Organic semiconductor element

Abstract

To provide a light-emitting element having excellent luminous efficiency. A light-emitting element with low driving voltage is provided. A novel compound that can be used for a transport layer, a host material, or a light-emitting material of a light-emitting element is provided.SOLUTION: To provide a new compound containing a benzofuropyrimidine skeleton. A light-emitting element including the compound with the benzofuropyrimidine skeleton between a pair of electrodes is provided.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] With advantages such as thinness and light weight, fast response to input signals, and low power consumption, Lighting devices and display devices use light-emitting elements (organic EL elements) that use organic compounds as light-emitting materials. The development of display devices is accelerating.

[0003] In an organic EL element, a light-emitting layer is sandwiched between electrodes, and when a voltage is applied, light is injected from the electrodes. The electrons and holes recombine to excite the luminescent material, and the excited state is converted to the ground state. The wavelength of light emitted by a luminescent material is unique to that material, and different By using a variety of organic compounds as luminescent materials, luminescence with various wavelengths can be obtained. The element can be obtained.

[0004] In the case of display devices designed to display images, such as monitors, full color To reproduce an image, it is necessary to obtain at least three colors of light: red, green, and blue. In addition, in order to obtain high color rendering, the lighting device is designed to emit light with wavelength components evenly distributed across the visible light range. Ideally, it would be best to obtain light with a wavelength of 2000 keV. In reality, it is best to synthesize two or more types of light with different wavelengths. The light obtained by this method is often used for lighting purposes. It is known that white light with high color rendering properties can be obtained by synthesizing light. are.

[0005] As mentioned earlier, the light emitted by a luminescent material is specific to that material. Important properties of light-emitting elements, such as power consumption and luminous efficiency, are determined only by the material that emits light. It does not depend on the layer other than the light-emitting layer, the device structure, and the relationship between the light-emitting material and the host material. The nature, compatibility, and career balance of the person also have a significant impact. There is no doubt that a wide variety of light-emitting element materials will be required to achieve this. For this reason, materials for light-emitting devices having various molecular structures have been proposed (for example, Patent Document 1 reference).

[0006] By the way, in the light-emitting element using electroluminescence, the generation rate of the excited state is as follows: It is generally known that the triplet excited state is 3, whereas the singlet excited state is 1. and a light-emitting device using a phosphorescent material as a light-emitting material, which can convert triplet excitation energy into light emission. Optical elements are light-emitting elements that use fluorescent materials as light-emitting materials to convert singlet excitation energy into light. In principle, a light-emitting element with higher luminous efficiency can be obtained compared to conventional light-emitting elements.

[0007] Here, the host material in the host-guest type light-emitting layer and the carriers in contact with the light-emitting layer The materials that make up the transport layer are designed to efficiently convert excitation energy into light emission from the luminescent material. The triplet excited state is higher than that of the luminescent material. A substance with a high energy level (energy difference from the singlet ground state) is used.

[0008] However, most of the substances used as host materials for the light-emitting element are fluorescent materials. The triplet excited state in the substance is at a lower energy position than the singlet excited state. For this reason, it is difficult to distinguish between using fluorescent materials and phosphorescent materials that emit light of the same wavelength as the light-emitting material. In comparison with the case where a material with a wider band gap is used as the host material, the latter case It is necessary to use it as such.

[0009] Therefore, in order to efficiently obtain short-wavelength phosphorescence, a very large band gap is required. However, a host material with a high luminous efficiency and a carrier transport material are required. While achieving a good balance between the requirements for important properties of light-emitting elements, such as efficiency, It is difficult to develop a material with a large band gap that can be used as a light-emitting device material. [Prior art documents] [Patent documents]

[0010] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-15933 Summary of the Invention [Problem to be solved by the invention]

[0011] In view of the above, an object of one embodiment of the present invention is to provide a light-emitting element with high emission efficiency. Another object of the present invention is to provide a light-emitting element with low driving voltage. The present invention aims to provide a light-emitting element that emits phosphorescence. It is an object of the present invention to provide a light-emitting element that exhibits color phosphorescence.

[0012] In one embodiment of the present invention, the compound is used as a carrier transport layer, a host material, or a light-emitting material of a light-emitting element. In particular, the present invention aims to provide a novel compound that can emit phosphorescence at wavelengths shorter than green. The present invention provides a novel compound that can be used in light-emitting devices that emit light with excellent characteristics. The goal is to

[0013] In addition, one aspect of the present invention provides a heterocyclic compound having a high triplet excited level (T1 level). In particular, by using the compound semiconductor in a light-emitting element that emits phosphorescence with a wavelength shorter than that of green, An object of the present invention is to provide a heterocyclic compound that enables a light-emitting element with high light efficiency to be obtained.

[0014] Another object of one embodiment of the present invention is to provide a heterocyclic compound having high carrier-transport properties. In particular, it can be used in a light-emitting element that emits phosphorescence with a wavelength shorter than that of green light, and An object of the present invention is to provide a heterocyclic compound that enables a light-emitting element with low voltage to be obtained.

[0015] Another embodiment of the present invention provides a light-emitting element using the heterocyclic compound. The following are the challenges.

[0016] In another embodiment of the present invention, a low-power-consumption display device using the heterocyclic compound is A play module, a lighting module, a light-emitting device, a lighting device, a display device, and an electronic device, respectively The objective is to provide

[0017] The description of these problems does not preclude the existence of other problems. In one embodiment, it is not necessary to solve all of these problems simultaneously. Other issues may become apparent from the description, drawings, claims, etc. be. [Means for solving the problem]

[0018] The above problem is solved by a compound containing a benzofuropyrimidine skeleton and by applying the compound to a light-emitting element. This can be achieved by:

[0019] That is, one embodiment of the present invention is a compound represented by the following general formula (G1).

[0020] [ka]

[0021] In the above general formula (G1), A 1 is a substituted or unsubstituted alkyl group having 6 to 100 carbon atoms. a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryl group; It represents a group having 6 to 100 carbon atoms containing a substituted or unsubstituted heteroaryl group. Ta, R 1 ~R 5 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted a monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic hydrocarbon having 7 to 10 carbon atoms, A saturated hydrocarbon or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Represents.

[0022] Another embodiment of the present invention is a compound represented by the following general formula (G2).

[0023] [ka]

[0024] In the above general formula (G2), R 1 ~R 5 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, alkyl group, substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or unsubstituted Substituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms or substituted or unsubstituted polycyclic saturated hydrocarbons having 6 to 13 carbon atoms In addition, α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. uni represents a skeleton having hole transport properties.

[0025] Another embodiment of the present invention is the above compound, wherein n is 2.

[0026] Another embodiment of the present invention is a compound represented by the following general formula (G3).

[0027] [ka]

[0028] In the above general formula (G3), R 1 ~R 5 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, alkyl group, substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, substituted or unsubstituted substituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted polycyclic saturated hydrocarbons having 6 to 10 carbon atoms 3 represents any one of the aryl groups. uni represents a skeleton having hole transport properties .

[0029] Another aspect of the present invention is the compound described above, wherein Ht uni is substituted or unsubstituted Benzothiophenyl group, substituted or unsubstituted dibenzofuranyl group and substituted or unsubstituted carbazole group The compound is one of the benzoyl groups.

[0030] Another aspect of the present invention is the compound described above, wherein Ht uni is represented by the following general formula (Ht- It is a compound represented by any one of the groups represented by (Ht-1) to (Ht-6).

[0031] [ka]

[0032] In the above general formula, R 6 ~R 15 are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms. or a substituted or unsubstituted phenyl group. 16 carbon number 1 to 6, or a substituted or unsubstituted phenyl group.

[0033] Another aspect of the present invention is the above-mentioned A 1 or a substituted or unsubstituted aryl group representing Carbon atoms of groups containing substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups It is a compound with 6 to 54 carbon atoms in prime numbers.

[0034] Another aspect of the present invention is the above-mentioned A 1 or a substituted or unsubstituted aryl group representing Carbon atoms of groups containing substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups In prime numbers, it is a compound having 6 to 33 carbon atoms.

[0035] Another aspect of the present invention is the compound described above, wherein R 6 ~R 15 is all hydrogen It is a compound.

[0036] Another aspect of the present invention is the compound described above, wherein R 2 and R 4 are both hydrogen It is a mixture.

[0037] Another aspect of the present invention is the compound described above, wherein R 1 ~R 5 are all hydrogen It is a compound.

[0038] Another aspect of the present invention is the compound described above, wherein R 2 , R4 and R 6 ~R 15 but It is a compound that is all hydrogen.

[0039] Another aspect of the present invention is the compound described above, wherein R 1 ~R 15 is all hydrogen It is a compound.

[0040] Another embodiment of the present invention is a compound represented by the following structural formula (100):

[0041] [ka]

[0042] Another embodiment of the present invention is a compound represented by the following structural formula (200):

[0043] [ka]

[0044] Another embodiment of the present invention is a compound represented by the following structural formula (300):

[0045] [ka]

[0046] Another embodiment of the present invention is a compound represented by the following structural formula (115):

[0047] [ka]

[0048] The compound of the present invention may be used as a host material for a light-emitting layer or as a material for a carrier transport layer. It is preferable to use it as such.

[0049] Another embodiment of the present invention is a compound containing the above-described compound as a partial structure.

[0050] Specifically, it is an organometallic complex containing the compound as a ligand.

[0051] Another embodiment of the present invention is a chemical compound having a benzofuropyrimidine skeleton between a pair of electrodes. The light-emitting device includes a compound.

[0052] Another aspect of the present invention is a light-emitting device having a light-emitting layer between a pair of electrodes, the light-emitting layer including at least The light-emitting element also includes a light-emitting substance and a compound having a benzofuropyrimidine skeleton.

[0053] Another embodiment of the present invention is a light-emitting device including a light-emitting layer between a pair of electrodes, the light-emitting layer being iridium. The light-emitting element includes a compound having a benzofuropyrimidine skeleton and a tungsten complex.

[0054] In another aspect of the present invention, a carrier transport layer, specifically, an electron transport layer, is provided between a pair of electrodes. The electron transport layer includes a light-emitting element containing a compound having a benzofuropyrimidine skeleton. He is a child.

[0055] Another embodiment of the present invention is a light-emitting element including a light-emitting layer and an electron-transporting layer between a pair of electrodes. and a light-emitting element containing a compound having a benzofuropyrimidine skeleton in at least one of the electron transport layers. It is an element.

[0056] In another aspect of the present invention, the benzofuropyrimidine skeleton is benzofuro[3,2- d] A light-emitting device having a pyrimidine skeleton.

[0057] In addition, specific compounds having the above benzofuro[3,2-d]pyrimidine skeleton are That's right.

[0058] Another embodiment of the present invention is a display module including the above-described light-emitting element.

[0059] Another embodiment of the present invention is a lighting module including the above-described light-emitting element.

[0060] Another embodiment of the present invention is a light-emitting device including the above light-emitting element and a means for controlling the light-emitting element. It is a device.

[0061] Another embodiment of the present invention is a display device including the light-emitting element in a display portion and a means for controlling the light-emitting element. The display device is provided with:

[0062] Another embodiment of the present invention is a lighting device including the light-emitting element in a lighting portion and a means for controlling the light-emitting element. The lighting device is provided with:

[0063] Another embodiment of the present invention is an electronic device including the above light-emitting element. [Effects of the Invention]

[0064] The light-emitting element according to the present invention is a light-emitting element having good light-emitting efficiency. Furthermore, it is a light-emitting element that emits light in the green to blue range with good luminous efficiency. be.

[0065] The heterocyclic compound according to the present invention has a wide energy gap. Therefore, it is suitable for use in the materials constituting the carrier transport layer of a light-emitting element and in the light-emitting layer. The compound can be suitably used as a host material or a light-emitting material in the organic EL device.

[0066] In another embodiment of the present invention, a low-power-consumption display device using the heterocyclic compound is A play module, a lighting module, a light-emitting device, a lighting device, a display device, and an electronic device, respectively can be provided. [Brief explanation of the drawings]

[0067] [Figure 1] 1 is a conceptual diagram of a light-emitting element. [Figure 2] Conceptual diagram of an organic semiconductor element. [Figure 3] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 4] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 5] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 6] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 7] 1 is a diagram showing an electronic device. [Figure 8] FIG. [Figure 9] FIG. [Figure 10] 10A and 10B illustrate a lighting device and an electronic device. [Figure 11] FIG. 2 is a diagram illustrating an in-vehicle display device and an illumination device. [Figure 12] 1 is a diagram showing an electronic device. [Figure 13] NMR chart of 4mDBTBPBfpm-II. [Figure 14] Absorption and emission spectra of 4mDBTBPBfpm-II. [Figure 15] LC / MS analysis results of 4mDBTBPBfpm-II. [Figure 16] NMR chart of 4mCzBPBfpm. [Figure 17] Absorption and emission spectra of 4mCzBPBfpm. [Figure 18] LC / MS analysis results of 4mCzBPBfpm. [Figure 19] Current density-luminance characteristics of light-emitting element 1. [Figure 20] Voltage-luminance characteristics of light-emitting element 1. [Figure 21] Luminance-current efficiency characteristics of light-emitting element 1. [Figure 22] Luminance-external quantum efficiency characteristics of light-emitting element 1. [Figure 23] Luminance-power efficiency characteristics of light-emitting element 1. [Figure 24] Emission spectrum of light-emitting element 1. [Figure 25] Normalized luminance time change characteristics of light-emitting element 1. [Figure 26] Current density-luminance characteristics of light-emitting element 2. [Figure 27] Voltage-luminance characteristics of light-emitting element 2. [Figure 28] Luminance-current efficiency characteristics of light-emitting element 2. [Figure 29] Luminance-external quantum efficiency characteristics of light-emitting element 2. [Figure 30] Luminance-power efficiency characteristics of light-emitting element 2. [Figure 31] Emission spectrum of light-emitting element 2. [Figure 32] Normalized luminance time change characteristics of light-emitting element 2. [Figure 33] Current density-luminance characteristics of light-emitting element 3. [Figure 34] Voltage-luminance characteristics of light-emitting element 3. [Figure 35] Luminance-current efficiency characteristics of light-emitting element 3. [Figure 36] Luminance-external quantum efficiency characteristics of light-emitting element 3. [Figure 37] Luminance-power efficiency characteristics of light-emitting element 3. [Figure 38] Emission spectrum of light-emitting element 3. [Figure 39] Normalized luminance time change characteristics of light-emitting element 3. [Figure 40] NMR chart of 4mFDBtPBfpm. DETAILED DESCRIPTION OF THE INVENTION

[0068] The following describes the preferred embodiments of the present invention, but the present invention can be embodied in many different ways. and the present invention may be modified in various forms and 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 may be made to the details. The present disclosure should not be construed as being limited to the contents of the preceding paragraph.

[0069] (Embodiment 1) The compound of one embodiment of the present invention described in this embodiment has a benzofuropyrimidine skeleton. Compounds having this skeleton have excellent carrier transport properties (particularly electron transport properties). This makes it possible to provide a light-emitting element with a low driving voltage.

[0070] In addition, the compound can have a high triplet excitation level (T1 level), which allows it to emit phosphorescent light. Specifically, the compound can be suitably used in a light-emitting element using the substance. When the compound has a higher excitation level (T1 level), the excitation energy of the phosphorescent material is transferred to the compound. This allows for the excitation energy to be effectively converted into light emission. A typical phosphorescent material is an iridium complex.

[0071] The benzofuropyrimidine skeleton is specifically benzofuro[3,2-d]pyrimidine. Examples of the amine skeleton include, but are not limited to, the amine skeleton.

[0072] Preferable specific examples of the compound having the benzofuropyrimidine skeleton include compounds represented by the following general formula (G1 ) is indicated.

[0073] [ka]

[0074] A in the formula 1 is a substituted or unsubstituted aryl group having 6 to 100 carbon atoms, A substituted heteroaryl group, or a substituted or unsubstituted aryl group and a substituted or unsubstituted represents a group having 6 to 100 carbon atoms containing a heteroaryl group represented by the formula:

[0075] The aryl group having 6 to 100 carbon atoms is typically represented by the following general formula (A 1 -1)No To(A 1 -6) are examples. The following are merely representative examples, and the number of carbon atoms The aryl group having 6 to 100 carbon atoms is not limited to these.

[0076] [ka]

[0077] R in the formula A1 ~R A6 each has 1 to 4 substituents, and the substituents are each independently hydrogen. a substituted or unsubstituted monocyclic saturated alkyl group having 5 to 7 carbon atoms; Hydrocarbons, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, substituted or It represents any one of unsubstituted aryl groups having 6 to 13 carbon atoms.

[0078] Furthermore, examples of the heteroaryl group or the group containing an aryl group and a heteroaryl group include: Representative examples include the following general formula (A 1 -10) or (A 1 -25) is an example of such a group. The following are just representative examples. 1 are not limited to these examples.

[0079] [ka]

[0080] [ka]

[0081] Also, R 1 ~R 5 are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted Substituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted monocyclic saturated hydrocarbons having 7 to 10 carbon atoms Polycyclic saturated hydrocarbon, substituted or unsubstituted aryl group having 6 to 13 carbon atoms Represents.

[0082] In addition, R 1 ~R 5 Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group. , ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group , tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert- Pentyl, neopentyl, hexyl, isohexyl, sec-hexyl, te rt-hexyl group, neohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2 -ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, etc. Specific examples of the substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms include cyclohexane. Propyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group , 2-methylcyclohexyl group, 2,6-dimethylcyclohexyl group, etc., Specific examples of unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms include decahydronaphthalene, naphthyl group and adamantyl group, and substituted or unsubstituted aryl groups having 6 to 13 carbon atoms. Specific examples of the tolyl group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, and a methyl group. Cityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, Examples include a 2-naphthyl group, a fluorenyl group, and a 9,9-dimethylfluorenyl group.

[0083] R 1 ~R 5 When these have a substituent, the substituent may have 1 or more carbon atoms. The group is assumed to be a group that does not significantly change the properties, such as alkyl groups of 1 to 3.

[0084] Further, regarding the benzofuropyrimidines described in this embodiment, more preferred specific examples include can be represented by the following general formula (G2).

[0085] [ka]

[0086] In the formula, R 1 ~R 5 Regarding the above, R in general formula (G1) 1 ~R 5 It is the same as Therefore, redundant description will be omitted. 1 ~R 5 Please refer to the description of I want to be.

[0087] In the general formula (G2), α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. When α has a substituent, the substituent has 1 to 10 carbon atoms. The group is assumed to be a group that does not significantly change the properties of the compound, such as the alkyl group in 3. .

[0088] In addition, Ht uni The interaction between the benzofuropyrimidine skeleton and the benzofuropyrimidine skeleton is suppressed, resulting in a high triplet excited state. In order to maintain the T1 level, n is preferably 1 or more, and the thermal properties are improved. In order to improve the stability of the molecule, n is preferably 2. Furthermore, when n is 2, In this case, the divalent group represented by α and n is a 1,1'-biphenyl-3,3'-diyl group. It is preferable.

[0089] In addition, in the general formula (G2), Ht uni represents a skeleton with hole transport properties. uni In order to maintain a high triplet excited level (T1 level), substituted or unsubstituted dibenzofurans are a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazo In addition, when these have a substituent, the substituent is preferably is assumed to be a group that does not significantly change the properties, such as an alkyl group having 1 to 3 carbon atoms. There are.

[0090] Ht uni Specific examples include those represented by the following general formulas (Ht-1) to (Ht-6): The group Ht is easy to synthesize and is a preferred example. uni The following example It is not limited to.

[0091] [ka]

[0092] R 6 ~R 15 are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted represents one of the substituted phenyl groups. 16 is an alkyl group having 1 to 6 carbon atoms; It represents either a substituted or unsubstituted phenyl group. When these have a substituent, The substituent is preferably an alkyl group having 1 to 3 carbon atoms, which does not significantly change the properties of the compound. We are assuming a low base.

[0093] In addition, the group represented by any one of the above general formulas (Ht-1) to (Ht-6) may be Ht un i The compound of one embodiment of the present invention having the formula: This is a preferred structure because it has hole transport properties. -6) acts as an electron donor moiety when combined with a benzofuropyrimidine skeleton. (benzofuropyrimidine acts as an electron acceptor site) and thus the charge transport in the membrane When focusing on the transportability, a group represented by any one of general formulas (Ht-1) to (Ht-6) Ht uni The compound of one embodiment of the present invention having the formula (I) is conductive in the bulk and has a carrier property at the interface. By improving the injection properties of each of these, low voltage driving becomes possible, and thus the light emitting device can be This is a preferable material configuration.

[0094] In addition, R in the groups represented by the above general formulae (Ht-1) to (Ht-6) 6 ~R 15 but The all-hydrogen structure is a preferred structure because it is easy to obtain raw materials and synthesize the structure. do.

[0095] For the same reason, in the compound represented by the general formula (G2), R 2 and R 4 and R are preferably hydrogen atoms. 1 ~R 5 All hydrogen More preferably,

[0096] Representative examples of the above-mentioned compounds are shown below. The compounds described in this embodiment are as follows: The examples below are not limiting.

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] The above-described compound of one embodiment of the present invention has excellent carrier-transport properties and therefore This makes it possible to provide a light-emitting device with a low driving voltage. Furthermore, the compound according to one embodiment of the present invention has a high triplet excitation level (T1 level). Therefore, a phosphorescent light emitting device with high luminous efficiency can be obtained. Even in phosphorescent light-emitting devices having an emission peak on the shorter wavelength side, it is possible to obtain light-emitting devices having good luminous efficiency. It is possible to provide optical elements. In addition, if the triplet excitation level (T1 level) is high, This also means that it has a wide band gap, and therefore exhibits blue fluorescence. The light emitting element can also be made to emit light efficiently.

[0102] Next, a method for synthesizing the compound represented by the above general formula (G1) will be described.

[0103] The compound represented by general formula (G1) can be synthesized by the following simple synthesis scheme: For example, as shown in the following synthesis scheme (a), the halogenation of a benzofuropyrimidine derivative can be The compound (A1) is a compound having an aryl group, a heteroaryl group, or an aryl group and a heteroaryl group. A is a group containing a group 1 The compound (A2) can be obtained by reacting the compound (A2) with the boronic acid compound (A3). In the formula, X represents a halogen element, and B represents a boronic acid, a boronic acid ester, or a cyclic In addition to lithium salts, cyclic triol borate salts also include potassium salts. A hydroxyl group salt or a sodium salt may also be used.

[0104] [ka]

[0105] In the synthesis scheme (a), R 1 ~R 5 are each independently hydrogen or a group having 1 to 6 carbon atoms. alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted is an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 6 to 10 carbon atoms, represents any one of 13 aryl groups.

[0106] In addition, boronic acid compounds of benzofuropyrimidine derivatives and A 1 Reacting with halogen compounds That's fine.

[0107] Since various types of the above-mentioned compounds (A1) and (A2) can be synthesized, the compounds represented by the general formula (G1) Therefore, the compound of the present invention can be synthesized in a large number of types. is characterized by a wide variety of options.

[0108] An example of a method for synthesizing a compound according to one embodiment of the present invention has been described above. However, the synthesis is not limited to this, and any other synthesis method may be used.

[0109] In addition, a compound including the compound described in this embodiment as a partial structure is also one embodiment of the present invention. Such compounds include, for example, organometallic complexes containing the structure as a ligand. Examples include:

[0110] That is, the compound contains a compound having a benzofuropyrimidine skeleton as a partial structure. The partial structure can be represented by the following general formula (G1).

[0111] [ka]

[0112] In the above general formula (G1), R 1 ~R 5 is the R mentioned in the above explanation. 1 ~R 5 Since the configuration is the same as that of the first embodiment, repeated explanation will be omitted.

[0113] Also, in the formula, A 1 is a substituted or unsubstituted aryl group having 6 to 100 carbon atoms, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryl group and a substituted or unsubstituted represents a group having 6 to 100 carbon atoms containing an unsubstituted heteroaryl group. 1 To use as Specific examples of groups that can be bonded to the aryl group are described in the explanation of the general formula (G1) above, so Abbreviated.

[0114] In addition, when the compound containing the partial structure represented by the above general formula (G1) is an organometallic complex, If iridium or platinum is used as the central metal, it can also be used as a phosphorescent material. is.

[0115] (Embodiment 2) In this embodiment, the compound represented by the following general formula (G1) described in Embodiment 1 is used as an organic The active layer of a vertical transistor (static induction transistor: SIT), a type of semiconductor element, Examples of forms in which it can be used are shown below.

[0116] [ka]

[0117] The structure of the element is as shown in Figure 2, which is a thin film containing a compound represented by general formula (G1) The active layer 1202 is sandwiched between a source electrode 1201 and a drain electrode 1203, and a gate electrode The gate electrode 1204 is embedded in the active layer 1202. The source electrode 1201 and the drain electrode 1202 are electrically connected to a means for applying a voltage. The source electrode 1203 is electrically connected to a means for controlling the voltage between the source and drain. It is being done.

[0118] In such a device structure, when no gate voltage is applied, the source-drain When a voltage is applied between them, current flows (the device is in the ON state). When voltage is applied, a depletion layer is generated around the gate electrode 1204, and current stops flowing (OFF (The state is changed to "transistor state"). The above mechanism allows it to function as a transistor.

[0119] In vertical transistors, similar to light-emitting devices, it is necessary to develop a material that has both carrier transport properties and good film quality. The active layer requires a material with the above properties, and the compound represented by general formula (G1) satisfies these conditions. It satisfies the requirements and can be used favorably.

[0120] (Embodiment 3) In this embodiment, one mode of a light-emitting element having a compound including a benzofuropyrimidine skeleton is described. This will be explained below with reference to FIG. 1(A).

[0121] The light-emitting element in this embodiment has a plurality of layers between a pair of electrodes. The light-emitting element includes a first electrode 101, a second electrode 102, and a light-emitting element including the first electrode 101 and the second electrode 102. The electrode 102 is connected to the EL layer 103. The first electrode 101 functions as an anode, and the second electrode 102 functions as a cathode. That is, the first electrode 101 has a higher potential than the second electrode 102. As shown in FIG. 1, when a voltage is applied between the first electrode 101 and the second electrode 102, light is emitted. Of course, the first electrode acts as a cathode and the second electrode acts as an anode. In this case, the stacking order of the EL layers is reversed from that described below. In the light-emitting element of this embodiment, benzopropyl ether is used in any of the layers of the EL layer 103. It is sufficient that the compound contains a compound having a benzofuropyrimidine skeleton. The layer containing the compound having the above-mentioned property is a light-emitting layer or an electron transport layer. This is preferable because it is possible to obtain a light-emitting element with good characteristics.

[0122] The electrode that functions as the anode is gold, which has a large work function (specifically, 4.0 eV or more). It is preferable to use metals, alloys, conductive compounds, and mixtures thereof. For example, indium tin oxide (ITO) , indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-oxide Examples include zinc oxide, 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 sol-gel deposition. For example, indium oxide-zinc oxide can be produced by applying the indium oxide method. A target containing 1 wt% to 20 wt% zinc oxide was used for sputtering. The film can be formed by a deposition method. Indium oxide (IWZO) is made by mixing 0.5 wt. of tungsten oxide with indium oxide. % or more and 5 wt% or less, and zinc oxide 0.1 wt% or more and 1 wt% or less. It can be formed by sputtering. , Nickel (Ni), Tungsten (W), Chromium (Cr), Molybdenum (Mo), Iron ( Nitrides of Fe, Cobalt (Co), Copper (Cu), Palladium (Pd), or metallic materials (For example, titanium nitride) etc. Graphene may also be used.

[0123] The stacked structure of the EL layer 103 is not particularly limited, and may be a layer containing a substance with high electron transport properties or a layer containing a material with high electron transport properties. a layer containing a substance with high hole transporting properties, a layer containing a substance with high electron injecting properties, a layer containing a substance with high hole injecting properties, A layer containing a material, a layer containing a bipolar material (a material with high electron and hole transport properties), a layer containing a carrier In this embodiment, the EL The layer 103 is made up of a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, and a cathode layer 114, from the electrode side that functions as an anode. The light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115 are laminated in this order. The materials constituting each layer are specifically described below.

[0124] The hole injection layer 111 is a layer containing a hole injection material. Ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPC) are also available. Phthalocyanine compounds, 4,4'-bis[N-(4-diphenylaminophenyl)- N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3 -methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl aromatic amine compounds such as diamine (diamino)-4,4'-diamine (abbreviation: DNTPD), or poly( Ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. The hole injection layer 111 can also be formed from such polymers.

[0125] In addition, as the hole-injection layer 111, a material having a hole-transporting property is used. It is also possible to use a composite material containing a substance that exhibits electron-accepting properties (hereinafter simply referred to as an electron-accepting substance). In this specification, a composite material simply means a material in which two materials are mixed. Instead, by mixing multiple materials, charge can be transferred between the materials. This charge transfer is only possible when an electric field is applied. This also includes cases where

[0126] In addition, by using a composite material in which an electron-accepting substance is contained in a substance having hole transport properties, This makes it possible to select the material for forming the electrode regardless of the work function of the material. Therefore, the electrode that functions as the anode should be made of a material with a large work function as well as a material with a small work function. Materials such as 7,7,8,8-tetramethyl-2-methyl-1,2,3,4-trimethyl-1,2,4,5-trimethyl-1,2,3 ... tetrafluoroquinodimethane (abbreviation: F4-TCNQ), Examples of the oxides include loranil. Transition metal oxides can also be used. Oxides of metals belonging to groups 4 to 8 of the periodic table can be suitably used. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide Rhenium oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferred because of their high electron accepting properties. Among these, molybdenum oxide is particularly stable in the atmosphere, has low hygroscopicity, and is easy to handle, making it suitable for use in electrical appliances. It can be suitably used as a denaturant-receptive substance.

[0127] The hole transporting substance used in the composite material includes aromatic amine compounds, carbazole compounds, and the like. compounds, aromatic hydrocarbons, polymeric compounds (oligomers, dendrimers, polymers, etc.) Various organic compounds can be used, such as: is preferably an organic compound with high hole transporting properties. -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. Other materials may be used as long as they have high transport properties. Specific examples of organic compounds that can be used as a substance having hole transport properties in the .

[0128] For example, the aromatic amine compound is N,N'-di(p-tolyl)-N,N'-diphenyl Phenyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N-(4- Diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N ,N'-Bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl Phenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), 1,3 ,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), etc.

[0129] Specific examples of carbazole compounds that can be used in the composite material include 3-[N- (9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol 3,6-bis[N-(9-phenylcarbazole-3 -yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) , 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino] -9-phenylcarbazole (abbreviation: PCzPCN1), etc.

[0130] Other carbazole compounds that can be used in composite materials include 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-carbazole (abbreviation: CzPA), 1,4-bis[ 4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. You can be there.

[0131] In addition, examples of aromatic hydrocarbons that can be used in the composite material include 2-tert -butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2- tert-Butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3, 5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9 ,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,1 0-Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene 2-tert-butylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAn th), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) , 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7- Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl 9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,1 0'-Diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) 10,10'-bis[(2,3,4,5,6-pentafluorophenyl)-9,9'-bianthryl, (phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. In addition, pentacene, coronene, etc. can also be used. -6 cm 2 / Vs or more and aromatic hydrocarbons with carbon numbers of 14 to 42 are used. It is more preferable that

[0132] The aromatic hydrocarbons that can be used in the composite material may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2- Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2- diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), and the like.

[0133] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl ether) Nylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. can.

[0134] The hole transport layer 112 is a layer containing a substance having a hole transport property. As a material, a material having hole transport properties that can be used as the above-mentioned composite material can be mentioned. The above can be used in the same way. Please refer to the description of the composite material. The hole transport layer may contain a compound having a skeleton.

[0135] The light-emitting layer 113 is a layer containing a light-emitting material. The light-emitting layer 113 is made of a film of a light-emitting material alone. The light-emitting element may be composed of a film in which a light-emitting substance is dispersed in a host material, or may be composed of a film in which a light-emitting substance is dispersed in a host material.

[0136] In the light-emitting layer 113, there is no particular limitation on the material that can be used as the light-emitting substance. The light emitted by these materials may be either fluorescent or phosphorescent. For example, the following fluorescent substances are listed: N,N'-bis[4-(9 -phenyl-9H-fluoren-9-yl)phenyl]-N,N'-diphenylpyrene- 1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis[4-(9H-cal (bazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine YGA2S, 4-(9H-carbazol-9-yl)-4'-(10-phenyl)- 4-(9H-carbamoyl-9-anthryl)triphenylamine (abbreviation: YGAPA), (9,10-diphenyl-2-anthryl)triphenyl amine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9 -anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), Rylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4 -(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert- Butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N' -triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl Phenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-chlor 2PCAPPA, N-[4-(9,10-diphenyl- 2-Anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenedia Min (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N''',N' ''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, 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 Phenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10 -diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylene Diamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2- N,N',N'-triphenyl-1,4-phenylenediamine 9,10-bis(1,1'-biphenyl-2-yl)- N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene- 2-Amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9- Amine (abbreviation: DPhAPhA) Coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)- 6,11-Diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethyl Amino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedi Nitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetramethyl- Hydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran -4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetramethylpropanedinitrile Kis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) , 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acetate Naphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD) , 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6, 7-Tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4 H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-te rt-Butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro- 4H-pyran-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl 4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[ 4-(Dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propane Dinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1 ,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij] Quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (Abbreviation: BisDCJTM), N,N'-bis[4-(9-phenyl-9H-fluorene -9-yl)phenyl]-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1, 6FLPAPrn) and blue phosphorescent materials include tris{2-[5-(2 -methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazo {Ir(mp)}(3-yl-κN2)phenyl-κC}iridium(III) (abbreviation: [Ir(mp) ptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4 -triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4 -(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazo 4H, such as [Ir(iPrptz-3b)3]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) -triazole-based organometallic iridium complexes and tris[3-methyl-1-(2 -methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(I II) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl -3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [I Organometallic iridium compounds with a 1H-triazole skeleton, such as [(Prpttz1-Me)3], complexes and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl [Ir-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) , tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenyl [Ir(dmpimpt-Me)3] Organometallic iridium complexes with imidazole skeletons, such as bis[2-(4',6' (difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1 -pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl) Nyl)pyridinato-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpi c) Bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N ,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pi c)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]stomach Electron-withdrawing groups such as lithium(III) acetylacetonate (abbreviated as FIracac) An example of an organometallic iridium complex is a phenylpyridine derivative having the following structure as a ligand. In addition, organometallic iridium complexes with a 4H-triazole skeleton have been shown to be highly reliable and highly efficient. Furthermore, an example of a green phosphorescent material is tris(4-methyl-6 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [I r(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpiperidinyl) Iridium(III) (abbreviation: [Ir(mppm)2(acac)]), ( Acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridine Ir(tBuppm)2(acac) (Ir(tBuppm)2(acac)), (acetylacetonate Nato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(II I) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[ 5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(I II) (Abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bi Bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm Organometallic iridium complexes with pyrimidine skeletons such as (a)2(acac)]) Cetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(I II) (Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonate) Bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes and tris(2-phenylpyridinato-N,C 2’ )iridium (III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac )]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate ( Abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinato)iridine Ir(bzq)3), tris(2-phenylquinolinato-N ,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinoxadiene) Norinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(p In addition to organometallic iridium complexes with a pyridine skeleton, such as q) 2(acac)]), Tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [ Examples of rare earth metal complexes include pyridinium phosphate (Tb(acac)3(Phen)]). Organometallic iridium complexes with an iridium skeleton are highly reliable and highly efficient. Therefore, it is particularly preferred. An example of a red phosphorescent material is (diisobutyrylmethanato)bis[4, 6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir( 5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl dinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm )2(dpm)]), bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipyr Valoylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)] ) and organometallic iridium complexes with pyrimidine skeletons such as (acetylacetonato) Bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(t ppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivalo Ir(tppr)2(dpm)), ( Acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]i Pyrazine skeletons such as rhodium(III) (abbreviation: [Ir(Fdpq)2(acac)]) Organometallic iridium complexes and tris(1-phenylisoquinolinato-N,C 2 ’ ) Iridium (III ) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)] In addition to organometallic iridium complexes with pyridine skeletons such as 2,3,7,8,12, 13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: Platinum complexes such as PtOEP and tris(1,3-diphenyl-1,3-propanediol). Nato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3( Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate ](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Ph en)]) are examples of rare earth metal complexes. The iridium complexes of the group Ir are particularly preferred because they are remarkably excellent in reliability and luminous efficiency. Organometallic iridium complexes with a pyrazine skeleton can emit red light with good chromaticity, By applying it to a white light emitting device, the color rendering properties can be improved. Compounds with an amine skeleton also emit light in the blue to ultraviolet range, making them suitable as light-emitting materials. Compounds having a benzofuropyrimidine skeleton may also be used.

[0137] In addition to the substances mentioned above, various substances may be selected.

[0138] The host material for dispersing the light-emitting substance includes a compound having a benzofuropyrimidine skeleton. It is preferable to use

[0139] Compounds with a benzofuropyrimidine skeleton have a wide band gap and high triplet excitation. Because it has a T1 level, it can emit blue light and colors between green and blue. Particularly as a host material for dispersing luminescent materials that emit high-energy light, such as phosphorescent materials. Of course, fluorescent materials that emit fluorescence at wavelengths longer than blue, and green It can also be used as a host material to disperse phosphorescent substances that emit phosphorescence with wavelengths longer than that of the In addition, since the compound has high carrier transport properties (especially electron transport properties), the driving voltage It is possible to realize a light emitting device with a small luminance.

[0140] In addition, the compound having a benzofuropyrimidine skeleton is used in the carrier transport layer ( Preferably, it is also effective to use the compound as a material for constituting the electron transport layer. The blue light-emitting material has a band gap or a high triplet excitation level (T1 level). Even if the material exhibits high-energy luminescence, such as fluorescent light or green to blue phosphorescence, and to efficiently transfer the energy of carriers recombined in the host material to the light-emitting material. This makes it possible to manufacture a light-emitting element with high luminous efficiency. When the compound is used as a host material or a material constituting a carrier transport layer, the compound is preferably used as a light-emitting material. The band gap is narrower than that of the compound, or the singlet excited level (S1 level) or triplet excited level It is preferable to select a material with a low starting level (T1 level), but this is not a limitation. .

[0141] When a compound having a benzofuropyrimidine skeleton is not used as the host material, Examples of materials that can be used are listed below.

[0142] As a material with electron transport properties, bis(10-hydroxybenzo[h]quinolinato)benzyl Lilium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4- Phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinol) bis[2-(2-benzoxazolyl)phenol]( ... [2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnPBO) and metal complexes such as 2-(4-biphenylyl)- 5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD ), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butyl) 1,3,4-oxadiazol-2-yl)benzene (abbreviation: OXD- 7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl ]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzene (1-phenyl-1H-benzimidazole) (TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzo Heterocyclization of polyazole skeletons such as imidazole (abbreviation: mDBTBIm-II) compounds and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]ky Noxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene- 4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBT BPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3- yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[ 3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm ), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6 Heterocyclic compounds with diazine skeletons such as mDBTP2Pm-II) and 3,5-bis[ 3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) , 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) Among the above, heterocyclic compounds having a pyridine skeleton, such as Heterocyclic compounds having a pyridine skeleton and heterocyclic compounds having a pyridine skeleton are preferred because of their high reliability. In particular, heterocyclic compounds with a diazine (pyrimidine or pyrazine) skeleton have electron transport properties. The above-mentioned benzofuropyrimidine structure has high conductivity and contributes to reducing the driving voltage. The compound has a relatively large electron transporting property and is classified as a material having electron transporting property.

[0143] In addition, examples of materials having hole transport properties that can be used as the host material include: ,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB ), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl] phenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9, 9'-Bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) , 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation Name: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)trimethylsilyl Phenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'- Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenyla PCBBi1BP, 4-(1-naphthyl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di (1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl PCBNBB, 9,9-dimethyl-N-phenyl-N-[4-(9 -phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviated : PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3- (phenyl)spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF) Compounds with aromatic amine skeletons such as 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3 ,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzT P), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), etc. Compounds with a carbazole skeleton and 4,4',4''-(benzene-1,3,5-trimethylsilyl) yl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl- 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene DBTFLP-III, 4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Compounds with thiophene skeletons and 4,4',4''-(benzene-1,3,5-thiazolinone) 4-[3-[3-(9- (phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: Examples of compounds having a furan skeleton include compounds having a furan skeleton such as furan dimers (mmDBFFLBi-II). However, compounds with aromatic amine skeletons and compounds with carbazole skeletons are not reliable. Furthermore, it has a high hole transporting property and contributes to reducing the driving voltage, which is preferable.

[0144] When the light-emitting substance is a phosphorescent substance, the host material is a triplet excited state of the phosphorescent substance. Select a substance with a triplet excitation level (T1 level) greater than the fluorescence level (T1 level) and In the case of a substance, it is preferable to select a substance having a larger band gap than the fluorescent substance. The light-emitting layer may contain a third material in addition to the host material and the phosphorescent material.

[0145] Here, when a phosphorescent material is used, in order to obtain a light-emitting element with higher luminous efficiency, Consider the energy transfer between the material and the phosphorescent material. The recombination of carriers occurs in the host material. Since the emission occurs in both the host material and the phosphorescent material, the emission efficiency can be improved by It is necessary to make the energy transfer to quality more efficient.

[0146] Two mechanisms have been proposed for the energy transfer from the host material to the phosphorescent material. The first mechanism is the Küster mechanism, and the second is the Förster mechanism. Each mechanism will be explained below. Here, the molecule that provides the excitation energy is called the host molecule, and the molecule that receives the excitation energy is called the host molecule. The child is referred to as the guest molecule.

[0147] <Förster mechanism (dipole-dipole interaction)> The Förster mechanism does not require direct contact between molecules for energy transfer. Energy transfer occurs through the resonance phenomenon of dipole vibration between the molecule and the guest molecule. The host molecule transfers energy to the guest molecule through the vibrational resonance phenomenon, and the host molecule The guest molecule enters the excited state. The rate constant of the Förster mechanism is k h * →g of This is shown in equation (1).

[0148]

number

[0149] In formula (1), ν represents the frequency, and f' h (ν) is the normalized Emission spectrum (fluorescence spectrum when discussing energy transfer from singlet excited states, When discussing energy transfer from triplet excited states, it represents the phosphorescence spectrum, and ε g (ν ) represents the molar extinction coefficient of the guest molecule, N represents Avogadro's number, and n represents the refractive index of the medium. represents the rate of excitation, R represents the intermolecular distance between the host molecule and the guest molecule, and τ represents the measured excitation state. represents the lifetime of the state (fluorescence lifetime or phosphorescence lifetime), c represents the speed of light, and φ represents the luminescence quantum yield (single When discussing energy transfer from single excited states, the fluorescence quantum yield is used, and when discussing energy transfer from triplet excited states, the fluorescence quantum yield is used. When discussing energy transfer, it represents the phosphorescence quantum yield, and K 2 is the ratio of the host molecule and the guest molecule This is a coefficient (0 to 4) that represents the orientation of the transition dipole moment. In the case of random orientation, K 2 =2 / 3.

[0150] Dexter mechanism (electron exchange interaction) The Dexter mechanism occurs when the host and guest molecules approach the effective contact distance where orbital overlap occurs. The energy is transferred through the exchange of electrons of the excited host molecule and the ground state guest molecule. -Transfer occurs. The rate constant of the Dexter mechanism is k h * →g is shown in equation (2).

[0151]

number

[0152] In equation (2), h is Planck's constant, and K is a constant with the dimension of energy. where ν represents the frequency and f' h (ν) is the normalized emission spectrum of the host molecule (When discussing energy transfer from the singlet excited state, the fluorescence spectrum, triplet excited state represents the phosphorescence spectrum when discussing energy transfer from g (ν) is a guest represents the normalized absorption spectrum of the molecule, L represents the effective molecular radius, and R represents the effective molecular radius of the host molecule. Represents the intermolecular distance between the child and guest molecules.

[0153] Here, the energy transfer efficiency from the host molecule to the guest molecule φ ET is expressed by equation (3). k r is the emission process (fluorescence when discussing energy transfer from a singlet excited state, triplet When discussing energy transfer from a single excited state, k represents the rate constant of phosphorescence, and k n is non represents the rate constant of the luminescence process (thermal deactivation and intersystem crossing), and τ represents the lifetime of the excited state measured. vinegar.

[0154]

number

[0155] First, from equation (3), the energy transfer efficiency Φ ET To increase the The rate constant k h * →g , other competing rate constants k r +k n (=1 / τ) The rate constant of the energy transfer, k h * →g Large In order to achieve this, from equations (1) and (2), the Förster mechanism and the Dexter mechanism In both of these mechanisms, the emission spectrum of the host molecule (energy from the singlet excited state) When discussing energy transfer, consider the fluorescence spectrum and energy transfer from triplet excited states. In this case, it is better to have a large overlap between the absorption spectrum of the guest molecule and the phosphorescence spectrum of the guest molecule. You can see that.

[0156] Here, we consider the overlap between the emission spectrum of the host molecule and the absorption spectrum of the guest molecule. In the absorption spectrum of the guest molecule, the absorption band at the longest wavelength (lowest energy) side is overlapped. It is essential.

[0157] In this embodiment, a phosphorescent compound is used as the guest material. In tors, the absorption band that is thought to contribute most strongly to luminescence is the triplet band from the ground state. It is near the absorption wavelength corresponding to the direct transition to the excited state, and it is the absorption that appears on the longest wavelength side. This indicates that the emission spectrum (fluorescence spectrum and phosphorescence spectrum) of the host material It is preferable that the absorption band of the phosphorescent compound overlaps with the absorption band on the longest wavelength side of the absorption spectrum of the phosphorescent compound. It is thought that this is the case.

[0158] For example, in organometallic complexes, especially in luminescent iridium complexes, the longest wavelength absorption band is In many cases, a broad absorption band appears around 500 to 600 nm. Mainly, triplet MLCT (Metal to Ligand Charge Transfer) However, this absorption band is due to the triplet π-π transition. * Transition or singlet MLCT This includes some absorption due to transitions, and these overlap to form the absorption spectrum at the longest wavelength side. It is thought that a broad absorption band is formed. Therefore, it is considered that the guest material is an organometallic complex. When using complexes (especially iridium complexes), the broad spectrum at the longest wavelength is It is preferable that the absorption band of the host material largely overlaps with the emission spectrum of the host material.

[0159] First, let us consider the energy transfer from the triplet excited state of the host material. From the theory, in the energy transfer from the triplet excited state, the phosphorescence spectrum of the host material It is sufficient that the overlap between the absorption band of the guest material on the longest wavelength side and the absorption band of the guest material is large.

[0160] However, the problem here is the energy from the singlet excited state of the host molecule. In addition to the energy transfer from the triplet excited state, the energy transfer from the singlet excited state From the above discussion, if we want to efficiently transfer electrons, we must consider not only the phosphorescence spectrum of the host material but also the Furthermore, the fluorescence spectrum must be designed to overlap with the longest wavelength absorption band of the guest material. In other words, the fluorescent spectrum of the host material must be similar to the phosphorescent spectrum. Unless the host material is designed to be at such a position, the singlet excited state and triplet excited state of the host material will not be This means that energy transfer from both the excited doublet states cannot be performed efficiently. do.

[0161] However, in general, the S1 level and the T1 level are significantly different (S1 level > T1 level). The emission wavelength of light and the emission wavelength of phosphorescence are also significantly different (emission wavelength of fluorescence < emission wavelength of phosphorescence). For example, 4,4'-di(N-carbazone) is often used in light-emitting devices using phosphorescent compounds. CBP has a phosphorescence spectrum around 500 nm. On the other hand, the fluorescence spectrum is around 400 nm, which is a difference of 100 nm. From this perspective, the fluorescence spectrum of the host material is in a similar position to the phosphorescence spectrum. It is extremely difficult to design a host material that exhibits such a property.

[0162] In addition, since the S1 level is higher than the T1 level, the fluorescence spectrum is at the longest wavelength side of the guest material. The T1 level of the host material at a wavelength close to the absorption spectrum of the guest material is It falls below level 1.

[0163] Therefore, when a phosphorescent material is used as a light-emitting material, the light-emitting layer contains a host material, a light-emitting material, and The third substance is included, and the host material and the third substance are in the form of an exciplex (also called an exciplex). It is preferable that the combination forms a compound represented by the formula (II).

[0164] In this case, the carriers (electrons and holes) in the light-emitting layer recombine with the host material. The substance 3 forms an exciplex. The fluorescence spectrum of the exciplex is similar to that of the host material alone and The emission spectrum has a longer wavelength side than the fluorescence spectrum of the third substance alone. The T1 levels of the first and third materials are kept higher than the T1 level of the guest material. This maximizes the energy transfer from the excited state. Since the S1 level and the S2 level are close to each other, the fluorescence spectrum and the phosphorescence spectrum are almost the same. This means that the guest molecule can be converted from its singlet ground state to its triplet excited state. The absorption corresponding to the transition (the block that exists on the longest wavelength side in the absorption spectrum of the guest molecule) The fluorescence and phosphorescence spectra of the exciplex are largely overlapped on the Therefore, a light-emitting element with high energy transfer efficiency can be obtained.

[0165] The third substance can be any of the above-mentioned host materials and additives. The host material and the third substance may be materials that generate an exciplex. However, it is necessary to combine a compound that easily accepts electrons (a compound with electron transport properties). It is possible to combine a compound that easily accepts holes (a compound that has hole transport properties) with the compound. preferable.

[0166] The host material and the third substance are composed of a compound with electron transport properties and a compound with hole transport properties. When the mixture is made of a polyimide, the carrier balance can be controlled by the mixture ratio. The ratio of the host material to the third substance (or additive) is preferably in the range of 1:9 to 9:1. In this case, the light-emitting layer in which one type of light-emitting material is dispersed is divided into two layers, and the host material and the third material are mixed. This allows the carrier balance of the light emitting element to be optimized. In addition, one of the light-emitting layers can be made of a hole transport material, which can improve the lifetime. The other light-emitting layer may be an electron-transporting layer.

[0167] When the light-emitting layer having the above-mentioned structure is made of a plurality of materials, it can be formed by vacuum deposition. Co-evaporation of the above, or mixed solution using inkjet method, spin coating method, dip coating method, etc. It can be prepared using

[0168] The electron transport layer 114 is a layer containing a substance having an electron transport property. Tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Alq), tris(4-methyl-8-quinolinolato) ) Aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato ) Beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenyl quinoline or benzoquinoline skeletons, such as (BAlq) The layer is made of a metal complex having a phosphorus skeleton. Bis[2-(2-phenyl)benzoxazolato]zinc (abbreviation: Zn(BOX)2), oxazolamides such as hydroxyphenyl)benzothiazolato]zinc (abbreviated as Zn(BTZ)2) Metal complexes having azole or thiazole ligands can also be used. In addition to the metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)- 1,3,4-oxadiazole (abbreviated as PBD) and 1,3-bis[5-(p-tert -butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OX D-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) nyl)-1,2,4-triazole (abbreviation: TAZ), bathophenanthroline (abbreviation: B Phen), vasocuproine (abbreviated as BCP), etc. can also be used. The substances that were found were 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 for the electron transport layer as long as it has a higher electron transporting property than the above-mentioned substances. No.

[0169] In addition, a compound having a benzofuropyrimidine skeleton is used as a material for forming the electron transport layer 114. The compound having a benzofuropyrimidine skeleton has a wide band gap. Since it is a material with a high triplet excitation level (T1 level), the excitation energy in the light-emitting layer is Effectively preventing migration to the electron transport layer 114 and suppressing the resulting decrease in luminous efficiency Therefore, it is possible to obtain a light-emitting element with high luminous efficiency. The compound having the formula (I) has excellent carrier transport properties and therefore provides a light-emitting element with a low driving voltage. This becomes possible.

[0170] The electron transport layer may be not only a single layer, but also a laminate of two or more layers made of the above-mentioned materials. It may also be something.

[0171] Furthermore, a layer for controlling the movement of electron carriers may be provided between the electron transport layer and the light emitting layer. This is achieved by adding a small amount of a substance with high electron trapping properties to a material with high electron transport properties as described above. It is a layer that adjusts the carrier balance by suppressing the movement of electron carriers. This type of structure prevents electrons from penetrating the light-emitting layer. This is highly effective in suppressing problems that arise (for example, a reduction in the device life).

[0172] In addition, the host material of the light-emitting layer and the material constituting the electron transport layer share a common skeleton. This allows smoother carrier movement and reduces the driving voltage. Furthermore, the host material and the material constituting the electron transport layer can be the same material. It is highly effective to configure it as follows.

[0173] In addition, an electron transport layer 114 is formed between the electron transport layer 114 and the second electrode 102. An electron injection layer 115 may be provided. The electron injection layer 115 may be formed of lithium, calcium, fluorine, or the like. Lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc. In addition, a substance having an electron transport property and a compound having an electron donating property to the substance can be used. A composite material with a substance having an electron donating property (hereinafter simply referred to as an electron donating substance) can also be used. The donor substances include alkali metals or alkaline earth metals or their compounds. By using such a composite material for the electron injection layer 115, This is a more preferable configuration because electrons are efficiently injected from the second electrode 102. By using this structure, it is possible to use not only materials with a low work function but also other conductive materials as the cathode. It is also possible to use materials.

[0174] The material that forms the electrode that functions as the cathode must have a low work function (specifically, 3. 8 eV or less) metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include those belonging to Group 1 or Group 2 of the periodic table. The elements that are present in the atmosphere are alkali metals such as lithium (Li) and cesium (Cs), and magnesium. Alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and alloys containing these (MgAg, AlLi), europium (Eu), ytterbium ( However, the second electrode is preferably a rare earth metal such as Yb, and an alloy containing the rare earth metal. By providing an electron injection layer between the electrode 102 and the electron transport layer, the Indium oxide-oxide containing Al, Ag, ITO, silicon or silicon oxide Various conductive materials, such as tin, can be used for the second electrode 102. The material can be deposited using methods such as sputtering, inkjet, and spin coating. It is possible.

[0175] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, a vacuum deposition method, an ink jet method, a spin coating method, or the like can be used. Also, each electrode or each layer may be formed using a different film formation method. .

[0176] The electrodes may also be formed by a sol-gel method or a wet method using a paste of a metal material. Alternatively, the film may be formed by a dry method such as sputtering or vacuum deposition.

[0177] The structure of the EL layer provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, the metals used in the light-emitting region, electrodes, and carrier injection layer are not limited to the above. The first electrode 101 and the second electrode 102 are spaced apart so as to suppress quenching caused by their proximity. A preferred configuration is to provide a light-emitting region where holes and electrons recombine at a location away from the electrode 102. .

[0178] In addition, the hole transport layer and the electron transport layer directly contacting the light emitting layer, particularly the light emitting region in the light emitting layer 113 The carrier transport layer, which is in contact with the side closer to the light-emitting layer, transfers energy from the excitons generated in the light-emitting layer. In order to suppress this, the energy gap is determined by the luminescent material that constitutes the luminescent layer or the Those with an energy gap larger than that of the luminescent material contained therein It is preferable to make it of quality.

[0179] The light-emitting element having the above-described structure has a first electrode 101 and a second electrode 102. The generated potential difference causes a current to flow, and the light-emitting layer 113, which is a layer containing a highly luminescent substance, The holes and electrons are recombined to emit light. It is structured so that

[0180] The light is emitted through either the first electrode 101 or the second electrode 102, or both. Therefore, either the first electrode 101 or the second electrode 102 Alternatively, both electrodes may be made of a light-transmitting electrode. Only the first electrode 101 may be made of a light-transmitting electrode. In this case, light is emitted through the first electrode 101 and extracted from the substrate side. When only the first electrode 102 is a light-transmitting electrode, light is emitted through the second electrode 102 and reaches the substrate. The light is extracted from the opposite side. Both the first electrode 101 and the second electrode 102 are transparent. In the case where the electrodes are the same, light is emitted through the first electrode 101 and the second electrode 102 and reaches the substrate side. and is taken out from both the substrate and the opposite side.

[0181] The light-emitting element in this embodiment is a benzofuropyrimidine Since compounds with a skeletal structure are used, the luminescent material has a large energy gap. Even fluorescent materials that emit blue light and phosphorescent materials that emit colors between green and blue can be efficiently This makes it possible to obtain a light-emitting element with good luminous efficiency. This makes it possible to provide a light-emitting element with lower power consumption. Compounds with an amide skeleton have excellent carrier transport properties, allowing for light emission with low driving voltage. It is possible to provide the element.

[0182] Such a light-emitting element is fabricated using a substrate made of glass, plastic, or the like as a support. By fabricating multiple light-emitting elements on one substrate, a passive matrix type A light-emitting device can be manufactured. A transistor is formed, and the light-emitting element is fabricated on an electrode electrically connected to the transistor. This allows for an active master that controls the driving of a light emitting element by a transistor. A trix-type light-emitting device can be manufactured. Note that the structure of the transistor is not particularly limited. The TFT may be a staggered type or an inverted staggered type. There is no particular limitation on the crystallinity of the TFT substrate. It may be composed of either N-type and P-type TFTs, or N-type TFTs or P-type TFTs. The semiconductor layer constituting the TFT may be either one of the two types. The materials used are silicon (Si) and germanium (Ge), which are the first of the elements in the periodic table. Group 14 elements, compounds such as gallium arsenide and indium phosphide, as well as zinc oxide and tin oxide Any material that exhibits semiconductor properties, such as oxides of the above, may be used. Oxides (oxide semiconductors) that exhibit these properties include indium, gallium, aluminum, and zinc. A composite oxide of an element selected from lead and tin can be used. For example, zinc oxide (Zn O), indium oxide containing zinc oxide (Indium Zinc Oxide), and Indium oxide, gallium oxide, and zinc oxide (IGZO) Gallium Zinc Oxide is an example of this. A semiconductor may be used. The semiconductor layer may have either a crystalline structure or an amorphous structure. Specific examples of the semiconductor layer having a crystalline structure include a single crystal semiconductor and a polycrystalline semiconductor. or a microcrystalline semiconductor.

[0183] (Fourth embodiment) In this embodiment, a light emitting element having a structure in which a plurality of light emitting units are stacked (hereinafter referred to as a stacked element) The embodiment of the light-emitting element (also referred to as a light-emitting element) will be described with reference to FIG. The light-emitting element has a plurality of light-emitting units between the first electrode and the second electrode. The EL layer 103 has the same structure as that of the EL layer 103 shown in the third embodiment. The light-emitting element shown in is a light-emitting element having one light-emitting unit, and in this embodiment, It can be said to be a light-emitting element having a plurality of light-emitting units.

[0184] In FIG. 1B, a first light-emitting unit is disposed between the first electrode 501 and the second electrode 502. The knit 511 and the second light-emitting unit 512 are stacked, and the first light-emitting unit 511 A charge generating layer 513 is provided between the first electrode and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 502 in the third embodiment, respectively. This corresponds to the pole 102, and the same one as that explained in the third embodiment can be applied. In addition, the first light emitting unit 511 and the second light emitting unit 512 may have the same configuration but different The configuration may be as follows.

[0185] The charge generating layer 513 contains a composite material of an organic compound and a metal oxide. The composite material of a compound and a metal oxide can be used for the hole injection layer shown in Embodiment 3. The organic compound can be an aromatic amine compound, a carbazoline compound, or a methyl methacrylate compound. aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.) As the organic compound, a compound having a hole mobility of 1 x10 -6 cm 2 It is preferable to apply a value of / Vs or more. Other materials may be used as long as they have a high hole transporting property. The composite material of these compounds has excellent carrier injection and transport properties, making it suitable for low-voltage operation and low Current driving can be realized. In the case of knitted devices, the charge generating layer can also function as a hole transport layer, so there is no need to provide a hole transport layer. It's also good.

[0186] The charge generation layer 513 is made of a layer containing a composite material of an organic compound and a metal oxide and other materials. For example, the organic compound and the A layer containing a composite material of a metal oxide and a compound selected from electron donating substances and an electron transporting substance. Alternatively, a layer containing an organic compound and a metal compound may be combined. A layer containing an oxide composite material and a transparent conductive film may be combined.

[0187] In any case, the electrode sandwiched between the first light-emitting unit 511 and the second light-emitting unit 512 When a voltage is applied to the first electrode 501 and the second electrode 502, the charge generation layer 513 generates a It is sufficient that the light-emitting element injects electrons into the light-emitting unit and injects holes into the other light-emitting unit. For example, in FIG. 1B, the potential of the first electrode is higher than the potential of the second electrode. When a voltage is applied so that the charge generation layer 513 generates electrons, the charge generation layer 513 generates electrons in the first light-emitting unit 511. The electron injection hole 514 may be injected into the second light-emitting unit 512.

[0188] In this embodiment, the light emitting element having two light emitting units has been described, but the light emitting element having three or more light emitting units may be used. The same can be applied to a light-emitting element in which the above light-emitting units are stacked. As in the light-emitting device according to the embodiment, a plurality of light-emitting units are disposed between a pair of electrodes by a charge generating layer. By separating the LEDs, high brightness light emission is possible while keeping the current density low, and the LEDs can be used for a long time. It is also possible to realize a light-emitting device that can be driven at a low voltage and consumes less power. It is possible.

[0189] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole For example, a light-emitting element having two light-emitting units can be used. In this case, the luminous color of the first luminous unit and the luminous color of the second luminous unit are in a complementary color relationship. By doing so, it is possible to obtain a light emitting element that emits white light as a whole. In addition, complementary colors are colors that become achromatic when mixed. By mixing light from materials that emit light of certain colors, white light can be obtained. The same applies to a light-emitting element having three light-emitting units. For example, the first light-emitting unit The light emitting color of the first light emitting unit is red, the light emitting color of the second light emitting unit is green, and the light emitting color of the third light emitting unit is red. When the emitted light color of the dot is blue, the light emitting element as a whole can emit white light. In addition, one light-emitting unit has a light-emitting layer using a phosphorescent material, and the other light-emitting unit has a light-emitting layer using a fluorescent material. By applying a light-emitting layer using a material, it is possible to emit both fluorescent and phosphorescent light in a single light-emitting element. For example, one light-emitting unit can emit red and green light more efficiently. The other light-emitting unit emits blue fluorescent light, resulting in a highly efficient luminous system. White light emission can be obtained.

[0190] Since the light-emitting element of this embodiment mode includes a compound having a benzofuropyrimidine skeleton, A light-emitting element having high luminous efficiency and a low driving voltage can be obtained. Furthermore, the light-emitting unit containing the compound can emit light from the light-emitting substance with good color purity. Therefore, it becomes easy to adjust the color of the light-emitting element as a whole.

[0191] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0192] (Embodiment 5) In this embodiment, a light-emitting element including a compound having a benzofuropyrimidine skeleton is used. The light emitting device will now be described.

[0193] In this embodiment, a light-emitting element including a compound having a benzofuropyrimidine skeleton is used. An example of the manufactured light-emitting device will be described with reference to FIG. 3. Note that FIG. 3(A) shows a light-emitting device. 3(B) is a cross-sectional view of FIG. 3(A) taken along lines AB and CD. This light emitting device includes a driving circuit shown by a dotted line that controls the light emission of the light emitting element 618. Path section (source side drive circuit) 601, pixel section 602, drive circuit section (gate side drive circuit) 60 3. Also, 604 is a sealing substrate, 625 is a desiccant, and 605 is a sealant. The inside surrounded by the sealing material 605 forms a space 607 .

[0194] The lead wiring 608 is connected to the source side driver circuit 601 and the gate side driver circuit 603. The wiring is for transmitting the input signal, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal from Lint Circuit 609 Although only the FPC is shown here, this FPC has a printed circuit board. A printed wiring board (PWB) may be attached. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0195] Next, the cross-sectional structure will be described with reference to FIG. A source side driver circuit 601, which is a driver circuit section, is formed in this example. , one pixel in the pixel section 602 is shown.

[0196] The source side driver circuit 601 includes an n-channel TFT 623 and a p-channel TFT 62 4 is combined to form a CMOS circuit. In addition, the drive circuit is a CMOS circuit Alternatively, the substrate may be formed of a PMOS circuit or an NMOS circuit. Although the driver integrated type with the drive circuit formed on the top is shown, this is not necessarily required. It may also be formed externally rather than on the substrate.

[0197] The pixel section 602 includes a switching TFT 611, a current control TFT 612, and The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive resin film of a mold.

[0198] In addition, in order to improve the coverage of the film formed thereon, the upper end of the insulator 614 Alternatively, a surface having a curvature is formed at the lower end. For example, the material of the insulator 614 is When a positive photosensitive acrylic is used, the radius of curvature (0. It is preferable that the insulating material 614 has a curved surface with a thickness of 2 μm to 3 μm. Either a negative-working photosensitive material or a positive-working photosensitive material can be used.

[0199] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function It is desirable to use a material with a large resistance. For example, an ITO film or an insulator containing silicon indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single layer films such as chromium film, tungsten film, Zn film, and Pt film, titanium nitride and aluminum film are also available. a titanium nitride film and an aluminum-based film; A three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the electrode can also function as an anode. .

[0200] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods, such as a method using a benzofuropyrimidine skeleton. The EL layer 616 also contains other materials such as low molecular weight compounds. The polymer may be a polymer or a polymer compound (including an oligomer or a dendrimer).

[0201] Furthermore, a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode is The materials used are those with a low work function (Al, Mg, Li, Ca, or their alloys or compounds). It is preferable to use a compound such as MgAg, MgIn, or AlLi. When the light generated in the second electrode 617 is transmitted through the second electrode 617, the film thickness of the second electrode 617 is set to Thinned metal film and transparent conductive film (ITO, indium oxide containing 2-20 wt% zinc oxide) It uses lamination of indium, silicon-containing indium tin oxide, zinc oxide (ZnO, etc.) It's better.

[0202] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting element. The light-emitting element has the configuration of the third embodiment or the fourth embodiment. It should be noted that the pixel portion is formed with a plurality of light emitting elements. The optical device includes a light emitting element having the configuration described in the third or fourth embodiment and other The light emitting element may have both a light emitting element having a different configuration.

[0203] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealing material 605, A space 607 surrounded by an element substrate 610, a sealing substrate 604, and a sealing material 605 contains a light-emitting element. The space 607 is filled with a filler. In addition to cases where inert gas (nitrogen, argon, etc.) is filled, resin, desiccant, or other Sometimes it is filled with both.

[0204] It is preferable to use epoxy resin or glass frit for the sealing material 605. In addition, it is desirable that these materials be as impermeable to moisture and oxygen as possible. The sealing substrate 604 may be made of glass or quartz, or may be made of FRP (Fiber Reinforced Plastic). Reinforced Plastics), PVF (Polyvinyl Fluoride), Polyethylene A plastic substrate made of stainless steel, acrylic or the like can be used.

[0205] As described above, a light-emitting element containing a compound having a benzofuropyrimidine skeleton was used. A manufactured light-emitting device can be obtained.

[0206] In FIG. 4, a light emitting element that emits white light is formed, and a colored layer (color filter) or the like is provided. FIG. 4(A) shows an example of a full-color light-emitting device. an insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first the first interlayer insulating film 1020, the second interlayer insulating film 1021, the peripheral portion 1042, the pixel portion 1040, The driving circuit unit 1041, the first electrodes 1024W, 1024R, 1024G, 10 24B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, and a sealing substrate 10 31, sealing material 1032, etc. are shown.

[0207] In addition, in FIG. 4(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on the transparent substrate 1033. A transparent substrate on which a colored layer and a black layer are provided may be further provided. 1033 is aligned and fixed to the substrate 1001. The colored layer and the black layer are In FIG. 4(A), the colored layer is covered with an overcoat layer 1036. There are light-emitting layers that emit light to the outside without passing through the color layers of each color, and light-emitting layers that emit light to the outside. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, blue, and green. Images can be expressed using pixels.

[0208] In FIG. 4(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020 As shown in the figure, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0209] In the light emitting device described above, light is taken in from the substrate 1001 side on which the TFT is formed. The light emitting device has a bottom emission structure, but the light is emitted from the sealing substrate 1031 side. It may also be a light emitting device with a structure where light is extracted (top emission type). A cross-sectional view of the light-emitting device is shown in FIG. 5. In this case, a substrate 1001 that does not transmit light is used. Until the connection electrode that connects the TFT and the anode of the light-emitting element is formed, the bottom The third interlayer insulating film 1037 is then formed in the same manner as in the case of an emission type light emitting device. The insulating film 1022 is formed to cover the insulating film 1022. This insulating film may also have a role of planarization. The insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as other known materials. It is possible.

[0210] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are positive electrodes. The cathode is also used as the top-emission type light-emitting diode, as shown in Figure 5. In the case of a device, it is preferable that the first electrode is a reflective electrode. In order to obtain white light emission, the configuration described in the third or fourth embodiment is adopted. The element structure is as follows.

[0211] In Figures 4 and 5, the EL layer configuration that can produce white light emission is a multi-layer EL layer. This can be achieved by using multiple light-emitting units. Of course, the configuration for obtaining this is not limited to these.

[0212] In the top emission structure shown in Figure 5, the colored layers (red colored layer 1034R, green The sealing is performed using a sealing substrate 1031 provided with a colored layer 1034G and a blue colored layer 1034B. The sealing substrate 1031 has a black layer (black A coloring layer (a red coloring layer 1034R, a green coloring layer 1035R) may be provided. The blue colored layer 1034G, the blue colored layer 1034B, and the black layer (black matrix) are shown in FIG. The sealing substrate 1031 may be covered with an overcoat layer as shown in FIG. A substrate having optical properties is used.

[0213] Although an example of full-color display using four colors, red, green, blue, and white, is shown here, the present invention is not particularly limited to this. Instead, a full color display using three colors, red, green, and blue, may be used.

[0214] The light emitting device of this embodiment is a light emitting device according to the third embodiment or the fourth embodiment. The light-emitting element contains a compound having a benzofuropyrimidine skeleton, which provides excellent characteristics. Specifically, a light-emitting device having a benzofuropyrimidine skeleton can be obtained. The compounds have a wide energy gap and a high triplet excited level (T1 level), making them suitable for luminescence. Since it is possible to suppress the transfer of energy from Therefore, a light emitting device with reduced power consumption can be provided. In addition, compounds with a benzofuropyrimidine skeleton have high carrier transport properties, so they can be used as driving currents. A light emitting element with low voltage can be obtained, and a light emitting device with low driving voltage can be obtained.

[0215] Up to this point, we have explained about active matrix type light emitting devices. A sub-matrix light-emitting device will be described. 6A is a perspective view of the light-emitting device, and FIG. 6B is a cross-sectional view of FIG. 6A taken along the XY line. An EL layer 955 is provided between the electrode 952 and the electrode 956. The insulating layer 953 is covered with a partition layer 954. The sidewalls of the partition layer 954 become thinner as they approach the substrate surface. That is, the cross section of the partition layer 954 in the short side direction has a slope such that the gap between the partition layers 954 becomes narrower. The trapezoidal shape has a base (which faces in the same direction as the surface of the insulating layer 953 and is in contact with the insulating layer 953) The upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953) ) is shorter than the distance . ) In this way, by providing the partition layer 954, the light emitting element caused by static electricity or the like can be prevented from In addition, in a passive matrix light emitting device, a low driving The light-emitting element (benzofuropyrimidine) according to embodiment 3 or 4 is operated by a voltage. By having a light-emitting element including a compound having a structure, it is possible to operate the light-emitting element with low power consumption. This can be done.

[0216] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix. Since it is possible to control the light, it can be suitably used as a display device for displaying images. It is an optical device.

[0217] (Embodiment 6) In this embodiment mode, a light-emitting element including the light-emitting element described in Embodiment 3 or 4 as a part thereof is used. The light-emitting device described in the third or fourth embodiment is a benzophenone-based light-emitting device. The light-emitting element has reduced power consumption because it contains a compound having a pyrimidine skeleton. As a result, the electronic device described in this embodiment has a display portion with reduced power consumption. The light-emitting element according to the third embodiment or the fourth embodiment can be used as a slave device. Since the light emitting element has a low driving voltage, it can be used as an electronic device with a low driving voltage. is.

[0218] As an electronic device to which the light-emitting element is applied, for example, a television set (television, (also called television receivers), computer monitors, digital cameras, digital digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) (c), portable game machines, personal digital assistants, audio playback devices, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are shown below.

[0219] 7A shows an example of a television device. The television device has a housing 71 A display unit 7103 is built into the case 7101. The display unit 7103 can display images. The display unit 7103 may be the same as that described in Embodiment 3 or 4. The light-emitting elements are arranged in a matrix. Since the compound having a zirconia skeleton is contained, a light-emitting element with high luminous efficiency can be obtained. In addition, a light-emitting element with low driving voltage can be obtained. The television device having the display unit 7103 configured as above can be a television device with reduced power consumption. Furthermore, it is possible to provide a television device with a low driving voltage.

[0220] The television device can be operated using an operation switch provided on the housing 7101 or a separate remote control. This can be done by the operation key 710 provided on the remote control operation device 7110. 9, the channel and volume can be controlled, and the image displayed on the display unit 7103 can be In addition, the remote control operation device 7110 can operate the remote control operation device 711. A display portion 7107 for displaying information output from the computer may be provided.

[0221] The television device is configured to include a receiver, a modem, etc. It can receive general television broadcasts and can also transmit via wired or wireless communication via a modem. By connecting to a communication network, it can be transmitted in one direction (sender to receiver) or two directions (transmit It is also possible to communicate information between a sender and a receiver, or between receivers themselves.

[0222] FIG. 7B shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. This computer is similar to the one described in the third or fourth embodiment. The display portion 7203 is fabricated by arranging light elements in a matrix. The optical element contains a compound having a benzofuropyrimidine skeleton, and therefore has good luminous efficiency. Furthermore, it is possible to provide a light-emitting element with a low driving voltage. Therefore, a computer having the display portion 7203 formed of the light-emitting element consumes less power. It is also possible to make a computer with a low drive voltage. It is possible to do this.

[0223] FIG. 7C shows a portable gaming machine, which is composed of two housings, a housing 7301 and a housing 7302. The housing 7301 is connected by a connecting portion 7303 so as to be openable and closable. The light-emitting elements similar to those described in the third or fourth embodiment are arranged in a matrix. A display portion 7304 manufactured by the method is incorporated, and a display portion 7305 is incorporated in the housing 7302. In addition, the portable gaming machine shown in FIG. 7(C) also includes a speaker unit 7306, a recording medium, Insertion section 7307, LED lamp 7308, input means (operation keys 7309, connection terminal 731 0, Sensor 7311 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, Magnetic, temperature, chemical, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity (including functions for measuring degree, gradient, vibration, smell or infrared rays), microphone 731 2) and the like. Of course, the configuration of the portable gaming machine is not limited to the above, and at least In either case, the display unit 7304 and / or the display unit 7305 may be A display unit is used in which light-emitting elements similar to those described in the fourth embodiment are arranged in a matrix. It is sufficient to have the above-mentioned equipment, and other auxiliary equipment may be provided as appropriate. The portable gaming machine shown in FIG. 1 reads out and displays a program or data recorded on a recording medium. It has the function of displaying information on the display unit and the function of sharing information with other portable gaming machines via wireless communication. The functions of the portable gaming machine shown in FIG. 7(C) are not limited to these, and various functions may be used. The portable gaming machine having the display unit 7304 as described above can have the following. The light-emitting element used in 304 contains a compound having a benzofuropyrimidine skeleton. As a result, the portable gaming machine has good luminous efficiency and consumes less power. In addition, the light-emitting element used in the display portion 7304 is a benzofuropyrimidine. By including a compound having an amine skeleton, it is possible to operate the device at a low driving voltage. This allows for a portable gaming machine with a low driving voltage.

[0224] FIG. 7D shows an example of a mobile phone. The mobile phone is built in a housing 7401. In addition to the display unit 7402, operation buttons 7403, an external connection port 7404, and a speaker 7405 are also included. 405, a microphone 7406, etc. The mobile phone is A display unit 7 is fabricated by arranging light-emitting elements similar to those described in the fourth embodiment in a matrix. 402. The light-emitting element includes a compound having a benzofuropyrimidine skeleton. Therefore, it is possible to provide a light-emitting element with good luminous efficiency. Therefore, the display portion 7402 including the light-emitting element can be used as a The mobile phone can be a mobile phone with reduced power consumption. It is possible to make a small mobile phone.

[0225] The mobile phone shown in FIG. 7D allows users to input information by touching the display portion 7402 with a finger or the like. In this case, it is possible to make a call or create an email. Operations such as making a setting can be performed by touching the display portion 7402 with a finger or the like.

[0226] The screen of the display unit 7402 has three main modes. The first is a mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines the display mode and the input mode.

[0227] For example, when making a call or creating an email, the display portion 7402 is used for inputting characters. In this case, you can input characters displayed on the screen. In this case, a keyboard or number buttons can be displayed on most of the screen of the display unit 7402. preferable.

[0228] The mobile phone also has sensors inside it that detect tilt, such as a gyro or acceleration sensor. By providing a detection device, the orientation of the mobile phone (portrait or landscape) can be determined and the display portion 7402 The screen display can be switched automatically.

[0229] The screen mode can be switched by touching the display portion 7402 or operating the housing 7401. The type of image displayed on the display unit 7402 can be selected by operating the create button 7403. For example, the image signal to be displayed on the display unit can be switched by If the data is text data, the mode switches to display mode, and if the data is text data, the mode switches to input mode.

[0230] In the input mode, a signal detected by the optical sensor of the display unit 7402 is detected and displayed. If there is no input by touch operation on the display unit 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0231] The display portion 7402 can also function as an image sensor. By touching 402 with the palm or fingers and capturing an image of the palm print, fingerprint, etc., personal authentication can be performed. In addition, a backlight that emits near-infrared light in the display unit or a sensing device that emits near-infrared light By using a light source, it is also possible to capture images of finger veins, palm veins, etc.

[0232] Note that the configuration described in this embodiment mode may be the same as that described in any of Embodiments 1 to 5. They can be used in combination.

[0233] As described above, the benzofuropyrimidines described in the third and fourth embodiments The range of application of light-emitting devices including light-emitting elements containing compounds having a skeleton is extremely wide. The device can be applied to electronic devices in all fields. By using a compound having the formula: Furthermore, electronic devices with low driving voltage can be obtained.

[0234] Furthermore, a light-emitting element containing a compound having a benzofuropyrimidine skeleton is used in a light source device. A light source device can also be formed by using a light emitting element containing a compound having a benzofuropyrimidine skeleton. An embodiment of the light source device will be described with reference to FIG. and a light emitting element including a compound having the formula: The light emitting element has an input / output terminal portion for supplying a current to the sealing means. Therefore, it is preferable that the device is isolated from the external atmosphere.

[0235] FIG. 8 shows a light-emitting device containing a compound having a benzofuropyrimidine skeleton applied to a backlight. The liquid crystal display device shown in FIG. 8 includes a housing 901, a liquid crystal layer 9 902, a backlight 903, and a housing 904. The liquid crystal layer 902 is connected to a driver IC 905. The backlight 903 uses a light-emitting element containing the above compound. The current is supplied by terminal 906.

[0236] By applying a light-emitting element containing the compound to the backlight of a liquid crystal display device, it is possible to reduce power consumption. A backlight with reduced power consumption can be obtained. This allows the creation of a surface-emitting lighting device, and also makes it possible to increase the area. It is possible to increase the area of ​​the crystal, and it is also possible to increase the area of ​​the liquid crystal display device. Backlights that use light-emitting elements containing substances can be made thinner than conventional backlights, making it possible to It also becomes possible to make the device thinner.

[0237] FIG. 9 shows a light-emitting element including a compound having a benzofuropyrimidine skeleton, which is used in a lighting device. This is an example of application to a desk lamp. The desk lamp shown in FIG. 9 includes a housing 2001 and a light source 20 02, and a light emitting element containing the above compound is used as a light source 2002.

[0238] FIG. 10 shows a light-emitting element containing a compound having a benzofuropyrimidine skeleton, which is used as an indoor lighting device. The light-emitting element containing the compound has a low power consumption. Since the compound is an element, it is possible to provide a lighting device with reduced power consumption. The light-emitting element containing the compound can be made large in area and can therefore be used as a large-area lighting device. In addition, since the light-emitting element containing the compound has a small thickness, it is possible to manufacture a thin lighting device. It becomes possible to do this.

[0239] The light-emitting element containing the compound having a benzofuropyrimidine skeleton is used for the windshield of an automobile. The light-emitting element containing the above compound can be installed in an automobile or dashboard. The display area 5000 is a display area for displaying a vehicle windshield or dashboard. The region 5005 is a display provided using a light-emitting element containing the above compound.

[0240] The display area 5000 and the display area 5001 are the above-mentioned compound provided on the windshield of the automobile. The light-emitting element containing the compound is a display device having a first electrode. By making the first and second electrodes from transparent electrodes, the opposite side can be seen through. It can be a so-called see-through display device. Even if it is installed on the windshield of a car, it can be installed without obstructing the view. In addition, when a transistor or the like is provided for driving, it is possible to use an organic semiconductor material. Light-transmitting transistors such as organic transistors and transistors using oxide semiconductors It is better to use star.

[0241] The display area 5002 is a display device equipped with a light-emitting element containing the above compound provided in the pillar portion. The display area 5002 displays an image captured by an imaging means provided on the vehicle body. This can compensate for the visibility obstructed by the pillars. The display area 5003 provided in the vehicle body allows the view outside the vehicle to be displayed. By projecting images from the installed imaging means, blind spots can be compensated for and safety can be improved. By projecting images that complement the invisible parts, the sense of incongruity is reduced more naturally. Safety checks can be performed without any need for manual intervention.

[0242] The display area 5004 and the display area 5005 are used to display navigation information, a speedometer, and a tachometer. Provides various information such as meter, mileage, fuel level, gear status, air conditioning settings, etc. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in display areas 5000 to 5003. In addition, the display areas 5000 to 5005 can be used as lighting devices. It is also possible.

[0243] A light-emitting element containing a compound having a benzofuropyrimidine skeleton can be obtained by containing the compound. Therefore, a light emitting element with a low driving voltage or a light emitting element with low power consumption can be obtained. Therefore, it is possible to display a large image such as the display area 5000 to the display area 5005. Even if you have many screens, it will not put a strain on the battery and you can use it comfortably. Therefore, a light emitting device or a lighting device using a light emitting element containing the compound can be used for an in-vehicle The light emitting device or lighting device can be suitably used as the above light emitting device or lighting device.

[0244] Figures 12(A) and 12(B) show an example of a foldable tablet terminal. 2(A) shows the tablet terminal in an open state, and the tablet terminal includes a housing 9630, a display unit 9631a, and a , display unit 9631b, display mode changeover switch 9034, power switch 9035, A power mode changeover switch 9036, a fastener 9033, and an operation switch 9038 are included. The tablet terminal displays a light-emitting device equipped with a light-emitting element using the compound. The insulating film is fabricated by using it in one or both of the portion 9631a and the display portion 9631b.

[0245] A part of the display unit 9631a can be used as a touch panel area 9632a. By touching the operation keys 9637, data can be input. In 1a, for example, half of the area has a display function only, and the other half The display unit 963 has a touch panel function, but is not limited to this. The entire area of ​​the display unit 96 may have a touch panel function. The entire surface of 31a is displayed as a keyboard button to serve as a touch panel, and the display part 9631b is displayed. It can be used as a screen.

[0246] In addition, in the display unit 9631b, as in the display unit 9631a, The part can be used as a touch panel area 9632b. By touching the area where the display switch button 9639 is displayed with your finger or a stylus, Keyboard buttons can be displayed on the display portion 9631b.

[0247] In addition, when touching the touch panel area 9632a and the touch panel area 9632b at the same time, You can also input the character.

[0248] A display mode changeover switch 9034 is used to change the display orientation, such as portrait or landscape. You can switch between black and white and color display. The switch 9036 is an external switch that is detected by a light sensor built into the tablet terminal. The display brightness can be optimized according to the amount of light. In addition to sensors, other detection devices such as gyros and acceleration sensors that detect tilt are also available. may be incorporated.

[0249] FIG. 12A shows an example in which the display area of ​​the display portion 9631b is the same as that of the display portion 9631a. However, there is no particular limitation, and one size may be different from the other size. The display quality may also differ. For example, one display panel may be able to display a higher resolution image than the other. It may also be used as a rule.

[0250] FIG. 12(B) shows the tablet terminal in the closed state. Body 9630, solar cell 9633, charge / discharge control circuit 9634, battery 9635, DCD 12B shows an example in which a charge / discharge control circuit 96 is provided. As an example of 34, a configuration having a battery 9635 and a DC-DC converter 9636 is shown. This shows that.

[0251] In addition, since the tablet device can be folded in half, when not in use, the case 9630 is closed. Therefore, the display portions 9631a and 9631b can be protected. This makes it possible to provide a tablet terminal that is highly durable and reliable for long-term use.

[0252] In addition, the tablet terminals shown in Figs. 12(A) and 12(B) can be used in various Functions that display information (still images, videos, text images, etc.), calendars, dates, or times The function to display information on the display unit, and the function to input or edit the information displayed on the display unit. It has input functions, functions to control processing using various software (programs), etc. It is possible.

[0253] The solar cell 9633 attached to the surface of the tablet terminal supplies power to the touch panel. The solar cell 9633 can be supplied to a display unit, a video signal processor, or the like. The battery 9635 can be efficiently charged by installing it on one or both sides of the housing 9630. This is preferable because it is possible to configure the device to perform the above.

[0254] The configuration and operation of the charge / discharge control circuit 9634 shown in FIG. 12(B) are shown in FIG. A block diagram is shown in Fig. 12(C) and will be explained. 635, DC-DC converter 9636, converter 9638, switches SW1 to SW3 , the display unit 9631, the battery 9635, the DC-DC converter 963 6. The converter 9638 and the switches SW1 to SW3 are configured to perform the charge / discharge control shown in FIG. 12(B). This corresponds to the circuit 9634.

[0255] First, an example of operation when power is generated by the solar cell 9633 using external light will be described. The power generated by the solar cell is converted to DC voltage to charge the battery 9635. The voltage is increased or decreased by the DC converter 9636. When the power charged by the solar cell 9633 is used, switch SW1 is turned on and the The inverter 9638 increases or decreases the voltage to the voltage required for the display unit 9631. When not displaying on the display unit 9631, turn SW1 off and SW2 on. The configuration may be such that the battery 9635 is charged.

[0256] Although the solar cell 9633 is shown as an example of a power generating means, the power generating means is not particularly Other power generating devices such as, but not limited to, piezoelectric elements (piezo elements) and thermoelectric conversion elements (Peltier elements) may also be used. The battery 9635 may be charged by wireless (contactless) means. It can be combined with a non-contact power transmission module that transmits and receives power to charge, or other charging methods. The power generating means may be omitted.

[0257] In addition, as long as the display unit 9631 is provided, the electronic device is not limited to the one having the shape shown in FIG. Needless to say, this is not fixed. [Example]

[0258] <Synthesis Example 1> In this synthesis example, the compound having the benzofuropyrimidine skeleton described in Embodiment 1 was synthesized. 4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]benzofuro[ 3,2-d]pyrimidine (abbreviation: 4mDBTBPBfpm-II) (structural formula (100)) The synthesis method of 4mDBTBPBfpm-II is explained below. The structural formula of 4mDBTBPBfpm-II is shown below.

[0259] [ka]

[0260] Step 1: Synthesis of 4-(3'-bromobiphenyl-3-yl)dibenzothiophene > First, 48g of 3-(dibenzothiophen-4-yl)phenylboronic acid, 3-iodobromine 54g of benzene, tris(2-methylphenyl)phosphine (abbreviation: P(o-toly l) 3) 1.9 g, 160 mL of 2 M potassium carbonate aqueous solution, 800 mL of toluene, ethanol 80 mL of the solution was placed in a 3 L three-neck flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. The mixture was heated to 8°C to dissolve the palladium (II) acetate (0.38 g). The mixture was stirred for 1 hour. Here, 0.92 g of tris(2-methylphenyl)phosphine and acetic acid were further added. 0.18 g of palladium (II) was added and stirred for 6 hours. Then, water was added to the solution. The organic layer was extracted with toluene, dried over magnesium sulfate, and The resulting solution was filtered. The solvent was distilled off from the solution, and the resulting residue was dissolved in hot toluene. However, Celite (Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855, same below) , alumina, Florisil (Wako Pure Chemical Industries, Ltd., Catalog No.: 540-00135 The mixture was then hot filtered through a filter aid layered in this order (hereinafter the same), followed by Celite. The solid was recrystallized in a mixed solvent of toluene and methanol to obtain a white solid. The synthesis scheme for step 1 is shown in formula (a-1) below.

[0261] [ka]

[0262] Step 2: Synthesis of 3'-(dibenzothiophen-4-yl)-3-biphenylboronic acid > 4-(3'-bromobiphenyl-3-yl)dibenzothiophene obtained in Step 1 above 30 g of the solution was placed in a 1 L three-neck flask equipped with a dropping funnel, and the atmosphere in the flask was replaced with nitrogen. The flask was then cooled to -78°C in a cryostat, with 300 mL of tetrahydrofuran (dehydrated) added. Then, 50 mL of n-butyllithium (1.6 M hexane solution) was added dropwise from the dropping funnel. Then, add 64 mL of tetrahydrofuran (dehydrated) to the dropping funnel and pour it into the reaction solution. After stirring the reaction solution at -78°C for 1 hour, 11 mL of trimethyl borate was added dropwise and the mixture was allowed to cool to room temperature. The temperature was raised to 100°C and the mixture was stirred at room temperature for 18 hours. The mixture was stirred for 1 hour, water was added to the resulting mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and then dried over magnesium sulfate. The solution was filtered, and the solvent was distilled off from the solution, and the resulting solid was washed with toluene. A white solid was obtained in a yield of 40%. The synthesis scheme of Step 2 is shown in the following formula (b-1). .

[0263] [ka]

[0264] Step 3: 4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Synthesis of benzofuro[3,2-d]pyrimidine (abbreviation: 4mDBTBPBfpm-II) 3'-(dibenzothiophen-4-yl)-3-biphenylborohydride obtained in Step 2 above 2.3g of phosphoric acid, 1.2g of 4-chlorobenzofuro[3,2-d]pyrimidine, 2M potassium carbonate 5.4 mL of aqueous sodium chloride solution, 27 mL of toluene, and 2.7 mL of ethanol were added to a 1 The contents were placed in a 00 mL three-neck flask, degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen. This mixture was added with tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd 68 mg of (PPh3)4) was added, and the mixture was heated at 80°C for 2 hours to react. The residue was washed with water and ethanol, and recrystallized from toluene to give 1.8 g of a white solid. The synthesis scheme of step 3 is shown in formula (c-1) below.

[0265] [ka]

[0266] The resulting white solid (2.3 g) was purified by train sublimation. The production conditions were a pressure of 3.2 Pa, argon gas flow rate of 15 mL / min, and The solid was heated at ° C. After purification by sublimation, 0.5 g of the target white solid was obtained with a recovery rate of 22%.

[0267] Furthermore, 1.5 g of the unsublimated solid from the above sublimation purification was subjected to the train sublimation method. The sublimation purification conditions were a pressure of 2.7 Pa and an argon gas flow rate of 5.0 mL / min. After sublimation purification, 1.4 g of the target white solid was obtained, with a recovery rate of 92%. Got it.

[0268] The white solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. This shows that 4mDBTBPBfpm-II was obtained. It was.

[0269] 1 H-NMR.δ(CDCl3):7.44-7.54(m,4H),7.60-7.6 1(m,2H),7.66-7.51(m,4H),7.78-7.84(m,2H), 7.91-7.92(d,1H),8.17(ts,1H),8.20-8.23(m, 2H),8.31-8.32(d,1H),8.62-8.63(d,1H),8.96 -8.97(t,1H),9.30(s,1H).

[0270] Also, 1 The H NMR charts are shown in Figures 13(A) and (B). Note that Figure 13(B) shows This is a chart showing an enlarged range from 7.2 ppm to 8.8 ppm in Figure 13(A). The measurement results confirmed that the target product, 4mDBTBPBfpm-II, was obtained. did.

[0271] <<Physical properties of 4mDBTBPBfpm-II>> Next, the absorption and emission spectra of 4mDBTBPBfpm-II in toluene were measured. The absorption spectrum and emission spectrum of the thin film are shown in Figure 14(A) and Figure 14(B). The spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation, V550 model). The spectrum of the toluene solution was obtained by measuring the toluene solution of 4mDBTBPBfpm-II on a quartz The spectrum of the thin film was measured by placing it in a cell. The sample was prepared by vapor deposition on a quartz substrate. The absorption spectrum of the toluene solution was measured using a quartz cell. The absorption spectrum obtained by subtracting the absorption spectrum measured by adding only toluene is shown in the figure. The absorption spectrum of the thin film is shown by subtracting the absorption spectrum of the quartz substrate. Ta.

[0272] As shown in Figure 14(A), the toluene solution of 4mDBTBPBfpm-II exhibited a peak near 282 nm and In addition, absorption peaks were observed around 320 nm and 320 nm. pm-II thin films are 244 nm, 268 nm, 290 nm, 326 nm, and 340 nm An absorption peak is observed around 410 nm (excitation wavelength 340 nm). Thus, 4mDBTBPBfpm-II absorbs and emits light in the very short wavelength region. It was found that

[0273] In addition, the ionization potential of 4mDBTBPBfpm-II in the thin film state was calculated using the The ionization potential was measured by photoelectron spectroscopy (Riken Keiki Co., Ltd., AC-2). As a result of converting the value of the HOMO level of 4mDBTBPBfpm-II to a negative value, the HOMO level of 4mDBTBPBfpm-II is -6 From the absorption spectrum data of the thin film in Figure 14(B), it is assumed that the direct transition The absorption edge of 4mDBTBPBfpm-II obtained from the Tauc plot is 3.50e V. Therefore, the solid-state optical energy gap of 4mDBTBPBfpm-II The energy gap is estimated to be 3.50 eV. From this value, the LUMO level of 4mDBTBPBfpm-II is estimated to be -2.88 eV. Thus, 4mDBTBPBfpm-II has a 3.50 eV It was found that it has a wide energy gap of

[0274] In addition, 4mDBTBPBfpm-II was analyzed by liquid chromatography mass spectrometry (LCMS). chromatography mass spectrometry,abbreviation:LC / MS The analysis was carried out using the following method.

[0275] LC / MS analysis was performed using a Waters Acquity UPLC and a Waters The analysis was carried out using a Xevo G2 Tof MS manufactured by Epson Corporation.

[0276] For MS analysis, electrospray ionization was used. The capillary voltage was set at 3 The voltage was 0.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The ionized components under the above conditions are collided with argon gas in a collision cell. The energy of the argon collision (collision) was The electron energy was set to 50 eV and 70 eV. The mass range measured was m / z = 10 The range is 0 to 1200.

[0277] The results are shown in Figures 15(A) and (B). Figure 15(A) shows the results at a collision energy of 50 eV. Figure 15(B) shows the results when the collision energy is 70 eV. is. [Example]

[0278] <Synthesis Example 2> In this synthesis example, the compound having the benzofuropyrimidine skeleton described in embodiment 1 4-{3-[3'-(9H-carbazol-9-yl)]biphenyl-3-yl}benzo Furo[3,2-d]pyrimidine (abbreviation: 4mCzBPBfpm) (structural formula (300)) A specific synthesis example is given below. The structural formula of 4mCzBPBfpm is shown below.

[0279] [ka]

[0280] Step 1: Synthesis of 9-[3-(3-bromophenyl)phenyl]-9H-carbazole > First, 16 g (56 mmol) of 3-(9H-carbazol-9-yl)phenylboronic acid , 3-iodobromobenzene 19g (67mmol), tri(ortho-tolyl)phosphine 0.68 g (2.2 mmol) of ethanol, 56 mL of 2 M potassium carbonate aqueous solution, 250 mL of toluene 30 mL of ethanol was placed in a 1 L three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 0.13 g (0.56 mmol) of palladium acetate was added to the mixture, and the mixture was heated and stirred at 80°C for 14 hours. The aqueous layer of the resulting reaction mixture was extracted with toluene, and the resulting extract solution was combined with the organic layer. The organic layer was washed with water and saturated saline. Magnesium sulfate was added to the organic layer to dry it. The resulting mixture was gravity filtered to obtain a filtrate, which was then concentrated to obtain an oily substance. The oil was purified by recycling preparative HPLC LC-SakuraNEXT. The resulting fraction was concentrated and washed with toluene and methanol to give 9-[3-(3-bromophenoxy)-2-methyl-2-propanol]. [(9H-phenyl)phenyl]-9H-carbazole was obtained (white solid 13 g, yield 58%). The synthesis scheme of Peptide 1 is shown in (a-2) below.

[0281] [ka]

[0282] Step 2: 3-[3'-(9H-carbazol-9-yl)]biphenylboronic acid Synthesis> Synthesis contents: 9-[3-(3'-bromophenyl)phenyl]-9H-carbazole 13g (33 mmol) was placed in a 500 mL three-neck flask, and the flask was degassed and replaced with nitrogen. 160 mL of tetrahydrofuran was added and stirred at -78°C. Add 24 mL (40 mmol) of ethyllithium (1.65 mol / L hexane solution) dropwise. The mixture was stirred at -78°C for 1 hour. After a predetermined time had passed, 4.7 ml of trimethyl borate was added to the mixture. L (43 mmol) was added, and the mixture was stirred for 18 hours while the temperature was raised to 20°C. 100 mL of 1 mol / L hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The aqueous layer was extracted with ethyl acetate, and the resulting extract was washed with saturated saline. Magnesium carbonate was added to dry the mixture, and the resulting mixture was gravity filtered. The filtrate was concentrated to obtain a solid. This solid was washed with toluene to give 3-[3'-(9H-carbazol-9-yl) ] Biphenylboronic acid was obtained (white solid 6.0 g, yield 51%). The team is shown in (b-2) below.

[0283] [ka]

[0284] Step 3: 4-{3-[3'-(9H-carbazol-9-yl)]biphenyl-3 Synthesis of {-yl}benzofuro[3,2-d]pyrimidine (abbreviation: 4mCzBPBfpm) 3-[3'-(9H-carbazol-9-yl)]biphenylboronic acid 3.0 g (8.3 mmol), 4-chlorobenzofuro[3,2-d]pyrimidine 1.7 g (8.3 mmol) ), 8.3 mL of 2 M potassium carbonate aqueous solution, 40 mL of toluene, and 4 mL of ethanol were added to 200 The mixture was placed in a 3-neck flask and the inside of the flask was replaced with nitrogen. Sphine)palladium(II) dichloride (Pd(PPh3)2Cl2) 68.3mg ( 0.059 mmol) was added, and the mixture was heated and stirred at 80°C for 6 hours. The mixture was extracted with toluene, and the resulting extract solution and the organic layer were combined and washed with saturated saline. Anhydrous magnesium sulfate was added to the mixture to dry it, and the resulting mixture was subjected to gravity filtration to obtain a filtrate. The filtrate was concentrated and the resulting solid was dissolved in toluene again, and celite, alumina, and celite were added. The filtrate was concentrated and the resulting solid was recrystallized from toluene to give a white solid. A white solid (2.0 g, 50% yield) was obtained. The sublimation purification was carried out by the sublimation method. The conditions for the sublimation purification were a pressure of 2.3 Pa and an argon gas flow rate of 1. The solid was heated to 250°C while the water was flowing at 0 mL / min. After purification by sublimation, the target white solid was obtained. The compound was obtained in an amount of 1.3 g with a recovery rate of 65%. The synthesis scheme for step 2 is shown below in (c-2). .

[0285] [ka]

[0286] The white solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below.

[0287] 1 H-NMR.δ(CDCl3):7.32(m,2H),7.44(m,2H),7. 52-7.55(m,3H),7.63-7.64(m,1H),7.69-7.77( m,4H),7.85-7.88(m,2H),7.97(t,1H),8.18(d, 2H),8.31(d,1H),8.65(m,1H),8.92(t,1H),9.2 7(s,1H).

[0288] Also, 1 The H NMR charts are shown in Figures 16(A) and (B). Note that Figure 16(B) shows This is a chart showing an enlarged range from 7.6 ppm to 9.4 ppm in Figure 16(A). The measurement results confirmed that the target substance, 4mCzBPBfpm, was obtained.

[0289] <<Physical properties of 4mCzBPBfpm>> Next, the absorption spectrum and emission spectrum of 4mCzBPBfpm in toluene are shown. The absorption spectrum and emission spectrum of the thin film are shown in Figure 17(A) and Figure 17(B). The Tor was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). The spectrum of the ene solution was measured by placing a toluene solution of 4mCzBPBfpm in a quartz cell. The spectrum of the thin film was obtained by depositing 4mCzBPBfpm on a quartz substrate. The absorption spectrum of the toluene solution was measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film is shown in Fig. 1. The absorption spectrum is shown after subtracting the absorption spectrum of the British substrate.

[0290] From Figure 17(A), the toluene solution of 4mCzBPBfpm has the following wavelengths: 294 nm, 324 nm, The absorption peaks are observed around 334 nm and 422 nm (excitation wavelength 3). 30 nm). Also, from Figure 17(B), the thickness of the 4mCzBPBfpm thin film was 207 nm. , around 243nm, 262nm, 289nm, 295nm, 326nm, and 341nm The absorption peak was observed at 440 nm (excitation wavelength 341 nm). Thus, 4mCzBPBfpm exhibits absorption and emission in the very short wavelength region. Understood.

[0291] In addition, the ionization potential of 4mCzBPBfpm in a thin film state was measured by photoelectric conversion in the atmosphere. The ionization potential was measured by atomic spectroscopy (Riken Keiki, AC-2). As a result of converting it to a negative value, the HOMO level of 4mCzBPBfpm was found to be -6.13 eV. From the absorption spectrum data of the thin film in Figure 17(B), the Tauc plan assuming direct transition was obtained. The absorption edge of 4mCzBPBfpm determined from the lot was 3.49 eV. The solid-state optical energy gap of CzBPBfpm is estimated to be 3.49 eV. From the HOMO level obtained earlier and this energy gap value, the L of 4mCzBPBfpm The UMO level can be estimated to be -2.64 eV. It was found that m has a wide energy gap of 3.49 eV in the solid state. Ta.

[0292] In addition, 4mCzBPBfpm was analyzed by liquid chromatography mass spectrometry (LCMS). LC / MS analysis) So, we analyzed it.

[0293] LC / MS analysis was performed using a Waters Acquity UPLC and a Waters The analysis was carried out using a Xevo G2 Tof MS manufactured by Epson Corporation.

[0294] For MS analysis, electrospray ionization was used. The capillary voltage was set at 3 The voltage was 0.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The ionized components under the above conditions are collided with argon gas in a collision cell. The energy of the argon collision (collision) was The electron energy was set to 50 eV and 70 eV. The mass range measured was m / z = 10 The range is 0 to 1200.

[0295] The results are shown in Figures 18(A) and (B). Figure 18(A) shows the results at a collision energy of 50 eV. Figure 18(B) shows the results when the collision energy is 70 eV. is. [Example]

[0296] In this example, the compound having a benzofuropyrimidine skeleton described in Embodiment 1 was The green-emitting phosphorescent material 4mDBTBPBfpm-II was used as a host material in the emitting layer. A light-emitting device (light-emitting device 1) using the fluorine-containing compound as a fluorine-containing compound will be described.

[0297] The molecular structures of the compounds used in this example are shown in the following structural formulas (i) to (v) and (100). The element structure is shown in Figure 1(A).

[0298] [ka]

[0299] <Fabrication of Light-Emitting Element 1> First, a silicon-containing indium tin oxide ( A glass substrate with an ITSO film was prepared. The ITSO surface was 2 mm square. The periphery was covered with a polyimide film so that the surface was exposed, and the electrode area was 2 mm × 2 mm. As a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water and heated at 200°C for 1 hour. After baking for 10 seconds, UV ozone treatment was performed for 370 seconds. -4 The inside is about Pa The substrate was introduced into a vacuum deposition apparatus under reduced pressure, and the substrate was heated to 170°C for 3 minutes in the heating chamber of the vacuum deposition apparatus. After vacuum baking for 10 minutes, the substrate was allowed to cool for about 30 minutes.

[0300] Next, the substrate was placed in a vacuum deposition apparatus with the surface on which ITSO was formed facing downward. The sample was fixed in a holder.

[0301] The vacuum deposition equipment was -4 After reducing the pressure to 100 Pa, the 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: D DBT3P-II) and molybdenum(VI) oxide were mixed. The hole injection layer 111 was formed by co-evaporation so that the weight ratio of the metal and the oxide was 4:2. The film thickness was set to 20 nm. Co-evaporation is the process of depositing different materials from different evaporation sources. This is a vapor deposition method in which the metal and the metal are evaporated simultaneously.

[0302] Next, 4-phenyl-4'-(9-phenylfluorene) represented by the above structural formula (ii) By depositing 20 nm of (benzo-9-yl)triphenylamine (abbreviation: BPAFLP), Thus, a hole transport layer 112 was formed.

[0303] Furthermore, on the hole transport layer 112, 4-[3'-(dibenzyl)-2-methyl-2-propanol] represented by the above structural formula (100) (benzothiophen-4-yl)biphenyl-3-yl]benzofuro[3,2-d]pyrimidin (abbreviation: 4mDBTBPBfpm-II) and tris(2-methyl-4-phenyl-2-propanol) represented by the above structural formula (iii). (2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy )3]) and 4mDBTBPBfpm-II:[Ir(ppy)3]=1:0.08( After co-evaporating 20 nm of 4mDBTBPBfpm-II and [Ir( ppy)3] and 4mDBTBPBfpm-II:[Ir(ppy)3] = 1:0.04 The light-emitting layer 113 was formed by co-evaporation so that the thickness was 20 nm (weight ratio).

[0304] Next, 4,6-bis[3-(4-dibenzothienyl)phenyl]phenyl]propanol represented by the above structural formula (iv) is prepared. 10 nm of phenylpyrimidine (abbreviation: 4,6mDBTP2Pm-II), followed by the above structure Bathophenanthroline (abbreviated as BPhen) represented by formula (v) was evaporated to a thickness of 15 nm. In this way, the electron transport layer 114 was formed.

[0305] Furthermore, lithium fluoride is vapor-deposited on the electron transport layer 114 to a thickness of 1 nm. Finally, an electron injection layer 115 was formed. An aluminum film of 200 nm was formed, completing the light-emitting element 1. The deposition was all carried out using a resistance heating method.

[0306] <Operating characteristics of light-emitting element 1> The light-emitting element 1 obtained as described above was placed in a glove box with a nitrogen atmosphere. After sealing the device to prevent it from being exposed to the atmosphere, the operating characteristics of this light-emitting device were The measurements were carried out at room temperature (an atmosphere maintained at 25°C).

[0307] FIG. 19 shows the current density-luminance characteristics of Light-emitting Element 1, FIG. 20 shows the voltage-luminance characteristics, and FIG. 21 shows the luminance-current characteristics. The efficiency characteristics are shown in Figure 21, the brightness-external quantum efficiency characteristics are shown in Figure 22, and the brightness-power efficiency characteristics are shown in Figure 2 Shown in 3.

[0308] As can be seen from FIG. 21, Light-emitting Element 1 exhibits favorable luminance-current efficiency characteristics and is a light-emitting element with favorable luminous efficiency. Therefore, 4mDBTBPBfpm-II, that is, the form of implementation The compounds with the benzofuropyrimidine skeleton described in Section 1 have a high triplet excited level (T1 level). Even phosphorescent materials that have a wide energy gap and emit green light can be excited effectively. 20, the light-emitting element 1 exhibits a good voltage-luminance relationship. It was found that the device exhibited the characteristics described above and had a low driving voltage. Bfpm-II, that is, the compound having a benzofuropyrimidine skeleton described in the first embodiment Similarly, the compound shown in FIG. 19 has excellent carrier transport properties. The current density-luminance characteristics and the luminance-external quantum efficiency characteristics shown in Figure 22 are also good. As shown in 23, the light-emitting element 1 exhibited very good power efficiency.

[0309] Next, the emission spectrum when a current of 0.1 mA was applied to the fabricated light-emitting element 1 was measured. The luminescence intensity is shown as a relative value with the maximum luminescence intensity set to 1. It was found that the compound 1 exhibited green luminescence due to the luminescent material [Ir(ppy)3].

[0310] In addition, the initial brightness is 5000 cd / m 2 The light-emitting element 1 is driven under the condition of a constant current density. The results of the reliability test are shown in Figure 25. In Figure 25, the initial luminance is set to 100%. From this result, it can be seen that the light-emitting element 1 exhibits a small decrease in luminance over driving time. It is clear that the light emitting element has good reliability. [Example]

[0311] In this example, the compound having a benzofuropyrimidine skeleton described in Embodiment 1 was The green-emitting phosphorescent material 4mDBTBPBfpm-II was used as a host material in the emitting layer. A light-emitting element (light-emitting element 2) using the fluorine-containing compound as a fluorine-containing compound will be described.

[0312] The molecular structures of the compounds used in this example are shown in the following structural formulas (i) to (iii) and (v). (vi) and (100). The device structure is that shown in Figure 1(A).

[0313] [ka]

[0314] <Fabrication of light-emitting element 2> First, a silicon-containing indium tin oxide ( A glass substrate with an ITSO film was prepared. The ITSO surface was 2 mm square. The periphery was covered with a polyimide film so that the surface was exposed, and the electrode area was 2 mm × 2 mm. As a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water and heated at 200°C for 1 hour. After baking for 10 seconds, UV ozone treatment was performed for 370 seconds. -4 The inside is about Pa The substrate was introduced into a vacuum deposition apparatus under reduced pressure, and the substrate was heated to 170°C for 3 minutes in the heating chamber of the vacuum deposition apparatus. After vacuum baking for 10 minutes, the substrate was allowed to cool for about 30 minutes.

[0315] Next, the substrate was placed in a vacuum deposition apparatus with the surface on which ITSO was formed facing downward. The sample was fixed in a holder.

[0316] 10 in the vacuum chamber -4 After reducing the pressure to 100 Pa, 4,4',4 ''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT 3P-II) and molybdenum(VI) oxide, DBT3P-II: molybdenum oxide = 4 :2 (weight ratio) to form the hole injection layer 111. The thickness was set to 20 nm. Co-evaporation is the process of simultaneously depositing multiple different substances from different evaporation sources. This is a vapor deposition method in which the material is evaporated.

[0317] Next, 4-phenyl-4'-(9-phenylfluorene) represented by the above structural formula (ii) By depositing 20 nm of (benzo-9-yl)triphenylamine (abbreviation: BPAFLP), Thus, a hole transport layer 112 was formed.

[0318] Furthermore, on the hole transport layer 112, 4-[3'-(dibenzyl)-2-methyl-2-propanol] represented by the above structural formula (100) (benzothiophen-4-yl)biphenyl-3-yl]benzofuro[3,2-d]pyrimidin (abbreviation: 4mDBTBPBfpm-II) and N-(1 ,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]-9H-fluoren-2-amine (abbreviated as PCB BiF) and tris(2-phenylpyridinatonato-N ,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]) and 4mDBTBP Bfpm-II:PCBBiF:[Ir(ppy)3]=0.5:0.5:0.05(heavy After co-evaporating 20 nm of PCBF PM-II with 4mDBTBPBfpm-II, PCBF PM ... iF and [Ir(ppy)3] were mixed with 4mDBTBPBfpm-II:PCBBiF:[ Ir(ppy)3] = 0.8:0.2:0.05 (weight ratio) Thus, the light-emitting layer 113 was formed.

[0319] Next, 4mDBTBPBfpm-II was added to 10 nm, followed by the An electron transport layer was formed by depositing 15 nm of bathophenanthroline (abbreviated as BPhen). 114 was formed.

[0320] Furthermore, lithium fluoride is vapor-deposited on the electron transport layer 114 to a thickness of 1 nm. Finally, an electron injection layer 115 was formed. An aluminum film of 200 nm was formed, completing the light-emitting element 2. The deposition was all carried out using a resistance heating method.

[0321] <Operating characteristics of light-emitting element 2> The light-emitting element 2 obtained as described above was placed in a glove box with a nitrogen atmosphere. After sealing the device to prevent it from being exposed to the atmosphere, the operating characteristics of this light-emitting device were The measurements were carried out at room temperature (an atmosphere maintained at 25°C).

[0322] FIG. 26 shows the current density-luminance characteristics of Light-emitting Element 2, FIG. 27 shows the voltage-luminance characteristics, and FIG. 28 shows the luminance-current characteristics. The efficiency characteristics are shown in Figure 28, the luminance-external quantum efficiency characteristics are shown in Figure 29, and the luminance-power efficiency characteristics are shown in Figure 3 Shown as 0.

[0323] As can be seen from FIG. 28, Light-emitting element 2 exhibits favorable luminance-current efficiency characteristics and is a light-emitting element with favorable luminous efficiency. Therefore, 4mDBTBPBfpm-II, that is, the form of implementation The compounds with the benzofuropyrimidine skeleton described in Section 1 have a high triplet excited level (T1 level). Even phosphorescent materials that have a wide energy gap and emit green light can be excited effectively. 27, the light-emitting element 2 exhibits a good voltage-luminance relationship. It was found that the device exhibited the characteristics described above and had a low driving voltage. Bfpm-II, that is, the compound having a benzofuropyrimidine skeleton described in the first embodiment Similarly, the compound shown in FIG. 26 has excellent carrier transport properties. The current density-luminance characteristics and the luminance-external quantum efficiency characteristics shown in Figure 29 are also good. As shown in 30, the light-emitting element 2 exhibited very good power efficiency.

[0324] Next, the emission spectrum when a current of 0.1 mA was applied to the fabricated light-emitting element 2 was measured. The luminescence intensity is shown as a relative value with the maximum luminescence intensity set to 1. It was found that the compound 2 exhibited green luminescence due to the luminescent material [Ir(ppy)3].

[0325] In addition, the initial brightness is 5000 cd / m 2 The light-emitting element 2 is driven under the condition of a constant current density. The results of the reliability test are shown in Figure 32. In Figure 32, the initial luminance is set to 100%. From this result, it can be seen that the decrease in luminance of the light-emitting element 2 with driving time is small. It is clear that the light emitting element has good reliability. [Example]

[0326] In this example, the compound having a benzofuropyrimidine skeleton described in Embodiment 1 was The phosphorescent layer of 4mDBTBPBfpm-II emits yellow-green light. The light-emitting element (light-emitting element 3) used as the stock material will be described.

[0327] The molecular structures of the compounds used in this example are represented by the following structural formulas (i), (ii), (v) to ( vii) and (100). The device structure is that shown in Figure 1(A).

[0328] [ka]

[0329] <Fabrication of Light-Emitting Element 3> First, a silicon-containing indium tin oxide ( A glass substrate with an ITSO film was prepared. The ITSO surface was 2 mm square. The periphery was covered with a polyimide film so that the surface was exposed, and the electrode area was 2 mm × 2 mm. As a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water and heated at 200°C for 1 hour. After baking for 10 seconds, UV ozone treatment was performed for 370 seconds. -4 The inside is about Pa The substrate was introduced into a vacuum deposition apparatus under reduced pressure, and the substrate was heated to 170°C for 3 minutes in the heating chamber of the vacuum deposition apparatus. After vacuum baking for 10 minutes, the substrate was allowed to cool for about 30 minutes.

[0330] Next, the substrate was placed in a vacuum deposition apparatus with the surface on which ITSO was formed facing downward. The sample was fixed in a holder.

[0331] 10 in the vacuum chamber -4 After reducing the pressure to 100 Pa, 4,4',4 ''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT 3P-II) and molybdenum(VI) oxide, DBT3P-II: molybdenum oxide = 4 :2 (weight ratio) to form the hole injection layer 111. The thickness was set to 20 nm. Co-evaporation is the process of simultaneously depositing multiple different substances from different evaporation sources. This is a vapor deposition method in which the material is evaporated.

[0332] Next, 4-phenyl-4'-(9-phenylfluorene) represented by the above structural formula (ii) By depositing 20 nm of (benzo-9-yl)triphenylamine (abbreviation: BPAFLP), Thus, a hole transport layer 112 was formed.

[0333] Furthermore, on the hole transport layer 112, 4-[3'-(dibenzyl)-2-methyl-2-propanol] represented by the above structural formula (100) (benzothiophen-4-yl)biphenyl-3-yl]benzofuro[3,2-d]pyrimidin (abbreviation: 4mDBTBPBfpm-II) and N-(1 ,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]-9H-fluoren-2-amine (abbreviated as PCB BiF) and bis[2-(6-tert-butyl-4- Pyrimidinyl-κN3)phenyl-κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]) and BTBPBfpm-II:PCBBiF:[Ir(tBuppm)2(acac)]=0 After co-evaporating 20 nm of the film at a weight ratio of 0.5:0.5:0.05, 4 mDBTBP was Bfpm-II, PCBBiF, and [Ir(tBuppm)2(acac)] were mixed for 4 mDBTBPBfpm-II:PCBBiF:[Ir(tBuppm)2(acac)] = 0.8:0.2:0.05 (weight ratio) An optical layer 113 was formed.

[0334] Next, 4mDBTBPBfpm-II was added to 10 nm, followed by the An electron transport layer was formed by depositing 15 nm of bathophenanthroline (abbreviated as BPhen). 114 was formed.

[0335] Furthermore, lithium fluoride is vapor-deposited on the electron transport layer 114 to a thickness of 1 nm. Finally, an electron injection layer 115 was formed. A 200 nm thick aluminum film was formed, completing the light-emitting element 3. The deposition was all carried out using a resistance heating method.

[0336] <Operation characteristics of light-emitting element 3> The light-emitting element 3 obtained as described above was placed in a glove box with a nitrogen atmosphere. After sealing the device to prevent it from being exposed to the atmosphere, the operating characteristics of this light-emitting device were The measurements were carried out at room temperature (an atmosphere maintained at 25°C).

[0337] FIG. 33 shows the current density-luminance characteristics of the light-emitting element 3, FIG. 34 shows the voltage-luminance characteristics, and FIG. The efficiency characteristics are shown in Figure 35, the luminance-external quantum efficiency characteristics are shown in Figure 36, and the luminance-power efficiency characteristics are shown in Figure 3 Shown in Figure 7.

[0338] As can be seen from FIG. 35, Light-emitting element 3 exhibits favorable luminance-current efficiency characteristics and is a light-emitting element with favorable luminous efficiency. Therefore, 4mDBTBPBfpm-II, that is, the form of implementation The compounds with the benzofuropyrimidine skeleton described in Section 1 have a high triplet excited level (T1 level). position) and has a wide energy gap, so even yellow-green phosphorescent materials can be excited effectively. 34, the light-emitting element 3 has good voltage-luminance characteristics. This indicates that the light-emitting device has a low driving voltage. pm-II, that is, the compound having a benzofuropyrimidine skeleton described in embodiment 1 Similarly, the current in FIG. The density-luminance characteristics and the luminance-external quantum efficiency characteristics shown in Figure 36 are also very good. As shown in FIG. 37, the light-emitting element 3 exhibited very good power efficiency.

[0339] Next, the emission spectrum when a current of 0.1 mA was applied to the fabricated light-emitting element 3 was shown in FIG. The luminescence intensity is shown as a relative value with the maximum luminescence intensity set to 1. Molecule 3 exhibits yellow-green luminescence due to the luminescent material [Ir(tBuppm)2(acac)]. I found that.

[0340] In addition, the initial brightness is 5000 cd / m 2 The light-emitting element 3 is driven under the condition of a constant current density. The results of the reliability test are shown in Figure 39. In Figure 39, the initial luminance is set to 100%. From this result, it can be seen that the decrease in luminance of the light-emitting element 3 with the driving time is small. It is clear that the light emitting element has good reliability. [Example]

[0341] <Synthesis Example 3> In this synthesis example, the compound having the benzofuropyrimidine skeleton described in embodiment 1 4-{3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophene-4- 4mFDBtPBfpm ) (Structural formula (115)) is specifically illustrated below. is shown below.

[0342] [ka]

[0343] Step 1: Synthesis of 4-(9,9-dimethylfluoren-2-yl)dibenzothiophene > First, 19g of 2-bromo-9,9-dimethylfluorene, dibenzothiophen-4-yl Boronic acid 16g, tris(2-methylphenyl)phosphine (abbreviation: P(o-tolyl )3) 0.43g, 2M potassium carbonate aqueous solution 35mL, toluene 270mL, ethanol 90 mL of the solution was placed in a three-necked flask equipped with a reflux condenser, the atmosphere in the flask was replaced with nitrogen, and paradiacetic acid was added. 0.16 g of ammonium chloride was added and heated at 90°C for 13 hours. 0.21 g of (abbreviation) and 79 mg of palladium acetate were added and heated at 90°C for 17 hours. Water was added to the resulting mixture, and extraction was carried out using toluene. The extracted solution was then washed with water, saturated saline, and The solvent was distilled off from the filtrate, and the resulting solution was washed with water, dried over magnesium sulfate, and then gravity filtered. The residue was dissolved in toluene and filtered through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531- 16855 (hereinafter the same), alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog no. The mixture was filtered through a filter aid layered in the order of (Product No.: 540-00135, same below). The solvent was evaporated and the mixture was extracted with toluene and hexane (volume ratio: 1:10) and then passed through a silica gel column. The solvent was removed from the resulting solution by distillation, and the residue was purified by chromatography using a mixture of toluene and hexane. By recrystallization from the mixed solvent, a white solid was obtained in 70% yield. The synthesis scheme is shown in (a-3) below.

[0344] [ka]

[0345] Step 2: 6-(9,9-dimethylfluoren-2-yl)dibenzothiophene-4 Synthesis of -ylboronic acids Next, 17 g of 4-(9,9-dimethylfluoren-2-yl)dibenzothiophene was added to three The flask was degassed with nitrogen. The flask was cooled to -40°C in a cryostat, and then n-butyllithium (1.6M 34 mL of the hexane solution was added dropwise, and the mixture was stirred at room temperature for 1 hour. Cool to °C, add 6.6 mL of trimethyl borate dropwise, warm to room temperature, and then keep at room temperature. The mixture was stirred for 21 hours, and then 50 mL of 1 M hydrochloric acid was added thereto, followed by stirring for 1 hour. Extract with ethyl acetate, wash with saturated aqueous sodium bicarbonate and saturated brine, and The solvent was removed from the filtrate by distillation, toluene was added, and the mixture was washed with ultrasound. After suction filtration, a yellowish-white solid was obtained in a yield of 34%. The team is shown in (b-3) below.

[0346] [ka]

[0347] Step 3: 4-(3-bromophenyl)-6-(9,9-dimethylfluorene-2- Synthesis of (I)yldibenzothiophene Subsequently, 6-(9,9-dimethylfluoren-2-yl)dibenzothiophen-4-yl Boronic acid 7.1g, 3-iodo-bromobenzene 5.2g, P(o-tolyl)30. 57g, potassium carbonate 5.1g, toluene 74mL, ethanol 19mL, water 19mL The flask was purged with nitrogen and palladium acetate 0.2 1 g of toluene was added and heated at 80°C for 8 hours. The resulting mixture was extracted with toluene and saturated brine. The solvent in the filtrate was distilled off, and the resulting residue was The residue was dissolved in toluene and a filter aid consisting of layers of Celite, alumina, and Florisil was added. The solvent was distilled off, and the mixture was mixed with toluene and hexane in a volume ratio of 1:10 as the developing solvent. The yellowish white solid was obtained in a yield of 74% by silica gel column chromatography. The synthesis scheme of step 3 is shown below in (c-3).

[0348] [ka]

[0349] Step 4: 3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophene Synthesis of [phenyl-4-yl]phenylboronic acid pinacol ester> Next, 4-(3-bromophenyl)-6-(9,9-dimethylfluoren-2-yl)di 2.5g of benzothiophene, 1.2g of bis(pinacol)diboron, 1.4g of potassium acetate g was placed in a three-necked flask equipped with a reflux condenser, the atmosphere in the flask was replaced with nitrogen, and 300 ml of dioxane was added. mL of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) di Add 0.19 g of chloromethane adduct (abbreviation: Pd(dppf)Cl2) and heat at 90°C for 9. After heating for 5 hours, water was added to the resulting mixture, which was then extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated from the filtrate, and the resulting residue was extracted with toluene. Dissolve in ethylene and filter through a filter aid consisting of Celite, alumina, and Florisil layered in that order. The solvent was distilled off, and the mixture was diluted with toluene and hexane (volume ratio: 1:10) as a developing solvent. The product was purified by column chromatography to give a colorless oil in 17% yield. The synthesis scheme of Step 4 is shown below in (d-3).

[0350] [ka]

[0351] <Step 5: Synthesis of 4mFDBtPBfpm> Finally, 3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophene-4 -yl]phenylboronic acid pinacol ester 0.45g, 4-chlorobenzofuro[3, 2-d]pyrimidine 0.14 g, potassium phosphate 0.45 g, dioxane 4 mL, t-bu 0.16 g of ethanol was placed in a three-necked flask, the atmosphere in the flask was replaced with nitrogen, and 1 g of palladium acetate was added. 0.8 mg and di(1-adamantyl)-n-butylphosphine 5.6 mg were added and refluxed. The reaction was allowed to proceed, and water was added to the resulting mixture, which was then extracted with ethyl acetate and washed with saturated brine. Magnesium sulfate was added, and the mixture was subjected to gravity filtration. The solvent in the filtrate was distilled off, and a toluene:hexane= Purify by flash column chromatography using a 1:5 (volume ratio) developing solvent. A yellow solid was obtained in a yield of 10%. The synthesis scheme for step 5 is shown in formula (e-3) below. show.

[0352] [ka]

[0353] The yellow solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below.

[0354] 1 H-NMR.δ(CDCl3):1.37(s,6H),7.28-7.31(dt, 2H),7.37(d,1H),7.44-7.50(m,2H),7.58-7.66 (m,5H),7.69-7.73(m,3H),7.75-7.78(t,1H),7 .82(s,1H),7.93(d,1H),8.23-8.28(m,3H),8.6 4(td,1H),9.02(ts,1H),9.27(s,1H).

[0355] Also, 1 The H NMR charts are shown in Figures 40(A) and (B). Note that Figure 40(B) shows This is a chart showing an enlarged range from 7.0 ppm to 9.5 ppm in Figure 40(A). The measurement results confirmed that the target value of 4mFDBtPBfpm was obtained. (Reference example 1)

[0356] In this reference example, the 4,6-bis[3-(4-dibenzothienyl)phenyl]phenyl ether used in Example 3 was This article explains the synthesis method of 4,6mDBTP2Pm-II. .

[0357] <4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6m Synthesis of DBTP2Pm-II) 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)phenylboron. carboxylic acid, 3.5 g (34 mmol) of sodium carbonate, and 20 mL of 1,3-dimethyl-3 ,4,5,6-tetrahydro-2(1H)pyrimidinone (abbreviation: DMPU) and 10 mL The mixture was degassed by stirring under reduced pressure. g (81 μmol) of bis(triphenylphosphine)palladium(II) dichloride The reaction vessel was then purged with argon. The mixture was heated and stirred for 30 minutes by irradiation. After heating, water was added to the mixture and filtered. The solid was washed with dichloromethane and ethanol. Toluene was added, and the mixture was suction filtered through Celite, alumina, and Florisil. The filtrate was concentrated. The obtained solid was recrystallized using toluene to give 2.52 g of a white solid. The yield was 63%. The synthetic scheme for the above reaction is shown below.

[0358] [ka]

[0359] 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%.

[0360] Nuclear magnetic resonance method ( 1 H-NMR confirmed that this compound was the target compound, 4,6-bis[3 -(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-I I) was confirmed.

[0361] of the obtained material 1 The 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).

[0362] (Reference example 2) In this Reference Example, the N-(1,1'-biphenyl-4-yl)-9-phenyl- ,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]phenyl This article explains the synthesis method of ]-9H-fluoren-2-amine (abbreviation: PCBBiF). .

[0363] Step 1: N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-phenyl Synthesis of 9H-nyl-2-fluoren-amine In a 1 L three-neck flask, add N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-9 H-Fluoren-2-amine 45g (0.13mol) and sodium tert-butoxide 36g (0.38mol) of bromobenzene, 21g (0.13mol) of bromobenzene, and toluene The mixture was degassed by stirring under reduced pressure. The inside of the flask was replaced with nitrogen. Then, bis(dibenzylideneacetone)palladium(0) 0. 8g (1.4mmol) and tri(tert-butyl)phosphine (10wt% hexane The synthesis scheme for Step 1 is shown below.

[0364] [ka]

[0365] The mixture was stirred at 90°C for 2 hours under a nitrogen atmosphere. The solid was filtered off by suction filtration. The obtained filtrate was concentrated to give about 200 mL of a brown liquid. This brown liquid was mixed with toluene, and the resulting solution was then passed through Celite, alumina, and fluorine. The resulting filtrate was concentrated to give a pale yellow liquid. The product was recrystallized from hexane to give 52 g of a pale yellow powder in 95% yield. Ta.

[0366] Step 2: N-(1,1'-biphenyl-4-yl)-N-(4-bromophenyl) Synthesis of 9,9-dimethyl-9H-fluoren-2-amine In a 1 L Meyer flask, add N-(1,1'-biphenyl-4-yl)-9,9-dimethyl 45 g (0.10 mol) of N-phenyl-9H-fluoren-2-amine was added to the flask. 225 mL of benzene was added and dissolved by stirring under heating. After allowing the solution to cool to room temperature, 225 mL of ethyl acetate was added to the solution, and 18 g of N-bromosuccinimide (abbreviation: NBS) was added. 0.10 mol) was added and stirred at room temperature for 2.5 hours. The organic layer was washed three times with an aqueous solution of sodium bicarbonate and once with saturated saline. Magnesium was added and the mixture was left to stand for 2 hours and dried. The filtrate was concentrated to give a yellow liquid. The solution was purified using Celite, alumina, and Florisil. The solution was concentrated to give a pale yellow solid, which was recrystallized from toluene / ethanol. The target product, a white powder, was obtained in an amount of 47 g and a yield of 89%. The system is shown below.

[0367] [ka]

[0368] <Step 3: Synthesis of PCBBiF> In a 1 L three-neck flask, add N-(1,1'-biphenyl-4-yl)-N-(4-bromopheny 41g (80mmol)-9,9-dimethyl-9H-fluoren-2-amine, 9- 25 g (88 mmol) of phenyl-9H-carbazol-3-ylboronic acid was added to the flask. 240 mL of benzene, 80 mL of ethanol, and 120 mL of potassium carbonate aqueous solution (2.0 mol / L) mL was added and the mixture was degassed by stirring under reduced pressure. After degassing, the contents of the flask were Nitrogen substitution was performed. In addition, 27 mg (0.12 mmol) of palladium (II) acetate and tri( 154 mg (0.5 mmol) of ortho-tolylphosphine was added, and the mixture was again reduced in pressure. The mixture was degassed by stirring, and after degassing, the atmosphere in the flask was replaced with nitrogen. The mixture was stirred at 110° C. for 1.5 hours. The synthesis scheme for Step 3 is shown below.

[0369] [ka]

[0370] After that, the mixture was allowed to cool to room temperature while stirring, and the aqueous layer was extracted twice with toluene. The resulting extract solution and the organic layer were combined and washed twice with water and twice with saturated saline. Magnesium sulfate was added to the solution and allowed to stand, and then dried. The magnesium was removed, and the resulting filtrate was concentrated to give a brown solution. After mixing with the above, the resulting solution was purified through Celite, alumina, and Florisil. The obtained filtrate was concentrated to give a pale yellow solid. This pale yellow solid was diluted with ethyl acetate / ethanol. The objective product was recrystallized using HCl to obtain 46 g of a pale yellow powder in a yield of 88%.

[0371] The resulting pale yellow powder (38 g) was purified by train sublimation. The light yellow powder was heated to 345°C under the conditions of a pressure of 3.7 Pa and an argon flow rate of 15 mL / min. After purification by sublimation, the target pale yellow solid was obtained in a yield of 31 g and a recovery rate of 83%.

[0372] Nuclear magnetic resonance (NMR) analysis confirmed that this compound was the target N-(1,1'-biphenyl) 4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9H-fluoren-2-amine (abbreviation: PCBBiF) I confirmed that.

[0373] The resulting pale yellow solid 1 The H-NMR data is shown below. 1 H-NMR (CDCl3,500MHz): δ=1.45(s, 6H), 7.18( d, J=8.0Hz, 1H), 7.27-7.32(m, 8H), 7.40-7.50( m, 7H), 7.52-7.53(m, 2H), 7.59-7.68(m, 12H), 8 .19(d, J=8.0Hz, 1H), 8.36(d, J=1.1Hz, 1H). [Explanation of symbols]

[0374] 101 first electrode 102 second electrode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 501 first electrode 502 Second electrode 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 601 Drive circuit section (source side drive circuit) 602 Pixel section 603 Drive circuit section (gate side drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching TFT 612 Current Control TFT 613 First electrode 614 Insulators 616 EL layer 617 Second electrode 618 Light-emitting element 623 n-channel TFT 624 p-channel TFT 901 Case 902 Liquid crystal layer 903 Backlight 904 Case 905 Driver IC 906 terminal 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode First electrode of 1024W light emitting element 1024R First electrode of light-emitting element 1024G First electrode of light-emitting element 1024B First electrode of light-emitting element 1025 Bulkhead 1028 EL layer 1029 Second electrode of light-emitting element 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black layer (black matrix) 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 1201 Source electrode 1202 Active layer 1203 Drain electrode 1204 gate electrode 2001 Case 2002 light source 3001 Lighting equipment 5000 display area 5001 Display area 5002 Display area 5003 Display area 5004 Display area 5005 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7301 Housing 7302 Housing 7303 Connection section 7304 Display section 7305 Display section 7306 Speaker section 7307 Recording medium insertion section 7308 LED Lamp 7309 Operation Key 7310 Connection terminal 7311 Sensor 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9630 chassis 9631 Display section 9631a Display section 9631b Display section 9632a Touch panel area 9632b Touch panel area 9633 Solar Cells 9634 Charge / Discharge Control Circuit 9635 Battery 9636 DC / DC Converter 9637 Operation Key 9638 Converter 9639 Keyboard display switch button 9033 Fasteners 9034 Display mode switch 9035 Power Switch 9036 Power saving mode switch 9038 Operation switch

Claims

[Claim 1] An organic semiconductor device comprising a compound represented by formula (G1): 【Chemistry 1】 (In the formula, A １ represents a group having 6 to 100 carbon atoms, and the group is composed of one or more of a benzene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a dibenzofuran ring, a carbazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, and a triphenylamine structure, and the ring or the structure may have a substituent. １ ~R ５ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

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