with oxazole or thiazole ligands, such as BTZ, are also used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-te rt-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD) and 1,3- Bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl] Benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-( 4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), Basof Also used are phenanthroline (abbreviated as BPhen) and bathocuproine (abbreviated as BCP). The substances mentioned here are mainly 10 -6 cm 2 / Vs or higher electron mobility The electron transport layer may be a single layer or a double layer of the above-mentioned material. It may be a laminate of more than one.

[0226] The organic compound shown in Embodiment 2 and the second compound shown in Embodiment 1 also have pyridine. It has a methyl group skeleton and is suitable for the electron transport layer 1140 .

[0227] The electron injection layer 1150 is a layer containing a substance with high electron injection properties. are lithium, cesium, calcium, lithium fluoride, cesium fluoride, and calcium fluoride. Alkali metals, alkaline earth metals, such as lithium oxide, lithium ions, etc., or their compounds It is also possible to use rare earth metal compounds such as erbium fluoride. In addition, the above-described substances for forming the electron transporting layer 1140 can also be used.

[0228] Alternatively, the electron injection layer 1150 may be formed by mixing an organic compound and an electron donor. Such composite materials may be made by adding an electron to an organic compound by an electron donor. Since electrons are generated, the organic compound has excellent electron injection and transport properties. In this case, it is preferable that the material is excellent in transporting the generated electrons. The electron transport layer 1140 is made of a material (metal complex, heteroaromatic compound, etc.) The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, Examples of such elements include smium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of suitable Lewis bases include magnesium oxide and barium oxide. It is also possible to use organic compounds such as tetrathiafulvalene (TTF). You can also be there.

[0229] The hole injection layer 1110, the hole transport layer 1120, the light emitting layer 1130, and the electron transport layer 1140 are The layer 1140 and the electron injection layer 1150 are formed by deposition (including vacuum deposition), inkjet deposition, and the like, respectively. The layer can be formed by a jet method, a coating method, or the like.

[0230] The second electrode 1030 has a small work function when it functions as a cathode. (preferably 3.8 eV or less) metals, alloys, conductive compounds, and mixtures thereof Specifically, it is preferable to form the material using an element belonging to Group 1 or 2 of the periodic table. Elements, namely alkali metals such as lithium and cesium, and calcium, strontium, etc. Alkaline earth metals, magnesium, and alloys containing these (e.g., Mg-Ag, Al -Li), europium, ytterbium, and other rare earth metals and alloys containing these, as well as a Aluminum, silver, etc. can be used.

[0231] However, the layer of the EL layer 1020 formed in contact with the second electrode 1030 is the above-described When using a composite material made by mixing an organic compound and an electron donor, Aluminum, silver, ITO, silicon or silicon oxide containing oxides, regardless of quantity A variety of conductive materials can be used, such as indium-tin oxide.

[0232] The second electrode 1030 is formed by vacuum deposition or sputtering. In addition, when using silver paste, etc., it is possible to use a coating method, an inkjet method, etc. etc. can be used.

[0233] In the light-emitting element described above, a potential difference generated between the first electrode 1010 and the second electrode 1030 This causes a current to flow, and holes and electrons recombine in the EL layer 1020, causing light to be emitted. This light emission is transmitted to either the first electrode 1010 or the second electrode 1030. Therefore, the electric current is taken out through both the first electrode 1010 and the second electrode 103. Either one or both of the electrodes 10 and 11 serve as electrodes that are transparent to visible light.

[0234] The structure of the layer provided between the first electrode 1010 and the second electrode 1030 is the same as that described above. In order to prevent quenching caused by the proximity of the light emitting region to the metal, Then, holes and electrons recombine at a location away from the first electrode 1010 and the second electrode 1030. Any other configuration may be used as long as it has a light-emitting region.

[0235] That is, the layer stack structure is not particularly limited, and a substance with high electron transporting properties, a substance with high hole transporting properties, materials with high electron injection properties, materials with high hole injection properties, bipolar properties (electron and In one embodiment of the present invention, a layer made of a material having a high hole transporting property or a hole blocking material is The light-emitting layer contains 4,6mDBTP2Pm-II (abbreviation) as a host material, and It may be possible to configure them in combination.

[0236] In addition, 4,6mDBTP2Pm-II (abbreviation) is a substance with high electron transport properties, 4,6mDBTP2Pm-II (abbreviation) can also be used for the electron transport layer 1140. That is, the organic compound of one embodiment of the present invention can be used for the electron-transport layer.

[0237] In addition, both the light-emitting layer 1130 (particularly the host material of the light-emitting layer) and the electron-transporting layer 1140 By using the organic compound of one embodiment of the present invention, an extremely low driving voltage can be achieved.

[0238] Next, the light-emitting element shown in FIG. 2B is formed by forming a first electrode 1010 and a second electrode 1020 on a substrate 1000. The EL layer 1020 is provided between a pair of electrodes, a first electrode 1030 and a second electrode 1030. 20 includes a hole injection layer 1110, a hole transport layer 1120, a light emitting layer 1130, and an electron transport layer 114 2B has a substrate 1000 and an electron injection layer 1150. The second electrode 1030 functions as a cathode, and the second electrode 1030 is laminated in this order. electron injection layer 1150, electron transport layer 1140, light emitting layer 1130, hole transport layer 1120, hole injection layer The first electrode 1010, which functions as an anode, is formed on the insulating layer 1110. It is composed of:

[0239] A specific method for forming the light emitting element will be described below.

[0240] The light emitting element of this embodiment has a structure in which an EL layer 1020 is sandwiched between a pair of electrodes. The EL layer 1020 has at least a light-emitting layer 1130, which has a 4.6 mD The EL layer 102 is formed using BTP2Pm-II (abbreviation) as a host material. In addition to the light-emitting layer 1130, the layer 1100 includes functional layers (hole injection layer 1110, hole transport layer 1120, electron The electrode (first electrode 1010) may include a transport layer 1140, an electron injection layer 1150, etc. The first electrode 1030, the light-emitting layer 1130, and the functional layer are formed by a droplet ejection method (ink-jet method). It may be formed by a wet method such as a vacuum deposition method, a spin coating method, or a printing method. It may be formed by a dry method such as a VD method or a sputtering method. Since it can be formed under atmospheric pressure, it can be formed using a simple device and process. On the other hand, the dry method does not require dissolving the material. Since there is no problem, materials that are hardly soluble in the solution can be used, allowing for a wide range of material choices.

[0241] All of the thin films constituting the light-emitting element may be formed by a wet method. The light-emitting element can be manufactured using only the necessary equipment. The functional layer and the first electrode 1010 are laminated on the light-emitting layer 1130 by a wet method. The second electrode 10 may be formed by a dry method before the light-emitting layer 1130 is formed. The light-emitting layer 1130 and the functional layer are formed by a dry process and laminated on the light-emitting layer 1130. The functional layer and the first electrode 1010 may be formed by a wet method. The method is not limited to this, and a wet method or a dry method may be used depending on the material used, the required film thickness, and the interface state. The light-emitting device can be fabricated by selecting and combining the methods.

[0242] In this embodiment, a light emitting element is fabricated on a substrate made of glass, plastic, or the like. By fabricating multiple light-emitting elements like this on one substrate, a passive matrix type In addition, a light-emitting device can be fabricated on a substrate made of glass, plastic, or the like. For example, a thin film transistor (TFT) is formed, and a light emitting element is generated on an electrode electrically connected to the TFT. An optical element may be fabricated, whereby an active element that controls the driving of a light-emitting element by a TFT is fabricated. It should be noted that the structure of the TFT is not particularly limited. The TFT may be a staggered type or an inverted staggered type. The crystallinity of the semiconductor is not particularly limited, and an amorphous semiconductor or a crystalline semiconductor may be used. In addition, the driving circuit formed on the TFT substrate may also be N-type and P-type TFTs. It may consist of either N-type or P-type. It is also possible.

[0243] As described above, using 4,6mDBTP2Pm-II (abbreviation) described in the second embodiment, A light-emitting element can be manufactured by using an organic compound according to one embodiment of the present invention. As a result, a light-emitting element with low driving voltage and high current efficiency can be obtained.

[0244] Furthermore, a light-emitting device (image display device) using the light-emitting element of one embodiment of the present invention obtained in this manner can be manufactured. The device) can achieve low power consumption.

[0245] Note that a passive matrix light-emitting device or Active matrix in which the driving of light-emitting elements is controlled by thin-film transistors (TFTs) A light-emitting device of this type can be fabricated.

[0246] This embodiment mode can be implemented in appropriate combination with other embodiment modes.

[0247] (Fourth embodiment) In this embodiment, as one aspect of the present invention, a phosphorescent iridium metal compound which is a first compound is The complex is a second compound, an organic compound containing a pyrimidine skeleton, and two or more other organic compounds. A light-emitting element using the compound in the light-emitting layer will be described with reference to FIG.

[0248] The light-emitting element described in this embodiment has a pair of electrodes (a first electrode 201 and a second electrode 202) as shown in FIG. The structure has an EL layer 203 between the first and second electrodes 202. The layer has at least a light-emitting layer 204, and also has a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, The layer may include a hole injection layer, a hole transport layer, an electron transport layer, and the like. The electron injection layer and the charge generation layer can be formed using the substances described in Embodiment 1. In this embodiment, the first electrode 201 is used as an anode, and the second electrode 202 is used as a cathode. Used as a pole.

[0249] The light-emitting layer 204 shown in this embodiment contains the phosphorescent compound which is the first compound shown in Embodiment 1. a phosphorescent compound 205 using a phosphorescent iridium metal complex, a first organic compound 206, and The light-emitting layer 204 contains a second organic compound 207. The phosphorescent compound 205 is The first organic compound 206 and the second organic compound 20 7, at least one of which contains an organic compound containing a pyrimidine skeleton as the second compound. The material contained in the light-emitting layer 204 at a higher ratio is used as the host material in the light-emitting layer 204. do.

[0250] In the light-emitting layer 204, the guest material is dispersed in the host material. This can suppress the crystallization of the light-emitting layer. Concentration quenching can be suppressed, and the luminous efficiency of the light-emitting device can be increased.

[0251] The triplet excited energies of the first organic compound 206 and the second organic compound 207 are The energy level (T1 level) of the phosphorescent compound 205 is preferably higher than the T1 level of the phosphorescent compound 205. The T1 level of the first organic compound 206 (or the second organic compound 207) is a phosphorescent compound. If the T1 level of 205 is lower than the triplet excitation energy of the phosphorescent compound 205 that contributes to the emission, The first organic compound 206 (or the second organic compound 207) quenches the ghee. This leads to a decrease in luminous efficiency.

[0252] Here, in order to increase the efficiency of energy transfer from the host material to the guest material, The Förster mechanism (dipole-dipole interaction) and the The emission spectrum of the host material ( When discussing energy transfer from the singlet excited state, the fluorescence spectrum is When discussing the energy transfer from the guest material, the phosphorescence spectrum is used. More specifically, the overlap with the spectrum in the absorption band on the longest wavelength (lowest energy) side However, in the case of a typical phosphorescent guest material, the host material The fluorescence spectrum of the guest material is calculated by the absorption band at the longest wavelength (lowest energy) side. It is difficult to overlap the spectrum with the host material. The phosphorescence spectrum of the material is located on the longer wavelength (lower energy) side than the fluorescence spectrum, The T1 level of the host material is lower than the T1 level of the phosphorescent compound, resulting in the above-mentioned quenching. On the other hand, to avoid the quenching problem, the T If the T1 level of the phosphorescent compound is designed to be higher than the T1 level of the host material, the fluorescence The fluorescence spectrum shifts to the short wavelength (high energy) side, so that the fluorescence spectrum The absorption spectrum no longer overlaps with that of the material in the absorption band on the longest wavelength (lowest energy) side. Therefore, the fluorescence spectrum of the host material is adjusted to the longest wavelength (lowest energy) side of the guest material. The energy from the singlet excited state of the host material is measured by superimposing the absorption spectrum in the absorption band of Maximizing mobility is usually difficult.

[0253] Therefore, in this embodiment, the first organic compound 206 and the second organic compound 207 In this case, in the light-emitting layer 204, Upon recombination of carriers (electrons and holes) in the first organic compound 206 and the second organic compound 207, The compound 207 forms an excited complex (also called an exciplex), which emits light. In the layer 204, the fluorescence spectrum of the first organic compound 206 and the fluorescence spectrum of the second organic compound 207 are The fluorescence spectrum of 07 is converted to the emission spectrum of the exciplex located at longer wavelengths. Furthermore, the emission spectrum of the exciplex and the absorption spectrum of the guest material overlap significantly. By selecting the first and second organic compounds so that It is possible to maximize the energy transfer of the triplet excited state. It is believed that energy transfer occurs from the exciplex rather than from the starting material.

[0254] As the phosphorescent compound 205, a phosphorescent iridium metal complex is used as the first compound. The first organic compound 206 and the second organic compound 207 are compounds that accept electrons. compounds that easily trap electrons (electron trapping compounds) and compounds that easily accept holes (hole trapping compounds). It is preferable to combine the second compound (pyrimidinyl compound) with the second compound. An organic compound containing an amine skeleton can be used as a compound that readily accepts electrons.

[0255] Compounds that readily accept holes include 4-phenyl-4'-(9-phenyl)- (9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3 -[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9 -phenylcarbazole (abbreviation: PCzPCN1), 4,4',4''-tris[N-( 1-Naphthyl-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA) , 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro[ N,N'-bis(9-phenylcarbamoyl) N,N'-diphenyl-1,3-diamine (abbreviated as PCA2B), N-(9,9-dimethyl-2-N',N'-diphenylamino-9H-furan N,N-diphenylamine (abbreviation: DPNF), N-phenyl- N-(4-phenylphenyl)-N-(9-phenyl-9H-carbazol-3-yl) Amine (abbreviation: PCA1BP), N,N',N''-triphenyl-N,N',N''- Tris(9-phenylcarbazol-3-yl)-benzene-1,3,5-triamine ( Abbreviation: PCA3B), 2-[N-(9-phenylcarbazol-3-yl)-N-phenyl 2-[N-(4- Diphenylaminophenyl)-N-phenylamino]-spiro-9,9'-bifluorene (abbreviation: DPASF), N,N-di(biphenyl-4-yl)-N-(9-phenyl-9 H-carbazol-3-yl)amine (abbreviation: PCzBBA1), N,N'-bis[4- (Carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluor 2,7-diaminediamine (abbreviation: YGA2F), 4,4'-bis[N-(3-methylphenyl)- phenyl)-N-phenylamino]biphenyl (TPD), 4,4'-bis[N-(4-diphenylamino)biphenyl phenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N- (9,9-dimethyl-9H-fluoren-2-yl)-N-[9,9-dimethyl-2-{ N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)}amino- 9H-Fluoren-7-yl]phenylamine (abbreviation: DFLADFL), 3-[N-( 9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazo (abbreviation: PCzPCA1), 3-[N-(4-diphenylaminophenyl)-N-phenyl]- phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[ N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazo (abbreviation: PCzDPA2), 4,4'-bis(N-{4-[N'-(3-methylphenyl) (Nyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl) ethyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3,6-bis[ N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol-3-yl Rubazole (abbreviation: PCzPCA2) is an example.

[0256] The first organic compound 206 and the second organic compound 207 can form an exciplex. The emission spectrum of the exciplex is an example of a combination of the phosphorescent compound 205. The emission spectrum of the exciplex overlaps with the absorption spectrum of the phosphorescent compound 205. It is sufficient that the wavelength is longer than the spectral peak.

[0257] The first organic compound is composed of a compound that readily accepts electrons and a compound that readily accepts holes. When the second organic compound 206 and the second organic compound 207 are mixed, the carrier balance is controlled by the mixing ratio. Specifically, the ratio of the first organic compound to the second organic compound is 1:9. A range of ∼9:1 is preferred.

[0258] The light-emitting element described in this embodiment has an emission spectrum of an exciplex and an absorption spectrum of a phosphorescent compound. Energy transfer efficiency is increased by utilizing spectral overlap. Therefore, a light emitting device with high external quantum efficiency can be realized.

[0259] As another configuration included in the present invention, the other two phosphorescent compounds 205 (guest materials) The types of organic compounds include hole-trapping host molecules and electron-trapping host molecules. The light-emitting layer 204 is formed using the molecules, and holes are generated in the guest molecules present in the two types of host molecules. and electrons to make the guest molecule excited (i.e., Guest Couple ed with Complementary Hosts (GCCH) It is also possible to form the light emitting layer 204 on the substrate.

[0260] In this case, the hole-trapping host molecule and the electron-trapping host molecule are: The compounds that readily accept holes and those that readily accept electrons are It can be used.

[0261] Note that the light-emitting element shown in this embodiment mode is an example of the structure of a light-emitting element, but A light-emitting element having a different structure shown in another embodiment can also be applied to the light-emitting device according to this embodiment. In addition, the light emitting device including the light emitting element may be a passive matrix light emitting device. In addition to the optical device and the active matrix type light emitting device, other devices different from those described in other embodiments may be used. A light emitting device having a microcavity structure including a light emitting element having the structure described above can be manufactured. and all of these are included in the present invention.

[0262] In the case of an active matrix type light emitting device, the structure of the TFT is not particularly limited. For example, a staggered or inverted staggered TFT can be used as appropriate. The driver circuit formed on the FT substrate can be made up of N-type and P-type TFTs. Alternatively, it may be composed of only one of N-type TFTs or P-type TFTs. Furthermore, there is no particular limitation on the crystallinity of the semiconductor film used in the TFT. An amorphous semiconductor film, a crystalline semiconductor film, an oxide semiconductor film, or the like can be used.

[0263] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0264] (Embodiment 5) In this embodiment, as one embodiment of the present invention, a structure having a plurality of EL layers sandwiching a charge generation layer is described. A light emitting device having such a structure (hereinafter referred to as a tandem light emitting device) will be described.

[0265] The light-emitting element shown in this embodiment has a pair of electrodes (first electrode 30) as shown in FIG. A plurality of EL layers (first EL layer 302(1), second EL layer 302(2), and second EL layer 304) are disposed between the first and second electrodes. It is a tandem light emitting device having an L layer 302(2).

[0266] In this embodiment, the first electrode 301 is an electrode that functions as an anode, and the second electrode The electrode 304 functions as a cathode. 304 can have the same structure as that of the first embodiment. The first EL layer 302(1) and the second EL layer 302(2) are the same as those in the first embodiment or the second embodiment. The EL layer may have the same structure as that shown in 3, or either of them may have the same structure. That is, the first EL layer 302(1) and the second EL layer 302(2) have the same structure. The configuration may be the same as that of the first or third embodiment. can be applied.

[0267] In addition, between the plurality of EL layers (the first EL layer 302(1) and the second EL layer 302(2)), The charge generating layer 305 is provided between the first electrode 301 and the second electrode 302. When a voltage is applied to the electrode 304, electrons are injected into one EL layer and positive charges are injected into the other EL layer. In this embodiment, the first electrode 301 is connected to the second electrode 302. When a voltage is applied so that the potential becomes higher than that of the charge generating layer 304, the charge Electrons are injected into 302(1) and holes are injected into the second EL layer 302(2).

[0268] The charge generating layer 305 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, the transmittance of visible light through charge generation layer 305 is preferably 40% or more.) In addition, the charge generating layer 305 has a lower conductivity than the first electrode 301 and the second electrode 304. It works even at a rate.

[0269] The charge generation layer 305 is made of an organic compound with high hole transport properties to which an electron acceptor is added. Even if an electron donor (donor) is added to an organic compound with high electron transport properties, Alternatively, both of these structures may be stacked.

[0270] In the case where an electron acceptor is added to an organic compound having a high hole transporting property, Examples of organic compounds with high transportability include NPB, TPD, TDATA, and MTDATA. , 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl Aromatic amine compounds such as bis(amino)biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 / Vs or more. However, if an organic compound has a higher hole transporting property than an electron transporting property, a substance other than those mentioned above can be used. It's okay.

[0271] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetramethyl ... Examples include fluoroquinodimethane (abbreviation: F4-TCNQ) and chloranil. Further, transition metal oxides can be used. Specifically, vanadium oxide and niobium oxide are examples of oxides of metals belonging to the group , tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, oxide Rhenium is preferred because of its high electron-accepting property. Among them, molybdenum oxide is particularly stable even in the atmosphere. It is preferable because it is stable, has low hygroscopicity, and is easy to handle.

[0272] On the other hand, in the case where an electron donor is added to an organic compound having high electron transport properties, Examples of organic compounds with high electron transport properties include Alq, Almq3, BeBq2, and B Metal complexes having a quinoline or benzoquinoline skeleton, such as Alq, can be used. In addition, oxazole-based compounds such as Zn(BOX)2 and Zn(BTZ)2, Metal complexes having azole-based ligands can also be used. However, PBD, OXD-7, TAZ, BPhen, BCP, etc. can also be used. The substances mentioned in are mainly 10 -6 cm 2 It is a substance with an electron mobility of 1 / Vs or more. Alternatively, an organic compound containing a pyrimidine skeleton may be used as the second compound. Any organic compound having a high electron transporting property may be used in addition to the above.

[0273] The electron donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or or metals belonging to Groups 2 and 13 of the periodic table, and their oxides and carbonates. Specifically, lithium (Li), cesium (Cs), magnesium (Mg) , calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, It is preferable to use cesium carbonate. The compound may be used as the electron donor.

[0274] By forming the charge generating layer 305 using the above-mentioned materials, an EL layer is laminated. When the voltage is increased, the increase in the driving voltage can be suppressed.

[0275] In this embodiment mode, a light-emitting element having two EL layers has been described. As shown above, the same can be said for a light-emitting device in which n (where n is 3 or more) EL layers are stacked. As in the light-emitting device according to the present embodiment, multiple layers are formed between a pair of electrodes. When the device has multiple EL layers, the current density can be improved by disposing a charge generating layer between the EL layers. It is possible to emit light in a high brightness range while keeping the current density low. In addition, when applied to lighting, the voltage drop due to the resistance of the electrode material It is possible to reduce the size of the LED, which allows for uniform light emission over a large area. A light emitting device with low power consumption can be realized.

[0276] In addition, by making the luminescent color of each EL layer different, the desired luminescence color can be obtained as a whole. For example, in a light-emitting element having two EL layers, the first By making the luminous color of the first EL layer and the luminous color of the second EL layer complementary to each other, It is also possible to obtain a light-emitting element that emits white light as a whole. In other words, the color that becomes achromatic when it is made of a substance that emits complementary colors. When the resulting light is mixed, white light can be obtained.

[0277] The same applies to a light-emitting element having three EL layers. For example, The luminescent color of the first EL layer is red, the luminescent color of the second EL layer is green, and the luminescent color of the third EL layer is blue. In this case, the light emitting element as a whole can emit white light.

[0278] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. You can be there.

[0279] (Embodiment 6) In this embodiment, the light-emitting element shown in Embodiment 1 and Embodiments 3 to 5 A light emitting device using the element will be described with reference to FIG.

[0280] The light-emitting device described in this embodiment mode is a micro-optical resonance device utilizing the optical resonance effect between a pair of electrodes. As shown in Figure 5, it has a microcavity structure and a pair of electrodes (reflection electrodes 4 51 and semi-transmissive / semi-reflective electrode 452) has at least an EL layer 455 between them. The EL layer 455 has at least a first light-emitting region. The light emitting layer 454B, the second light emitting layer 454G, and the third light emitting layer 454R are also included. It may also include an injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like. In addition, at least one of the first light-emitting layer 454B, the second light-emitting layer 454G, and the third light-emitting layer 454R At least one layer contains a phosphorescent iridium metal complex and an organic compound containing a pyrimidine skeleton. , is included.

[0281] In this embodiment, as shown in FIG. 5, a light emitting element having a different structure (first light emitting element 450R A light emitting device having a first light emitting element 450G and a third light emitting element 450B will be described. do.

[0282] The first light emitting element 450R has a first transparent conductive layer 453a and an EL layer 453b on a reflective electrode 451. The second electrode 455 and the semi-transmissive / semi-reflective electrode 452 are laminated in this order. The light emitting element 450G includes a second transparent conductive layer 453b and an EL layer 455 on a reflective electrode 451. , and a semi-transmissive / semi-reflective electrode 452 are laminated in this order. 450B is a display device in which an EL layer 455 and a semi-transmissive / semi-reflective electrode 452 are sequentially formed on a reflective electrode 451. It has a layered structure.

[0283] The light emitting elements (first light emitting element 450R, second light emitting element 450G, and third light emitting element 450R) In the light-emitting element 450B), a reflective electrode 451, an EL layer 455, a semi-transmissive and semi-reflective electrode 45 2 is common.

[0284] The EL layer 455 includes a first light-emitting layer 454B, a second light-emitting layer 454G, and a third light-emitting layer 454G. The first light-emitting layer 454B has a structure including a first light-emitting layer 454R. Light with a peak in the wavelength range below 480 nm (λ B ) and the second light-emitting layer 454G emits , light with a peak in the wavelength range of 500 nm to 550 nm (λ G ) and the third The light-emitting layer 454R emits light (λ R ) As a result, both the light emitting elements (first light emitting element 450R, second light emitting element 450R) emit light. 450G, and the third light-emitting element 450B), the first light-emitting layer 454B, the second light-emitting layer 454 G and the light emitted from the third light-emitting layer 454R are overlapped, i.e., the light emitted from the third light-emitting layer 454R is in the visible light region. From the above, the wavelength is λ B <λ G <λ R Let us suppose that the relationship is as follows:

[0285] Each light emitting element shown in this embodiment has a reflective electrode 451 and a semi-transparent and semi-reflective electrode 45 2 and an EL layer 455 is sandwiched between the EL layer 455 and the The light emitted from the layer in all directions functions as a micro-optical resonator (microcavity). The resonant frequency is generated by the reflective electrode 451 having the reflective layer and the semi-transparent and semi-reflective electrode 452. The electrode 451 is made of a conductive material having reflectivity, and the reflection of visible light on the film is The conductivity is 40% to 100%, preferably 70% to 100%, and the resistivity is 1×10 -2 The semi-transmitting and semi-reflective electrode 452 has a reflectivity of Ωcm or less. It is made of a conductive material and a light-transmitting conductive material, and the film reflects visible light. The emissivity is 20% to 80%, preferably 40% to 70%, and the resistivity is 1×10 - 2 It is assumed that the film has a resistance of Ωcm or less.

[0286] In this embodiment, the first light emitting element 450R and the second light emitting element 4 50G, the transparent conductive layers (first transparent conductive layer 453a, second transparent conductive layer By changing the thickness of 453b), the reflective electrode 451 and the semi-transparent / semi-reflective electrode can be formed for each light-emitting element. The optical distance between the electrodes 452 is changed. The light travels through the reflective electrode 451 and the semi-transparent and semi-reflective electrode 452, forming a resonant wave. This allows the device to strengthen light with a wavelength that is longer than the resonance wavelength and attenuate light with a wavelength that does not resonate. By changing the optical distance between the electrode 51 and the semi-transparent / semi-reflective electrode 452, light of different wavelengths can be transmitted. can be extracted.

[0287] The optical distance (also called the optical path length) is the actual distance multiplied by the refractive index, In this embodiment, it is expressed as the actual film thickness multiplied by n (refractive index). "Optical distance = actual film thickness x n".

[0288] In the first light emitting element 450R, the reflective electrode 451 and the semi-transmissive and semi-reflective electrode 452 are The optical distance at mλ R / 2 (where m is a natural number equal to or greater than 1), and the second light-emitting element 450G Let mλ be the optical distance from the reflective electrode 451 to the semi-transparent and semi-reflective electrode 452. G / 2( In the third light emitting element 450B, a semi-transparent electrode 451 is formed. The optical distance to the semi-reflective electrode 452 is mλ. B / 2 (where m is a natural number greater than or equal to 1) are.

[0289] As a result, the first light-emitting element 450R emits the third light-emitting element contained in the EL layer 455. The light emitted in the optical layer 454R (λ R ) is extracted, and from the second light-emitting element 450G, The light (λ ) emitted from the second light-emitting layer 454G included in the EL layer 455 G ) is extracted, The third light-emitting element 450B is mainly composed of the first light-emitting layer 454B included in the EL layer 455. The light emitted at (λ B The light extracted from each light-emitting element is semi-transparent. The light is emitted from the semi-reflective electrode 452 side.

[0290] In the above configuration, the optical element from the reflective electrode 451 to the semi-transmissive and semi-reflective electrode 452 Strictly speaking, the distance is from the reflective area of ​​the reflective electrode 451 to the semi-transparent and semi-reflective area of ​​the semi-transparent and semi-reflective electrode 452. However, in the reflective electrode 451 and the semi-transparent / semi-reflective electrode 452, Since it is difficult to precisely determine the position of the reflective area in the reflective electrode 451, The above-mentioned effect can be fully obtained by assuming that any position of the semi-reflective electrode 452 is a reflective region. It is assumed that this is possible.

[0291] Next, in the first light emitting element 450R, the reflected light from the third light emitting layer 454R is The light reflected by the reflective electrode 451 and returned (first reflected light) is incident on the third light emitting layer 454. This causes interference with the light (first incident light) that is directly incident on the semi-transmissive / semi-reflective electrode 452 from R. , the optical distance between the reflective electrode 451 and the third light-emitting layer 454R is (2n R -1)λ R / 4(just s,n R is a natural number greater than or equal to 1). By adjusting the optical distance, and amplifying the light emitted from the third light-emitting layer 454R by adjusting the phase of the light and the first incident light. can be done.

[0292] Strictly speaking, the optical distance between the reflective electrode 451 and the third light-emitting layer 454R is The optical distance between the reflective area in the third light-emitting layer 451 and the light-emitting area in the third light-emitting layer 454R is However, the reflection area of ​​the reflective electrode 451 and the third light-emitting layer 454R Since it is difficult to precisely determine the position of the light-emitting region, the reflective electrode 451 and the third light-emitting It is sufficient to assume that any position on the layer 454R is a reflective region and a luminous region, respectively, to realize the above-mentioned The effect can be obtained.

[0293] Next, in the second light emitting element 450G, the reflected light from the second light emitting layer 454G is The light reflected by the reflective electrode 451 and returned (second reflected light) is incident on the second light emitting layer 454. The light (second incident light) coming from G directly incident on the semi-transmissive / semi-reflective electrode 452 interferes with the light. , the optical distance between the reflective electrode 451 and the second light-emitting layer 454G is (2n G -1)λ G / 4(just s,n G is a natural number greater than or equal to 1). By adjusting the optical distance, the second reflection and amplifying the light emitted from the second light-emitting layer 454G by adjusting the phase of the light and the second incident light. can be done.

[0294] Strictly speaking, the optical distance between the reflective electrode 451 and the second light-emitting layer 454G is The optical distance between the reflection area in the second light-emitting layer 451 and the light-emitting area in the second light-emitting layer 454G is However, the reflective region of the reflective electrode 451 and the second light-emitting layer 454G Since it is difficult to precisely determine the position of the light-emitting region, the reflective electrode 451 and the second light-emitting It is sufficient to assume that any position on the layer 454G is a reflective region and a light-emitting region, respectively, to realize the above-mentioned The effect can be obtained.

[0295] Next, in the third light emitting element 450B, the reflected light from the first light emitting layer 454B is The light reflected by the reflective electrode 451 and returned (third reflected light) is incident on the first light emitting layer 454. This causes interference with the light (third incident light) that is directly incident on the semi-transmissive / semi-reflective electrode 452 from B. , the optical distance between the reflective electrode 451 and the first light-emitting layer 454B is (2n B -1)λ B / 4(just s,n B is a natural number greater than or equal to 1). By adjusting the optical distance, the third reflection and amplifying the light emitted from the first light-emitting layer 454B by adjusting the phase of the light and the third incident light. can be done.

[0296] Strictly speaking, the optical distance between the reflective electrode 451 and the first light-emitting layer 454B is The optical distance between the reflective area in 451 and the light-emitting area in the first light-emitting layer 454B is However, the reflective region of the reflective electrode 451 and the first light-emitting layer 454B Since it is difficult to precisely determine the position of the light-emitting region, the reflective electrode 451 and the first light-emitting It is sufficient to assume that any position on layer 454B is a reflective region and a light-emitting region, respectively, to achieve the above-mentioned The effect can be obtained.

[0297] In the above-described configuration, each of the light-emitting elements has a structure in which a plurality of light-emitting layers are provided in the EL layer. However, the present invention is not limited to this. For example, the tank described in the fifth embodiment may be used. In combination with the structure of a DEM type (stacked type) light emitting element, a charge generating layer is sandwiched between one light emitting element. A configuration in which a plurality of EL layers are provided and a single or a plurality of light-emitting layers are formed in each EL layer. Good too.

[0298] The light-emitting device shown in this embodiment has a microcavity structure, and Even if there are layers, it is possible to extract light of different wavelengths for each light-emitting element, so RGB coating Therefore, it is easy to achieve high definition, and for this reason, full color It is also advantageous in realizing the luminescence of specific wavelengths in the front direction. This configuration uses pixels of three or more colors, which allows for low power consumption. It is particularly useful when applied to color displays (image display devices), but it is also useful for lighting, etc. It may also be used for the following purposes.

[0299] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0300] (Embodiment 7) In this embodiment, a light-emitting device including a light-emitting element according to one embodiment of the present invention will be described with reference to FIGS. 7. First, the light emitting device shown in FIG. 6 will be described, and then the light emitting device shown in FIG. 7 will be described. The light emitting device shown in FIG.

[0301] FIG. 6(A) is a top view showing a light-emitting device, and FIG. 6(B) is a cross-sectional view of FIG. 6(A) taken along lines AB and CD. FIG.

[0302] In FIG. 6A, 401 indicated by a dotted line is a driving circuit section (source side driving circuit), 40 2 is a pixel section, 403 is a driving circuit section (gate side driving circuit), and 404 is a sealing substrate. , 405 is a sealing material, and the inside surrounded by the sealing material 405 is a space.

[0303] The lead wiring 408 is connected to the source side driver circuit 401 and the gate side driver circuit 403. The wiring is for transmitting the input signal, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal from Lint Circuit 409 Although only the FPC is shown here, this FPC has a printed circuit board. A printed wiring board (PWB) may be attached. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0304] Next, the cross-sectional structure will be described with reference to Fig. 6(B). A source side driver circuit 401, which is a driver circuit section, is formed in this example. , one pixel in the pixel section 402 is shown.

[0305] The source side driver circuit 401 includes an n-channel TFT 423 and a p-channel TFT 42 4 is combined to form a CMOS circuit. The driving circuit is also formed by TFT. It may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In this form, a driver integrated type in which a drive circuit is formed on a substrate is shown, but this is not necessarily required. In addition, the driving circuitry can be formed externally rather than on the substrate.

[0306] The pixel section 402 includes a switching TFT 411, a current control TFT 412, and The pixel is formed by a plurality of pixels including a first electrode 413 electrically connected to the drain. An insulator 414 is formed to cover the end of the first electrode 413. It is formed by using a photosensitive acrylic resin film of a mold.

[0307] In order to improve the covering property, the upper end or the lower end of the insulator 414 has a curvature. For example, the material of the insulator 414 is a positive photosensitive adhesive. When a rill is used, only the upper end of the insulator 414 has a radius of curvature (0.2 μm to 3 μm). It is preferable that the insulator 414 has a curved surface. Negative type that becomes insoluble in etching solution, or polymer type that becomes soluble in etching solution when irradiated with light. Any of the above types can be used.

[0308] A light-emitting layer 416 and a second electrode 417 are formed on the first electrode 413. Here, the material used for the first electrode 413 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 silicon-containing indium. Tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, chromium In addition to single layer films such as titanium nitride film and aluminum film, Lamination of a film containing aluminum as the main component, a titanium nitride film, a film containing aluminum as the main component, and a titanium nitride film A three-layer structure with a laminated structure can be used. This allows for good ohmic contact.

[0309] The light-emitting layer 416 can be formed by a deposition method using a deposition mask, a droplet ejection method such as an inkjet method, etc. The light-emitting layer 416 is formed by various methods such as a photolithography method, a printing method, a spin coating method, etc. The light-emitting layer 416 contains an organic compound having a pyrimidine skeleton, as described in the embodiment. Other materials constituting the present invention include low molecular weight materials, oligomers, dendrimers, and polymer materials. may be.

[0310] Furthermore, a material used for the second electrode 417 formed on the light-emitting layer 416 and functioning as a cathode is The material is a material with a small work function (Al, Mg, Li, Ca, or an alloy or compound thereof). It is preferable to use a material such as an alloy of Mg—Ag, Mg—In, or Al—Li. When the light generated in 16 is transmitted through the second electrode 417, the second electrode 417 is made of a film. Thin metal thin films and transparent conductive films (ITO, indium oxide containing 2-20 wt% zinc oxide) Indium oxide containing indium, silicon or silicon oxide, such as indium tin oxide or zinc oxide) It is preferable to use a laminate of the above.

[0311] Furthermore, by bonding the sealing substrate 404 to the element substrate 410 with a sealing material 405, A light-emitting element is disposed in a space 407 surrounded by an element substrate 410, a sealing substrate 404, and a sealant 405. The space 407 is filled with a filler material. In addition to the case where an inert gas (nitrogen, argon, etc.) is filled, the sealing material 405 is filled. There are cases like this.

[0312] It is preferable to use an epoxy resin for the sealing material 405. It is desirable that the sealing substrate 404 be made of a material that is as impermeable to moisture and oxygen as possible. Materials used for this include glass substrates, quartz substrates, and FRP (Fiberglass-Reinforced Plastics). Enforced Plastics), PVF (Polyvinyl Fluoride), Polyester Alternatively, a plastic substrate made of acrylic or the like can be used.

[0313] As described above, an active matrix light-emitting device having the light-emitting element of one embodiment of the present invention can be manufactured. The device can be obtained.

[0314] The light-emitting element of the present invention can be used not only in the above-mentioned active matrix light-emitting device but also in a panel light-emitting device. The present invention can also be used in a passive matrix light emitting device.

[0315] FIG. 7 shows a perspective view and a cross-sectional view of a passive matrix light-emitting device using a light-emitting element of the present invention. 7(A) is a perspective view showing a light emitting device, and FIG. 7(B) is a perspective view showing FIG. 7(A) in the XY plane. FIG.

[0316] In FIG. 7, an EL layer is disposed between a first electrode 502 and a second electrode 503 on a substrate 501. The end of the first electrode 502 is covered with an insulating layer 505. A partition layer 506 is provided on the insulating layer 505. The sidewalls of the partition layer 506 are in contact with the substrate surface. As the distance between the side walls approaches , the distance between the side walls becomes narrower. That is, the cross section of the partition layer 506 in the short side direction is trapezoidal, and the bottom side (the surface direction of the insulating layer 505) The side that faces the same direction as the insulating layer 505) faces the upper side (the side that faces the same direction as the insulating layer 505). The side of the partition wall layer 506 is oriented in the same direction as the insulating layer 505 and is shorter than the side of the partition wall layer 506 that is not in contact with the insulating layer 505. By providing the protective film, defects in the light-emitting element due to static electricity or the like can be prevented.

[0317] Through the above steps, a passive matrix light-emitting device having a light-emitting element of one embodiment of the present invention can be obtained. It is possible.

[0318] Note that the light-emitting device (active matrix type, passive matrix type) shown in this embodiment mode Since the light-emitting element of one embodiment of the present invention is used in both of the above-mentioned types, power consumption is low. Therefore, a light emitting device with good light emitting properties can be obtained.

[0319] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0320] (Embodiment 8) In this embodiment, a light-emitting device according to one embodiment of the present invention shown in the above embodiment is included as a part thereof. The electronic devices include cameras such as video cameras and digital cameras. goggle-type displays, navigation systems, sound reproduction devices (car audio , audio components, computers, game devices, personal digital assistants (mobile computers computer, mobile phone, portable game machine or electronic book, etc.), image playback device equipped with recording medium (device Specifically, it is a device that plays back recording media such as Digital Versatile Disc (DVD). These electronic devices include devices equipped with a display device that can generate and display the image. A specific example of the vessel is shown in Figure 8.

[0321] FIG. 8A illustrates a television device according to one embodiment of the present invention, which includes a housing 611, a support base 612, a display, and a display panel. This television device includes a display unit 613, a speaker unit 614, a video input terminal 615, etc. In this case, the light-emitting device of one embodiment of the present invention can be applied to the display portion 613. The light-emitting device of one embodiment of the present invention can achieve high current efficiency at a low driving voltage. By applying the optical device, a television set with reduced power consumption can be obtained.

[0322] FIG. 8B shows a computer according to one embodiment of the present invention, which includes a main body 621, a housing 622, a display display unit 623, keyboard 624, external connection port 625, pointing device 626 In this computer, the light emitting device of the present invention is applied to the display unit 623. The light-emitting device according to one embodiment of the present invention can achieve high current efficiency at a low driving voltage. Therefore, by applying the light-emitting device of one embodiment of the present invention, a computer with reduced power consumption can be realized. can be obtained.

[0323] FIG. 8C shows a mobile phone according to one embodiment of the present invention, which includes a main body 631, a housing 632, a display unit 633, an audio input unit 634, an audio output unit 635, operation keys 636, and an external connection port 637 In this mobile phone, the display unit 633 includes a light emitting device according to the present invention. The light-emitting device of one embodiment of the present invention can be driven at a low voltage and has high current efficiency. Therefore, by using the light-emitting device of one embodiment of the present invention, a portable device with reduced power consumption can be obtained. You can get a mobile phone.

[0324] FIG. 8D shows a camera according to one embodiment of the present invention, which includes a main body 641, a display unit 642, a housing 643, and a 43, external connection port 644, remote control receiver 645, image receiver 646, battery 647 , a voice input unit 648, operation keys 649, an eyepiece unit 650, etc. The light-emitting device of one embodiment of the present invention can be applied to the display portion 642. The light-emitting device of one embodiment of the present invention can achieve high current efficiency at a low driving voltage. By applying this, a camera with reduced power consumption can be obtained.

[0325] As described above, the light-emitting device of one embodiment of the present invention has an extremely wide range of application. The light-emitting device according to one embodiment of the present invention can be used in electronic devices in various fields. As a result, an electronic device with reduced power consumption can be obtained.

[0326] The light-emitting device of one embodiment of the present invention can also be used as a lighting device. 1 is an example of a liquid crystal display device using a light-emitting device of one embodiment of the present invention as a backlight. The liquid crystal display device shown in FIG. 9A includes a housing 701, a liquid crystal layer 702, a backlight 703, The display device has a housing 704, and the liquid crystal layer 702 is connected to a driver IC 705. The light-emitting device of one embodiment of the present invention is used for the light 703, and a current is supplied to the light 703 through a terminal 706. is being supplied.

[0327] In this way, the light-emitting device of one embodiment of the present invention can be used as a backlight of a liquid crystal display device. In addition, the light-emitting device of one embodiment of the present invention has a surface Since it is a light-emitting lighting device and can be made large, it is also possible to make the backlight large. Therefore, it is possible to obtain a liquid crystal display device with low power consumption and a large area.

[0328] Next, FIG. 9B shows a light-emitting device of one embodiment of the present invention used as a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9(B) has a housing 801 and a light source 802. The light-emitting device of one embodiment of the present invention is used as the light source 802. Since current efficiency can be obtained, low power consumption can be achieved by applying the light-emitting device of one embodiment of the present invention. It is possible to obtain a standing stand.

[0329] Next, FIG. 9C shows a case where the light-emitting device of one embodiment of the present invention is used as an indoor lighting device 901. The light-emitting device of one embodiment of the present invention can be made large in area, and therefore, a large-area lighting device Furthermore, the light-emitting device of one embodiment of the present invention can be driven at a low voltage and can be used as a light-emitting device having a high current density. Since current efficiency can be obtained, the application of the light-emitting device of one embodiment of the present invention can achieve lighting with low power consumption. In this way, the light-emitting device of one embodiment of the present invention can be used as an indoor lighting device. In the room used as the device 901, a television set according to one embodiment of the present invention as described with reference to FIG. 8(A) was installed. You can install unit 902 and watch public broadcasts and movies.

[0330] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0331] The organic compound (second compound) having a pyrimidine skeleton according to one embodiment of the present invention may be It can be used in organic thin-film solar cells. More specifically, because it has carrier transport properties, It can be used as a carrier transport layer or a carrier injection layer. It can be used as follows. [Example]

[0332] In this example, as one embodiment of the organic compound including a pyrimidine skeleton, which is the second compound, 4,6-bis[3-(phenanthrene-9-yl)phenanthren-9-yl] ... This paper describes a method for synthesizing 4,6mPnP2Pm.

[0333] [ka]

[0334] 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4, Synthesis of 6mPnP2Pm≫ 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4, The synthesis scheme of 6mPnP2Pm is shown in (C-1).

[0335] [ka]

[0336] In a 100 mL round-bottom flask, add 0.64 g (4.3 mmol) of 4,6-dichloropyrimidine. and 3.2 g (11 mmol) of 3-(phenanthren-9-yl)phenylboron Add the acid and 2.3 g (21 mmol) of sodium carbonate to the mixture and add 10 mL of acetone. Acetonitrile and 20 mL of water were added. The mixture was degassed by stirring under reduced pressure. To this mixture was added 30 mg (43 μmol) of bis(triphenylphosphine)palladium. This was heated in a microwave (2.45 GHz) under an argon atmosphere. The mixture was heated and stirred by irradiation with a 100W (100W) lamp for 1 hour and 30 minutes. 3.4 mmol) of 3-(9-phenanthryl)phenylboronic acid and 0.71 g (6.7 mmol) sodium carbonate, 28 mg (40 μmol) bis(triphenylphosphine Palladium (II) dichloride was added and the mixture was heated and stirred for another hour. Water was added to the mixture, and the organic layer was extracted with dichloromethane. The mixture was washed with an aqueous sodium chloride solution and saturated saline, and magnesium sulfate was added to adsorb moisture. This mixture was separated by gravity filtration, and the filtrate was concentrated to obtain a solid. The product was purified by column chromatography. The obtained fraction was concentrated to give a solid. Recrystallization using ethyl acetate yielded 4,6-bis[3-(phenanthrene-9-yl)phenyl]piperidin. 0.99 g of a white solid, limidine (abbreviation: 4,6mPnP2Pm), was obtained in a yield of 40%.

[0337] The obtained 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation The white solid (name: 4,6mPnP2Pm) was purified by train sublimation. The sublimation purification was carried out under the conditions of a pressure of 3.7 Pa and an argon flow rate of 5.0 mL / min. Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP 2Pm) was heated at 280°C for 14 hours. After purification by sublimation, 4,6-bis[3-(phenanthroline)] White solid of [(nanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm) The total mass was 0.80 g, with a recovery rate of 79%.

[0338] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(Phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm) It was confirmed that this is the case.

[0339] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.50-7.75(m,14H) ,7.87-7.91(m,4H),8.21-8.31(m,5H),8.73(d, J1=8.4Hz,2H),8.78(d,J1=8.4Hz,2H),9.36(d, J1=0.9Hz,1H).

[0340] Also, 1 The H NMR chart is shown in Figure 10. Note that Figure 10(B) is the same as Figure 10(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0341] Next, the 4,6-bis[3-(phenanthrene-9-yl)phenyl ]pyrimidine (abbreviation: 4,6mPnP2Pm) was analyzed by liquid chromatography mass spectrometry (LCMS). id Chromatography Mass Spectrometry, abbreviation: L The samples were analyzed by C / MS analysis.

[0342] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Dissolve 4,6mPnP2Pm (abbreviation) in toluene and dilute with acetonitrile. The injection volume was adjusted to 5.0 μL.

[0343] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0344] For MS analysis, electrospray ionization was used. Ionization was performed using electrospray ionization (ESI). The capillary voltage was 3.0 kV. The sample cone voltage was 30 V, and detection was performed in positive mode. The range was m / z = 100 to 1200.

[0345] The component m / z=584.23 separated and ionized under the above conditions was placed in the collision chamber. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0346] From the results of FIG. 97, 4,6mPnP2Pm (abbreviation), which is one embodiment of the present invention, is mainly Partial skeleton products around m / z=252, m / z=277, and m / z=541 The ion peak is near m / z=585 and the precursor ion peak is near m / z= It was found that a peak derived from a dimer ion was detected around 1169. The results shown in Figure 97 show the characteristic results derived from 4,6mPnP2Pm (abbreviation). Therefore, it is important to identify 4,6mPnP2Pm (abbreviation) contained in the mixture. This can be said to be important data.

[0347] The fragment around m / z=541 is 4,6mPnP2Pm (abbreviation) It is thought that this is a product ion generated by the cleavage of the pyrimidine ring. The product ion pattern is similar to that of the present invention, where the 4- and 6-positions of the pyrimidine ring are substituted. Therefore, this is one of the characteristics of the organic compound of one embodiment of the present invention. 6mPnP2Pm (abbreviation) contains a pyrimidine ring substituted at the 4- and 6-positions. This suggests that:

[0348] In addition, 4,6mPnP2Pm (abbreviation), which is one aspect of the present invention, is used as a time-of-flight secondary ion mass spectrometer. Time-of-Flight Secondary Ion Mass Spectrometer Qualitative spectra (positive and negative intensities) measured by ToF-SIMS On) are shown in Figures 98(A) to (D).

[0349] FIG. 98(A) shows the measurement results for positive ions, with the horizontal axis representing m / s in the range of 0 to 500. The vertical axis represents z, and the vertical axis represents intensity (arbitrary units). Also, Figure 98(B) shows the measurement results for positive ions. The horizontal axis represents the m / z range of 400 to 1200, and the vertical axis represents the intensity (arbitrary units). Also, Figure 98(C) shows the measurement results for negative ions, with the horizontal axis representing m in the range of 0 to 500. The vertical axis represents the intensity (arbitrary unit) of the ion beam. The horizontal axis represents the m / z range of 400 to 1200, and the vertical axis represents the intensity (arbitrary units). represent.

[0350] The equipment used was a TOF SIMS5 (manufactured by ION-TOF), and the primary ion source was Bi3 ++ The primary ions were irradiated in pulses with a pulse width of 7 to 12 nm, and the irradiation dose was 8.2×10 10 ~6.7×10 11 ions / cm 2 (1×10 12 ions / c m 2 The accelerating voltage was 25 keV and the current was 0.2 pA. Measurements were carried out using PnP2Pm (abbreviation) powder.

[0351] From the results of Figures 98(A) and (B), it is clear that 4,6mPnP2Pm (abbreviation ) mainly has partial skeleton product ions around m / z=252 and m / z=276. It was found that a peak was detected.

[0352] Furthermore, from the results of Figures 98(C) and (D), it is clear that the 4,6mPnP2Pm (abbreviation) is a peak of partial skeleton product ions mainly around m / z=571, The peaks derived from precursor ions are around m / z=585 and m / z=595, respectively. The results shown in Figure 98(C) and (D) indicate that 4,6mPnP Since it shows the characteristic results derived from 2Pm (abbreviation), it is This is important data for identifying 4,6mPnP2Pm (abbreviation).

[0353] The absorption spectrum of the toluene solution of 4,6mPnP2Pm (abbreviation) is shown in Figure 11(A). The emission spectrum is shown in Figure 11(B). The absorption spectrum of the thin film of ) is shown in Figure 12(A), and the emission spectrum is shown in Figure 12(B). The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation, V550 model). The solution was placed in a quartz cell, and the thin film was evaporated onto a quartz substrate to prepare the sample for measurement. The absorption spectrum was measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film is the absorption spectrum of the quartz substrate. 11 and 12, the horizontal axis represents the wavelength. The vertical axis represents the length (nm), and the vertical axis represents the intensity (arbitrary units). In the case of the toluene solution, An absorption peak is observed around 99 nm, and emission wavelength peaks are observed at 322 nm, 342, and 3 In the case of thin films, the wavelengths were around 206, 257, 304, and 353 nm. An absorption peak was observed at 406 nm, and the emission wavelength peak was 406 nm.

[0354] In addition, the glass transition temperature of 4,6mPnP2Pm (abbreviation) synthesized in this example is as follows: The results were obtained using a differential scanning calorimeter (DSC). The glass transition temperature of (abbreviation) was 126°C. It was found that the 4 ,6mPnP2Pm (abbreviation) does not have any peaks indicating crystallization, and is a substance that is difficult to crystallize. It was found that...

[0355] In addition, the electrochemical properties (thin film) of 4,6mPnP2Pm (abbreviation) were measured (measurement equipment (Product of Riken Keiki, AC-2). The electrochemical properties (thin film) were measured as follows: Ta.

[0356] The HOMO level was measured by photoelectron spectroscopy (Riken Keiki, AC-2) in air. The value of the ionization potential was obtained by converting it to a negative value. The value of the LUMO level was also obtained. is calculated by assuming direct transition using the absorption spectrum data of the thin films shown in the above examples. The absorption edge is calculated from the Tauc plot and used as the optical energy gap. It was obtained by adding it to the value of the HOMO level.

[0357] From the results of electrochemical characterization (thin film), the HOMO level of 4,6mPnP2Pm (abbreviation) The highest occupied molecular orbital level (LUMO level) is -5.95 eV, and the lowest unoccupied molecular orbital level (LUMO level) is - The surface area was 2.70 eV, and the band gap (Bg) was 3.25 eV.

[0358] From the above results, 4,6mPnP2Pm (abbreviation) has a relatively deep HOMO level and It was confirmed that the compound has a relatively shallow LUMO level and a relatively wide Bg. [Example]

[0359] In this example, 4,6-bis[3-(naphthalene-1, 2-diol]-1, 2-diol]-1, 2-diol, ... -yl)phenyl]-2-phenylpyrimidine (abbreviation: 2Ph-4,6mNP2Pm) The synthesis method will be described.

[0360] [ka]

[0361] <4,6-bis[3-(naphthalen-1-yl)phenyl]-2-phenylpyrimidine( Synthesis of 2Ph-4,6mNP2Pm (abbreviation: 2Ph-4,6mNP2Pm) 4,6-bis[3-(naphthalen-1-yl)phenyl]-2-phenylpyrimidine ( The synthesis scheme of 2Ph-4,6mNP2Pm (abbreviation: 2Ph-4,6mNP2Pm) is shown in (D-1).

[0362] [ka]

[0363] In a 100 mL three-neck flask, add 1.80 g (3.86 mmol) of 4,6-bis(3-bromo-2-methyl-2-methylpropional). (bromophenyl)-2-phenylpyrimidine and 4.50 g (9.65 mmol) of 1-naphthalene Phthaleneboronic acid and 117 mg (386 μmol) of tris(2-methylphenyl)boronic acid Add 10 mL of 2.0 M potassium carbonate solution and 15 mL of thiazolinone to the mixture. 5 mL of toluene and 5 mL of ethanol were added, and the mixture was degassed by stirring under reduced pressure. 17 mg (77.2 μmol) of palladium(II) acetate was added to the mixture, and the mixture was heated at 90 The mixture was stirred at ℃ for 8 hours. After stirring, the resulting mixture was filtered to recover the solid. The aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined and washed with saturated saline. Magnesium sulfate was added to adsorb the water. The mixture was separated by gravity filtration. The mixture was concentrated to obtain solids. Toluene was added to these solids, and the mixture was filtered through Celite (Wako Pure Chemical Industries, Ltd.). Co., Ltd., Catalog No.: 531-16855), alumina, Florisil (Wako Pure Chemical Industries, Ltd. The filtrate was concentrated to remove the solids. Got it. This solid was purified by silica gel column chromatography (eluent: hexane, then toluene The resulting solid was recrystallized using toluene to give a white solid. The compound was obtained in an amount of 1.84 g in a yield of 85%.

[0364] The resulting solid (1.66 g) was purified by train sublimation at a pressure of 2. The purification was carried out at 260°C under conditions of 9 Pa and an argon flow rate of 5 mL / min. 1.52 g of a white solid was obtained with a recovery rate of 92%.

[0365] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(naphthalen-1-yl)phenyl]-2-phenylpyrimidine (abbreviation: 2Ph-4, It was confirmed that the compound was 6mNP2Pm.

[0366] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.42-7.60(m,11H) ,7.65-7.72(m,4H),7.90-7.96(m,6H),8.10(s, 1H), 8.36-8.40(m, 4H), 8.69-8.73(m, 2H).

[0367] Also, 1 The H NMR chart is shown in Figure 13. Note that Figure 13(B) is the same as Figure 13(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0368] Next, the 4,6-bis[3-(naphthalen-1-yl)phenyl]- obtained in this example 2-Phenylpyrimidine (abbreviation: 2Ph-4,6mNP2Pm) was analyzed by liquid chromatography. The results were analyzed by quantitative analysis (LC / MS analysis).

[0369] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Dissolve 2Ph-4,6mNP2Pm (abbreviation) in toluene and dilute with acetonitrile. The injection volume was adjusted to 5.0 μL.

[0370] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0371] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0372] The component m / z=560.23 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0373] From the results of Figure 99, 2Ph-4,6mNP2Pm (abbreviation), which is one embodiment of the present invention, around m / z=202, around m / z=230, around m / z=253, and around m / z=441 The peak of the partial skeleton product ion is around m / z=561, and the peak of the precursor ion is around m / z=562. A peak due to the dimer ion was detected around m / z=1121. The results shown in Figure 99 were obtained from 2Ph-4,6mNP2Pm (abbreviation ) and therefore, the results are characteristic of the 2Ph-4, This is important data for identifying 6mNP2Pm (abbreviation).

[0374] The fragment around m / z=441 corresponds to 2Ph-4,6mNP2Pm (abbreviation). The pyrimidine ring in the hydroxyl group is cleaved (and the phenyl group at position 2 is lost at the same time). This product ion pattern is considered to be a pyrimidine product ion. One of the features of the organic compound according to one embodiment of the present invention is that the 4- and 6-positions of the ring are substituted. Therefore, 2Ph-4,6mNP2Pm (abbreviation), which is one embodiment of the present invention, has This suggests that the compound contains a pyrimidine ring substituted at the 1st and 6th positions.

[0375] The absorption spectrum of the toluene solution of 2Ph-4,6mNP2Pm (abbreviation) is shown in Figure 14. The emission spectrum is shown in Figure 14(A) and the emission spectrum is shown in Figure 14(B). The absorption spectrum of the thin film of 2Pm (abbreviation) is shown in Figure 15(A), and the emission spectrum is shown in Figure 15(B). The absorption spectra were measured using an ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. The absorption spectrum was measured by placing a solution of toluene in a quartz cell. The absorption spectrum is the absorption spectrum measured with the filter subtracted from the absorption spectrum measured with the filter. The absorption spectrum is shown after subtracting the absorption spectrum of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 82 nm, and the emission wavelength peak was 361 nm. In the case of thin films, absorption peaks were observed around 228, 266, 279, 316, and 357 nm. The peak emission wavelength was 393 nm. [Example]

[0376] In this example, 4,6-bis[3-(triphenylene)] represented by the following structural formula (314) was used. Synthetic method for [4,6m-2-yl]phenylpyrimidine (abbreviation: 4,6mTpP2Pm) explain.

[0377] [ka]

[0378] <4,6-bis[3-(triphenylen-2-yl)phenyl]pyrimidine (abbreviation: 4, Synthesis of 6mTpP2Pm) 4,6-bis[3-(triphenylen-2-yl)phenyl]pyrimidine (abbreviation: 4, The synthesis scheme of 6mTpP2Pm is shown in (E-1).

[0379] [ka]

[0380] In a 100 mL round-bottom flask, add 0.65 g (4.38 mmol) of 4,6-dichloropyridine. 3.83 g (11.0 mmol) of 3-(triphenylen-2-yl)phenyl Add 2.33 g (22.0 mmol) of boronic acid and sodium carbonate to the mixture. 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidino DMPU and 10 mL of water were added. The mixture was stirred under reduced pressure. The mixture was degassed with 41 mg (52.6 μmol) of bis(triphenylphosphine) (vinyl)palladium (II) dichloride was added and the atmosphere was replaced with argon. The specimen was heated by irradiating it with microwaves (2.45 GHz, 100 W) under an argon atmosphere for 1 hour and 30 minutes. After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The obtained solid was dissolved in ethanol. Toluene was added to the solid, and the solid was filtered through Celite (Wako Pure Chemical Industries, Ltd., catalog number :531-16855), alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog no. The mixture was filtered through a filter (Product No.: 540-00135) under reduced pressure, and the filtrate was concentrated to give a white solid. The product was purified by silica gel column chromatography (developing solvent: toluene, then toluene:acetic acid The resulting solid was recrystallized using toluene to give a white solid. was obtained in 1.12 g, 37% yield.

[0381] The resulting solid (0.88 g) was purified by train sublimation at a pressure of 2. The purification was carried out at 370°C under conditions of 8 Pa and an argon flow rate of 5 mL / min. 0.71 g of a pale yellow solid was obtained with a recovery rate of 81%.

[0382] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(Triphenylen-2-yl)phenyl]pyrimidine (abbreviation: 4,6mTpP2Pm) It was confirmed that this is the case.

[0383] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.66-7.76(m,10H) ,7.98-8.02(m,4H),8.23(d,J1=7.8Hz,2H),8.3 4(s,1H),8.62-8.81(m,12H),8.95(s,2H),9.46 (s,1H).

[0384] Also, 1 The H NMR chart is shown in Figure 16. Note that Figure 16(B) is the same as Figure 16(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0385] Next, the 4,6-bis[3-(triphenylen-2-yl)phenyl] obtained in this example ]pyrimidine (abbreviation: 4,6mTpP2Pm) was analyzed by liquid chromatography mass spectrometry (LC / MS) The results were analyzed using the S analysis.

[0386] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Dissolve 4,6mTpP2Pm (abbreviation) at a concentration of chloroform and dilute with acetonitrile. The injection volume was adjusted to 5.0 μL.

[0387] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0388] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0389] The component m / z=684.26 separated and ionized under the above conditions was placed in the collision chamber. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0390] From the results of FIG. 100, it can be seen that 4,6mTpP2Pm (abbreviation), which is one embodiment of the present invention, is mainly The peaks of partial skeleton product ions are around m / z=327 and m / z=641. It was found that precursor ions were detected around m / z=685. The results shown in Figure 100 show the characteristic results derived from 4,6mTpP2Pm (abbreviation). Therefore, it is important to identify 4,6mTpP2Pm (abbreviation) contained in the mixture. This can be said to be important data.

[0391] The product ion around m / z=641 is 4,6mTpP2Pm (abbreviation). This is thought to be a product ion generated by the cleavage of the pyrimidine ring in Such product ion patterns are due to the substitution of the 4th and 6th positions of the pyrimidine ring. This is one of the characteristics of the organic compound according to one aspect of the present invention. 4,6mTpP2Pm (abbreviation) contains a pyrimidine ring substituted at the 4th and 6th positions. This suggests that

[0392] The absorption spectrum of the toluene solution of 4,6mTpP2Pm (abbreviation) is shown in Figure 17(A). The emission spectrum is shown in Figure 17(B). The absorption spectrum of the thin film of ) is shown in Figure 18(A), and the emission spectrum is shown in Figure 18(B). The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation, V550 model). The solution was placed in a quartz cell, and the thin film was evaporated onto a quartz substrate to prepare the sample for measurement. The absorption spectrum was measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film is the absorption spectrum of the quartz substrate. 17 and 18, the horizontal axis represents the wavelength. The vertical axis represents the length (nm), and the vertical axis represents the intensity (arbitrary units). In the case of a toluene solution, the wavelength is around 281 nm. The absorption peak was observed at 363 nm, and the emission wavelength peak was 363 nm. The absorption peaks are observed around 271 and 320 nm, and the emission wavelength peak is at 423 nm. there were. [Example]

[0393] In this example, 4,6-bis[3-(dibenzothiophene)] represented by the following structural formula (400) was used. Synthesis of 4,6m(phenyl-4-yl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II) The method will be explained.

[0394] [ka]

[0395] 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: Synthesis of 4,6mDBTP2Pm-II) 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: The synthesis scheme of 4,6mDBTP2Pm-II) is shown in (F-1).

[0396] [ka]

[0397] In a 100 mL recovery flask, add 1.0 g (6.7 mmol) of 4,6-dichloropyrimidinium chloride. and 5.1 g (17 mmol) of 3-(dibenzothiophen-4-yl)-phenylboronic acid. uronic acid, 3.5 g (34 mmol) sodium carbonate, and 20 mL of 1,3-dimethyl- 3,4,5,6-tetrahydro-2(1H)-pyrimidinone (abbreviation: DMPU) and 10 5 mL of water was added. The mixture was degassed by stirring under reduced pressure. 6 mg (81 μmol) of bis(triphenylphosphine)palladium(II) dichloride The reaction vessel was then purged with argon gas. The mixture was heated and stirred by irradiating with 1.5 hours of heat. After heating, water was added to the mixture. The residue was obtained by filtration, and the obtained solid was washed with dichloromethane and ethanol. Toluene was added to the solid, and the solid was filtered through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-16 855), alumina, Florisil (Wako Pure Chemical Industries, Ltd., Catalog No.: 540-0 The resulting mixture was filtered through a filter (0135) with suction, and the filtrate was concentrated to give a solid. The mixture was recrystallized using HCl to give 2.52 g of a white solid in a yield of 63%.

[0398] The resulting solid (2.50 g) was purified by train sublimation at a pressure of 3. The purification was carried out at 300°C under conditions of 6 Pa and an argon flow rate of 5 mL / min. 1.98 g of a white solid was obtained with a recovery rate of 79%.

[0399] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(Dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2 It was confirmed that the ion was Pm-II.

[0400] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.41-7.51(m,4H), 7.58-7.62(m,4H),7.68-7.79(m,4H),8.73(dt, J1=8.4Hz,J2=0.9Hz,2H),8.18-8.27(m,7H),8. 54(t,J1=1.5Hz,2H),9.39(d,J1=0.9Hz,1H).

[0401] Also, 1 The H NMR chart is shown in Figure 19. Note that Figure 19(B) is the same as Figure 19(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0402] Next, the 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]phenyl ether obtained in this example was 4,6mDBTP2Pm-II was analyzed by liquid chromatography. The product was analyzed by LC / MS analysis.

[0403] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. 4,6mDBTP2Pm-II (abbreviation) of a concentration of The injection volume was adjusted to 5.0 μL.

[0404] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0405] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0406] The component m / z=596.14 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0407] From the results of Figure 101, 4,6mDBTP2Pm-II (abbreviation), which is one embodiment of the present invention, , mainly around m / z=252, around m / z=258, around m / z=284, and around m / z=3 The peaks of partial skeleton product ions are around m / z=59 and m / z=553. The peak at m / z=7 is derived from the precursor ion, and the peak at m / z=1193 is derived from the dimer ion. The results shown in Figure 101 show that the peaks 4 and 6 are detected. Since this shows the characteristic results derived from mDBTP2Pm-II (abbreviation), Important data for identifying 4,6mDBTP2Pm-II (abbreviation) contained in the compound It can be said that this is the case.

[0408] The product ion at m / z=553 is 4,6mDBTP2Pm-II (abbreviated It is thought to be a fragment generated by cleavage of the pyrimidine ring in The product ion pattern shown above is due to substitution at the 4th and 6th positions of the pyrimidine ring. This is one of the characteristics of the organic compound according to one embodiment of the present invention. 4,6mDBTP2Pm-II (abbreviation) is a pyrimidine substituted at the 4th and 6th positions. This suggests that it contains a ring.

[0409] In addition, 4,6mDBTP2Pm-II (abbreviation), which is one embodiment of the present invention, was used as a time-of-flight secondary electron microscope. Qualitative spectra (positive and negative ions) measured by a time-of-flight (ToF)-SIMS mass spectrometer were Shown in Figures 102(A) to (D).

[0410] Note that Figure 102(A) shows the measurement results for positive ions, and the horizontal axis is m in the range of 0 to 500. The vertical axis represents the intensity (arbitrary unit) of the ion beam. The horizontal axis represents m / z in the range of 400 to 1200, and the vertical axis represents intensity (arbitrary units). Also, FIG. 102(C) shows the measurement results for negative ions, with the horizontal axis ranging from 0 to 500. The vertical axis represents the m / z range, and the vertical axis represents the intensity (arbitrary unit). The horizontal axis represents the m / z range of 400 to 1200, and the vertical axis represents the intensity (arbitrary Units).

[0411] The equipment used was a TOF SIMS5 (manufactured by ION-TOF), and the primary ion source was Bi3 ++ The primary ions were irradiated in pulses with a pulse width of 7 to 12 nm, and the irradiation dose was 8.2×10 10 ~6.7×10 11 ions / cm 2 (1×10 12 ions / c m 2 The accelerating voltage was 25 keV and the current was 0.2 pA. Measurements were carried out using DBTP2Pm-II (abbreviation) powder.

[0412] From the results of Figures 102(A) and (B), it is clear that 4,6mDBTP2Pm- II (abbreviation) is mainly around m / z=184, m / z=258, and m / z=271. Near m / z=284, near m / z=296, near m / z=309, and m / z=59 It was found that peaks of partial skeleton product ions were detected around 7.

[0413] Furthermore, from the results of Figures 102(C) and (D), it is clear that 4,6mDBTP2, which is one embodiment of the present invention, Pm-II (abbreviation) has peaks of partial skeleton product ions mainly around m / z=583. The peaks are located near m / z=597, m / z=607, and m / z=627. It was found that peaks derived from the ion were detected. The results shown in (D) are characteristic results derived from 4,6mDBTP2Pm-II (abbreviation). Since this indicates that 4,6mDBTP2Pm-II (abbreviation) is contained in the mixture, This data is important for identifying the

[0414] Furthermore, 4,6mDBTP2Pm-II (abbreviation), which is one embodiment of the present invention, was analyzed by GC / MS. Extractor (Thermo Fisher, ITQ1100 ion trap GC / MS) n of The measurement was performed using a direct sample introduction system (DEP). The mode was EI+, and the ionization voltage was 7 The voltage was set to 0 eV, the emission current was set to 250 μA, and the electron lens was set to 15 V. The sample temperature was set at a heating rate of 10°C / sec. The temperature was raised to ° C. From the measurement results, it was found that 4,6mDBTP2Pm- II (abbreviation) (m / z=596.14) is mainly around m / z=184 and m / z=28 Around 2, around m / z=298, around m / z=310, around m / z=552, m / z=56 The peak of the partial skeleton product ion is around m / z=8, and the peak of the precursor ion is around m / z=596. It was found that peaks derived from 4, Since this shows the characteristic results derived from 6mDBTP2Pm-II (abbreviation), Important data for identifying 4,6mDBTP2Pm-II (abbreviation) contained in the mixture It can be said that it is a

[0415] The product ion around m / z=184 is 4,6mDBTP2Pm-II (abbreviated It is thought to be a fragment derived from dibenzothiophene in the product (named The pattern of the photo-ion is obtained by analyzing the organic compound having a dibenzothiophene skeleton, which is one embodiment of the present invention. Therefore, 4,6mDBTP2Pm-I, which is one aspect of the present invention, This suggests that I (abbreviation) contains a dibenzothiophene skeleton.

[0416] The product ions around m / z=552 and m / z=568 are 4,6mDB Fragmentation of the pyrimidine ring in TP2Pm-II (abbreviation) This product ion pattern is thought to be due to the 4- and 5-positions of the pyrimidine ring. This is one of the characteristics of the heterocyclic compound according to one embodiment of the present invention, in which the 1- and 6-positions are substituted. Therefore, 4,6mDBTP2Pm-II (abbreviation), which is one embodiment of the present invention, has 4- and 6-positions. This suggests that the compound contains a substituted pyrimidine ring.

[0417] The absorption spectrum of the toluene solution of 4,6mDBTP2Pm-II (abbreviation) is shown in Figure 2. The emission spectrum is shown in Figure 20(A) and the emission spectrum is shown in Figure 20(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 21(A), and the emission spectrum is shown in Figure 21 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. The absorption spectrum is shown after subtracting the absorption spectrum of the quartz substrate.

[0418] In Figures 20 and 21, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). In the case of the toluene solution, an absorption peak is observed around 282 nm, and the emission wavelength peak is around 3 In the case of thin films, the values ​​were 244, 265, 290, 317, and 334 nm. An absorption peak was observed around 100 nm, and the emission wavelength peak was 396 nm. [Example]

[0419] In this example, 2,4-bis[3-(dibenzothiophene)] represented by the following structural formula (401) was used. Synthesis of 2,4m(phenyl-4-yl)pyrimidine (abbreviation: 2,4mDBTP2Pm-II) The method will be explained.

[0420] [ka]

[0421] 2,4-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: Synthesis of 2,4mDBTP2Pm-II) 2,4-Bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: The synthesis scheme of 2,4mDBTP2Pm-II) is shown in (G-1).

[0422] [ka]

[0423] In a 100 mL recovery flask, add 0.75 g (5.03 mmol) of 2,4-dichloropyrrolidone. 3.82 g (12.6 mmol) of 3-(dibenzothiophen-4-yl) fluoride Add phenylboronic acid and 2.67 g (25.2 mmol) of sodium carbonate to this mixture. 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone Dimethyl methyl methacrylate (DMPU) and 10 mL of water were added. The mixture was stirred under reduced pressure. To this mixture, 42 mg (60.3 μmol) of bis(triphenylphosphine) was added. Sphine)palladium(II) dichloride was added and the atmosphere was replaced with argon. The specimen was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 55 minutes under an argon atmosphere. After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The obtained solid was dissolved in ethanol and distilled water. The solid was washed with chloromethane, and toluene was added to the solid. , Catalog number: 531-16855), alumina, Florisil (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (Chemical Engineering Co., Ltd., Catalog No. 540-00135) under reduced pressure, and the filtrate was concentrated to give a white solid. This solid was purified by silica gel column chromatography (developing solvent: toluene). The obtained solid was recrystallized using toluene to give 1.87 g of a white solid in a yield of 62%. I got it.

[0424] The resulting solid (1.80 g) was purified by train sublimation at a pressure of 5. The purification was carried out by heating at 300°C under conditions of 1 Pa and an argon flow rate of 10 mL / min. After that, 1.98 g of a white solid was obtained with a recovery rate of 68%.

[0425] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 2,4-bis[3 -(Dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 2,4mDBTP2 It was confirmed that the ion was Pm-II.

[0426] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.39-7.76(m,13H) ,7.90(dt,J1=7.8Hz,J2=1.5Hz,2H),8.13-8.20 (m,4H),8.32(dt,J1=8.1Hz,J2=1.5Hz,1H),8.6 8(dt,J1=7.8Hz,J2=1.5Hz,1H),8.72(t,J1=1.5 Hz,1H),8.92(d,J1=5.4Hz,1H),9.07(t,J1=1.5 Hz,1H).

[0427] Also, 1 The H NMR chart is shown in Figure 22. Note that Figure 22(B) is the same as Figure 22(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0428] The absorption spectrum of the toluene solution of 2,4mDBTP2Pm-II (abbreviation) is shown in Figure 2. 3(A) and the emission spectrum is shown in Figure 23(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 24(A), and the emission spectrum is shown in Figure 24 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. The absorption spectrum is shown after subtracting the absorption spectrum of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 283 nm, and the emission wavelength peak was 356 nm. In the case of thin films, absorption peaks are observed around 244, 226, 287, 318, and 335 nm. was observed, and the peak emission wavelength was 385 nm. [Example]

[0429] In this example, 2,5-bis[3-(dibenzothiophene)] represented by the following structural formula (402) was used. Synthesis of 2,5m(phenyl-4-yl)pyrimidine (abbreviation: 2,5mDBTP2Pm-II) The method will be explained.

[0430] [ka]

[0431] 2,5-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: Synthesis of 2,5mDBTP2Pm-II) 2,5-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: The synthesis scheme of 2,5mDBTP2Pm-II) is shown in (H-1).

[0432] [ka]

[0433] In a 100 mL recovery flask, add 0.97 g (5.03 mmol) of 5-bromo-2-chloro 3.82 g (12.6 mmol) of 3-(dibenzothiophene-4-yl)pyrimidine (I) phenylboronic acid and 2.67 g (25.2 mmol) of sodium carbonate were added to this To the mixture, 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)- Pyrimidinone (abbreviated as DMPU) and 10 mL of water were added. The mixture was degassed by stirring. 42 mg (60.3 μmol) of bis(triphenylphosphine) (Nylphosphine)palladium(II) dichloride was added and the reaction mixture was purged with argon. The vessel was irradiated with microwaves (2.45 GHz, 100 W) under an argon atmosphere for 1 hour and 30 minutes. After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The solid was washed with ethanol and dichloromethane. Toluene was added to the solid, and the solid was filtered through Celite (Wako Pure Chemical Industries, Ltd.). Industrial Co., Ltd., Catalog No.: 531-16855), Alumina, Florisil (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (Yaku Kogyo Co., Ltd., Catalog No.: 540-00135) and the filtrate was concentrated. This solid was purified by silica gel column chromatography (eluent: toluene). The resulting solid was recrystallized using toluene to give 1.87 g of a white solid. , was obtained in a yield of 62%.

[0434] The resulting solid (1.81 g) was purified by train sublimation at a pressure of 5. The purification was carried out by heating at 335°C under conditions of 1 Pa and an argon flow rate of 10 mL / min. After that, 1.52 g of a white solid was obtained with a recovery rate of 84%.

[0435] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 2,5-bis[3 -(Dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 2,5mDBTP2 It was confirmed that the ion was Pm-II.

[0436] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.46-7.51(m,4H), 7.55-7.75(m,7H),7.82-7.88(m,3H),7.92(dt, J1=7.8Hz,J2=1.5Hz,1H),8.09(t,J1=1.5Hz,1H) ),8.18-8.23(m,4H),8.60(dt,J1=8.4Hz,J2=1. 5Hz, 1H), 8.92 (t, J1=1.8Hz, 1H), 9.17 (s, 2H).

[0437] Also, 1 The H NMR chart is shown in Figure 25. Note that Figure 25(B) is the same as Figure 25(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0438] Next, the 2,5-bis[3-(dibenzothiophen-4-yl)phenyl]phenyl ether obtained in this example was 2,5mDBTP2Pm-II) was analyzed by liquid chromatography. The product was analyzed by LC / MS analysis.

[0439] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Dissolve 2.5mDBTP2Pm-II (abbreviation) in chloroform and add acetonitrile. The injection volume was adjusted to 5.0 μL.

[0440] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0441] For MS analysis, electrospray ionization was used. Ionization was performed using electrospray ionization (ESI). The capillary voltage was 3.0 kV. The sample cone voltage was 30 V, and detection was performed in positive mode. The range was m / z = 100 to 1200.

[0442] The component m / z=596.14 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0443] From the results of Figure 103, 2,5mDBTP2Pm-II (abbreviation), which is one embodiment of the present invention, , and peaks of partial skeleton product ions mainly appear around m / z=271 and m / z=284. The peak originating from the precursor ion is around m / z=597, and the peak originating from the precursor ion is around m / z=1193. It was found that peaks derived from dimer ions were detected near the peaks. The results shown in Fig. 1 are characteristic results derived from 2,5mDBTP2Pm-II (abbreviation). Therefore, 2,5mDBTP2Pm-II (abbreviation) contained in the mixture was identified. This is important data for the future.

[0444] The absorption spectrum of the toluene solution of 2,5mDBTP2Pm-II (abbreviation) is shown in Figure 2. 6(A) and the emission spectrum is shown in Figure 26(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 27(A), and the emission spectrum is shown in Figure 27 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. In Figures 26 and 27, the absorption spectrum is subtracted from that of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 287 nm, and the emission wavelength peak was 353 nm. In the case of thin films, absorption peaks are observed around 244, 268, 289, 326, and 334 nm. was observed, and the peak emission wavelength was 391 nm. [Example]

[0445] In this example, 4,6-bis[3-(2,8-diphenyl)-2-methyl-2-propanol] represented by the following structural formula (412) was used. 4,6m-dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP The synthesis method of 2Pm-III) will be explained.

[0446] [ka]

[0447] <4,6-bis[3-(2,8-diphenyl-dibenzothiophen-4-yl)phenyl]phenyl ]Synthesis of pyrimidine (abbreviation: 4,6mDBTP2Pm-III)> 4,6-bis[3-(2,8-diphenyl-dibenzothiophen-4-yl)phenyl] The synthesis scheme of pyrimidine (abbreviation: 4,6mDBTP2Pm-III) is shown in (I-1). show.

[0448] [ka]

[0449] In a 100 mL round-bottom flask, add 0.50 g (3.33 mmol) of 4,6-dichloropyridine. 3.80 g (8.33 mmol) of 3-(2,8-diphenyl-dibenzothiophene) (phen-4-yl)phenylboronic acid and 1.77 g (16.7 mmol) of sodium carbonate Add 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydrofuran to the mixture. DMPU and 10 mL of water were added to this mixture. The mixture was degassed by stirring under reduced pressure. Bis(triphenylphosphine)palladium(II) dichloride was added and the mixture was purged with argon. The reaction vessel was heated with microwaves (2.45 GHz, 100 W) under an argon atmosphere for 1 hour. After heating, water was added to the mixture, which was then filtered to obtain a residue. The solid was washed with ethanol and dichloromethane. Toluene was added to the solid, and the ceramic Ito (Wako Pure Chemical Industries, Ltd., Catalog No.: 531-16855), alumina, fluorine Suction filtration through Zeal (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135) The filtrate was concentrated to give a white solid. This solid was purified by silica gel column chromatography ( The resulting solid was recrystallized using toluene to give a white solid. The compound was obtained in an amount of 1.74 g in a yield of 58%.

[0450] The resulting solid (1.19 g) was purified by train sublimation at a pressure of 2. The purification was carried out at 380°C under conditions of 5 Pa and an argon flow rate of 5 mL / min. 1.04 g of a white solid was obtained with a recovery rate of 87%.

[0451] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(2,8-diphenyl-dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviated :4,6mDBTP2Pm-III).

[0452] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.37-7.42(m,4H), 7.50(t,J1=7.5Hz,8H),7.65-7.83(m,16H),7.9 7(dt,J1=7.8Hz,J1=1.5Hz,2H),8.29-8.33(m,3 H),8.43(t,J1=1.5Hz,4H),8.62(t,J1=1.5Hz,2 H), 9.41 (d, J1 = 1.2 Hz, 1 H).

[0453] Also, 1 The H NMR chart is shown in Figure 28. Note that Figure 28(B) is the same as Figure 28(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0454] Next, the 4,6-bis[3-(2,8-diphenyl-dibenzothiophene] (4,6m-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-III) The compounds were analyzed by liquid chromatography-mass spectrometry (LC / MS).

[0455] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. 4,6mDBTP2Pm-III (abbreviation) of a concentration of The injection volume was adjusted to 5.0 μL by dilution with ethanol.

[0456] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0457] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0458] The component m / z=900.26 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0459] From the results of Figure 104, 4,6mDBTP2Pm-III (abbreviation), which is one embodiment of the present invention, The partial skeletons are mainly located around m / z=421, m / z=437, and m / z=857. The product ion peak of m / z=901 is accompanied by a precursor ion peak. It was found that each of the following was detected. Since this shows the characteristic results derived from P2Pm-III (abbreviation), This is important data for identifying 4,6mDBTP2Pm-III (abbreviation) contained in It can be said that.

[0460] The product ion around m / z=857 is 4,6mDBTP2Pm-III( It is thought to be a product ion generated by the cleavage of the pyrimidine ring in However, such a product ion pattern is due to substitution at the 4th and 6th positions of the pyrimidine ring. This is one of the characteristics of the organic compound according to one embodiment of the present invention. The embodiment, 4,6mDBTP2Pm-III (abbreviation), is a peptide having substitutions at the 4th and 6th positions. This suggests that it contains a lysine ring.

[0461] In addition, the absorption spectrum of 4,6mDBTP2Pm-III (abbreviation) in toluene is shown in Fig. 29(A) and the emission spectrum are shown in Figure 29(B). The absorption spectrum of the thin film of 2Pm-III (abbreviation) is shown in Figure 30(A), and the emission spectrum is shown in Figure 30(B). The absorption spectra were measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell. The absorption spectrum measured by adding only fluorine is subtracted from the absorption spectrum measured by adding only fluorine. The absorption spectrum is shown after subtracting the absorption spectrum of the quartz substrate. In 30, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). In this case, an absorption peak was observed around 292 nm, and the emission wavelength peak was 372 nm. In addition, in the case of thin films, absorption peaks are observed around 264, 301, and 354 nm. The peak light wavelength was 402 nm. [Example]

[0462] In this example, 4,6-bis[3-(dibenzofuran)] represented by the following structural formula (430) was used. Method for synthesizing 4,6m-(4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBFP2Pm-II) This article explains:

[0463] [ka]

[0464] <4,6-bis[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 4, Synthesis of 6mDBFP2Pm-II) 4,6-bis[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 4, The synthesis scheme of 6mDBFP2Pm-II) is shown in (J-1).

[0465] [ka]

[0466] In a 100 mL recovery flask, add 0.79 g (5.31 mmol) of 4,6-dichloropyrrolidone. 3.82 g (13.3 mmol) of 3-(dibenzofuran-4-yl)-phenyl Add 2.82 g (26.6 mmol) of sodium carbonate and add the mixture. , 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone Add DMPU and 10 mL of water. Stir the mixture under reduced pressure. To this mixture, 45 mg (63.7 μmol) of bis(triphenylphosphine) was added. (Phth)palladium(II) dichloride was added and the atmosphere was replaced with argon. Heating by irradiating with microwaves (2.45GHz 100W) under argon gas flow for 1 hour and 30 minutes After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The obtained solid was dissolved in ethanol. The solid was washed with dichloromethane and toluene was added, and the solid was filtered through Celite (Wako Pure Chemical Industries, Ltd.). Company, Catalog Number: 531-16855), Alumina, Florisil (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (manufactured by the Company, Catalog No. 540-00135) and the filtrate was concentrated to a white This solid was purified by silica gel column chromatography (developing solvent: toluene). The resulting solid was recrystallized using toluene to give 1.56 g of a white solid in a yield of 5%. Got it at 2%.

[0467] The resulting solid (1.51 g) was purified by train sublimation at a pressure of 3. The purification was carried out at 280°C under conditions of 5 Pa and an argon flow rate of 5 mL / min. 1.23 g of a white solid was obtained with a recovery rate of 81%.

[0468] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 4,6-bis[3 -(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBFP2Pm -II).

[0469] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.34-7.50(m,6H), 7.57(d,J1=8.4Hz,2H),7.73(t,J1=7.8Hz,4H), 7.98-8.01(m,4H),8.11(d,J1=7.8Hz,2H),8.26 (d,J1=7.8Hz,2H),8.33(d,J1=0.9Hz,1H),8.69 (t,J1=1.5Hz,2H),9.41(s,1H).

[0470] Also, 1 The H NMR chart is shown in Figure 31. Note that Figure 31(B) is the same as Figure 31(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0471] Next, the 4,6-bis[3-(dibenzofuran-4-yl)phenyl ]pyrimidine (abbreviation: 4,6mDBFP2Pm-II) was analyzed by liquid chromatography mass spectrometry ( The analysis was carried out by LC / MS.

[0472] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. 4,6mDBFP2Pm-II (abbreviation) with a concentration of The injection volume was adjusted to 5.0 μL.

[0473] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0474] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0475] The component m / z=564.18 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0476] From the results of Figure 105, 4,6mDBFP2Pm-II (abbreviation), which is one embodiment of the present invention, , mainly around m / z=215, around m / z=239, around m / z=270, and m / z=5 The peak of the partial skeleton product ion is around m / z=21, and the peak of the precursor is around m / z=565. A peak due to the ion is located at m / z=1129, and a peak due to the dimer ion is located at m / z=1129. The results shown in Figure 105 are for 4,6mDBFP2Pm-I Since this shows the characteristic results derived from I (abbreviation), 4, This is important data for identifying 6mDBFP2Pm-II (abbreviation).

[0477] The product ion at m / z=521 is 4,6mDBFP2Pm-II (abbreviated It is thought to be a product ion generated by the cleavage of the pyrimidine ring in Such a product ion pattern is due to substitution at the 4th and 6th positions of the pyrimidine ring. This is one of the characteristics of the organic compound according to one embodiment of the present invention. The 4,6mDBFP2Pm-II (abbreviation) is a pyrimidine derivative substituted at the 4th and 6th positions. This suggests that it contains an azido ring.

[0478] The absorption spectrum of the toluene solution of 4,6mDBFP2Pm-II (abbreviation) is shown in Figure 3. 2(A) and the emission spectrum is shown in Figure 32(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 33(A), and the emission spectrum is shown in Figure 33 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. The absorption spectrum is shown after subtracting the absorption spectrum of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 289 nm, and the emission wavelength peak was 383 nm. In the case of thin films, absorption peaks are observed around 206, 248, 290, 303, and 315 nm. was observed, and the peak emission wavelength was 383 nm. [Example]

[0479] In this example, 2,4-bis[3-(dibenzofuran)] represented by the following structural formula (431) was used. Method for synthesizing 2,4mDBFP2Pm-II (2,4m-4-yl)phenylpyrimidine This article explains:

[0480] [ka]

[0481] <2,4-bis[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2, Synthesis of 4mDBFP2Pm-II) 2,4-bis[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2, The synthesis scheme of 4mDBFP2Pm-II) is shown in (K-1).

[0482] [ka]

[0483] In a 100 mL recovery flask, add 0.79 g (5.31 mmol) of 2,4-dichloropyrrolidone. 3.82 g (13.3 mmol) of 3-(dibenzofuran-4-yl)-phenyl Add 2.82 g (26.6 mmol) of sodium carbonate and add the mixture. , 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone Add DMPU and 10 mL of water. Stir the mixture under reduced pressure. To this mixture, 45 mg (63.7 μmol) of bis(triphenylphosphine) was added. (Phth)palladium(II) dichloride was added and the atmosphere was replaced with argon. The sample was heated by irradiating it with microwaves (2.45 GHz, 100 W) under an argon atmosphere for 1 hour. After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The obtained solid was dissolved in ethanol and distilled water. The solid was washed with chloromethane, and toluene was added to the solid. , Catalog number: 531-16855), alumina, Florisil (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (Chemical Engineering Co., Ltd., Catalog No. 540-00135) under reduced pressure, and the filtrate was concentrated to give a white solid. This solid was purified by silica gel column chromatography (developing solvent: toluene). The obtained solid was recrystallized using toluene to give 1.89 g of a white solid in a yield of 63%. I got it.

[0484] The resulting solid (1.93 g) was purified by train sublimation at a pressure of 3. The purification was carried out at 270°C under conditions of 3 Pa and an argon flow rate of 5 mL / min. 1.43 g of a white solid was obtained with a recovery rate of 74%.

[0485] Nuclear magnetic resonance method ( 1 H NMR) confirmed that this compound was the target compound, 2,4-bis[3 -(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2,4mDBFP2Pm -II).

[0486] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.31-7.45(m,6H), 7.54-7.57(m,2H),7.68-7.77(m,5H),7.92-8.0 0(m,4H),8.07-8.13(m,2H),8.33(dt,J1=7.8Hz ,J2=1.2Hz,1H),8.70(dt,J1=8.1Hz,J2=1.5Hz, 1H),8.89(t,J1=1.5Hz,1H),8.93(d,J1=5.4Hz, 1H), 9.22(t,J1=1.5Hz,1H).

[0487] Also, 1 The H NMR chart is shown in Figure 34. Note that Figure 34(B) is the same as Figure 34(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0488] Next, the 2,4-bis[3-(dibenzofuran-4-yl)phenyl ]pyrimidine (abbreviation: 2,4mDBFP2Pm-II) was analyzed by liquid chromatography mass spectrometry ( The analysis was carried out by LC / MS.

[0489] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. 2,4mDBFP2Pm-II (abbreviation) with a concentration of The injection volume was adjusted to 5.0 μL.

[0490] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 40:60 until 10 minutes. After that, the ratio was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. was changed linearly.

[0491] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0492] The component m / z=564.18 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0493] From the results of FIG. 106, 2,4mDBFP2Pm-II (abbreviation), which is one embodiment of the present invention, , and peaks of partial skeleton product ions mainly appear around m / z=239 and m / z=268. The peak originating from the precursor ion is around m / z=565, and the peak originating from the precursor ion is around m / z=1129. It was found that peaks derived from dimer ions were detected near the peaks. The results shown in Fig. 1 are characteristic results derived from 2,4mDBFP2Pm-II (abbreviation). Therefore, 2,4mDBFP2Pm-II (abbreviation) contained in the mixture was identified. This is important data for the future.

[0494] The absorption spectrum of 2,4mDBFP2Pm-II (abbreviation) in toluene is shown in Figure 3. 5(A) and the emission spectrum is shown in Figure 35(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 36(A), and the emission spectrum is shown in Figure 36 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. In the figures, the absorption spectrum is subtracted from the absorption spectrum of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 283 nm, and the emission wavelength peak was 413 nm. In the case of the thin film, an absorption peak is observed around 316 nm, and the emission wavelength peak is around 387 nm. It was m. [Example]

[0495] In this example, 2,5-[3-(dibenzofuran-4-yl)-4-(4-methyl ... -yl)phenyl]pyrimidine (abbreviation: 2,5mDBFP2Pm-II) and explain.

[0496] [ka]

[0497] <2,5-[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2,5m Synthesis of DBFP2Pm-II) 2,5-[3-(dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2,5m The synthesis scheme of DBFP2Pm-II) is shown in (L-1).

[0498] [ka]

[0499] In a 100 mL recovery flask, add 1.03 g (5.31 mmol) of 5-bromo-2-chloro 3.82 g (13.3 mmol) of 3-(dibenzofuran-4-yl) -Phenylboronic acid and 2.82 g (26.6 mmol) of sodium carbonate were added to this mixture. To the mixture, 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyridinone was added. DMPU and 10 mL of water were added. The mixture was stirred under reduced pressure. The mixture was degassed by stirring. 45 mg (63.7 μmol) of bis(triphenylphosphine) (Dimethylphosphine)palladium(II) dichloride was added and the atmosphere was replaced with argon. The sample was irradiated with microwaves (2.45GHz, 100W) for 2 hours and 30 minutes under an argon atmosphere. After heating, water was added to the mixture, and the mixture was filtered to obtain a residue. The solid was washed with alcohol and dichloromethane. Toluene was added to the solid, and the solid was filtered through Celite (Wako Pure Chemical Industries, Ltd.). Co., Ltd., Catalog No.: 531-16855), alumina, Florisil (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (Koyo Co., Ltd., Catalog No.: 540-00135) and the filtrate was concentrated. This solid was purified by silica gel column chromatography (eluent: toluene). The resulting solid was recrystallized using toluene to give 1.80 g of a white solid. The yield was 60%.

[0500] The resulting solid (1.80 g) was purified by train sublimation at a pressure of 3. The purification was carried out at 300°C under conditions of 3 Pa and an argon flow rate of 5 mL / min. 1.51 g of a white solid was obtained with a recovery rate of 84%.

[0501] Nuclear magnetic resonance method ( 1 1 H NMR) confirmed that this compound was the target compound, 2,5-[3-( Dibenzofuran-4-yl)phenyl]pyrimidine (abbreviation: 2,5mDBFP2Pm-I I) was confirmed.

[0502] of the obtained material 1 The 1 H NMR data is shown below. 1 H NMR(CDCl3,300MHz):δ=7.35-7.41(m,2H), 7.45-7.52(m,4H),7.62-7.78(m,7H),7.96-8.0 3(m,5H),8.14(dt,J1=7.8Hz,J2=1.5Hz,1H),8. 21(dd,J1=2.7Hz,J2=1.5Hz,1H),8.59(dt,J1=7 .8Hz,J2=1.5Hz,1H),9.03(t,J1=1.2Hz,1H),9. 18(s,2H).

[0503] Also, 1 The H NMR chart is shown in Figure 37. Note that Figure 37(B) is the same as Figure 37(A). This is an enlarged chart showing the range of 7.0 ppm to 9.5 ppm.

[0504] Next, the 2,5-[3-(dibenzofuran-4-yl)phenyl]pyridinium chloride obtained in this example was Limidine (abbreviation: 2,5mDBFP2Pm-II) was analyzed by liquid chromatography mass spectrometry (LC The results were analyzed by HPLC / MS analysis.

[0505] LC / MS analysis was performed using a Waters Acqu (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo G2 T The column used for LC separation was Acquity UPLC BEH The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. 2,5mDBFP2Pm-II (abbreviation) with a concentration of The injection volume was adjusted to 5.0 μL.

[0506] A gradient method was used for LC separation, which changes the composition of the mobile phase. The mobile phase A:mobile phase B ratio was 40:60 until 10 minutes, and then the composition was changed. The ratio of mobile phase A to mobile phase B was set to mobile phase A:mobile phase B=95:5. It changed to linear.

[0507] In MS analysis, ionization was performed using electrospray ionization (ESI), and the resulting The column voltage was 3.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The mass range for measurement was m / z=100 to 1200.

[0508] The component m / z=564.18 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of MS analysis of the ions using a time-of-flight (ToF) MS are shown in FIG.

[0509] From the results of FIG. 107, 2,5mDBFP2Pm-II (abbreviation), which is one embodiment of the present invention, , mainly around m / z=239, m / z=255, and m / z=268 The product ion peak is near m / z=565, and the precursor ion peak is near m / z=565. It was found that a peak derived from a dimer ion was detected around m / z = 1129. The results shown in Figure 107 are derived from 2,5mDBFP2Pm-II (abbreviation). Since this shows a characteristic result, it is possible to confirm that the 2,5mDBFP2Pm- This is important data for identifying II (abbreviation).

[0510] The absorption spectrum of the toluene solution of 2,5mDBFP2Pm-II (abbreviation) is shown in Figure 3. 8(A) and the emission spectrum is shown in Figure 38(B). The absorption spectrum of the thin film of Pm-II (abbreviation) is shown in Figure 39(A), and the emission spectrum is shown in Figure 39 The absorption spectra were measured using an ultraviolet-visible spectrophotometer (Japan Spectroscopic Corporation). The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate. For the absorption spectrum, the solution was placed in a quartz cell and measured with tolue. The absorption spectrum is the one obtained by subtracting the absorption spectrum measured with only the thin film. In Figures 38 and 39, the absorption spectrum is subtracted from that of the quartz substrate. In the figure, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary units). An absorption peak was observed around 287 nm, and the emission wavelength peak was 425 nm. In the case of thin films, absorption peaks are observed around 205, 247, 280, 302 and 316 nm. The peak emission wavelength was 390 nm.

[0511] As shown in Examples 1 to 10, the second compound of the present invention, which contains a pyrimidine skeleton, The band gap (Bg) between HOMO and LUMO is determined from the absorption spectrum of organic compounds. It was found that the absorption is almost nonexistent in the visible region and the transparency is high, making it suitable for use as a light-emitting device. When used in this way, it is difficult for the luminous energy to be reabsorbed, and a highly efficient element can be expected. It has a higher S1 level than the spectrum and can be used as a host material for fluorescent luminescent materials in the visible region. It is expected that the high S1 level will also result in a high T1 level. It was found that the compound can also be used as a light-emitting material because it emits purple to blue light. [Example]

[0512] In this example, as one embodiment of the organic compound including a pyrimidine skeleton, which is the second compound, The structural formulae (300), (311), (314), (400), ( 401), (402), (412), (430), (431), and (432), and the first The compounds of the structural formulas (200) to (204), (210) to (21 The electrochemical properties (solution) of (3), (250), and (251) were measured. The chemical formulas of the materials used in this example are shown below.

[0513] [ka]

[0514] [ka]

[0515] [ka]

[0516] [ka]

[0517] The measurement was carried out by cyclic voltammetry (CV). The measurements were performed using an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 60 The measurement results are shown in Table 1.

[0518] [Table 1]

[0519] The oxidation side (potential of one-electron oxidation) shown in Table 1 corresponds to the value of the HOMO level. 4,6mPnP2Pm (abbreviation), which is one embodiment of an organic compound containing a pyrimidine skeleton. The HOMO level is deeper (smaller) than that of the iridium metal complex, which is the dopant. It was found that holes can be efficiently injected into these iridium metal complexes as dopants. In addition, if the HOMO level of the iridium metal complex is -6.0 to -5.0 eV, The iridium metal complex is a compound of formula 2, which is an organic compound containing a pyrimidine skeleton. It was found that the ion trap can efficiently trap the ions.

[0520] The reduction side (potential of one-electron reduction) shown in Table 1 corresponds to the value of the LUMO level. 4,6mPnP2Pm( The LUMO levels of the phosphorescent iridium metal complexes are similar to or slightly different from those of the dopants. Since the values ​​are close to each other, electrons can be efficiently transferred to the iridium metal complex, which is the dopant. In addition, the iridium complex dopant was found to be easily injected into the host material. It does not interfere with the electron transport properties of 4,6mPnP2Pm (abbreviation), and has a low driving voltage It was suggested that a device could be fabricated.

[0521] From the above results, it can be seen that the organic compound having a pyrimidine skeleton of the present invention has a relatively deep HOMO It has a suitable LUMO level and is therefore suitable as a host material for iridium metal complexes. In particular, diazine skeletons, specifically pyrimidine skeletons, having close LUMO levels are preferred. This is suitable for iridium metal complexes.

[0522] The phosphorescent compounds represented by the structural formulas (200) to (204), (250), and (251) Iridium metal complexes have a pyrimidine skeleton and are represented by structural formulas (210) to (213). The phosphorescent iridium metal complexes have a pyrazine skeleton, so they all have a diazine skeleton. do.

[0523] The measurement method for the above cyclic voltammetry (CV) measurement is as follows: The following is an explanation of 4,6mPnP2Pm (abbreviation), but other chemicals The mixture was also measured in the same manner.

[0524] The solution used in the CV measurement was dehydrated dimethylformamide (DMF) (Asahi Chemical Industries, Ltd.). The supporting electrolyte was 0.1% sucrose (manufactured by Rudrich, 99.8%, catalog number: 22705-6). Tetra-n-butylammonium perchlorate (n-Bu4NClO4) (Tokyo Chemical Industry Co., Ltd.) Catalog number: T0836) was dissolved to a concentration of 100 mmol / L, and The measurement target was dissolved to a concentration of 2 mmol / L. A platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.) was used as the electrode, and a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.) was used as the auxiliary electrode. The electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS Co., Ltd.) was used as a reference. The electrode used was an Ag / Ag+ electrode (manufactured by BAS Co., Ltd., RE7 non-aqueous solvent reference electrode). The measurements were carried out at room temperature (20-25°C). The scan rate was set to 0.1 V / sec.

[0525] (Calculation of potential energy relative to the vacuum level of the reference electrode) First, the potential of the reference electrode (Ag / Ag+ electrode) used in this example with respect to the vacuum level The Fermi energy (eV) of the Ag / Ag+ electrode was calculated. The redox potential of ferrocene in methanol is +0.61 vs. the standard hydrogen electrode. 0 [V vs. SHE] (references; Christian R.Goldsmith et al., J.Am.Chem.Soc., Vol. 124, No.1,83-96, 2002).

[0526] On the other hand, the reference electrode used in this example was used to measure the oxidation reduction of ferrocene in methanol. The initial potential was found to be +0.11 V [vs. Ag / Ag+]. The potential energy of the reference electrode used in the examples is 0.50 [ eV] was found to be lower.

[0527] Here, the potential energy of the standard hydrogen electrode from the vacuum level is -4.44 eV. It is known that (Reference: Toshihiro Onishi and Tamami Koyama, Polymer EL Materials (Kyoritsu Shuppan) , pp.64-67). From the above, the potential of the reference electrode used in this example relative to the vacuum level The potential energy can be calculated as -4.44-0.50=-4.94[eV]. Ta.

[0528] The oxidation reaction characteristics of the compound in this example were measured by setting the potential of the working electrode relative to the reference electrode to approximately 0. Scanning was performed from 3V to about 1.5V, and then from about 1.5V to about 0.3V.

[0529] Next, we will explain in detail how to calculate the HOMO level from the CV measurement of the target substance. Position (neutral to oxidized) E pa [V] and the reduction peak potential (between the oxidizing side and neutral side) E pc [ V] was calculated. pa and E pc The intermediate potential between (E pa +E pc) / 2 [V]. This means that the compound of this example has a half-wave potential value [V v This shows that Ag is oxidized by the electrical energy of [s.Ag / Ag+]. corresponds to the HOMO level.

[0530] The reduction reaction characteristics of the compound in this example were measured by adjusting the potential of the working electrode relative to the reference electrode to about -1 After scanning from 0.5V to approximately -2.2V, it scans from approximately -2.2V to approximately -1.5V. It was.

[0531] Next, we will explain in detail how to calculate the LUMO level from the CV measurement of the target substance. Position (neutral to reducing side) E pa [V] and the oxidation peak potential (between the reduction side and neutral side) E pc [ V] was calculated. pa and E pc The intermediate potential between (E pa +E pc ) / 2 [V]. This means that the compound of this example has a half-wave potential value [V v This shows that Ag is reduced by the electrical energy of [s.Ag / Ag+]. corresponds to the LUMO level. [Example]

[0532] In this example, a phosphorescent iridium metal complex containing a pyrimidine skeleton was used as the first compound. and a second compound represented by the structural formula (300) shown in Embodiment 1 and Example 1. The organic compound containing the pyrimidine skeleton and the light-emitting element 1 using the compound as a light-emitting material were evaluated. The chemical formulas of the materials used in this example are shown below.

[0533] [ka]

[0534] The light-emitting element 1 will be described with reference to Fig. 40. The fabrication of the light-emitting element 1 of this example will be described below. Here's how.

[0535] (Light-emitting element 1) First, on the substrate 1100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITO-SiO2, hereafter abbreviated as ITSO) was formed into a film by sputtering. The first electrode 1101 was formed. The composition of the target used was In2O3:Sn The ratio of O2:SiO2 was 85:10:5 [wt %]. The thickness of the first electrode 1101 was , 110 nm, and the electrode area was 2 mm × 2 mm. This electrode functions as an anode of the light-emitting element.

[0536] Next, as a pretreatment for forming a light emitting element on the substrate 1100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0537] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition apparatus, the substrate 1100 It was left to cool for about 30 minutes.

[0538] Next, the first electrode 1101 is placed on the substrate 1101 so that the surface on which the first electrode 1101 is formed faces downward. The formed substrate 1100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and 10 -4 After the pressure was reduced to about Pa, 1,3,5-tri(dibenzothiophene) was (4-phenyl-4-yl)-benzene (abbreviation: DBT3P-II) and molybdenum oxide are co-evaporated. The hole injection layer 1111 was formed by the above process. The thickness of the layer was set to 40 nm. The weight ratio of DBT3P-II to molybdenum oxide was 4:2 (=DBT3P-II:molybdenum oxide). The co-evaporation method is a method in which multiple evaporation sources are used in one processing chamber. This is a deposition method in which deposition is performed simultaneously on the surface and the substrate.

[0539] Next, 4-phenyl-4'-(9-phenylfluorene-9 -yl)triphenylamine (abbreviation: BPAFLP) to a thickness of 20 nm. Thus, a hole transport layer 1112 was formed.

[0540] Furthermore, the 4,6-bis[3-(phenanthrene-9-yl)phenanthren-1-yl]phenanthren-2-yl]phenanthren-3-yl]phenanthren-4-yl]phenanthren-5 ... 4-phenyl-4'-(9-phenyl)pyrimidine (abbreviation: 4,6mPnP2Pm) (9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP) , (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)i Iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]) and A first light-emitting layer 1113a was formed on the hole-transporting layer 1112. 2Pm (abbreviation), PCBA1BP (abbreviation), and [Ir(tBuppm)2(acac) The weight ratio of PCBA1BP is 0.7:0.3:0.05 (=4.6mPnP2Pm:PCBA1BP: [Ir(tBuppm)2(acac)]). The film thickness of 1113a was set to 15 nm.

[0541] Next, 4,6mPnP2Pm (abbreviation) and PCBA1BP (abbreviation), and [Ir(tBuppm)2(acac)] were co-deposited to form a first light-emitting layer 11 The second light-emitting layer 1113b was formed on the first light-emitting layer 1113a. , PCBA1BP (abbreviation), and [Ir(tBuppm)2(acac)] (abbreviation) The ratio of the amounts was 0.8:0.2:0.05 (=4,6mPnP2Pm:PCBA1BP:[Ir (tBuppm)2(acac)]). The film thickness of 3b was set to 25 nm.

[0542] Next, 4,6mPnP2Pm (abbreviation) was deposited on the second light-emitting layer 1113b to a thickness of 10 nm. Thus, a first electron transport layer 1114a was formed.

[0543] Next, bathophenanthroline (abbreviation: BPhen) was applied to the first electron transport layer 1114a. A film was formed to a thickness of 20 nm to form the second electron transport layer 1114b.

[0544] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 1114b to a thickness of 1 nm. The electron injection layer 1115 was formed by vapor deposition using a method similar to that described above.

[0545] Finally, a 200 nm thick aluminum film was deposited as the second electrode 1103, which served as the cathode. The light-emitting element 1 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0546] The element structure of the light-emitting element 1 obtained as described above is shown in Table 2.

[0547] [Table 2]

[0548] The light-emitting element 1 is sealed in a nitrogen atmosphere glove box so that it is not exposed to the atmosphere. (Sealing material was applied around the element, and heat treatment was performed at 80°C for 1 hour during sealing.) Thereafter, the operating characteristics of the light-emitting element 1 were measured. The measurements were carried out at room temperature (25°C). The event was held in an atmosphere maintained at a comfortable level.

[0549] The current density-luminance characteristics of the light-emitting element 1 are shown in FIG. 41. In FIG. 41, the horizontal axis represents the current density (mA / cm 2 ) and the vertical axis is luminance (cd / m 2 ) and the voltage-luminance of the light-emitting element 1. The characteristics are shown in Figure 42. In Figure 42, the horizontal axis represents voltage (V) and the vertical axis represents brightness (cd / m 2 ) 43 shows the luminance-current efficiency characteristics of the light-emitting element 1. In FIG. is the luminance (cd / m 2 ) and the vertical axis represents the current efficiency (cd / A). The voltage-current characteristics are shown in FIG. 44. In FIG. 44, the horizontal axis represents voltage (V) and the vertical axis represents current (mA). ) is shown. Furthermore, the luminance-chromaticity coordinate characteristics of the light-emitting element 1 are shown in FIG. 45. In FIG. 45, The horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates chromaticity (x-coordinate and y-coordinate). The luminance-power efficiency characteristics of the device 1 are shown in Figure 46. In Figure 46, the horizontal axis represents luminance (cd / m 2 ) and the vertical axis represents power efficiency (lm / W).

[0550] Furthermore, the luminance of the light-emitting element 1 is 1000 cd / m 2 Voltage (V) and current density near (mA / cm 2 ), CIE chromaticity coordinates (x, y), luminance (cd / m 2 ), current efficiency (cd / A) and external quantum efficiency (%) are shown in Table 3.

[0551] [Table 3]

[0552] The current density of the light-emitting element 1 was 2.5 mA / cm 2 The emission spectrum when As shown in Figure 47, the emission spectrum of Light-Emitting Device 1 has a peak at 547 nm. do.

[0553] Furthermore, as shown in Table 3, the luminance of the light-emitting element 1 was 1300 cd / m 2 CIE chromaticity coordinates at The target was (x, y) = (0.43, 0.56). It was found that the original light emission was obtained.

[0554] As described above, the first compound is a phosphorescent iridium metal complex containing pyrimidine, The present invention uses the second compound, an organic compound containing a pyrimidine skeleton, as a light-emitting substance. The light-emitting element 1, which is one embodiment of the present invention, is shown to be capable of efficiently emitting light in the green wavelength region. In addition, 4,6mPnP2Pm (abbreviation) has a higher T1 level than green. Therefore, 4,6mPnP2Pm (abbreviation) is a wavelength longer than green, including green. It has been found that the compound is suitable as a host for a light-emitting material that emits light.

[0555] 41 and 42, the light-emitting element 1 is an element with low driving voltage and low power consumption. 43 and 46, it was found that the light-emitting element 1 was a highly efficient element. FIG. 45 shows that the light-emitting element 1 has a good carrier balance at each luminance level. It was.

[0556] Next, a reliability test was carried out on the light-emitting element 1. The results of the reliability test are shown in FIG. 8 and FIG.

[0557] In Figure 48, the reliability test was performed using an initial luminance of 5000 cd / m 2 Set it to The light-emitting element 1 was driven under the condition of a constant current density. The horizontal axis represents the driving time (h) of the element, and the vertical axis represents the initial The normalized luminance (%) is shown when the initial luminance is set to 100%. The time it took for the brightness to drop below 70% was approximately 290 hours.

[0558] FIG. 48 shows that the light-emitting element 1 has a long life.

[0559] From the above results, the first compound was a phosphorescent iridium metal complex containing pyrimidine. and a second compound, an organic compound containing a pyrimidine skeleton, as a light-emitting material. The light-emitting element 1, which is one embodiment of the present invention, is a light-emitting element that has high efficiency, low driving voltage, low power consumption, and a long lifetime. I discovered something.

[0560] Next, in FIG. 49, the measurement method for the reliability test is as follows: initial luminance is 5000 cd / m 2 Set in The time change in the voltage of the light-emitting element 1 was measured under the condition of a constant current density. The vertical axis represents the operating time (h), and the vertical axis represents the voltage (V). It was confirmed that the increase was small. [Example]

[0561] In this example, a compound represented by structural formula (400) synthesized in Example 4, which is one aspect of the present invention, was used. Light-emitting element 2 and light-emitting element 3 using organic compounds were evaluated. The chemical formula of the material of the light-emitting element 2 is shown below.

[0562] [ka]

[0563] The light-emitting element 2 will be described with reference to FIG. 50(A). The method for producing the above is shown below.

[0564] (Light-emitting element 2) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0565] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0566] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0567] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, 1,3,5-tri(dibenzothiophene) was (4-phenyl-4-yl)-benzene (abbreviation: DBT3P-II) and molybdenum oxide are co-evaporated. The hole injection layer 2111 was formed by the above process. The thickness of the layer was set to 40 nm. The weight ratio of DBT3P-II to molybdenum oxide was 4:2 (=DBT3P-II:molybdenum oxide). The co-evaporation method is a method in which multiple evaporation sources are used in one processing chamber. This is a deposition method in which deposition is performed simultaneously on the surface and the substrate.

[0568] Next, 4-phenyl-4'-(9-phenylfluorene-9 -yl)triphenylamine (abbreviation: BPAFLP) to a thickness of 20 nm. Thus, a hole transport layer 2112 was formed.

[0569] Furthermore, the 4,6-bis[3-(dibenzothiophen-4-yl) phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 4-phenyl-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCB A1BP) and (acetylacetonato)bis(6-tert-butyl-4-phenylpyridine) Iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]) , were co-evaporated to form a first light-emitting layer 2113a on the hole transport layer 2112. ,6mDBTP2Pm-II (abbreviation), PCBA1BP (abbreviation), and [Ir(tBup The weight ratio of [(acac)] was 0.7:0.3:0.05 (=4.6mDBTP2 Pm-II:PCBA1BP:[Ir(tBuppm)2(acac)]) The thickness of the first light emitting layer 2113a was adjusted to 15 nm.

[0570] Next, 4,6mDBTP2Pm-II (abbreviation) and PCB A1BP (abbreviation) and [Ir(tBuppm)2(acac)] were co-evaporated, and the first A second light-emitting layer 2113b was formed on the optical layer 2113a. m-II (abbreviation), PCBA1BP (abbreviation), and [Ir(tBuppm)2(acac )] (abbreviation) weight ratio is 0.8:0.2:0.05 (= 4,6mDBTP2Pm-II :PCBA1BP:[Ir(tBuppm)2(acac)]). The thickness of the second light emitting layer 2113b was 25 nm.

[0571] Next, 4,6mDBTP2Pm-II (abbreviation) was deposited on the second light-emitting layer 2113b to a thickness of 10 The first electron transport layer 2114a was formed to a thickness of 100 nm.

[0572] Next, bathophenanthroline (abbreviation: BPhen) was applied to the first electron transport layer 2114a. A film was formed to a thickness of 20 nm to form the second electron transport layer 2114b.

[0573] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 2114b to a thickness of 1 nm. The electron injection layer 2115 was formed by vapor deposition using a method similar to that described above.

[0574] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 2 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0575] The element structure of the light-emitting element 2 obtained as described above is shown in Table 4.

[0576] [Table 4]

[0577] Next, the chemical formulas of the materials of the light-emitting element 3 used in this example are shown below.

[0578] [ka]

[0579] The light-emitting element 3 will be described with reference to FIG. 50(B). The method for producing the above is shown below.

[0580] (Light-emitting element 3) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0581] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0582] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0583] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, 4,4'-di(N-carbazolyl) The hole injection layer 2111 is formed by co-evaporating biphenyl (abbreviation: CBP) and molybdenum oxide. The film thickness was 60 nm, and the ratio of CBP (abbreviation) to molybdenum oxide was The ratio was adjusted to 4:2 (CBP:molybdenum oxide). This is a deposition method in which deposition is carried out simultaneously from multiple evaporation sources in one processing chamber.

[0584] Next, 1,3-bis(N-carbazolyl)benzene (abbreviation: A film of mCP was formed to a thickness of 20 nm to form a hole transport layer 2112 .

[0585] Furthermore, the 4,6-bis[3-(dibenzothiophen-4-yl) phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 9-phenyl-9H -3-(9-phenyl-9H-carbazol-3-yl)-carbazole (abbreviation: PCC P) and tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1, 2,4-Triazolate]iridium(III) (abbreviation: [Ir(Mptz1-mp)3] ) was co-evaporated to form a first light-emitting layer 2113a on the hole-transporting layer 2112. , 4,6mDBTP2Pm-II (abbreviation), PCCP (abbreviation), and [Ir(Mptz1 -mp)3] (abbreviation) weight ratio is 1:0.3:0.08 (=4.6mDBTP2Pm- II:PCCP:[Ir(Mptz1-mp)3]). The thickness of the light-emitting layer 2113a was set to 30 nm.

[0586] Next, 2-[3-(dibenzothiophen-4-yl)phenyl]phenyl]propane was deposited on the first light-emitting layer 2113a. mDBTBIm-II) and [Ir(Mptz1-mp)3] (abbreviation) was co-deposited on the first light-emitting layer 2113a. The light-emitting layer 2113b was formed using mDBTBIm-II (abbreviation) and [Ir( The weight ratio of mDBTBIm-II to mDBTBIm-II was 1:0.08 (= mDBTBIm-II: Mptz1-mp)3 (abbreviation). [Ir(Mptz1-mp)3]). The film thickness of b was set to 10 nm.

[0587] Next, bathophenanthroline (abbreviation: BPhen) was applied to the second light-emitting layer 2113b to a thickness of 1000 μm. The film was formed to a thickness of 15 nm to form the electron transport layer 2114 .

[0588] Furthermore, lithium fluoride (LiF) was vapor-deposited on the electron transport layer 2114 to a thickness of 1 nm. Then, an electron injection layer 2115 was formed.

[0589] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 3 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0590] The element structure of the light-emitting element 3 obtained as described above is shown in Table 5.

[0591] [Table 5]

[0592] The light-emitting element 2 and the light-emitting element 3 fabricated as described above were placed in a glove box with a nitrogen atmosphere. The process involves sealing each light-emitting element so that it is not exposed to the atmosphere (applying a sealant around the element). After that, the light-emitting element 2 and the light-emitting element 3 were The operating characteristics of the device 3 were measured. The measurements were carried out at room temperature (an atmosphere maintained at 25°C). So I went.

[0593] The current density-luminance characteristics of the light-emitting element 2 and the light-emitting element 3 are shown in FIGS. 51 and 58, respectively. In Figures 51 and 58, the horizontal axis represents the current density (mA / cm 2 ) and the vertical axis is brightness ( cd / m 2 ) are shown. The voltage-luminance characteristics of the light-emitting element 2 and the light-emitting element 3 are shown in FIG. 52 and 59, the horizontal axis represents voltage (V) and the vertical axis represents brightness. degree (cd / m 2 ) is shown. The luminance vs. current efficiency characteristics of Light-emitting Elements 2 and 3 are shown in FIG. 53 and 60, respectively. In Fig. 53 and Fig. 60, the horizontal axis is luminance (cd / m 2 ) The vertical axis represents the current efficiency (cd / A), and the vertical axis represents the voltage-voltage relationship of the light-emitting element 2 and the light-emitting element 3. The current characteristics are shown in Figures 54 and 61, respectively. In Figures 54 and 61, the horizontal axis represents voltage ( The vertical axis represents the luminance (V) and the vertical axis represents the current (mA). The target characteristics are shown in Figures 55 and 62, respectively. In Figures 55 and 62, the horizontal axis is the brightness. degree (cd / m 2 ), and the vertical axis represents chromaticity (x coordinate and y coordinate). The luminance-power efficiency characteristics of the light-emitting element 1 and the light-emitting element 2 are shown in FIG. 56 and FIG. 63, respectively. In Figure 63, the horizontal axis is luminance (cd / m 2 ) and the vertical axis represents power efficiency (lm / W). .

[0594] 56 and 63, it can be seen that the light-emitting elements 2 and 3 are highly efficient elements. 55 and 62, the light-emitting element 2 and the light-emitting element 3 exhibited different brightness levels. It was found that the element had good carrier balance. It was found that the optical element 2 and the light-emitting element 3 are elements with low driving voltage and low power consumption. Ta.

[0595] Furthermore, the luminance of the light-emitting element 2 and the light-emitting element 3 was 1000 cd / m 2 Voltage when near (V), current density (mA / cm 2 ), CIE chromaticity coordinates (x, y), luminance (cd / m 2 ), Table 6 shows the current efficiency (cd / A) and external quantum efficiency (%).

[0596] [Table 6]

[0597] The current density of the light-emitting elements 2 and 3 was set to 2.5 mA / cm 2 When The spectra are shown in Figures 57 and 64, respectively. As shown in Figures 57 and 64, the emission The emission spectra of the light-emitting element 2 and the light-emitting element 3 have peaks at 548 nm and 472 nm, respectively. It has the following characteristics.

[0598] Furthermore, as shown in Table 6, the luminance of light-emitting element 2 was 723 cd / m 2 CIE chromaticity coordinates at The values ​​were (x, y)=(0.43, 0.56). The luminance of the light-emitting element 3 was 735c d / m 2 The CIE chromaticity coordinates at this time were (x,y) = (0.20,0.35). From these findings, it was found that both Light-Emitting Device 2 and Light-Emitting Device 3 emitted light derived from the dopant. It was found that...

[0599] As described above, the light-emitting element 2 according to one embodiment of the present invention can efficiently emit light in the yellow wavelength range. Furthermore, the light-emitting element 3 according to one embodiment of the present invention can emit light in the blue wavelength region. It was shown that the 4,6mDBTP2Pm-I region can be efficiently luminesced. I (abbreviation) has been found to have a higher T1 level than blue. DBTP2Pm-II (abbreviation) is a host material that emits light in the visible region (blue to red). It was found to be suitable for this purpose. [Example]

[0600] In this example, a compound represented by structural formula (400) synthesized in Example 4, which is one aspect of the present invention, was used. Light-emitting devices 4, 5, and 6 using organic compounds, and 4,6-bis[ 3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2 Light-emitting device 7 using Pm) was evaluated.

[0601] First, the chemical formulas of the materials used in the light-emitting element 4 of this example are shown below.

[0602] [ka]

[0603] The light-emitting element 4 will be described with reference to FIG. 50(A). The method for producing the above is shown below.

[0604] (Light-emitting element 4) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0605] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0606] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0607] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, DBT3P-II (abbreviation) and oxide molybdenum were placed on the first electrode 2101. The hole injection layer 2111 was formed by co-evaporation of lysine and bismuth. The thickness of the layer was 40 nm. The weight ratio of DBT3P-II (abbreviation) to molybdenum oxide is 4:2 (=DBT3 P-II: molybdenum oxide).

[0608] Next, BPAFLP (abbreviation) was deposited on the hole injection layer 2111 to a thickness of 20 nm. A film was formed to form a hole transporting layer 2112.

[0609] Furthermore, the 4,6-bis[3-(dibenzothiophen-4-yl) phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 4,4'-di(1- naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl PCBNBB and (acetylacetonato)bis(6-tert-butyl- 4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2( acac)]) was co-evaporated to form a first light-emitting layer 2113a on the hole transport layer 2112. Here, 4,6mDBTP2Pm-II (abbreviation), PCBNBB (abbreviation), and [ The weight ratio of Ir(tBuppm)2(acac)] (abbreviation) is 0.5:0.5:0.05 (=4,6mDBTP2Pm-II:PCBNBB:[Ir(tBuppm)2(aca The thickness of the first light-emitting layer 2113a was adjusted to 20 nm. .

[0610] Next, 4,6mDBTP2Pm-II (abbreviation) and PCB NBB (abbreviation) and [Ir(tBuppm)2(acac)] (abbreviation) were co-evaporated. A second light-emitting layer 2113b was formed on the first light-emitting layer 2113a. P2Pm-II (abbreviation), PCBNBB (abbreviation), and [Ir(tBuppm)2(ac ac)] (abbreviation) weight ratio is 0.8:0.2:0.05 (= 4,6mDBTP2Pm- II: PCBNBB: [Ir(tBuppm)2(acac)] The thickness of the second light emitting layer 2113b was set to 20 nm.

[0611] Next, 4,6mDBTP2Pm-II (abbreviation) was deposited on the second light-emitting layer 2113b to a thickness of 10 The first electron transport layer 2114a was formed to a thickness of 100 nm.

[0612] Next, BPhen (abbreviation) was deposited on the first electron transport layer 2114a to a thickness of 20 nm. A second electron transport layer 2114b was formed.

[0613] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 2114b to a thickness of 1 nm. The electron injection layer 2115 was formed by vapor deposition using a method similar to that described above.

[0614] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 4 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0615] The element structure of the light-emitting element 4 obtained as described above is shown in Table 7.

[0616] [Table 7]

[0617] Next, the chemical formulas of the materials used in the light-emitting element 5 of this example are shown below.

[0618] [ka]

[0619] The light-emitting element 5 will be described with reference to FIG. 50(C). The method for producing the above is shown below.

[0620] (Light-emitting element 5) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0621] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0622] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0623] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, DBT3P-II (abbreviation) and oxide molybdenum were placed on the first electrode 2101. The hole injection layer 2111 was formed by co-evaporation of lysine and bismuth. The thickness of the layer was 40 nm. The weight ratio of DBT3P-II (abbreviation) to molybdenum oxide is 4:2 (=DBT3 P-II: molybdenum oxide).

[0624] Next, on the hole injection layer 2111, 9-[3-(9-phenyl-9H-fluorene-9- mCzFLP) and PCCP (abbreviation) The hole transport layer 2112 was formed by co-evaporation. The weight ratio of FLP (abbreviation) to PCCP (abbreviation) was 1:1 (= mCzFLP:PCCP P).

[0625] Furthermore, 4,6mDBTP2Pm-II (abbreviation) synthesized in Example 4 and PCCP ( abbreviation) and tris(2-phenylpyridinato-N,C 2’) Iridium(III) (abbreviation :[Ir(ppy)3]) and a light-emitting layer 2113 are formed on the hole transport layer 2112 by co-evaporation. Here, 4,6mDBTP2Pm-II (abbreviation), PCCP (abbreviation), and [I The weight ratio of [r(ppy)3] (abbreviation) was 0.8:0.2:0.05 (=4.6mDBTP The composition was adjusted to be 2Pm-II:PCCP:[Ir(ppy)3]. The film thickness of 2113 was set to 40 nm.

[0626] Next, 4,6mDBTP2Pm-II (abbreviation) was deposited on the light-emitting layer 2113 to a thickness of 10 nm. The first electron transport layer 2114a was formed in this manner.

[0627] Next, BPhen (abbreviation) was deposited on the first electron transport layer 2114a to a thickness of 20 nm. A second electron transport layer 2114b was formed.

[0628] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 2114b to a thickness of 1 nm. The electron injection layer 2115 was formed by vapor deposition using a method similar to that described above.

[0629] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 5 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0630] The element structure of the light-emitting element 5 obtained as described above is shown in Table 8.

[0631] [Table 8]

[0632] Next, the chemical formulas of the materials used in the light emitting element 6 of this example are shown below.

[0633] [ka]

[0634] The light-emitting element 6 will be described with reference to FIG. 50(A). The method for producing the above is shown below.

[0635] (Light emitting element 6) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0636] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0637] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0638] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, DBT3P-II (abbreviation) and oxide molybdenum were placed on the first electrode 2101. The hole injection layer 2111 was formed by co-evaporation of lysine and bismuth. The thickness of the layer was 30 nm. The weight ratio of DBT3P-II (abbreviation) to molybdenum oxide is 4:2 (=DBT3 P-II: molybdenum oxide).

[0639] Next, BPAFLP (abbreviation) was deposited on the hole injection layer 2111 to a thickness of 20 nm. A film was formed to form a hole transporting layer 2112.

[0640] Furthermore, the 4,6-bis[3-(dibenzothiophen-4-yl) Phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and PCCP (abbreviation) , tris[2-methyl-3-(6-tert-butyl-4-pyrimidinyl-κN3)pyrimidinyl] [Ir(tBumpypm)3] and iridium(III) (abbreviation: [Ir(tBumpypm)3]). The first light-emitting layer 2113a was formed on the hole transport layer 2112 by evaporation. DBTP2Pm-II (abbreviation), PCCP (abbreviation), and [Ir(tBumpypm)3 The weight ratio of ] (abbreviation) is 0.5:0.5:0.05 (= 4,6mDBTP2Pm-II: PCCP:[Ir(tBumpypm)3]). The thickness of the layer 2113a was set to 20 nm.

[0641] Next, 4,6mDBTP2Pm-II (abbreviation) and PCC P (abbreviation) and [Ir(tBumpypm)3] (abbreviation) were co-deposited to form a first light-emitting layer 2 A second light-emitting layer 2113b was formed on the first light-emitting layer 113a. Weight ratio of I (abbreviation), PCCP (abbreviation), and [Ir(tBumpypm)3] (abbreviation) is 0.8:0.2:0.05(=4,6mDBTP2Pm-II:PCCP:[Ir( The thickness of the second light-emitting layer 2113b was adjusted to be tBumpypm)3). was set to 20 nm.

[0642] Next, 4,6mDBTP2Pm-II (abbreviation) was deposited on the second light-emitting layer 2113b to a thickness of 10 The first electron transport layer 2114a was formed to a thickness of 100 nm.

[0643] Next, BPhen (abbreviation) was deposited on the first electron transport layer 2114a to a thickness of 15 nm. A second electron transport layer 2114b was formed.

[0644] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 2114b to a thickness of 1 nm. The electron injection layer 2115 was formed by vapor deposition using a method similar to that described above.

[0645] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 6 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0646] The element structure of the light-emitting element 6 obtained as described above is shown in Table 9.

[0647] [Table 9]

[0648] Next, the chemical formulas of the materials used in the light-emitting element 7 of this example are shown below.

[0649] [ka]

[0650] The light-emitting element 7 will be described with reference to FIG. 50(A). The method for producing the above is shown below.

[0651] (Light-emitting element 7) First, on the substrate 2100, indium oxide-tin oxide containing silicon or silicon oxide is formed. A compound (ITSO) was deposited by sputtering to form a first electrode 2101. The composition of the target used was In2O3:SnO2:SiO2=85:10:5 [heavy The thickness of the first electrode 2101 was 110 nm, and the electrode area was 2 mm The first electrode 2101 is an electrode that functions as an anode of the light-emitting element. be.

[0652] Next, as a pretreatment for forming a light emitting element on the substrate 2100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0653] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition device, the substrate 2100 It was left to cool for about 30 minutes.

[0654] Next, the first electrode 2101 is placed on the substrate 101 so that the surface on which the first electrode 2101 is formed faces downward. The formed substrate 2100 was fixed to a substrate holder provided in a vacuum deposition apparatus, and -4 After the pressure was reduced to about Pa, DBT3P-II (abbreviation) and oxide molybdenum were placed on the first electrode 2101. The hole injection layer 2111 was formed by co-evaporation of lysine and bismuth. The thickness of the layer was 40 nm. The weight ratio of DBT3P-II (abbreviation) to molybdenum oxide is 4:2 (=DBT3 P-II: molybdenum oxide).

[0655] Next, mCzFLP (abbreviation) was deposited on the hole injection layer 2111 to a thickness of 20 nm. A film was formed to form a hole transporting layer 2112.

[0656] Furthermore, 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), PCCP (abbreviation), and bis[2-methyl-3-(6 -tert-butyl-4-pyrimidinyl-κN3)pyridyl-κC](2,4-pentane Geonato-κ 2 0,0') Iridium(III) (abbreviation: [Ir(tBumpypm)2 (acac)]) was co-evaporated to form a first light-emitting layer 2113a on the hole transport layer 2112. Here, 4,6mCzP2Pm (abbreviation), PCCP (abbreviation), and [Ir(tB The weight ratio of ethanol to ethanol is 0.8:0.2:0.05 (=4 ,6mCzP2Pm:PCCP:[Ir(tBumpypm)2(acac)]) The thickness of the first light emitting layer 2113a was adjusted to 20 nm.

[0657] Next, 4,6mCzP2Pm (abbreviation) and [Ir(tBu mpypm)2(acac)] (abbreviation) was co-deposited on the first light-emitting layer 2113a. The light-emitting layer 2113b was formed using 4,6mCzP2Pm (abbreviation) and [Ir The weight ratio of (tBumpypm)2(acac)] (abbreviation) is 1:0.05 (=4.6m The mixture was adjusted to give CzP2Pm:[Ir(tBumpypm)2(acac)]. The thickness of the second light emitting layer 2113b was 20 nm.

[0658] Next, 4,6mCzP2Pm (abbreviation) was deposited on the second light-emitting layer 2113b to a thickness of 10 nm. The first electron transport layer 2114a was formed in this manner.

[0659] Next, BPhen (abbreviation) was deposited on the first electron transport layer 2114a to a thickness of 20 nm. A second electron transport layer 2114b was formed.

[0660] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 2114b to a thickness of 1 nm. The electron injection layer 2115 was formed by vapor deposition using a method similar to that described above.

[0661] Finally, a 200 nm thick aluminum film was deposited as the second electrode 2103, which served as the cathode. The light-emitting element 7 of this example was fabricated by vapor deposition so as to have a film thickness of .

[0662] The element structure of the light-emitting element 7 obtained as described above is shown in Table 10.

[0663] [Table 10]

[0664] The light-emitting elements 4 to 7 fabricated as described above were placed in a glove box with a nitrogen atmosphere. The process involves sealing each light-emitting element to prevent it from being exposed to the atmosphere (applying a sealant around the element). Then, a heat treatment was performed at 80° C. for 1 hour during sealing. The operating characteristics were measured. The measurements were carried out at room temperature (an atmosphere maintained at 25°C). .

[0665] The current density-luminance characteristics of the light-emitting elements 4, 5, 6, and 7 are shown in FIG. , 72, 79, and 86, respectively. The horizontal axis represents the current density (mA / cm 2 ) and the vertical axis is luminance (cd / m 2 ) and 66, 67, and 68 show the voltage-luminance characteristics of the light-emitting elements 4, 5, 6, and 7. 66, 73, 80, and 87. The horizontal axis represents voltage (V) and the vertical axis represents brightness (cd / m 2 ) and the light-emitting element 4, The luminance-current efficiency characteristics of the light-emitting element 5, the light-emitting element 6, and the light-emitting element 7 are shown in FIGS. 67, 74, 81, and 82. 67, 74, 81, and 88, the horizontal axis represents the luminance ( cd / m 2 ), and the vertical axis represents the current efficiency (cd / A). The voltage-current characteristics of the light-emitting element 6 and the light-emitting element 7 are shown in FIGS. 68, 75, 82, and 89. 68, 75, 82, and 89, the horizontal axis represents voltage (V), The vertical axis represents current (mA). The luminance-chromaticity coordinate characteristics of 7 are shown in Figures 69, 76, 83, and 90, respectively. 9, Fig. 76, Fig. 83, and Fig. 90, the horizontal axis is luminance (cd / m 2 ) and the vertical axis is chromaticity ( The x and y coordinates are also shown. The luminance-power efficiency characteristics of the device 7 are shown in Figures 70, 77, 84, and 91, respectively. 70, 77, 84, and 91, the horizontal axis represents luminance (cd / m 2 ) and the vertical axis is power -Represents efficiency (lm / W).

[0666] 70, 77, 84, and 91, the light-emitting elements 4 to 7 are highly efficient elements. 69, 76, 83, and 90, it is clear that the light-emitting element 4 It was found that Light-emitting element 7 was an element with a good carrier balance at each luminance level. 68, 75, 82, and 89, the light-emitting elements 4 to 7 are driven at a driving voltage of It was found that the device has low power consumption and low temperature.

[0667] Furthermore, the luminance of light-emitting elements 4 to 7 was 1000 cd / m 2 The voltage when V), current density (mA / cm 2 ), CIE chromaticity coordinates (x, y), luminance (cd / m 2 ), electric The current efficiency (cd / A) and external quantum efficiency (%) are shown in Table 11.

[0668] [Table 11]

[0669] The current density of the light-emitting elements 4 to 7 was set to 2.5 mA / cm 2 The light emission The spectra are shown in Figures 71, 78, 85, and 92, respectively. 5 and 92, the emission spectra of the light-emitting elements 4 to 7 are It has peaks at 48 nm, 513 nm, 493 nm, and 508 nm.

[0670] In this way, light emission from each dopant material (iridium complex) was obtained. It was found that the second compound of the present invention, an organic compound containing a pyrimidine skeleton, The compound has a high T1 level, so it is possible to obtain phosphorescent materials with longer wavelengths, including blue-green. It was found that it can be used as a test material.

[0671] Furthermore, as shown in Table 11, the luminance of light-emitting element 4 was 694 cd / m 2 CIE chromaticity coordinates at The values ​​were (x, y) = (0.43, 0.56). The luminance of the light-emitting element 4 was 694 d / m 2 The voltage, current density, current efficiency, and external quantum efficiency at this time were 2.7 V, 0.9mA / cm 2 , 79 cd / A, and 22%. 54cd / m 2 The CIE chromaticity coordinates at this time were (x,y)=(0.33,0.62). In addition, the luminance of the light-emitting element 5 is 954 cd / m 2 The voltage, current density, current efficiency, and external The partial quantum efficiency was 3.1 V and 1.4 mA / cm, respectively. 2 , 69cd / A, and 20% The luminance of the light-emitting element 6 was 797 cd / m 2 The CIE chromaticity coordinates are (x,y )=(0.25, 0.52). The luminance of the light-emitting element 6 was 797 cd / m 2 At the time The voltage, current density, current efficiency, and external quantum efficiency of the cm 2 , 60 cd / A, and 24%. The luminance of the light-emitting element 7 was 810 cd / m 2 The CIE chromaticity coordinates at this time were (x,y) = (0.30,0.61). The luminance of element 7 is 810 cd / m 2 The voltage, current density, current efficiency, and external quantum efficiency are , 3.3V, 1.1mA / cm, respectively 2 , 77cd / A, and 24%.

[0672] As described above, the light-emitting elements 4 to 7 of one embodiment of the present invention can be driven at a low voltage. It was also shown that the carrier balance was good.

[0673] The second compound of the present invention, an organic compound containing a pyrimidine skeleton, has a high electric potential. It has been found that when used in the electron transport layer, a device with low driving voltage can be obtained. It was.

[0674] As shown in Light-emitting Elements 4 to 7, the light-emitting layer contains the second compound of one embodiment of the present invention. and organic compounds containing pyrimidine skeletons, which are highly hole-transporting compounds (PCBNBBs (abbreviation When using a dopant (PCCP) or a PCCP (abbreviation), the electrons and holes are It was found that this can be efficiently injected into the lithium complex, resulting in a highly efficient device with low driving voltage. Ta.

[0675] As shown in the light-emitting element 5, the hole transport layer is made of a material with high hole transport properties (PCCP ) and a material with a high T1 level (mCzFLP (abbreviation)), holes are generated efficiently. The excitation energy injected into the light emitting layer and generated in the light emitting layer is prevented from being transmitted to the hole transport layer. It was found that this could be controlled, resulting in devices with lower driving voltage and higher efficiency.

[0676] Next, the reliability test was carried out on the light-emitting elements 4 and 5. The results of the experiment are shown in FIGS.

[0677] In Figures 93 and 95, the reliability test was performed with an initial luminance of 5000 cd / m 2 The horizontal axis represents the driving time of the element. The vertical axis represents the operating time (h), and the vertical axis represents the normalized brightness (%) when the initial brightness is 100%. From FIG. 95, the normalized luminance of Light-emitting Element 4 after 300 hours was 87%. The normalized luminance of Light-emitting Device 5 after 420 hours was 83%.

[0678] Next, in FIG. 94 and FIG. 96, the measurement method of the reliability test is as follows: initial luminance is 5000 cd / m 2 The time change of the voltage of the light-emitting element 4 and the light-emitting element 5 was measured under the condition of a constant current density. The horizontal axis represents the device operation time (h) and the vertical axis represents the voltage (V). From this, it was confirmed that the increase in voltage over time in the light-emitting elements 4 and 5 was small.

[0679] As described above, it was found that the light-emitting elements 4 and 5 are long-life elements.

[0680] (Reference example 1) The (acetylacetonato)bis(6-tert- butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBupp The synthesis method of [Ir(tBup The structure of [(acac)] (abbreviation) is shown below.

[0681] [ka]

[0682] Step 1: 4-tert-butyl-6-phenylpyrimidine (abbreviation: HtBuppm ) Synthesis First, 22.5 g of 4,4-dimethyl-1-phenylpentane-1,3-dione and formaldehyde were mixed. 50 g of amide was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The reaction solution was refluxed for 5 hours by heating the vessel. Then, the solution was diluted with sodium hydroxide. The resulting organic layer was extracted with dichloromethane, and then washed with water and saturated brine. The solution was washed with water and dried over magnesium sulfate. The dried solution was filtered. After distilling off the solvent, the resulting residue was extracted with hexane:ethyl acetate=10:1 (volume ratio). The pyrimidine derivative HtBup was purified by silica gel column chromatography using the solvent The synthesis scheme of step 1 is shown below (M-1). show.

[0683] [ka]

[0684] Step 2: Di-μ-chloro-bis[bis(6-tert-butyl-4-phenylpyridine] Synthesis of [Ir(tBuppm)2Cl]2 > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the HtBup obtained in step 1 above were added. Add 1.49g of PM, 1.04g of iridium chloride hydrate (IrCl3·H2O) and a reflux condenser. The mixture was placed in a recovery flask equipped with a microwave oven (2. The reaction was carried out by irradiating the mixture with a 45 GHz (100 W) for 1 hour. After distilling off the solvent, the resulting residue The solution was filtered off with suction and washed with ethanol to obtain the binuclear complex [Ir(tBuppm)Cl] ( Yellow-green powder, 73% yield. The synthesis scheme for Step 2 is shown below (M-2).

[0685] [ka]

[0686] Step 3: (acetylacetonato)bis(6-tert-butyl-4-phenylpyridine) Iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]) > Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(t Buppm)2Cl]2 1.61 g, acetylacetone 0.36 g, sodium carbonate 1 0.27g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. Thereafter, the mixture was irradiated with microwaves (2.45 GHz, 120 W) for 60 minutes to cause a reaction. The resulting residue was filtered off with ethanol and washed with water and ethanol. It was dissolved in dichloromethane and then coated with Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531- The solvent was filtered through a filter aid consisting of layers of 16855), alumina, and celite in that order. The solid obtained by distillation was recrystallized in a mixed solvent of dichloromethane and hexane. The target product was obtained as a yellow powder (yield 68%). The synthesis scheme of Step 3 is shown below (M- 3) is shown.

[0687] [ka]

[0688] The yellow powder obtained in step 3 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) The measurement data is shown below. From the measurement results, [Ir(tBuppm)2(acac)] It was found that (abbreviation) was obtained.

[0689] of the obtained material 1 The 1 H NMR data is shown below. 1 H-NMR.δ(CDCl3):1.50(s,18H),1.79(s,6H), 5.26(s,1H),6.33(d,2H),6.77(t,2H),6.85(t, 2H),7.70(d,2H),7.76(s,2H),9.02(s,2H).

[0690] (Reference example 2) The tris[3-methyl-1-(2-methylphenyl)-5-phenylene] used in Example 13 above [Ir(Mpt The synthesis method of [Ir(Mptz1-mp)3]) will be specifically described below. The structure of [mp)3] (abbreviation) is shown below.

[0691] [ka]

[0692] <Step 1: Synthesis of N-(1-ethoxyethylidene)benzamide> First, 15.5 g of ethyl acetimidate hydrochloride, 150 mL of toluene, and triethylamine were mixed. 1.9 g of EtN was placed in a 500 mL three-neck flask and stirred at room temperature for 10 minutes. Add 50 mL of a mixed solution of 17.7 g of benzoyl chloride and 30 mL of toluene to this mixture. The mixture was added dropwise from the dropping funnel and stirred at room temperature for 24 hours. After the predetermined time had elapsed, the reaction mixture was filtered by suction. The solid was filtered and washed with toluene. The obtained filtrate was concentrated to give N-(1-ethoxyethyl) (Decanol)benzamide was obtained (red oil, 82% yield). The synthesis scheme for Step 1 is shown below. The following is shown in (N-1).

[0693] [ka]

[0694] Step 2: 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2 Synthesis of ,4-triazole (abbreviation: HMptz1-mp) Next, 8.68 g of o-tolylhydrazine hydrochloride, 100 mL of carbon tetrachloride, and triethylamine were added. 35 mL of EtN was placed in a 300 mL recovery flask and stirred at room temperature for 1 hour. After a certain time has passed, the mixture is added with N-(1-ethoxyethylidene) obtained in step 1 above. 8.72 g of benzamide was added and stirred at room temperature for 24 hours. Water was added to the mixture, and the aqueous layer was extracted with chloroform. This organic layer was washed with saturated saline and The resulting mixture was gravity filtered, and the filtrate was concentrated to give an oily The oily product was purified by silica gel column chromatography. The solvent used was dichloromethane. The obtained fraction was concentrated to give 3-methyl-1- (2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HM ptz1-mp) was obtained (orange oil, 84% yield). The synthesis scheme for step 2 is shown below. Shown in (N-2).

[0695] [ka]

[0696] Step 3: Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp Synthesis of )3]) Next, 2.71 g of the ligand HMptz1-mp (abbreviation) obtained in step 2 above, tri 1.06 g of bis(acetylacetonato)iridium(III) was added to a reaction vessel equipped with a three-way stopcock. The reaction vessel was purged with argon and heated at 250°C for 48 hours to carry out the reaction. The reaction mixture was dissolved in dichlo...

Claims

1. A pair of electrodes and a light-emitting layer are included, the light-emitting layer includes a guest material, a first organic compound having a pyrimidine skeleton, and a second organic compound that forms an exciplex with the first organic compound; the LUMO level of the first organic compound is −3.5 eV or more and −2.5 eV or less; the guest material is an iridium complex having any one of a pyrimidine skeleton, a pyrazine skeleton, a pyridine skeleton, a quinoline skeleton, a quinoxaline skeleton, and a triazine skeleton; The light-emitting device is one in which the emission spectrum of the exciplex overlaps with the absorption spectrum of the guest material.

2. A pair of electrodes and a light-emitting layer are included, the light-emitting layer includes a guest material, a first organic compound, and a second organic compound that forms an exciplex with the first organic compound; the LUMO level of the first organic compound is −3.5 eV or more and −2.5 eV or less; the first organic compound is an organic compound having at least one of a benzene skeleton, a biphenyl skeleton, a naphthalene skeleton, a carbazole skeleton, a phenanthrene skeleton, a triphenylene skeleton, a dibenzothiophene skeleton, and a dibenzofuran skeleton, and a pyrimidine skeleton; the guest material is an iridium complex having any one of a pyrimidine skeleton, a pyrazine skeleton, a pyridine skeleton, a quinoline skeleton, a quinoxaline skeleton, and a triazine skeleton; The light-emitting device is one in which the emission spectrum of the exciplex overlaps with the absorption spectrum of the guest material.

3. In claim 1 or claim 2, The LUMO level of the guest material is −3.5 eV or more and −2.5 eV or less.

4. In any one of claims 1 to 3, The second organic compound is an organic compound having a carbazole skeleton.

5. In any one of claims 1 to 3, The second organic compound is an organic compound having an amine skeleton.

6. In any one of claims 1 to 5, the T1 level of the first organic compound is higher than the T1 level of the guest material; A light-emitting element in which the T1 level of the second organic compound is higher than the T1 level of the guest material.

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