Light-emitting element

Abstract

To provide a novel organic compound, benzofuropyrimidine derivative or benzothienopyrimidine derivative.SOLUTION: An organic compound is represented by the general formula (G1). Q represents oxygen or sulfur. Ar1, Ar2, Ar3, and Ar4 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring, the substituent of which is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the aromatic hydrocarbon ring contains 6 to 25 carbon atoms.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one embodiment of the present invention is not limited to the above technical fields. The present invention relates to an object, a method, a manufacturing method, or a driving method. Process, Machine, Manufacture, or Composition of Matter Specific examples include semiconductor devices, display devices, and liquid crystal display devices. It is possible. [Background technology]

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

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

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

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-182699 Summary of the Invention [Problem to be solved by the invention]

[0006] Therefore, one embodiment of the present invention provides a novel organic compound. In this paper, we present novel organic compounds, benzofuropyrimidine derivatives or benzothienopyrimidines. In addition, in one embodiment of the present invention, a novel fluorine derivative that can be used for a light-emitting element is provided. In one embodiment of the present invention, an organic compound that can be used in an EL layer of a light-emitting element is provided. Furthermore, the present invention provides a novel organic compound that can be used to produce a photocatalytic reaction. The present invention provides a novel light-emitting device, a novel electronic device, and a novel light-emitting element having high reliability. Alternatively, a novel lighting device is provided. Note that the description of these problems does not preclude the existence of other problems. It should be noted that one embodiment of the present invention does not necessarily solve all of these problems. It is not necessary to provide a detailed description of the invention. Other issues can be identified from the description, drawings, claims, etc. It is possible to do this. [Means for solving the problem]

[0007] One aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative. It is an organic compound represented by the following general formula (G1). The aromatic group is attached to the 8-position of the benzofuropyrimidine or benzothienopyrimidine skeleton. A structure in which multiple aromatic hydrocarbon rings are linked (specifically, 2 to 4 aromatic hydrocarbon rings are linked). Has.

[0008] [ka]

[0009] In the above general formula (G1), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is a benzene ring, a naphthalene ring, a fluorene ring, heteroaromatic rings including a phenylene ring, a phenanthrene ring, a triphenylene ring, and a dibenzothiophene ring; Heteroaromatic rings containing dibenzofuran rings, heteroaromatic rings containing carbazole rings, benzimidazo It has one or more of a phenyl ring or a triphenylamine structure. 1 is hydrogen , an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated carbon atom having 5 to 7 carbon atoms, a hydrogen group, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted an unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 12 carbon atoms; represents a heteroaryl group of the formula:

[0010] Another aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative. It is an organic compound represented by the following general formula (G2). As represented by G2), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton Multiple aromatic hydrocarbon rings are linked to the 8th position (specifically, 2 to 4 aromatic hydrocarbon rings are linked). It has a structure in which the 4-position has a skeleton that has at least hole transport properties.

[0011] [ka]

[0012] In the above general formula (G2), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 represent the same group, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring. and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or 7 to 10 polycyclic saturated hydrocarbon groups, or a cyano group, The number of carbon atoms forming the hydrogen ring is 6 to 25. In addition, m and n are each 0 or is 1. In addition, α represents a substituted or unsubstituted phenylene group, and t is an integer of 0 to 4. Also, Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, , a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted an aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 12 carbon atoms; represents an aryl group.

[0013] Another aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative. It is an organic compound represented by the following general formula (G3). As shown in G3), Multiple aromatic hydrocarbon rings are linked to the 8th position (specifically, 2 to 4 aromatic hydrocarbon rings are linked). It has a structure with a skeleton that has hole transport properties via a phenylene group at the 4-position.

[0014] [ka]

[0015] In the above general formula (G3), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. , Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon number 1 to 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbon groups having 5 to 7 carbon atoms, substituted or unsubstituted is an unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 6 or more carbon atoms, an aryl group having from 1 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms; Represents.

[0016] Another aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative. It is an organic compound represented by the following general formula (G4). G4) as a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton Multiple aromatic hydrocarbon rings are linked to the 8th position (specifically, 2 to 4 aromatic hydrocarbon rings are linked). It has a structure with a skeleton that has hole transport properties via a biphenyldiyl group at the 4-position.

[0017] [ka]

[0018] In the above general formula (G4), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. , Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon number 1 to 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbon groups having 5 to 7 carbon atoms, substituted or unsubstituted is an unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 6 or more carbon atoms, an aryl group having from 1 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms; Represents.

[0019] In each of the above structures, Ht in the general formulae (G2), (G3), and (G4) u ni are each independently a pyrrole ring structure, a furan ring structure, or a thiophene ring structure. Have one of them.

[0020] In each of the above structures, Ht in the general formulae (G2), (G3), and (G4) u ni are each independently any one of the following general formulae (Ht-1) to (Ht-26):

[0021] [ka]

[0022] In the above general formulas (Ht-1) to (Ht-26), Q is oxygen or sulfur. Also, R 2 ~R 71 each represents 1 to 4 substituents, and each independently represents a hydrogen atom; It represents any one of a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. Also, Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0023] In each of the above structures, A in the general formulae (G1), (G2), (G3), and (G4) r 1 , Ar 2 , Ar 3 , and Ar 4 are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0024] In each of the above structures, the general formulae (G1), (G2), (G3), and (G4) Among them, Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical.

[0025] In each of the above structures, the general formulae (G1), (G2), (G3), and (G4) Among them, Ar 1 , Ar 2 , Ar 3 , and Ar 4 is unsubstituted.

[0026] In each of the above structures, the general formulae (G1), (G2), (G3), and (G4) The partial structure of the general formula (GX) in the formula (GX) is represented by the following structural formulas (GX-p1) to (GX- p12) and (GX-n1) to (GX-n6).

[0027] [ka]

[0028] [ka]

[0029] Another aspect of the present invention is a compound represented by any one of structural formulas (100), (101), and (102). It is an organic compound represented by one of the following:

[0030] [ka]

[0031] Note that another embodiment of the present invention is a light-emitting element using the organic compound according to one embodiment of the present invention. The present invention also includes a light-emitting element having a guest material in addition to the above organic compound. The present invention also includes a light-emitting element having a phosphorescent material in addition to the organic compound. The present invention also provides a light-emitting element that includes a phosphorescent material and a carbazole derivative in addition to the organic compound. The carbazole derivatives are bicarbazole derivatives or derivatives containing a carbazolyl group. The aromatic amines include those having the following structure:

[0032] Another embodiment of the present invention is a light-emitting element using the organic compound according to any one of the above embodiments of the present invention. In one embodiment of the present invention, the EL layer between the pair of electrodes or the light-emitting layer included in the EL layer may be formed of a material other than the organic EL material. The present invention also includes a light-emitting element formed using a certain organic compound. In addition to the light-emitting element, a layer containing an organic compound (for example, a cap layer) is provided in contact with the electrode. In addition to the light emitting element, a transistor is also included in the present invention. The invention also includes light-emitting devices having a photodiode, a substrate, etc. microphone, camera, operation buttons, external connectors, housing, cover, support base or speaker. Electronic devices and lighting devices that have a function such as a light source are also included in the scope of the invention.

[0033] Another embodiment of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device. Therefore, the light-emitting device in this specification includes an image display device. It also refers to a light source (including lighting equipment) that is connected to a light-emitting device, such as an FPC (Fl extensible printed circuit) or TCP (Tape Carrier Modules with connectors such as the ier Package, A module with a printed wiring board or a light emitting element with COG (Chip On Glass) All modules in which ICs (integrated circuits) are directly mounted using the OLED (LED) method are also included in the category of light-emitting devices. It shall be. [Effects of the Invention]

[0034] In one embodiment of the present invention, a novel organic compound can be provided. In an embodiment, novel organic compounds, benzofuropyrimidine derivatives or benzothienopyrimidine derivatives, are used. In addition, in one embodiment of the present invention, a fluorine-containing compound can be used in a light-emitting element. In addition, in one embodiment of the present invention, a novel organic compound capable of emitting light can be provided. It is possible to provide a novel organic compound that can be used in the EL layer of the element. A novel light-emitting element with high reliability can be provided by using a novel organic compound that is one embodiment of the present invention. Furthermore, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. can be provided. [Brief explanation of the drawings]

[0035] [Figure 1] 1A to 1C illustrate a structure of a light-emitting element. [Figure 2] 1A and 1B illustrate a light-emitting device. [Figure 3] 1A and 1B illustrate a light-emitting device. [Figure 4] 1A and 1B are diagrams illustrating electronic devices. [Figure 5] 1A and 1B are diagrams illustrating electronic devices. [Figure 6] FIG. [Figure 7] 1A and 1B are diagrams illustrating a lighting device. [Figure 8] 1H-NMR chart of the organic compound shown in structural formula (100). [Figure 9] (A) UV-visible absorption and emission spectra of the organic compound represented by structural formula (100) in toluene solution. (B) UV-visible absorption and emission spectra of the solid thin film of the organic compound represented by structural formula (100). [Figure 10] 1H-NMR chart of the organic compound shown in structural formula (101). [Figure 11] (A) UV-visible absorption and emission spectra of the organic compound represented by structural formula (101) in toluene solution. (B) UV-visible absorption and emission spectra of the solid thin film of the organic compound represented by structural formula (101). [Figure 12] 1H-NMR chart of the organic compound shown in structural formula (102). [Figure 13] (A) UV-visible absorption and emission spectra of the organic compound represented by structural formula (102) in toluene solution. (B) UV-visible absorption and emission spectra of the solid thin film of the organic compound represented by structural formula (102). [Figure 14] 1A and 1B are diagrams illustrating light-emitting elements. [Figure 15] 10 is a graph showing current density-luminance characteristics of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 16] 10 shows voltage-luminance characteristics of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 17] 10 shows luminance-current efficiency characteristics of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 18]10 shows voltage-current characteristics of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 19] 10 shows emission spectra of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 20] 10 is a graph showing the reliability of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. [Figure 21] 10 is a graph showing current density-luminance characteristics of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. FIG. [Figure 22] 10 is a graph showing voltage-luminance characteristics of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. [Figure 23] 10 shows luminance-current efficiency characteristics of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. [Figure 24] 10 is a graph showing voltage-current characteristics of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. [Figure 25] 10 shows emission spectra of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. FIG. [Figure 26] 10 shows the reliability of the light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7. [Figure 27] 10 is a graph showing current density-luminance characteristics of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. FIG. [Figure 28] 10 is a graph showing voltage-luminance characteristics of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. [Figure 29] 10 is a graph showing luminance-current efficiency characteristics of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. [Figure 30] 10 is a graph showing voltage-current characteristics of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. [Figure 31] 10 shows emission spectra of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. FIG. [Figure 32] 10 is a graph showing the reliability of the light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11. [Figure 33] 1H-NMR chart of the organic compound shown in structural formula (103). [Figure 34] UV-visible absorption and emission spectra of the organic compound shown in structural formula (103) in toluene solution. [Figure 35] UV-visible absorption and emission spectra of a solid thin film of the organic compound represented by structural formula (103). [Figure 36] 1H-NMR chart of the organic compound shown in structural formula (105). [Figure 37] UV-visible absorption and emission spectra of the solid thin film of the organic compound represented by structural formula (105). [Figure 38] 1H-NMR chart of the organic compound shown in structural formula (126). [Figure 39] UV-visible absorption and emission spectra of the organic compound shown in structural formula (126) in toluene solution. [Figure 40] UV-visible absorption and emission spectra of the solid thin film of the organic compound represented by structural formula (126). [Figure 41] 1H-NMR chart of the organic compound shown in structural formula (128). [Figure 42] 1H-NMR chart of the organic compound shown in structural formula (143). [Figure 43] 10 is a graph showing current density-luminance characteristics of the light-emitting elements 12 and 13. FIG. [Figure 44] 10 is a graph showing voltage-luminance characteristics of the light-emitting elements 12 and 13. FIG. [Figure 45] 10 is a graph showing luminance-current efficiency characteristics of the light-emitting elements 12 and 13. FIG. [Figure 46] 10 is a graph showing voltage-current characteristics of the light-emitting element 12 and the light-emitting element 13. FIG. [Figure 47] FIG. 10 shows emission spectra of the light-emitting elements 12 and 13. [Figure 48] 10 is a graph showing the reliability of the light-emitting element 12 and the light-emitting element 13. FIG. [Figure 49]10 is a graph showing current density-luminance characteristics of the light-emitting elements 14 and 15. FIG. [Figure 50] 10 is a graph showing voltage-luminance characteristics of the light-emitting element 14 and the light-emitting element 15. FIG. [Figure 51] 10 is a graph showing luminance-current efficiency characteristics of the light-emitting elements 14 and 15. FIG. [Figure 52] 10 is a graph showing voltage-current characteristics of the light-emitting element 14 and the light-emitting element 15. FIG. [Figure 53] FIG. 10 is a graph showing emission spectra of the light-emitting elements 14 and 15. [Figure 54] 10 is a graph showing the reliability of the light-emitting element 14 and the light-emitting element 15. FIG. DETAILED DESCRIPTION OF THE INVENTION

[0036] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the embodiments described below. It is not to be construed as being limited to the

[0037] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as those in the actual embodiment for ease of understanding. Therefore, the disclosed invention may not necessarily represent the actual position, size, range, etc. The position, size, range, etc. are not necessarily limited to those disclosed in the drawings, etc.

[0038] In addition, in this specification and the like, when explaining the configuration of the invention using drawings, the same The reference numerals are commonly used even among different drawings.

[0039] (Embodiment 1) In this embodiment, an organic compound according to one embodiment of the present invention will be described. The organic compound in one embodiment is a benzofuropyrimidine derivative represented by the following general formula (G1): The organic compound according to one embodiment of the present invention is a benzothienopyrimidine derivative. is a benzofuropyrimidine skeleton or a benzothieno skeleton as represented by the following general formula (G1). Multiple aromatic hydrocarbon rings are connected to the 8th position of the pyrimidine skeleton (specifically, 2 to 4 aromatic hydrocarbon rings). It has a structure in which hydrogen hydride rings are linked.

[0040] [ka]

[0041] In the general formula (G1), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is a benzene ring, a naphthalene ring, a fluorene ring, heteroaromatic rings including a phenylene ring, a phenanthrene ring, a triphenylene ring, and a dibenzothiophene ring; Heteroaromatic rings containing dibenzofuran rings, heteroaromatic rings containing carbazole rings, benzimidazo It has one or more of a phenyl ring or a triphenylamine structure. 1 is hydrogen , an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated carbon atom having 5 to 7 carbon atoms, a hydrogen group, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted an unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 12 carbon atoms; represents a heteroaryl group of the formula:

[0042] Another embodiment of the present invention is an organic compound represented by the following general formula (G2): The organic compound represented by the following general formula (G2) has a benzofuropyrimidine skeleton or a benzothiamine skeleton. Multiple aromatic hydrocarbon rings (specifically, 2 to 4 aromatic hydrocarbon rings) are connected to the 8-position of the enopyrimidine skeleton. It has a structure in which aromatic hydrocarbon rings are linked together, and has a skeleton that has at least hole transport properties at the 4-position. do.

[0043] [ka]

[0044] In the above general formula (G2), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 represent the same group, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring. and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or 7 to 10 polycyclic saturated hydrocarbon groups, or a cyano group, The number of carbon atoms forming the hydrogen ring is 6 to 25. In addition, m and n are each 0 or is 1. In addition, α represents a substituted or unsubstituted phenylene group, and t is an integer of 0 to 4. Also, Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, , a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted an aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 12 carbon atoms; represents an aryl group.

[0045] Another embodiment of the present invention is an organic compound represented by the following general formula (G3): The organic compound represented by the following general formula (G3) has a benzofuropyrimidine skeleton or a benzothiamine skeleton. Multiple aromatic hydrocarbon rings (specifically, 2 to 4 aromatic hydrocarbon rings) are connected to the 8-position of the enopyrimidine skeleton. It has a structure in which aromatic hydrocarbon rings are linked together, and has hole transport properties via a phenylene group at the 4-position. It has a skeleton.

[0046] [ka]

[0047] In the above general formula (G3), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. , Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon number 1 to 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbon groups having 5 to 7 carbon atoms, substituted or unsubstituted is an unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 6 or more carbon atoms, an aryl group having from 1 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms; Represents.

[0048] Another embodiment of the present invention is an organic compound represented by the following general formula (G4): The organic compound represented by the following general formula (G4) has a benzofuropyrimidine skeleton or a benzothiamine skeleton. Multiple aromatic hydrocarbon rings (specifically, 2 to 4 aromatic hydrocarbon rings) are connected to the 8-position of the enopyrimidine skeleton. It has a structure in which aromatic hydrocarbon rings are linked together, and has hole transport properties via a biphenyldiyl group at the 4-position. It has a skeleton with

[0049] [ka]

[0050] In the above general formula (G4), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh Call Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 or more and 25 or less. Furthermore, m and n are each 0 or 1. , Ht uni represents a skeleton having hole transport properties. 1 is hydrogen, carbon number 1 to 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbon groups having 5 to 7 carbon atoms, substituted or unsubstituted is an unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 6 or more carbon atoms, an aryl group having from 1 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms; Represents.

[0051] In addition, Ht in the above general formulas (G2), (G3), and (G4) uni is the hole transport property each independently represents a skeleton having a pyrrole ring structure, a furan ring structure, or a thiophene ring structure It is one of the following:

[0052] In addition, Ht in the above general formulae (G2), (G3), and (G4) uni is the hole transport property Each of the following general formulas (Ht-1) to (Ht-26) represents a skeleton having the following structure: It is one.

[0053] [ka]

[0054] In the above general formulas (Ht-1) to (Ht-26), Q is oxygen or sulfur. Also, R 2 ~R 71 each represents 1 to 4 substituents, and each independently represents a hydrogen atom; It represents any one of a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. Also, Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0055] In addition, Ht in the above general formulas (G2), (G3), and (G4) uni is the hole transport property This structure allows the compound to be combined with other substances (e.g., luminescent substances). When used in a light emitting device, the device characteristics can be improved.

[0056] In the above general formulae (G1), (G2), (G3), and (G4), When the unsubstituted or unsubstituted aromatic hydrocarbon ring has a substituent, the substituent may be a group having 1 to 6 carbon atoms. an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated alkyl group having 5 to 7 carbon atoms; a saturated hydrocarbon group, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group It is one of, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Examples include an isobutyl group, a sec-butyl group, a tert-butyl group, and a pentyl group.

[0057] In the above general formulae (G1), (G2), (G3), and (G4), or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, substituted or unsubstituted monocyclic saturated hydrocarbon group having 7 or more carbon atoms a polycyclic saturated hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a substituted or unsubstituted When the phenylene group has a substituent, the substituent may be a methyl group, an ethyl group, a propyl group, or the like. group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group alkyl groups having 1 to 7 carbon atoms such as pentyl and hexyl groups; cyclopentyl groups; cyclohexyl group, cycloheptyl group, 8,9,10-trinorbornanyl group, etc. a cycloalkyl group having 5 to 7 carbon atoms, a phenyl group, a naphthyl group, a biphenyl group, etc. Examples include aryl groups having 6 to 12 carbon atoms.

[0058] In addition, Ar in the above general formulae (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring. The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 5 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a monocyclic saturated hydrocarbon group having 7 carbon atoms a polycyclic saturated hydrocarbon group of any one of the groups 1 to 10, or a cyano group; The number of carbon atoms forming the ring is 6 or more and 25 or less. The aromatic hydrocarbon ring may be monovalent or divalent. The specific example of a substituted aromatic hydrocarbon group having 6 to 25 carbon atoms. Examples include a phenyl group, a phenylene group, a naphthyl group, a naphthylene group, a fluorenyl group, Fluorenediyl group, spirofluorenyl group, spirofluorenediyl group, triphenyl However, it is important to avoid excessive lowering of the T1 level. Therefore, it is preferable that the polyacene does not have three or more rings constituting the aromatic hydrocarbon ring. The above fluorenyl and fluorenediyl groups have an alkyl group or a phenyl group at the 9-position. It is preferred that the alkyl group has a substituent such as a methyl group.

[0059] In addition, Ar in the above general formulae (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; a saturated hydrocarbon group or a cyano group, and a carbon atom forming an aromatic hydrocarbon ring. By setting the prime number to be between 6 and 25, the T1 level of the organic compound can be set to a desired value. In addition, it is possible to maintain a moderate degree of sublimation, and decomposition during sublimation purification and vacuum deposition is suppressed. Furthermore, as shown in one embodiment of the present invention, the aromatic hydrocarbon rings can be connected in a series of multiple rings. By bonding, when used in a light-emitting device, the aromatic hydrocarbon ring is reduced compared to when there is only one aromatic hydrocarbon ring. In particular, the benzofuropyrimidine skeleton or the benzothieno skeleton can improve reliability. Compared with the case where a substituent containing a heteroaromatic ring was introduced at the 8th position of the pyrimidine skeleton, This can suppress periodic deterioration.

[0060] In addition, Ar in the above general formulae (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 are each independently a substituted or unsubstituted benzene ring or naphthyl It may also be a talen ring.

[0061] In addition, Ar in the above general formulae (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 may be the same.

[0062] In addition, the partial structures in the general formulae (G1), (G2), (G3), and (G4) below The general formula (GX) can be represented by the following structural formulae (GX-p1) to (GX-p12) and (G- It may be any one of (X-n1) to (GX-n6).

[0063] [ka]

[0064] [ka]

[0065] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 But carbon Specific examples of the monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms include a cyclopropyl group, ... cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-methylcyclohexyl group, Examples include a chloroheptyl group.

[0066] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 But carbon Specific examples of the polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms include a norbornyl group, an aza-substituted aryl group, and an aza-substituted aryl group. Examples include a damantyl group, a decalin group, and a tricyclodecyl group.

[0067] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 But carbon Specific examples of the aryl group having 6 to 13 carbon atoms include a phenyl group, an o-tolyl group, and -tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group Examples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a fluorenyl group.

[0068] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 But carbon Specific examples of the alkyl group having 1 to 6 include a methyl group, an ethyl group, and a propyl group. , isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, Pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group methylpentyl, hexyl, isohexyl, 3-methylpentyl, 2-methylpentyl, 2 1,2-ethylbutyl group, 2,3-dimethylbutyl group, etc. can be.

[0069] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 But carbon Specific examples of the heteroaryl group having a number of 3 to 12 include a triazinyl group, a pyrazinyl group, and a cyclohexyl group. nyl group, pyrimidinyl group, pyridinyl group, quinolinyl group, isoquinolinyl group, benzothie a benzoyl group, a benzofuranyl group, an indolyl group, a dibenzothienyl group, a dibenzofuranyl group, or a carbazolyl group, and the like.

[0070] In addition, R in the above general formulae (G1), (G2), (G3), and (G4) 1 However, as mentioned above By using the specific example, the organic compound according to one embodiment of the present invention has a high T1 level. do.

[0071] Next, specific structural formulas of the organic compounds according to embodiments of the present invention are shown below. However, the present invention is not limited to these.

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] The organic compounds represented by the structural formulas (100) to (144) are represented by the general formula (G1) However, the organic compound of one embodiment of the present invention is not limited to this. I can't.

[0077] Next, one embodiment of the present invention is a benzofuropyrimidine derivative represented by the following general formula (G1): The present invention also describes a method for synthesizing the benzothienopyrimidine derivative.

[0078] [ka]

[0079] In the general formula (G1), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the hydrogen ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. group, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms a cyano group or a hydroxyl group, and the carbon atom forming the aromatic hydrocarbon ring is Prime numbers are between 6 and 25. m and n are either 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is a benzene ring, a naphthalene ring, a fluorene ring Heteroaromatic rings including phenanthrene ring, triphenylene ring, and dibenzothiophene ring, Heteroaromatic rings containing benzofuran rings, heteroaromatic rings containing carbazole rings, benzimidazole It has one or more of a ring or a triphenylamine structure. 1 is hydrogen, carbon Alkyl groups having 1 to 6 prime numbers, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted a substituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 12 carbon atoms; represents a heteroaryl group.

[0080] <Method for synthesizing organic compound represented by general formula (G1)> Various reactions can be applied to synthesize the organic compound represented by the general formula (G1) above. For example, an organic compound represented by general formula (G1) can be prepared by a simple method shown in the following synthesis scheme. The compounds can be synthesized.

[0081] As shown in the following scheme (A-1), a benzofuropyrimidine skeleton having a substituent at the 8-position Or, a halogen compound (A1) containing a benzothienopyrimidine skeleton and a boronation reaction of A By reacting the compound (A2) with the compound (A3), an organic compound represented by general formula (G1) can be obtained. can.

[0082] [ka]

[0083] In the above synthesis scheme (A-1), X represents a halogen, and Q represents oxygen or sulfur. Represents Ar 1 , Ar 2 , Ar 3 , and Ar 4are each independently substituted or unsubstituted The aromatic hydrocarbon ring is an aromatic hydrocarbon ring having 1 to 6 carbon atoms. an alkyl group, an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms; a cyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. The number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Each n is 0 or 1. A is a group having a total of 12 to 100 carbon atoms, and Benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, triphenylene ring, dibenzyl ring Heteroaromatic rings containing benzothiophene rings, heteroaromatic rings containing dibenzofuran rings, carbazole Heteroaromatic rings containing rings, benzimidazole rings, or triphenylamine structures has multiple. Also, R 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a polycyclic saturated hydrocarbon group, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted and represents a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0084] As shown in the following synthesis scheme (A-2), a benzofuropyrimidine skeleton or a benzopyrimidine skeleton can be prepared. Dihalogen compounds containing thienopyrimidine skeletons (B1) and boronic acid compounds of A (A2 ), to obtain intermediate (B2), which is then reacted with boronic acid compound (B3). By this, the organic compound represented by the general formula (G1) can also be obtained.

[0085] [ka]

[0086] In the above synthesis scheme (A-2), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring. The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 5 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a monocyclic saturated hydrocarbon group having 7 carbon atoms 10 to 11, or a cyano group, and The number of carbon atoms forming the hydrogen ring is 6 to 25. In addition, m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is not a benzene ring, naphthalene ring, or the like. containing a fluorene ring, a phenanthrene ring, a triphenylene ring, or a dibenzothiophene ring heteroaromatic rings containing a dibenzofuran ring, heteroaromatic rings containing a carbazole ring, It has one or more of a benzimidazole ring and a triphenylamine structure. , R 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 7 carbon atoms, Monocyclic saturated hydrocarbon groups, substituted or unsubstituted polycyclic saturated hydrocarbon groups having 7 to 10 carbon atoms a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted carbon It represents a heteroaryl group having 3 to 12 prime numbers.

[0087] As shown in the following synthesis scheme (A-3), a benzofuropyrimidine skeleton or a benzopyrimidine skeleton can be prepared. A trihalogen compound (C1) containing a zothienopyrimidine skeleton and a boronic acid compound (A 2) to obtain intermediate (C2), and then react with R 1 The reaction of boronic acid compound (C3) with After obtaining intermediate (C4) through the reaction, boronic acid compound (B3) is reacted to give In this case, an organic compound represented by general formula (G1) can also be obtained.

[0088] [ka]

[0089] In the above synthesis scheme (A-3), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring. The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 5 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a monocyclic saturated hydrocarbon group having 7 carbon atoms 10 to 11, or a cyano group, and The number of carbon atoms forming the hydrogen ring is 6 to 25. In addition, m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is not a benzene ring, naphthalene ring, or the like. containing a fluorene ring, a phenanthrene ring, a triphenylene ring, or a dibenzothiophene ring heteroaromatic rings containing a dibenzofuran ring, heteroaromatic rings containing a carbazole ring, It has one or more of a benzimidazole ring and a triphenylamine structure. , R 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 7 carbon atoms, Monocyclic saturated hydrocarbon groups, substituted or unsubstituted polycyclic saturated hydrocarbon groups having 7 to 10 carbon atoms a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted carbon represents a heteroaryl group having a prime number of 3 to 12. 1is a boronic acid or boronic acid ester The cyclic triol borate salt represents lithium or cyclic triol borate salt. In addition to the potassium salt, the potassium salt and the sodium salt may also be used.

[0090] In addition, the 8 used in the above synthesis schemes (A-1), (A-2), and (A-3) It contains a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton having a substituent at the Halogen compounds (A1), boronic acid compounds (A2), benzofuropyrimidine skeletons or The compounds are dihalogen compounds (B1) containing a benzothienopyrimidine skeleton, intermediates (B2), and borohydrides. Phosphoric acid compound (B3), containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton Trihalogen compounds (C1), intermediates (C2), R 1 Boronic acid compound (C3), and Various types of intermediate (C4) are commercially available or can be synthesized. A benzofuropyrimidine derivative or a benzothienopyrimidine derivative represented by the general formula (G1) Many types of conductors can be synthesized. The compounds are characterized by a wide variety.

[0091] The organic compound according to one embodiment of the present invention and an example of a synthesis method thereof have been described above. The present invention is not limited to this, and other synthesis methods may be used for synthesis.

[0092] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiments. can be done.

[0093] (Embodiment 2) In this embodiment mode, a light-emitting element using the organic compound shown in Embodiment Mode 1 will be described with reference to FIG. and explain.

[0094] <Basic structure of light-emitting element> First, the basic structure of a light-emitting element will be described. Specifically, the first electrode 101 and the second electrode 102 are connected to each other. It has a structure in which an EL layer 103 is sandwiched between an electrode 102 .

[0095] In addition, in FIG. 1(B), a plurality of EL layers (two layers in FIG. 1(B)) are disposed between a pair of electrodes. a, 103b), and a stacked structure (tandem structure) having a charge generating layer 104 between the EL layers. A light-emitting element having a tandem structure can be driven at a low voltage and consumes less power. A light emitting device with low light emission can be realized.

[0096] When a voltage is applied to the first electrode 101 and the second electrode 102, the charge generating layer 104 generates a Electrons are injected into one EL layer (103a or 103b) and the other EL layer (103b or 1B, the first electrode 1 When a voltage is applied to the charge generating layer 101 so that the potential of the charge generating layer 101 is higher than that of the second electrode 102, Electrons are injected from the electrode 4 into the EL layer 103a, and holes are injected into the EL layer 103b. .

[0097] The charge generating layer 104 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the transmittance of visible light through the charge generating layer 104 is 40% or more.) In addition, the charge generating layer 104 has a lower conductivity than the first electrode 101 and the second electrode 102. It still works.

[0098] 1(C) shows the EL layer 103 shown in FIG. 1(A) (EL layer 103 shown in FIG. 1(B)). a, 103b) has a laminated structure) shows an example of a laminated structure In this case, however, the first electrode 101 functions as an anode. The EL layer 103 On the first electrode 101, a hole injection layer 111, a hole transport layer 112, It has a structure in which a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are laminated in this order. In addition, even in the case of a tandem structure having a plurality of EL layers as shown in FIG. 1(B), each EL layer is The structure is such that the layers are stacked in order from the anode side as described above. The first electrode 101 is the cathode, When the second electrode 102 is an anode, the stacking order of the EL layers is reversed.

[0099] The light-emitting layers 113 included in the EL layers (103, 103a, 103b) each contain a light-emitting material or By appropriately combining multiple substances, fluorescent or phosphorescent light of the desired color can be obtained. Furthermore, the light-emitting layer 113 may have a laminated structure that emits light of different colors. In this case, the luminescent material and other materials used in each of the laminated luminescent layers are different from each other. In addition, the plurality of EL layers (103a, 103b) shown in FIG. In this case, different luminescent colors may be obtained from the respective luminescent layers. The light-emitting material and other materials may be different materials.

[0100] In the light-emitting element of one embodiment of the present invention, the EL layer (103, 103a, 103b) The light emission obtained in the above can be made to resonate between the two electrodes, thereby enhancing the light emission obtained. For example, in FIG. 1C, the first electrode 101 is a reflective electrode, and the second electrode 10 By using 2 as a semi-transmissive and semi-reflective electrode, a micro-optical resonator (microcavity) structure is formed. This can enhance the light emission from the EL layer 103.

[0101] The first electrode 101 of the light-emitting element is made of a conductive material having reflectivity and a conductive material having light-transmitting property. When the reflective electrode has a laminated structure with a transparent conductive material (transparent conductive film), the thickness of the transparent conductive film must be controlled. Specifically, the light emitting layer 113 can be optically adjusted by controlling the light emitting layer 113. The distance between the first electrode 101 and the second electrode 102 is mλ / 2 where λ is the wavelength of light. (where m is a natural number)

[0102] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to the region (light-emitting region) of the light-emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to the region (light-emitting region) of the light-emitting layer 113 where desired light is obtained, , and are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). It is preferable that the light-emitting region is a region where holes in the light-emitting layer 113 and The recombination region with electrons is shown.

[0103] By performing such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be adjusted. This narrows the line width of the light source, thereby enabling light emission with good color purity to be obtained.

[0104] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is difficult to precisely define the reflective areas of the first electrode 101 and the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, The above effect can be obtained by assuming the first The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 1 / 3 of the optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained. The optical distance is the distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained. However, it is possible to reduce the reflection area in the first electrode 101 and the emission area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light emitting layer where the desired light is obtained is assumed to be the reflective region, and any position of the light emitting layer where the desired light is obtained is assumed to be the emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0105] When the light-emitting element shown in FIG. 1C has a microcavity structure, the EL layer is common. Therefore, different wavelengths of light (monochromatic light) can be extracted. This eliminates the need for separate coloring (for example, RGB) for the color layer, enabling high definition. It is also possible to combine it with a color filter. This makes it possible to strengthen the signal, thereby reducing power consumption.

[0106] The light-emitting element shown in FIG. 1(E) is an example of the light-emitting element having the tandem structure shown in FIG. 1(B). As shown in the figure, three EL layers (103a, 103b, 103c) are connected to a charge generating layer (10 The three EL layers (103a, 104a, 104b) are stacked on top of each other. Each of the light-emitting layers (113a, 113b, 113c) has a light-emitting layer (113a, 113b, 113c). Therefore, the light emitting colors of the light emitting layers can be freely combined. The light-emitting layer 113b is red, green, or yellow, and the light-emitting layer 113c is blue. However, the light-emitting layer 113a can be red, and the light-emitting layer 113b can be blue, green, or yellow. Either of these may be used, and the light-emitting layer 113c may be red.

[0107] In the light-emitting element according to one embodiment of the present invention, the first electrode 101 and the second electrode At least one of the electrodes 102 is a light-transmitting electrode (transparent electrode, semi-transmitting / semi-reflective electrode, etc.). When the electrode having light transmission is a transparent electrode, the visible light transmittance of the transparent electrode shall be 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of the semi-transmissive / semi-reflective electrode for visible light is The ratio is 20% or more and 80% or less, preferably 40% or more and 70% or less. , resistivity is 1×10 -2 It is preferable to set it to Ωcm or less.

[0108] In the above-described light-emitting element which is one embodiment of the present invention, the first electrode 101 and the second electrode When one of the electrodes 102 is a reflective electrode, the possibility of the reflective electrode The reflectance of visible light is set to 40% or more and 100% or less, preferably 70% or more and 100% or less. In addition, this electrode has a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.

[0109] <Specific structure of light-emitting element and manufacturing method> Next, a specific structure and a manufacturing method of the light-emitting element shown in FIG. 1, which is one embodiment of the present invention, will be described. Here, as shown in FIG. 1(A) and FIG. 1(C), the EL layer 103 is a single layer. In addition to the light-emitting device with the structure, the tandem structure shown in Figs. 1(B), 1(D), and 1(E) The light emitting devices shown in Figure 1 are also described. In the case of a cavity structure, for example, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a reflective electrode. The electrode 102 may be formed as a semi-transmissive and semi-reflective electrode. Alternatively, a plurality of electrodes can be used, and the second electrode 102 can be formed as a single layer or a stacked layer. After the EL layer (103, 103b) is formed, the material is selected and formed in the same manner as above. These electrodes can be fabricated by sputtering or vacuum deposition.

[0110] <First Electrode and Second Electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from those having the above-mentioned functions of both electrodes. If the requirements are met, the following materials can be used in combination. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (IT SO), In-Zn oxide, and In-W-Zn oxide. Aluminum (Al), Titanium (Ti), Chromium (Cr), Manganese (Mn), Iron (Fe), Cobalt (Co), Nickel (Ni), Copper (Cu), Gallium (Ga), Zinc (Zn), Indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten Tin (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium Metals such as yttrium (Y), neodymium (Nd), and alloys containing these in appropriate combinations are used. In addition, elements belonging to Group 1 or Group 2 of the periodic table that are not listed above can also be used. Elements (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium rare earth metals such as strontium (Sr), europium (Eu), ytterbium (Yb) and An alloy containing an appropriate combination of these, graphene, etc. may also be used.

[0111] The light-emitting element shown in FIG. 1 has an EL layer 103 having a stacked structure as shown in FIG. 1(C). When the first electrode 101 is an anode, the hole injection layer of the EL layer 103 is formed on the first electrode 101. 111 and a hole transport layer 112 are sequentially formed by vacuum deposition. As shown in the figure, a plurality of EL layers (103a, 103b) having a laminated structure sandwiches a charge generating layer 104. When the first electrode 101 is an anode, the EL layer 103 is formed on the first electrode 101. The hole injection layer 111a and the hole transport layer 112a are sequentially formed by vacuum deposition. In addition, after the EL layer 103a and the charge generation layer 104 are formed in this order, the charge generation layer 10 4, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are similarly laminated in this order. will be done.

[0112] <Hole injection layer and hole transport layer> The hole injection layer (111, 111a, 111b) is connected to the first electrode 101, which is an anode, and the charge generation A layer that injects holes from the layer (104) into the EL layers (103, 103a, 103b). and is a layer containing a material with high hole injection properties.

[0113] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. Examples of oxides of transition metals include oxides of tungsten, manganese, and the like. Phthalocyanine (abbreviated as HPc) and copper phthalocyanine (abbreviated as CuPC) Nin-based compounds, etc. can be used.

[0114] In addition, the low molecular weight compound 4,4',4''-tris(N,N-diphenylamino)trimethylsilyl Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl 4,4-Triphenylamine (MTDATA), '-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl( Abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' -phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD) , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl Nylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9- (phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCz Aromatic amine compounds such as PCN1) and the like can be used.

[0115] In addition, poly(N-vinyl alcohol), which is a polymer compound (oligomer, dendrimer, polymer, etc.), Poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl]phenyl] (Nyl-N'-phenylamino)phenyl methacrylamide] (abbreviation: PTPDMA), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] ] (abbreviation: Poly-TPD), etc. can be used. PEDOT / PSS) / poly(styrenesulfonic acid) Acid-added polymers such as polyaniline / poly(styrene sulfonic acid) (PAni / PSS) It is also possible to use a diol-based compound, etc.

[0116] In addition, materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptor materials). In this case, a composite material containing an acceptor material can be used. Electrons are extracted from the hole transport material and holes are formed in the hole injection layer (111, 111a, 111b). are generated and are transported through the hole transport layers (112, 112a, 112b) to the light emitting layers (113, 113 Holes are injected into the hole injection layers (111, 111a, 111b). is a single layer consisting of a composite material containing a hole transport material and an acceptor material (electron acceptor material). The layer may be formed of a hole transport material and an acceptor material (electron acceptor material). Each of these layers may be formed by laminating different layers.

[0117] The hole transport layer (112, 112a, 112b) is formed by the hole injection layer (111, 111a, 111 The holes injected from the first electrode 101 are transported to the light-emitting layer (113, 113a, 11b). The hole transport layer (112, 112a, 112b) is a layer that transports holes to the The hole transport layer (112, 112a, 112b) is a layer containing a transport material. The insulating material has the same HOMO level as that of the hole injection layer (111, 111a, 111b). It is preferable to use one having a HOMO level close to that of the other.

[0118] The acceptor material used in the hole injection layer (111, 111a, 111b) is an element Oxides of metals belonging to Groups 4 to 8 of the periodic table can be used. are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tantalum oxide Among them, molybdenum oxide is particularly It is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. The organic acceptors used are chloranil derivatives, hexaazatriphenylene derivatives, etc. As the compound having an electron-withdrawing group (halogen group or cyano group), 7, 7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4 -TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5, 8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7 ,8-Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. In particular, fused aromatic rings having multiple heteroatoms such as HAT-CN are preferred. Compounds to which electron-withdrawing groups are bonded are preferred because they are thermally stable. Radialene derivatives with halogen groups such as fluoro groups or cyano groups in the It is preferred because it has a very high acceptability, specifically α,α',α''-1,2,3-cyclopropanediol. Propantriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetate nitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2 ,6-Dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonite aryl], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3, 4,5,6-pentafluorobenzeneacetonitrile].

[0119] The hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 As the hole transport material used in 2b), 10 -6 cm 2 / Vs or higher hole mobility In addition, other materials that have a higher hole transporting property than electron transporting property are also suitable. can be used.

[0120] As the hole transport material, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives, Furan derivatives and thiophene derivatives) and aromatic amines (chemicals with aromatic amine skeletons) A material having a high hole transporting property, such as a compound, is preferred.

[0121] The carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole derivatives (e.g., 3,3'-bicarbazole derivatives), aromatic compounds having a carbazolyl group amines and the like.

[0122] The bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) include Specifically, 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-Bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazo 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carba 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4 -yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-( 2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: β NCCP) and others.

[0123] Specific examples of aromatic amines having a carbazolyl group include 4-phenyl-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCB A1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2 -yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole -3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: P CBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazo (3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl -(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N ,N'-Bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene -1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N' ,N''-Tris(9-phenylcarbazol-3-yl)benzene-1,3,5-tri Amine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl) 9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PC BAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl) Phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 3- [N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl Carbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole [N-3-yl]-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC A2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)a 3-[N-(4-diphenylamino)-9-phenylcarbazole (abbreviation: PCzPCN1), N-phenylaminophenyl)-9-phenylcarbazole (abbreviation: PC zDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenyla 3,6-bis[N-(4 -diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazo (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4 -(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline N,N'-bis[4-(carbazol-9-yl)phenyl]phenanthrin (abbreviation: YGA1BP) ]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: Y GA2F), 4,4',4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) and others.

[0124] In addition to the above, the carbazole derivatives include 3-[4-(9-phenanthryl)-phenanthroline]- 3-[4-(1-naphthyl)]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 1,3-Phenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN) -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl) Biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- Phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl) 9-[4-(10-phenyl-9-anthracene]phenyl)benzene (abbreviation: TCPB), (racenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like.

[0125] Specific examples of the thiophene derivatives and furan derivatives include 1,3,5-tri( Dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphen Nyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiazolinone Fluorophen (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene [6-phenyl-9-yl]phenyldibenzothiophene (abbreviation: DBTFLP-I V), 4,4',4''-(benzene-1,3,5 -triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-( 9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation Examples include compounds with a furan skeleton such as mmDBFFLBi-II.

[0126] Specific examples of the aromatic amine include 4,4'-bis[N-(1-naphthyl)-N -phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3 -methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-di Amine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2 -yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'- (9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4 -phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9 ,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene -2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLA DFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluorene-7-yl) 2-[N-(4-diphenylaminophenyl)- ... )-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2, 7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9, 9'-Bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-na 4,4-triphenylamine (abbreviation: 1-TNATA), ',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDAT A), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino] Triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl)-N,N '-Diphenyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N -(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPA B) N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N '-Diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviation: DPA3B) and the like.

[0127] As hole transport materials, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4 -vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4- (4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)meth acrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl) -N,N'-bis(phenyl)benzidine (abbreviation: Poly-TPD) A mixture can also be used.

[0128] However, the hole transport material is not limited to the above, and one or more of various known materials may be used. In combination, the hole injection layer (111, 111a, 111b) and the hole transport layer (111, 111a, 111b) are It can be used for the hole transport layer (112, 112a, 112b). Each of the layers 112, 112a, and 112b may be formed from a plurality of layers. For example, a first hole transport layer and a second hole transport layer may be laminated.

[0129] In the light-emitting device shown in FIG. 1, the hole transport layer (112, 113) of the EL layer (103, 103a) 2a) by vacuum deposition. In the case of a light-emitting element having a tandem structure shown in After the formation, a light-emitting layer 113b is also formed on the hole transport layer 112b of the EL layer 103b by vacuum deposition. It is formed by

[0130] <Light-emitting layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing a light-emitting substance. Luminescent materials include blue, purple, blue-purple, green, yellow-green, yellow, orange, and red. In addition, a material exhibiting different properties is appropriately used for the plurality of light-emitting layers (113a, 113b, 113c). By using luminescent materials having different luminescent colors (for example, complementary colors), It is possible to obtain white light by combining different luminescent colors. It may also have a laminated structure containing different light-emitting materials.

[0131] The light-emitting layers (113, 113a, 113b, 113c) contain a light-emitting material (guest material). In addition, one or more organic compounds (host materials, etc.) may be contained. The organic compound or compounds may be an organic compound according to one embodiment of the present invention or a compound according to the present embodiment. One or both of the hole transporting material and the electron transporting material described in the embodiment can be used.

[0132] As a luminescent material that can be used in the luminescent layer (113, 113a, 113b, 113c), , without particular limitation, a light-emitting material that converts singlet excitation energy into light emission in the visible light region; or A luminescent material that converts triplet excitation energy into luminescence in the visible light region can be used.

[0133] Other light-emitting materials include, for example, the following:

[0134] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples thereof include pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, and the like. Olene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives Pyrene derivatives are particularly well known for their The photon yield is high, which is preferable. Specific examples of pyrene derivatives include N,N'-bis(3- methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl N,N'-diphenylpyrene-1,6-diamine (abbreviation) Name: 1,6FrAPrn), N,N'-bis(dibenzothiophen-2-yl)-N,N '-Diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( Pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura N,N'-(pyrene-1,6-diamine) (abbreviation: 1,6BnfAPrn), yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyren-1,6-diyl)bis[ (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation :1,6BnfAPrn-03).

[0135] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-calcium (bazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-di N,9-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA) Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo PCAPA, 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), Perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP) , N,N'-(2-tert-butylanthracene-9,10-diyldi-4,1-phenyl) N,N',N'-triphenyl-1,4-phenylenediamine)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation :DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-an tolyl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) can be used. .

[0136] Furthermore, examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials. materials (phosphorescent materials) and thermally activated delayed fluorescence (TAF) tivated delayed fluorescence (TADF) materials are can be.

[0137] Phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. These emit different colors (emission peaks) depending on the substance, so they should be selected appropriately as needed. Select and use.

[0138] It has a blue or green color and the peak wavelength of the emission spectrum is between 450 nm and 570 nm. Some phosphorescent materials include the following:

[0139] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN 2 ]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrp)] tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl [Ir(iPr5 btz)3]), organometallic complexes with a 4H-triazole skeleton, such as tris[3- Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato ]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl Iridium(II) I) (abbreviation: [Ir(Prtz1-Me)3]) Organometallic complexes containing fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl]propanol [phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] [Ir(dmpimpt-Me)3 organometallic complexes with imidazole skeletons, such as bis[2-(4',6'-difluoromethyl] (O-phenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazoline) aryl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pi Lysinato-N,C 2’ ] Iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’ }Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) , bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium (III) Acetylacetonate (abbreviation: FIr(acac)) Examples of suitable organometallic complexes include those having phenylpyridine derivatives as ligands.

[0140] It is green or yellow and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0141] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(trimethylsilyl) Bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Ir(mpmppm)2(acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl (phenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}iridium(III) (abbreviation :[Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( organometallic iridium complexes with pyrimidine skeletons, such as (acetyl acac)] cetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)( Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: Organometallic pyrazine skeletons such as [Ir(mppr-iPr)2(acac)] Iridium complex, tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iriji Ir(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), (benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato- N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(a cac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] Organometallic iridium complexes with pyridine skeletons, bis(2,4-diphenyl-1,3-o Xazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir( dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl] Pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ]), as well as organometallic complexes such as tris(acetylacetonato)(monophenanthroline) Rare earth metals such as terbium(III) (abbreviated as [Tb(acac)3(Phen)]) Examples include complexes of the aryl group.

[0142] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0143] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmethyl Thanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III ) (abbreviation: [Ir(d1npm)2(dpm)]) Metal complex, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridide Ir(tppr)2(acac)], bis(2,3,5-trimethylsilyl) (triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethyl {(2,6-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC} ... thyl-3,5-heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir (dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4- Cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazine {(2,2,6,6-tetramethyl-3,5-heptanedioic acid)-N-phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedioic acid) Nat-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalate Nat-N,C 2’ ]Iridium(III) (abbreviation: [Ir(mpq)2(acac)]) , (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ ) Iri Ir(dpq)2(acac) (acetylacetonate) ) Bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) Organometallic compounds with a pyrazine skeleton, such as [Ir(Fdpq)2(acac)] complexes and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium (III) (abbreviation Name: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iriji Ir(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentaerythroyl) Tandione-κ 2O,O') Iridium(III) and other organic compounds with a pyridine skeleton Metal complex, 2,3,7,8,12,13,17,18-octaethyl-21H,23H- Platinum complexes such as porphyrin platinum(II) (abbreviation: [PtOEP]), tris(1,3 -diphenyl-1,3-propanedionato)(monophenanthroline)europium(I II) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)- 3,3,3-Trifluoroacetonato](monophenanthroline)europium(III) ) (abbreviation: [Eu(TTA)3(Phen)]).

[0144] Organic compounds (host materials, etc.) used in the light-emitting layers (113, 113a, 113b, 113c) The energy gap is larger than that of the luminescent material (guest material). One or more substances having the above formula may be selected and used.

[0145] Therefore, the luminescent material used in the luminescent layers (113, 113a, 113b, 113c) is a fluorescent material. In this case, the organic compound (host material) used in combination with the light-emitting substance is a singlet excited Organic compounds with a high energy level in the excited triplet state and a low energy level in the triplet excited state It is preferable to use the following organic compound (host material) in combination with the light-emitting substance. As the material, a hole transporting material (described above) or an electron transporting material (described later) shown in this embodiment mode can be used. In addition, bipolar materials and the like can be used.

[0146] Although some of the above examples overlap, preferred combinations with luminescent materials (fluorescent materials, phosphorescent materials) From this viewpoint, specific examples of organic compounds are shown below.

[0147] When the luminescent material is a fluorescent material, an organic compound that can be used in combination with the luminescent material (Host materials) include anthracene derivatives, tetracene derivatives, and phenanthrene derivatives condensed polycyclic aromatic hydrocarbons such as pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives aromatic compounds.

[0148] Specific examples of organic compounds (host materials) used in combination with fluorescent light-emitting substances include: is 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H- Carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl -9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4 -(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN ), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl- 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3- Amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenyl Amine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4 -[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol N-(9,10-diphenyl-2-anthryl)-3-amine (abbreviation: PCAPBA), )-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6 ,12-Dimethoxy-5,11-diphenylchrysene, N,N,N',N',N'',N '',N''',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10 ,15-tetraamine (abbreviation: DBC1), 9-[4-(10-phenyl-9-anthracene 7-[4-(10-phenyl)phenyl]-9H-carbazole (abbreviation: CzPA), [c,g]carbazole (abbreviation: c gDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]- Benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl- 10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl }-anthracene (abbreviation: FLPPA), 9,10-bis(3,5-diphenylphenyl) ) anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: :DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation :t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(styryl) 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 1,3,5-triphenyl-4,4'-diyldiphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1 -pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyltetracene, 5,12 -bis(biphenyl-2-yl)tetracene.

[0149] In addition, when the luminescent material is a phosphorescent material, the organic compound (phosphor) used in combination with the luminescent material The triplet excitation energy (energy between the ground state and the triplet excited state) of the luminescent material is It is sufficient to select an organic compound with triplet excitation energy greater than the energy difference. A plurality of organic compounds (e.g., a first host material and a second When a host material (or an assist material, etc.) is used in combination with a light-emitting substance, It is preferable to use a mixture of a plurality of organic compounds described above with a phosphorescent material.

[0150] By using this structure, the energy transfer from the exciplex to the luminescent material, Ex Using TET (Exciplex-Triplet Energy Transfer) It is possible to efficiently obtain light emission with high excitation power. A compound that easily forms an electron-transporting complex and easily accepts holes (hole transport material) is preferable. It is particularly preferable to combine it with a compound that readily accepts electrons (electron transporting material). Note that the organic compound of one embodiment of the present invention described in Embodiment 1 has a stable triplet excited state. Therefore, it is suitable as a host material when the light-emitting material is a phosphorescent material. When used in combination with phosphorescent materials that emit green light from triplet excited energy levels, It is suitable.

[0151] In addition, when the light-emitting substance is a phosphorescent material, an organic compound that can be used in combination with the light-emitting substance is Compounds (host materials, assist materials) include aromatic amines, carbazole derivatives, diamines, and Benzothiophene derivatives, dibenzofuran derivatives, zinc and aluminum metal complexes, Quinoxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline Derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, etc.

[0152] Among the above, aromatic amines (aromatic amine skeletons) which are organic compounds with high hole transport properties are Specific examples of the compound having the formula (I) include the same as the specific examples of the hole transport material shown above. Examples include:

[0153] Specific examples of carbazole derivatives, which are organic compounds with high hole transport properties, include the following: Specific examples of the hole transport material are the same as those shown in 1.

[0154] In addition, dibenzothiophene derivatives and dibenzofuran derivatives, which are organic compounds with high hole transport properties, Specific examples of derivatives include 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)- (phenyl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4 ',4''-(Benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DB F3P-II), 1,3,5-tri(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene phenyl-9-yl)dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Thiophene (abbreviation: DBTFLP-IV), 4-[3-(triphenylen-2-yl)phenyl] phenyl]dibenzothiophene (abbreviation: mDBTPTp-II), and the like.

[0155] In addition, specific examples of zinc and aluminum metal complexes, which are organic compounds with high electron transport properties, are: Examples include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato)aluminum(III) (Almq3), bis (10-hydroxybenzo[h]quinolinato)beryllium(II) (BeBq2) , bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(I II) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), etc. and metal complexes having a quinoline skeleton or a benzoquinoline skeleton.

[0156] In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Zn PBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Zn Metal complexes with oxazole or thiazole ligands such as BTZ can also be used. can be done.

[0157] In addition, oxadiazole derivatives and triazole derivatives, which are organic compounds with high electron transport properties, compounds, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, Specific examples of phenanthroline derivatives include 2-(4-biphenylyl)-5-(4-tert-butyl)- ... t-Butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl] Benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazo 3-(4-phenyl-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), (4-tert-butylphenyl)-5-(4-tert-butylphenyl)-4-phenyl-1,2,4-trimethylphenyl Azole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)triazole (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzimidazole) (benzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation Name: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2-yl) stilbene (abbreviation: BzOS), bathophenanthroline (abbreviation: Bphen), batho Cuproine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7-difluoro Phenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiazolinone) [4-(4-(4-phenyl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTP DBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl ]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3' -(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxazone Sarin (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carba [f,h]quinoxaline (abbreviation: 2CzPDBq -III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h ]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophene (4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDB q-II) and others.

[0158] In addition, heterocyclic compounds having a diazine skeleton, triazine, and thiazolinone, which are organic compounds with high electron transport properties, Specific examples of heterocyclic compounds having an amine skeleton and heterocyclic compounds having a pyridine skeleton include: 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6 mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (Abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole- 9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-( N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl {nyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9 -[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9' -phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35 DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB).

[0159] Furthermore, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridinyl) fluorene-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene -2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: P Polymer compounds such as F-BPy can also be used.

[0160] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), , two types of compounds (first compound and second compound) that form exciplexes, and an organometallic In this case, various organic compounds may be used in appropriate combination. However, to efficiently form an exciplex, a compound that readily accepts holes ( A compound that easily accepts electrons (electron transport material) is combined with a compound that easily accepts electrons (hole transport material). Specific examples of the hole transporting material and the electron transporting material are as follows: The materials described in this embodiment can be used. You can realize both lives at the same time.

[0161] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the electrons into electrons (reverse intersystem crossing) and efficiently emit light (fluorescence) from the singlet excited state. In addition, the conditions for efficiently obtaining thermally activated delayed fluorescence are three The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably The delayed fluorescence in TADF materials is between 0 eV and 0.1 eV. The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of -6 seconds or more, preferably 10 -3 More than a second.

[0162] TADF materials include, for example, fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium Cd, Sn, Pt, In, or Palladium Examples of metal-containing porphyrins include metal-containing porphyrins containing Pd, etc. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviated as SnF2(Meso IX)), hematopoietin Hematoxyl tin fluoride complex (abbreviated as SnF2 (Hemato IX)), coproporf Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethene Examples include thylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0163] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl] 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4 -(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5- Diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-diphenyl Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (Acr XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a π electrons of clidin-9,9'-anthracen]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having an excess type heteroaromatic ring and a π-electron deficient type heteroaromatic ring can be used. In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded is The donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings are both strong. This is particularly preferred because it reduces the energy difference between the singlet excited state and the triplet excited state. stomach.

[0164] When using a TADF material, it can also be used in combination with other organic compounds. In particular, it can be combined with the above-mentioned host material, hole transport material, and electron transport material. The organic compound according to one embodiment of the present invention shown in the first embodiment is used as a host material for the TADF material. It is preferable to use it as

[0165] In addition, the above materials can be used in combination with low molecular weight materials or polymer materials to form a light emitting layer (113 , 113a, 113b, 113c). The above methods (such as vapor deposition, coating, and printing) can be used appropriately.

[0166] In the light-emitting element shown in FIG. ) on which the electron transport layer (114, 114a) is formed. In the case of a light-emitting element having the structure, after the EL layer 103a and the charge generating layer 104 are formed, An electron transport layer 114b is also formed on the light emitting layer 113b of the L layer 103b.

[0167] <Electron transport layer> The electron transport layer (114, 114a, 114b) is formed by the electron injection layer (115, 115a, 115 b) transfers electrons injected from the second electrode 102 to the light-emitting layers (113, 113a, 11b). The electron transport layer (114, 114a, 114b) is a layer that transports electrons to the The electron transport layer (114, 114a, 114b) is a layer containing a transport material. The conductive material is 1×10 -6 cm 2A substance having an electron mobility of 1 / Vs or more is preferred. Any other material can be used as long as it has a higher electron transporting property than hole transporting property. Furthermore, the organic compound of one embodiment of the present invention described in Embodiment 1 has an excellent electron-transporting property. Therefore, it can also be used as an electron transport layer.

[0168] As the electron transporting material, metal complexes having a quinoline skeleton, Metal complexes, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives conductors, thiazole derivatives, phenanthroline derivatives, quinoline derivatives with quinoline ligands Conductors, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing heteroaromatic compounds. A material having high electron transporting properties, such as a π-electron deficient heteroaromatic compound, can be used.

[0169] A specific example of an electron transporting material is tris(8-quinolinolato)aluminum(III). (Abbreviation: Alq3), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium ( II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenyl) (Enolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq) and other metal complexes having a quinoline or benzoquinoline skeleton , bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO ), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ ), bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(II) (abbreviation: Z n(BTZ)2) and other metal complexes having an oxazole or thiazole skeleton. can be done.

[0170] In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl) 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) oxadiazole derivatives such as phenyl]-9H-carbazole (abbreviation: CO11), 3- (4-biphenylyl)-5-(4-tert-butylphenyl)-4-phenyl-1,2 ,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-( 4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), triazole derivatives such as 2,2',2''-(1,3,5-benzene triyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2 -[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzoyl Imidazole derivatives (benzimidazoline) such as midazole (abbreviation: mDBTBIm-II) and 4,4'-bis(5-methylbenzoxazol-2-yl)styrene derivatives. Oxazole derivatives such as ruben (abbreviation: BzOS), bathophenanthroline (abbreviation: B phen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalene-2-yl) )-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) Phenanthroline derivatives, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo 2-[3'-(dibenzo[f,h]quinoxaline] (abbreviation: 2mDBTPDBq-II) [4-( ... Name: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)bis(2-methyl-2-propanol) phenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo [f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophene) phen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPD Bq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo [f,h]quinoxaline derivatives such as quinoxaline (abbreviation: 6mDBTPDBq-II), or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazole-9-yl] phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-phenyl)phenyl]pyridine pyridine derivatives such as 4,6-bis(lysyl)phenyl]benzene (abbreviation: TmPyPB), [3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2P m), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4, 6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl] pyrimidine derivatives such as 2-[4-phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), [3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl] phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTz n) and other triazine derivatives can be used.

[0171] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' -bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) You can also be there.

[0172] The electron transport layer (114, 114a, 114b) is not limited to a single layer, but may be formed of any of the above materials. The layer may have a structure in which two or more layers made of the above are laminated.

[0173] Next, in the light-emitting element shown in FIG. 1(D), an electron transport layer 114a of the EL layer 103a is formed on the electron transport layer 114a. The electron injection layer 115a is formed by vacuum deposition. After the green layer 104 is formed and the electron transport layer 114b of the EL layer 103b is formed, The implantation layer 115b is formed by vacuum deposition.

[0174] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing a substance with high electron injection properties. The electron injection layers (115, 115a, 115b) are made of lithium fluoride (LiF), cerium fluoride, CsF, calcium fluoride (CaF2), lithium oxide (LiO x ) etc. Such alkali metals, alkaline earth metals, or compounds thereof can be used. Alternatively, rare earth metal compounds such as erbium fluoride (ErF3) can be used. In addition, electride may be used for the electron injection layer (115, 115a, 115b). For example, a mixed oxide of calcium and aluminum with high electron concentration is used as a catalyst. In addition, the above-mentioned electron transport layer (114, 114a, 114b) It is also possible to use a substance that constitutes the above.

[0175] In addition, the electron injection layer (115, 115a, 115b) contains an organic compound and an electron donor (donor ) may be used. Such a composite material may be formed by mixing Since electrons are generated in the organic compound, the organic compound has excellent electron injection and electron transport properties. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, for example, the electron transporting layer (114, 114a, 114b) described above may be used. Materials such as metal complexes and heteroaromatic compounds can be used as electron donors. Any substance that exhibits electron donating properties to organic compounds is acceptable. Preferred are lithium earth metals and rare earth metals, and lithium, cesium, magnesium, calcium, Examples include erbium and ytterbium. In addition, alkali metal oxides and alkaline earth metals Metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as thiafulvalene (abbreviation: TTF) can also be used.

[0176] In the light-emitting element shown in FIG. 1D, the light obtained from the light-emitting layer 113b is amplified. In this case, the optical distance between the second electrode 102 and the light-emitting layer 113b is In this case, the electron transport layer 1 is preferably formed so that the wavelength λ of the light is less than ¼. This can be adjusted by changing the film thickness of 14b or electron injection layer 115b.

[0177] <Charge generation layer> In the light-emitting element shown in FIG. 1(D), the charge generation layer 104 is When a voltage is applied between the second electrode (cathode) 102 and the EL layer 103a, electrons are injected into the EL layer 103a. The charge generating layer 104 has a function of injecting holes into the EL layer 103b. Even if an electron acceptor is added to the electron transport material, It may also have a structure in which an electron donor (donor) is added. The charge generation layer 104 may be formed using the above-mentioned materials. This makes it possible to suppress an increase in driving voltage when an EL layer is stacked.

[0178] In the charge generation layer 104, when an electron acceptor is added to a hole transport material, As the hole transporting material, the materials shown in this embodiment mode can be used. The acceptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinoline. Examples include dimethane (abbreviation: F4-TCNQ), chloranil, etc. Examples of the oxides of metals belonging to Groups 4 to 8 in the table include: Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples include tin oxide, manganese oxide, and rhenium oxide.

[0179] In the charge generating layer 104, when an electron donor is added to an electron transporting material, As the electron transporting material, the materials shown in this embodiment mode can be used. The donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or a periodic element. Metals belonging to Groups 2 and 13 in the table, as well as their oxides and carbonates, can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium Ca, Yb, In, Lithium oxide, Cesium carbonate It is preferable to use an organic compound such as tetrathianaphthacene. It may also be used as a donor.

[0180] The EL layer 103c in FIG. 1(E) is the same as the EL layer (103, 103a, 103b) described above. The charge generating layers 104a and 104b may also be configured in the same manner as described above. The charge generating layer 104 may have the same structure as the charge generating layer 104 .

[0181] <Substrate> The light-emitting element shown in this embodiment mode can be formed over various substrates. The type of substrate is not limited to a specific one. An example of the substrate is a semiconductor substrate (e.g., Single crystal substrate or silicon substrate), SOI substrate, glass substrate, quartz substrate, plastic substrate , metal substrate, stainless steel substrate, substrate with stainless steel foil, Tungsten substrate, substrate with tungsten foil, flexible substrate, lamination film, Examples include paper containing fibrous materials and base films.

[0182] Examples of the glass substrate include barium borosilicate glass and aluminoborosilicate glass. Glass or soda lime glass, etc. Flexible substrates, lamination films, etc. Examples of base films include polyethylene terephthalate (PET), polyethylene terephthalate (PE ... Plastics such as polyethylene naphthalate (PEN) and polyethersulfone (PES) Synthetic resins such as acrylic resin, polypropylene, polyester, polyvinyl fluoride, Or polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition Examples of the material include film and paper.

[0183] Note that the light-emitting element shown in this embodiment mode can be manufactured by a vacuum process such as evaporation or a spin-coil method. Solution processes such as the ink jet method and the ink jet method can be used. In this case, sputtering, ion plating, ion beam deposition, molecular beam deposition, Physical vapor deposition (PVD) methods such as vacuum deposition and chemical vapor deposition (CVD) methods can be used. In particular, the functional layer (hole injection layer (111, 111a, 111)) included in the EL layer of the light-emitting element b), hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113 b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 1 15a, 115b)), and the charge generating layer (104, 104a, 104b), Vacuum deposition method (vacuum deposition method, etc.), coating method (dip coating method, die coating method, bar coating method, strip coating method, etc.) Pin coating method, spray coating method, etc.), printing method (inkjet method, screen (stencil printing offset (lithographic printing), flexographic (relief printing), gravure, micro- The film can be formed by a method such as a contact method or a nanoimprint method.

[0184] Note that the EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are Each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a) , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), electron injection layer (115, 115a, 115b)) and charge generation layer ( 104, 104a, 104b) are not limited to the above-mentioned materials, and may be other materials. However, they can be used in combination as long as they fulfill the functions of each layer. Examples include high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds), Compounds in the intermediate range between molecules and polymers: molecular weight 400 to 4000), inorganic compounds (quantum dots As the quantum dot material, colloidal quantum dots can be used. alloy-type quantum dot materials, core-shell-type quantum dot materials, core-type quantum dot materials etc. can be used.

[0185] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments. It shall be possible.

[0186] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light emitting device shown in FIG. 1 comprises a transistor (FET) 202 and a light emitting element (2 203R, 203G, 203B, 203W) are electrically connected to form an active matrix. The light-emitting device is a light-emitting device of the type in which a plurality of light-emitting elements (203R, 203G, 203B, 203W) are , a common EL layer 204 is provided, and the electrodes of each light-emitting element are electrically connected to each other depending on the color of light emitted by each light-emitting element. The EL layer 204 has a microcavity structure in which the optical path length is adjusted. The emitted light is reflected by the color filters (206R, 206G, 206 It is a top-emission type light-emitting device in which light is emitted through a

[0187] In the light-emitting device shown in FIG. 2(A), the first electrode 207 is formed to function as a reflective electrode. In addition, the second electrode 208 is formed so as to function as a semi-transmissive and semi-reflective electrode. In other embodiments, the electrode material for forming the first electrode 207 and the second electrode 208 may be the same as that of the first electrode 207 or the second electrode 208. Please refer to the description of the state and use it as appropriate.

[0188] In addition, in FIG. 2(A), for example, the light emitting element 203R is a red light emitting element, and the light emitting element 203 G is a green light emitting element, light emitting element 203B is a blue light emitting element, and light emitting element 203W is a white light emitting element. In this case, the light-emitting element 203R has a first electrode 207 and a second electrode 208 as shown in FIG. 2(B). The light emitting element 203G is adjusted so that the optical distance between the light emitting element 203G and the electrode 208 is 200R. The optical distance between the first electrode 207 and the second electrode 208 is adjusted to 200G. 03B is arranged so that the optical distance between the first electrode 207 and the second electrode 208 is 200B. As shown in FIG. 2(B), the conductive layer 210R in the light-emitting element 203R is adjusted. The conductive layer 210G is laminated on the first electrode 207, and in the light emitting element 203G, the conductive layer 210G is laminated on the first electrode 207. By laminating the film on the substrate 7, optical adjustment can be performed.

[0189] Color filters (206R, 206G, 206B) are formed on the second substrate 205. Color filters allow specific wavelength ranges of visible light to pass through and block specific wavelength ranges. Therefore, as shown in FIG. 2(A), the filter overlaps with the light emitting element 203R. By providing a color filter 206R that passes only the red wavelength region at the position Red light can be emitted from the light emitting element 203R. By providing a color filter 206G that passes only the wavelength range of the light emitting element 203 Green light can be obtained from G. Also, a blue wavelength region is obtained at a position overlapping with the light emitting element 203B. By providing a color filter 206B that passes only blue light, the light emitting element 203B However, the light emitting element 203W does not need to be provided with a color filter. It is possible to obtain white light emission. In addition, a black layer (black A color filter (206R) may be provided. , 206G, 206B) and the black layer 209 are covered with an overcoat layer made of a transparent material. It is okay to use it.

[0190] In FIG. 2(A), a structure (top emission type) in which light is extracted to the second substrate 205 side is used. The light emitting device is shown, but as shown in FIG. 2(C), the first substrate on which the FET 202 is formed is The light emitting device may have a structure in which light is extracted from the 201 side (bottom emission type). In the case of a bottom emission type light emitting device, the first electrode 207 is a semi-transmissive and semi-reflective electrode. The first electrode 206 is formed to function as a reflecting electrode, and the second electrode 208 is formed to function as a reflecting electrode. The first substrate 201 is at least a light-transmitting substrate. (206R', 206G', 206B') are the light emitting elements (203 R, 203G, 203B) may be provided closer to the first substrate 201 than the other components.

[0191] In addition, in FIG. 2(A), the light emitting elements are red light emitting elements, green light emitting elements, blue light emitting elements, Although the case of a white light-emitting element has been described, the light-emitting element that is one embodiment of the present invention is not limited to this structure. The light emitting element may be a yellow light emitting element or an orange light emitting element. In order to fabricate these light-emitting devices, EL layers (light-emitting layer, hole injection layer, hole transport layer, electron transport layer) For materials used in the layer (e.g., electron injection layer, charge generation layer, etc.), see the descriptions in other embodiments. In this case, a color filter may be used depending on the color of light emitted from the light emitting element. The filter must be selected appropriately.

[0192] By adopting the above-described configuration, a light-emitting device having light-emitting elements that emit light of a plurality of colors can be obtained. can be obtained.

[0193] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0194] (Fourth embodiment) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0195] By applying the element structure of the light-emitting element according to one embodiment of the present invention, A light-emitting device or a passive matrix light-emitting device can be manufactured. A matrix-type light-emitting device is a device that combines light-emitting elements and transistors (FETs). Therefore, the light emitting device may be a passive matrix type light emitting device or an active matrix type light emitting device. Note that the light-emitting device described in this embodiment may include other The light-emitting element described in the embodiment can be applied.

[0196] In this embodiment mode, an active matrix light-emitting device will be described with reference to FIG.

[0197] 3A is a top view showing the light emitting device, and FIG. 3B is a top view showing the light emitting device along the dashed line AA in FIG. 3A. The active matrix light emitting device is A pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate The pixel section 302 and the driver circuit section (304a, 304b) are connected to the pixel section 302. The first substrate 301 and the second substrate 302 are connected by a sealing material 305. It is sealed between the plate 306 .

[0198] Furthermore, lead wiring 307 is provided on the first substrate 301. is electrically connected to the FPC 308, which is an external input terminal. An external signal (for example, a video signal, a clock signal) is input to the driving circuit unit (303, 304a, 304b). The FPC308 also transmits signals such as lock signals, start signals, and reset signals, as well as electrical potentials. A printed wiring board (PWB) may be attached. The state in which the light emitting device is attached is included in the light emitting device.

[0199] Next, a cross-sectional structure is shown in FIG.

[0200] The pixel section 302 includes a FET (switching FET) 311, a FET (current control FET) 312, and a plurality of pixels having a first electrode 313 electrically connected to the FET 312. The number of FETs that each pixel has is not particularly limited, and It can be provided as needed.

[0201] The FETs 309, 310, 311, and 312 are not particularly limited, and may be, for example, staggered. In addition, top gate and bottom gate transistors can be used. The transistor structure may be a Tom-gate type or the like.

[0202] The semiconductor crystals that can be used for these FETs 309, 310, 311, and 312 are The crystallinity is not particularly limited, and may be an amorphous semiconductor, a crystalline semiconductor (microcrystalline semiconductor, Any of polycrystalline semiconductors, single-crystalline semiconductors, and semiconductors having crystalline regions in part may be used. It is noted that the use of a crystalline semiconductor can suppress the deterioration of transistor characteristics. This is preferable.

[0203] In addition, these semiconductors include, for example, elements of Group 14, compound semiconductors, and oxide semiconductors. , organic semiconductors, etc. can be used. Typically, semiconductors containing silicon, gallium, A semiconductor containing arsenic, an oxide semiconductor containing indium, or the like can be used.

[0204] The driving circuit section 303 includes an FET 309 and an FET 310. The ET310 is a circuit containing transistors of one polarity (either N-type or P-type only). It may be formed by a CMOS circuit including N-type transistors and P-type transistors. Alternatively, a configuration may be adopted in which a driving circuit is provided externally.

[0205] The end of the first electrode 313 is covered with an insulator 314. , organic compounds such as negative photosensitive resins and positive photosensitive resins (acrylic resins), and acids Inorganic compounds such as silicon nitride, silicon oxynitride, and silicon nitride can be used. The upper or lower end of the edge 314 preferably has a curved surface. As a result, the coverage of the film formed on the insulator 314 can be improved.

[0206] An EL layer 315 and a second electrode 316 are stacked on the first electrode 313. 315 is a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. Has.

[0207] Note that the structure of the light-emitting element 317 shown in this embodiment mode may be the same as the structures and materials described in other embodiment modes. Although not shown here, the second electrode 316 is connected to an external input. It is electrically connected to the terminal FPC308.

[0208] In addition, although only one light emitting element 317 is shown in the cross-sectional view of FIG. 3B, the pixel portion 3 02, a plurality of light-emitting elements are arranged in a matrix. 2, light-emitting elements that can emit three types of light (R, G, B) are selectively formed, and It is possible to form a light-emitting device capable of displaying three colors (R, G, B). In addition to the light-emitting element from which light is obtained, for example, white (W), yellow (Y), magenta (M For example, a light-emitting element that emits three kinds of light (R, A light-emitting element that can emit the above-mentioned several types of light is added to a light-emitting element that can emit G and B light. This can improve color purity and reduce power consumption. By combining it with a filter, a light emitting device capable of full color display may be formed. The types of color filters are red (R), green (G), blue (B), cyan (C), and magenta. Colors such as ink (M), ink (Y), etc. can be used.

[0209] The FETs (309, 310, 311, 312) and the light emitting element 317 on the first substrate 301 are The second substrate 306 and the first substrate 301 are bonded together with a sealing material 305. A space 318 surrounded by the first substrate 301, the second substrate 306, and the sealing material 305 is formed. The space 318 is filled with an inert gas (nitrogen, argon, etc.) It may be filled with an organic material (including a sealant 305).

[0210] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material that is as impermeable to moisture and oxygen as possible for the cooling material 305. In addition, the second substrate 306 may be made of the same material as the first substrate 301. Therefore, various substrates described in other embodiments can be used as appropriate. The substrates used are glass substrates, quartz substrates, and FRP (Fiber-Reinforced Plastics). ced Plastics), PVF (Polyvinyl Fluoride), polyester or aluminum A plastic substrate made of acrylic resin or the like can be used. When a lit is used, the first substrate 301 and the second substrate 306 are made of glass from the viewpoint of adhesiveness. A lath substrate is preferred.

[0211] In this manner, an active matrix light emitting device can be obtained.

[0212] In addition, when an active matrix light emitting device is formed on a flexible substrate, The FET and the light emitting element may be formed directly, or the FET and the light emitting element may be formed on a separate substrate having a release layer. After forming the element, the FET and the light emitting element are separated from each other by applying heat, force, laser irradiation, etc. The peeling layer may be formed by peeling it off with a film and then transferring it onto a flexible substrate. , lamination of inorganic films such as tungsten film and silicon oxide film, or organic resin films such as polyimide. In addition, as the flexible substrate, a substrate on which a transistor can be formed can be used. In addition to boards, paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, Fabric substrate (natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester, etc.) , leather substrate, or rubber substrate. By using these substrates, durability It has excellent heat resistance and can be made lighter and thinner.

[0213] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0214] (Embodiment 5) In this embodiment, a light-emitting element according to one embodiment of the present invention and a light-emitting element having the light-emitting element according to one embodiment of the present invention will be described. Examples of various electronic devices and automobiles that have been completed using the light emitting device will be described below. Note that the light-emitting device is mainly applied to a display portion in the electronic device described in this embodiment mode. This can be done.

[0215] The electronic device shown in FIGS. 4A to 4C includes a housing 7000, a display portion 7001, a speaker, and a 7003, LED lamp 7004, operation key 7005 (power switch or operation switch ), connection terminal 7006, sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity , rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage , including the ability to measure power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays. ), a microphone 7008, etc.

[0216] FIG. 4(A) shows a mobile computer, which includes the above-mentioned components, a switch 7009, a red It may have an outside line port 7010, etc.

[0217] FIG. 4(B) shows a portable image playback device (for example, a DVD playback device) equipped with a recording medium. In addition to the above, it may have a second display unit 7002, a recording medium reading unit 7011, etc. This can be done.

[0218] Figure 4(C) is a digital camera with a TV receiving function, and in addition to the above, it also has an antenna 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0219] FIG. 4D shows a portable information terminal. The portable information terminal displays information on three or more screens of a display portion 7001. Here, information 7052, information 7053, and information 7054 are respectively For example, the user may have a mobile information terminal in his / her breast pocket. When the terminal is stored, information 7053 is displayed in a position that can be observed from above the mobile information terminal. Users can check the display without taking the mobile information terminal out of their pocket. and can decide, for example, whether to answer the call or not.

[0220] FIG. 4E shows a portable information terminal (including a smartphone), in which a display unit 7 is mounted in a housing 7000. 001, operation keys 7005, etc. The portable information terminal may have a speaker, The portable information terminal may be provided with a connection terminal, a sensor, etc. It can be displayed on the side of the number. Here is an example showing three icons 7050. Also, information 7051 shown in a dashed rectangle can be displayed on another surface of the display unit 7001. Examples of information 7051 include notifications of incoming e-mails, SNS, and phone calls, Subject of e-mail or SNS, sender name, date and time, remaining battery level, antenna reception Or, the icon 7050 or the like is displayed at the position where the information 7051 is displayed. Any of the above may be displayed.

[0221] Figure 4(F) shows a large television set (also called a television or television receiver). The device may have a housing 7000, a display unit 7001, and the like. The housing 7000 is supported by a support 7018. The operation of the display unit 7111 can be performed by a separate remote control unit 7111. The display unit 7001 may be provided with a touch sensor, and the operation can be performed by touching the display unit 7001 with a finger or the like. The remote control device 7111 may output information The remote control unit 7111 may have a display unit that displays the operation keys or buttons. The channel and volume can be controlled by the touch panel, and the display unit 7001 The image displayed can be manipulated.

[0222] The electronic devices shown in FIGS. 4A to 4F can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display, Functions such as calendar, date or time display, various software (programs) It has the functions of controlling processing by wireless communication, and It has the function of connecting to a data network, and the function of transmitting or receiving various data using wireless communication. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. Furthermore, in an electronic device having multiple display units, One display mainly displays image information, and the other mainly displays text information. or the ability to display images that take parallax into account on multiple displays to create a three-dimensional image. Furthermore, in an electronic device having an image receiving unit, Functions for taking still images, shooting videos, and automatically or manually correcting captured images Function, function to save the captured image to a recording medium (external or built-in to the camera), It should be noted that the functions shown in FIGS. 4(A) to 4(F) can be implemented by the following methods. The functions that the electronic device shown in the figure can have are not limited to these, and it may have various functions. can be done.

[0223] FIG. 4(G) shows a wristwatch-type mobile information terminal that can be used as a smart watch, for example. This wristwatch-type portable information terminal is made up of a housing 7000, a display unit 7001, and operation buttons. Tan 7022, 7023, Connection terminal 7024, Band 7025, Microphone 7026 , a sensor 7029, a speaker 7030, etc. The display unit 7001 has a curved display surface. This allows the display to be displayed along the curved display surface. For example, hands-free calling is possible by communicating with a wireless headset. The connection terminal 7024 allows data to be transmitted to and from other information terminals. Charging can also be performed by wireless power supply.

[0224] The display unit 7001 mounted on the housing 7000, which also serves as a bezel, has a non-rectangular display area. The display unit 7001 can display an icon representing the time, other icons, etc. The display unit 7001 is a touch panel equipped with a touch sensor (input device). It may also be an input / output device.

[0225] The smart watch shown in FIG. 4G can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display, Functions such as calendar, date or time display, various software (programs) It has the functions of controlling processing by wireless communication, and It has the function of connecting to a data network, and the function of transmitting or receiving various data using wireless communication. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It can have functions such as:

[0226] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity) Degrees, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, electricity Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared. ), a microphone, etc.

[0227] Note that the light-emitting device according to one embodiment of the present invention and the display device including the light-emitting element according to one embodiment of the present invention The display device can be used for each display portion of the electronic device shown in this embodiment, and has a long life. This can be achieved.

[0228] In addition, as an electronic device to which a light-emitting device is applied, a folding type as shown in FIGS. 5A shows a portable information terminal 93 in an unfolded state. 10. Also, FIG. 5(B) shows the state of folding from one of the unfolded state to the other. 5C shows the mobile information terminal 9310 in the process of changing from the folded state to the folded state. The portable information terminal 9310 is shown in a folded state. The portable information terminal 9310 is shown in a folded state. It is highly portable when unfolded, and when unfolded, the seamless, wide display area allows for easy viewing of the display. Excellent.

[0229] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the space between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display state. The display portion 931 can be used for the display unit 9311. In addition, a long-life electronic device can be realized. The display area 9312 in FIG. 1 is located on the side of the portable information terminal 9310 in the folded state. The display area 9312 is a display area where information icons and frequently used apps and programs are displayed. You can display shortcuts for programs, check information, and launch apps. It can be done smoothly.

[0230] In addition, an automobile to which a light emitting device is applied is shown in Fig. 6(A)(B). The device can be provided integrally with the automobile. Outer lights 5101 (including the rear of the vehicle), tire wheels 5102, and doors 5103 It can be applied to a part or the whole of the car. display part 5104, a steering wheel 5105, a shift lever 5106, a seat 5107, an inner - Can be applied to rear view mirrors 5108, etc. Also, it can be applied to some glass windows. You may do so.

[0231] As described above, electronic devices and automobiles to which the light-emitting device or the display device of one embodiment of the present invention is applied can be manufactured. In this case, it is possible to realize a long-life electronic device. The electronic devices and automobiles that can be used are not limited to those shown in this embodiment, but can be used in a variety of fields. It can be applied as follows.

[0232] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0233] (Sixth embodiment) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is used. The structure of a lighting device manufactured using this method will be described with reference to FIG.

[0234] 7(A) and (B) show an example of a cross-sectional view of a lighting device. Note that FIG. 7(A) shows a lighting device with a light source on the substrate side. The bottom emission type lighting device extracts light from the encapsulation substrate side. It is a top-emission lighting device that emits light.

[0235] A lighting device 4000 shown in FIG. 7A has a light-emitting element 4002 on a substrate 4001. The light emitting element 4002 has a substrate 4003 having an uneven surface on the outer side of the substrate 4001. It has a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0236] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0237] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light emitting element 4002. It is preferable that the substrate 4003 has the unevenness as shown in FIG. The efficiency of extracting light generated in 02 can be improved.

[0238] A lighting device 4200 in FIG. 7B has a light-emitting element 4202 over a substrate 4201. The element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. .

[0239] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4206 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0240] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 4211 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has unevenness as shown in FIG. The extraction efficiency of light generated in the light emitting element 4202 can be improved.

[0241] An example of the application of these lighting devices is a ceiling light for indoor lighting. There are two types of ceiling lights: direct ceiling mounted and recessed ceiling lights. Such a lighting device is constructed by combining a light-emitting device with a housing and a cover.

[0242] Other applications include footlights that can irradiate light onto the floor, improving safety at the feet. It is also possible to use a foot lamp in a bedroom, on stairs, or in a hallway. In this case, the size and shape can be changed appropriately according to the size and structure of the room. It is also possible to combine the device with a support stand to create a stationary lighting device. .

[0243] It can also be used as a sheet-type lighting device (sheet-type lighting). The lighting is attached to the wall, so it doesn't take up much space and can be used for a wide range of purposes. It is also easy to make it larger, and it can be used on curved walls and enclosures.

[0244] In addition to the above, a light-emitting device according to one embodiment of the present invention may be attached to a part of furniture installed in a room. By applying the light-emitting element, which is a part of the technology, it is possible to create a lighting device that also functions as furniture. Cut.

[0245] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0246] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible. [Example]

[0247] <Synthesis Example 1> In this example, an organic compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophene-4 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4m This section explains how to synthesize 8BP-4mDBtPBfpm. The structure is shown below.

[0248] [ka]

[0249] <8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophene-4-yl) Synthesis of [1-(triphenyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzophenone 1.37g of 3,2-d-pyrimidine, 0.657g of 4-biphenylboronic acid, phosphoric acid Tripotassium 1.91g, Diethylene glycol dimethyl ether (diglyme) 30 mL, 0.662 g of t-butanol is placed in a three-neck flask and stirred under reduced pressure. The mixture was degassed and replaced with nitrogen.

[0250] The mixture was heated to 60° C., and 23.3 mg of palladium(II) acetate, di(1-adamant) 66.4 mg of (ethyl)-n-butylphosphine was added, and the mixture was stirred at 120°C for 27 hours. Water was added to the reaction mixture, which was then subjected to suction filtration. The residue was washed with water, ethanol, and toluene. The filtered material was dissolved in hot toluene and packed in the order of celite, alumina and celite. The resulting solution was concentrated to dryness and recrystallized from toluene to obtain The target product, a white solid, was obtained in an amount of 1.28 g and a yield of 74%.

[0251] 1.26 g of this white solid was purified by train sublimation. The conditions were a pressure of 2.56 Pa, argon gas flow rate of 10 mL / min, and The solid was heated at ℃. After purification by sublimation, 1.01 g of the target pale yellow solid was obtained with a recovery rate of 80%. The synthesis scheme is shown in the following formula (a-1).

[0252] [ka]

[0253] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in Figure 8. From these results, In the present invention, the organic compound represented by the structural formula (100) is 8BP- It was found that 4mDBtPBfpm was obtained.

[0254] 1 H-NMR.δ(CDCl3):7.39(t,1H), 7.47-7.53(m,4 H), 7.63-7.67(m,2H), 7.68(d,2H), 7.75(d,2H) , 7.79-7.83(m,4H), 7.87(d,1H), 7.98(d,1H), 8 .02(d,1H), 8.23-8.26(m,2H), 8.57(s,1H), 8.7 3(d,1H), 9.05(s,1H), 9.34(s,1H).

[0255] <Physical properties of 8BP-4mDBtPBfpm> Next, the UV-visible absorption spectra of 8BP-4mDBtPBfpm in toluene solution and solid thin film were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0256] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). A fluorometer (V550 type) was used to measure the emission spectrum in toluene solution. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption and emission spectra are shown in Figure 9(A). The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. and luminescence intensity.

[0257] As shown in Figure 9(A), the toluene solution of 8BP-4mDBtPBfpm exhibited 332nm and 316nm Absorption peaks are observed at 281 nm and 406 nm (excitation wavelength). 318nm).

[0258] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and emission spectrum are shown in Figure 9(B). The horizontal axis is the wavelength, and the vertical axis is the absorption The absorption and emission intensities are shown. The measurement temperature was 10 K and the excitation light was 1000 W. A He-Cd laser with a wavelength of 325 nm was used, and a CCD detector was used for the detector. The emission spectrum of 1000kJ / cm2 was measured.

[0259] From Figure 9(B), the solid thin film of 8BP-4mDBtPBfpm has 341nm and 308n Absorption peaks were observed at 428 nm (excitation The emission wavelength peak was observed around the emission wavelength of 340 nm. From the spectral results, it was found that the phosphorescent component of the emission spectrum of 8BP-4mDBtPBfpm is the most The wavelength of the peak (including the shoulder) on the short wavelength side was 482 nm. From the peak wavelength, the T1 level of 8BP-4mDBtPBfpm was calculated to be 2.57 eV. .

[0260] The organic compound 8BP-4mDBtPBfpm, which is one embodiment of the present invention, has a high T1 level. It is also said to be a suitable host material for phosphorescent materials (guest materials) that emit light in the green to red range. The organic compound 8BP-4mDBtPBfpm, which is one embodiment of the present invention, is a visible It can also be used as a host material or an emitting material for phosphorescent emitting materials in the range of 1000 to 15000 nm. [Example]

[0261] <Synthesis Example 2> In this example, an organic compound represented by structural formula (101) in Embodiment 1, which is one embodiment of the present invention, Compound, 8-(1,1'-biphenyl-3-yl)-4-[3-(dibenzothiophene-4 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviated as 8mBP-4 The synthesis method for 8mBP-4mDBtPBfpm is explained below. The structure of pm is shown below.

[0262] [ka]

[0263] <8-(1,1'-biphenyl-3-yl)-4-[3-(dibenzothiophene-4-yl)] Synthesis of [1-(triphenyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzophenone 1.37g of 3-biphenylboronic acid, 0.664g of phosphoric acid 1.90 g of tripotassium chloride, 0.663 g of t-butanol, and 30 mL of diglyme were placed in a three-neck flask. The mixture was heated to 60°C and stirred under reduced pressure to degas the mixture and replace with nitrogen. Palladium(II) acetate 21.4 mg and di(1-adamantyl)-n-butylphosphine 65.6 mg was added, and the mixture was stirred at 120°C for 21 hours.

[0264] To this reaction mixture was added 23.5 mg of palladium(II) acetate and di(1-adamantyl)-n-butyl. 66.4 mg of ethylphosphine was added, and the mixture was stirred at 120° C. for 8 hours. Water was added to the reaction mixture. The residue was washed with water, ethanol, and toluene. The solution was dissolved in toluene and passed through a filter aid filled in the order Celite, alumina, and Celite. The resulting solution was concentrated to dryness and recrystallized with toluene to obtain the target white product. The solid was obtained in an amount of 1.10 g, a yield of 64%.

[0265] 1.10 g of this white solid was purified by train sublimation. The conditions were a pressure of 2.57 Pa, argon gas flow rate of 10 mL / min, and a temperature of 300 The solid was heated at ℃. After purification by sublimation, 0.895 g of the target pale yellow solid was obtained, with a recovery rate of 81%. The synthesis scheme is shown in formula (b-1) below.

[0266] [ka]

[0267] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in Figure 10. From the results, In the above, the organic compound represented by the structural formula (101) according to one embodiment of the present invention, 8mB It was found that P-4mDBtPBfpm was obtained.

[0268] 1 H-NMR.δ(CDCl3):7.39(t,1H), 7.47-7.50(m,4 H), 7.57(t,1H), 7.62-7.64(m,3H), 7.67-7.69( m,3H), 7.77-7.80(m,2H), 7.86(d,1H), 7.92(s, 1H), 7.79(d,1H), 8.00(d,1H), 8.21-8.23(m,2H ), 8.57(s,1H), 8.71(d,1H), 9.03(s,1H), 9.32( s,1H).

[0269] <<Physical properties of 8mBP-4mDBtPBfpm>> Next, the UV-visible absorption spectra of 8mBP-4mDBtPBfpm in toluene solution and solid thin film were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0270] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). A fluorometer (V550 type) was used to measure the emission spectrum in toluene solution. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption and emission spectra are shown in Figure 11(A). The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. The values ​​represent the degree and luminescence intensity.

[0271] As shown in Figure 11(A), the toluene solution of 8mBP-4mDBtPBfpm has a peak intensity of 331 nm and 31 Absorption peaks are observed around 5 nm and 280 nm, and the emission wavelength peak is 389 nm (excitation The wavelength was 320 nm.

[0272] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and the emission spectrum are shown in Figure 11(B). The horizontal axis is the wavelength, and the vertical axis is The absorption and emission intensities are shown. bRAM HR-PL (Horiba Ltd.) was used, the measurement temperature was 10K, and the excitation light was A He-Cd laser with a wavelength of 325 nm was used, and a CCD detector was used to measure the temperature (1 The emission spectrum was measured at 100 K.

[0273] From Figure 11(B), the solid thin film of 8mBP-4mDBtPBfpm has 343nm and 31 Absorption peaks are observed around 9 nm and 245 nm, and 411 nm (excitation wavelength 320 nm) The emission spectrum at low temperature (10K) showed a peak in the emission wavelength. The shortest wavelength peak of the phosphorescent component in the emission spectrum of 8mBP-4mDBtPBfpm ( The wavelength of the peak (including the shoulder) was 456 nm. The T1 level of mBP-4mDBtPBfpm was calculated to be 2.72 eV.

[0274] The organic compound 8mBP-4mDBtPBfpm, which is one embodiment of the present invention, has a high T1 level. It is a suitable host material for phosphorescent materials (guest materials) that emit light in the green to red range. It can be said that the organic compound 8mBP-4mDBtPBfpm according to one embodiment of the present invention is It can also be used as a host material or luminescent material for phosphorescent luminescent materials in the visible range. [Example]

[0275] <Synthesis Example 3> In this example, an organic compound represented by structural formula (102) in Embodiment 1, which is one embodiment of the present invention, Compound, 8-[(2,2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophene) 8(βN-4-yl)phenyl-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN 2)-4mDBtPBfpm) synthesis method will be explained. The structure of DBtPBfpm is shown below.

[0276] [ka]

[0277] <8-[(2,2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophene- Synthesis of (4-yl)phenyl-[1]benzofuro[3,2-d]pyrimidine 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzophenone 1.21g of 2,2'-binaphthalen-6-ylboron Acid 0.857g, tripotassium phosphate 1.67g, diglyme 26mL, t-butanol 0. 583 g was placed in a three-necked flask, and the contents of the flask were degassed by stirring under reduced pressure and replaced with nitrogen. Ta.

[0278] The mixture was heated to 60° C., and 18.9 mg of palladium(II) acetate, di(1-adamantanium) 61.1 mg of (ethyl)-n-butylphosphine was added, and the mixture was stirred at 120°C for 10 hours. Water was added to the reaction mixture, which was then subjected to suction filtration. The residue was washed with water, ethanol, and toluene. The residue was dissolved in hot toluene and packed in the order of celite, alumina, and celite. The resulting solution was passed through a filter aid and concentrated to dryness to give a white solid.

[0279] The total amount of the solid obtained was 0.348 g of [2,2'-binaphthalen]-6-ylboronic acid, phosphorus 0.621 g of tripotassium carbonate, 13 mL of diglyme, and 0.239 g of t-butanol were added to a three-port flask. The mixture was placed in a flask, and the inside of the flask was degassed by stirring under reduced pressure, and the atmosphere was replaced with nitrogen. Heat to 0°C and add 8.7 mg of palladium (II) acetate and di(1-adamantyl)-n-butyl 25.1 mg of methylphosphine was added, and the mixture was stirred at 120° C. for 18.5 hours. The mixture was added and subjected to suction filtration, and the residue was washed with water, ethanol and toluene.

[0280] The residue was dissolved in hot toluene and filtered through a filter packed in the order of celite, alumina, and celite. The resulting solution was concentrated to dryness and recrystallized in toluene to obtain the target compound. A white solid was obtained in an amount of 1.16 g, a yield of 65%. The sublimation purification was carried out by rain sublimation. The conditions for the sublimation purification were a pressure of 2.64 Pa and The solid was heated to 365°C while flowing argon gas at a flow rate of 10 mL / min. After that, 0.958 g of 8(βN2)-4mDBtPBfpm of the present invention (recovery rate 83%, The synthesis scheme is shown in formula (c-1) below.

[0281] [ka]

[0282] The white solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results are shown below. 1 The H-NMR chart is shown in Figure 12. From these results, In the present invention, the organic compound represented by the structural formula (102) is an embodiment of the present invention. 2)-4mDBtPBfpm was obtained.

[0283] 1 H-NMR.δ(CDCl3):7.50-7.7.57(m,4H), 7.64-7 .67(m,2H), 7.82(t,1H), 7.86-8.00(m,9H), 8.0 5-8.09(m,2H), 8.14(d,1H), 8.22-8.26(m,5H), 8.69(s,1H), 8.74(d,1H), 9.07(s,1H), 9.35(s, 1H).

[0284] <Physical properties of 8(βN2)-4mDBtPBfpm> Next, the UV-visible absorption spectra of the toluene solution and solid thin film of 8(βN2)-4mDBtPBfpm were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured.

[0285] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). A fluorometer (V550 type) was used to measure the emission spectrum in toluene solution. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption and emission spectra are shown in Figure 13(A). The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. The values ​​represent the degree and luminescence intensity.

[0286] From Figure 13(A), the toluene solution of 8(βN2)-4mDBtPBfpm has a peak at 333 nm, Absorption peaks are observed around 325 nm and 280 nm, and the emission wavelength peak is 414 nm ( The excitation wavelength was 329 nm.

[0287] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and the emission spectrum are shown in Figure 13(B). The horizontal axis is the wavelength, and the vertical axis is The absorption and emission intensities are shown. bRAM HR-PL (Horiba Ltd.) was used, the measurement temperature was 10K, and the excitation light was A He-Cd laser with a wavelength of 325 nm was used, and a CCD detector was used to measure the temperature (1 The emission spectrum was measured at 100 K.

[0288] From Figure 13(B), for the solid thin film of 8(βN2)-4mDBtPBfpm, Absorption peaks were observed around 266 nm and 245 nm, and 451 nm (excitation wavelength 340 nm) ) and the emission spectrum at low temperature (10 K) The shortest wavelength side of the phosphorescent component in the emission spectrum of 8(βN2)-4mDBtPBfpm The wavelength of the peak (including the shoulder) was 543 nm. From this, the T1 level of 8(βN2)-4mDBtPBfpm was calculated to be 2.28 eV.

[0289] The organic compound 8(βN2)-4mDBtPBfpm, which is one embodiment of the present invention, has a high T1 level. It is a suitable host material for phosphorescent materials (guest materials) that emit light in the yellow to red range. It can be said that the organic compound 8(βN2)-4mDBtPBfp, which is one embodiment of the present invention, m can also be used as a host material or emitting material for phosphorescent materials emitting light in the visible region. [Example]

[0290] In this example, the 8-[(2, 2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl Nyl-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtP Bfpm) (structural formula (102)) in the light-emitting layer. Dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzyl 8βN-4mDBtPBfpm (structural formula ( 301)) as an emitting layer, and Thiophen-4-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8 Comparative light-emitting device 3 using mDBtP2Bfpm) (structural formula (302)) as the light-emitting layer The device structure, manufacturing method, and characteristics of the light-emitting device used in this example will be described. The device structure of the device is shown in FIG. 14, and the specific configuration is shown in Table 1. The chemical formula of the material is shown below:

[0291] [Table 1]

[0292] [ka]

[0293] <Fabrication of light-emitting device> The light emitting element shown in this example has a first electrode 9 formed on a substrate 900 as shown in FIG. 01, a hole injection layer 911, a hole transport layer 912, a light emitting layer 913, an electron transport layer 914, and an electron A structure in which an electron injection layer 915 is sequentially stacked, and a second electrode 903 is stacked on the electron injection layer 915. It has.

[0294] First, a first electrode 901 was formed on a substrate 900. The electrode area was 4 mm 2 (2mm x 2 The thickness of the first electrode 901 was 1 / 2 mm. , indium tin oxide containing silicon oxide (ITSO) was deposited by sputtering to a thickness of 70 nm. The film was formed to a thickness of .

[0295] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV- The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition chamber and vacuum baked at 170°C for 30 minutes. After this, the substrate was allowed to cool for about 30 minutes.

[0296] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was co-deposited at a mass ratio of 2:1 to form a film with a thickness of 60 nm. .

[0297] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was formed by 4,4 '-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl Formed by vapor deposition using polyisopropylamine (abbreviated as PCBBi1BP) to a film thickness of 20 nm. did.

[0298] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0299] In the case of the light-emitting element 1, the light-emitting layer 913 is made of 8(βN2)-4mDBtPBfpm and N- (1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole -3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: P In addition to CBBiF), bis[4,6-dimethyl- 2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O, O') Iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]) The weight ratio is 8(βN2)-4mDBtPBfpm:PCBBiF:[Ir(dmpqn)2 (acac)] = 0.75:0.25:0.1. In the case of comparative light-emitting element 2, 8βN-4mDBtPBfpm and In addition to PCBBiF, [Ir(dmpqn)2( acac)] with a weight ratio of 8βN-4mDBtPBfpm:PCBBiF:[Ir( The mixture was co-evaporated so that the ratio of dmpqn)2(acac)] was 0.75:0.25:0.1. The film thickness was set to 40 nm. In addition to fpm and PCBBiF, [Ir(dm pqn)2(acac)] with a weight ratio of 4.8mDBtP2Bfpm:PCBBiF :[Ir(dmpqn)2(acac)]=0.75:0.25:0.1 The film thickness was 40 nm.

[0300] Next, an electron transport layer 914 was formed on the light emitting layer 913 .

[0301] In the case of the light-emitting element 1, the electron transport layer 914 has a thickness of 8(βN2)-4mDBtPBfpm. 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10- Phenanthroline (NBphen) was deposited in order to form a film with a thickness of 15 nm. In the case of comparative light-emitting element 2, the film thickness of 8βN-4mDBtPBfpm was 25 nm. The film thickness of NBphen was 15 nm. In the case of element 3, the thickness of the 4.8mDBtP2Bfpmm is 25 nm, and the thickness of the NBphen is The layers were formed by sequential evaporation so that the thickness was 15 nm.

[0302] Next, an electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was made of a fluoride Lithium (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0303] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. The film was formed by vapor deposition so as to have a thickness of 200 nm. Thus, the second electrode 903 functions as a cathode.

[0304] By the above steps, a light emitting element having an EL layer 902 sandwiched between a pair of electrodes is formed on the substrate 900. The hole injection layer 911, the hole transport layer 912, and the light emitting layer 91 described in the above steps were formed. 3. The electron transport layer 914 and the electron injection layer 915 constitute the EL layer in one embodiment of the present invention. In addition, all of the vapor deposition steps in the above-mentioned manufacturing method were performed by resistance heating. The deposition method was used.

[0305] The light emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. Then, another substrate (not shown) coated with a sealant that hardens when exposed to ultraviolet light is placed on the substrate 900. The substrates are fixed together so that the sealant adheres to the periphery of the light emitting element formed on the substrate 900. During sealing, 365 nm ultraviolet light was applied at 6 J / cm. 2 Irradiate the sealant to harden it, and then The sealant was stabilized by heat treatment at 0°C for 1 hour.

[0306] <Operating characteristics of light-emitting element> The operating characteristics of each fabricated light-emitting device were measured. The current density-luminance characteristics of each light-emitting element are shown in Figure 1. 5. Voltage-brightness characteristics are shown in Figure 16, brightness-current efficiency characteristics are shown in Figure 17, and voltage-current characteristics are shown in Figure 18. Each is shown.

[0307] Also, 1000 cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 2 below. .

[0308] [Table 2]

[0309] Furthermore, the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 were each supplied with an electric current of 2.5 mA / cm 2 Current density of The emission spectrum when a current was passed through the light-emitting element 1 at 1000 Hz is shown in FIG. The emission spectra of the comparative light-emitting element 2 and the comparative light-emitting element 3 have a peak at around 626 nm. and [Ir(dmpqn)2(acac) It is suggested that this is due to the emission of ].

[0310] Next, reliability tests were performed on the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. The results of the reliability test are shown in Figure 20. In Figure 20, the vertical axis represents the initial brightness, with 100%. The horizontal axis shows the normalized luminance (%) at the time of operation, and the horizontal axis shows the driving time (h) of the element. , 75mA / cm 2 A constant current drive test was conducted in which a constant current was applied at a current density of 1000 kJ / s.

[0311] The reliability test results showed that the light-emitting element 1 had the following characteristics compared to the comparative light-emitting elements 2 and 3: It was found that there was little deterioration in the initial stage of operation. The use of βN2)-4mDBtPBfpm (structural formula (102)) improves the device characteristics of the light-emitting device. It can be said that this is useful for improving the light-emitting performance. BtPBfpm (structural formula (301)) has a naphthyl group at the 8-position of the benzofuropyrimidine skeleton. The comparative light-emitting element 3 used in the present invention has a structure in which 302)) is a compound in which a dibenzothiophene is attached to the 8-position of the benzofuropyrimidine skeleton via a phenyl group. The 8(βN2)-4mDBtPBfpm used in light-emitting device 1 has a structure in which βN is bonded. is a structure in which multiple arylene groups are linked to the 8-position of a benzofuropyrimidine skeleton, specifically, It has a molecular structure with a binaphthyl group in which two identical naphthyl groups are linked together.

[0312] Therefore, the organic compound of the present invention has a benzofuropyrimidine skeleton or a benzofuropyrimidine skeleton. An organic compound with a biarylene group at the 8th position of the zothienopyrimidine skeleton is used as a light-emitting device. By using this, the time it takes for the initial luminance of Light-emitting element 1 to decrease by 5% (LT95) is reduced to 173 hours. In contrast, the LT95 of the comparative light-emitting element 2 was 86 hours and the LT95 of the comparative light-emitting element 3 was 32 hours. To provide a highly reliable light emitting element which is effective in suppressing initial deterioration of the light emitting element over time. It can be said that this is possible. [Example]

[0313] In this example, the 8BP-4m light-emitting element described in Example 1 was used as a light-emitting element according to one embodiment of the present invention. The light-emitting device 4 using DBtPBfpm (structural formula (100)) as the light-emitting layer was described in Example 2. Light-emitting device 5 using 8mBP-4mDBtPBfpm (structural formula (101)) as the light-emitting layer. For comparison, a comparative emission layer was used in which 8Ph-4mDBtPBfpm (structural formula (300)) was used as the emission layer. Optical element 6, for comparison, 8DBt-4mDBtPBfpm (structural formula (303)) as the light-emitting layer A comparative light-emitting element 7 was fabricated using the same, and the characteristics thereof were measured. The results are shown below.

[0314] The light-emitting element 4, the light-emitting element 5, the comparative light-emitting element 6, and the comparative light-emitting element 7 were fabricated in this example. The element structure of the element 7 is the same as that shown in FIG. 14 in the fourth embodiment, but The specific structure of each layer is shown in Table 3. The academic formula is shown below.

[0315] [Table 3]

[0316] [ka]

[0317] <Operating characteristics of each light-emitting element> The operating characteristics of the fabricated light-emitting element 4, light-emitting element 5, comparative light-emitting element 6, and comparative light-emitting element 7 were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0318] The current density-luminance characteristics of each light-emitting element are shown in FIG. 21, the voltage-luminance characteristics are shown in FIG. 22, and the luminance-current efficiency characteristics are shown in FIG. The characteristics are shown in Figure 23 and the voltage-current characteristics are shown in Figure 24.

[0319] Also, 1000 cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 4 below. .

[0320] [Table 4]

[0321] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of 25. As shown in FIG. 25, the emission spectrum of each light-emitting element has a peak at around 560 nm. The peak of [Ir(ppy)2(4dppy)] contained in the light-emitting layer 913 This suggests that it is due to luminescence.

[0322] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in Figure 26. In 6, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is conducted at 50mA / cm 2 At a constant current density of A constant current drive test was carried out.

[0323] From the results of the reliability test, the organic compound 8BP-4mDBtPBfp, which is one embodiment of the present invention, The light-emitting element 4 using m (structural formula (100)) in the light-emitting layer had a luminance reduction time of 5% from the initial luminance. (LT95) was 131 hours, and 8mBP-4mDBtPBfpm (structural formula (101) The light-emitting device 5 using the organic compound 8) in the light-emitting layer had a LT95 of 112 hours. Comparative light-emitting element 6, which uses Ph-4mDBtPBfpm (structural formula (300)) in the light-emitting layer, The LT95 was 98 hours, and 8DBt-4mDBtPBfpm (structural formula (303)) was produced. The comparative light-emitting element 7 used in the optical layer had a LT95 of 62 hours, and The initial deterioration of the light-emitting element using the compound for the light-emitting layer was suppressed. The organic compounds 8BP-4mDBtPBfpm and 8mBP-4mDBtPBfpm a structure in which multiple arylene groups are linked to the 8-position of a benzofuropyrimidine skeleton, more preferably This is the effect of having a biphenyl group in which two identical phenyl groups are linked. Use of an organic compound according to one embodiment of the present invention is useful in improving the reliability of a light-emitting element. It can be said that there is. [Example]

[0324] In this example, the light-emitting element according to one embodiment of the present invention is the 8BP-4mD The light-emitting device 8 using BtPBfpm (structural formula (100)) as the light-emitting layer, which was described in Example 2 Light-emitting device 9 using 8mBP-4mDBtPBfpm (structural formula (101)) as the light-emitting layer. For comparison, 8Ph-4mDBtPBfpm (structural formula (300)) was used as the emitting layer. Device 10, for comparison, with 8DBt-4mDBtPBfpm (structural formula (303)) as the emissive layer A comparative light-emitting element 11 was fabricated using the above-mentioned compound, and the characteristics thereof were measured. The results are shown below.

[0325] The light-emitting element 8, the light-emitting element 9, the comparative light-emitting element 10, and the comparative light-emitting element 11 were fabricated in this example. The element structure of the element 11 is the same as that shown in FIG. 14 in Example 4, but the element structure is The specific configuration of each layer is shown in Table 5. The materials used in this example are The chemical formula is shown below:

[0326] [Table 5]

[0327] [ka]

[0328] <Operating characteristics of each light-emitting element> The operation characteristics of the fabricated light-emitting element 8, light-emitting element 9, comparative light-emitting element 10, and comparative light-emitting element 11 were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0329] The current density-luminance characteristics of each light-emitting element are shown in FIG. 27, the voltage-luminance characteristics are shown in FIG. 28, and the luminance-current efficiency characteristics are shown in FIG. The characteristics are shown in Figure 29 and the voltage-current characteristics are shown in Figure 30.

[0330] Also, 1000 cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 6 below. .

[0331] [Table 6]

[0332] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of 31. As shown in FIG. 31, the emission spectrum of the light-emitting element has a peak around 524 nm. The light-emitting layer 913 has a peak, and the [2-(4-methyl-5-phenyl-2- bis[2-(2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC] C] is derived from the luminescence of iridium (abbreviated as [Ir(ppy)2(mdppy)]). This suggests that...

[0333] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in Figure 32. In Figure 2, the vertical axis shows the normalized brightness (%) when the initial brightness is 100%, and the horizontal axis shows the The reliability test is conducted at 50mA / cm 2 At a constant current density of A constant current drive test was carried out.

[0334] From the results of the reliability test, the organic compound 8BP-4mDBtPBfp, which is one embodiment of the present invention, The light-emitting element 8 using m (structural formula (100)) in the light-emitting layer had a time required for the luminance to decrease by 5% from the initial luminance. (LT95) was 30 hours, and 8mBP-4mDBtPBfpm (structural formula (10 The light-emitting device 9 using the organic compound 1)) in the light-emitting layer had a LT95 of 28 hours. Comparative light-emitting element 1 using 8DBt-4mDBtPBfpm (structural formula (303)) as the light-emitting layer 1 has a LT95 of 15 hours, and is an embodiment of the present invention in which initial deterioration of the organic compound is suppressed. In addition, the comparative organic compound, 8Ph-4mDBtPBfpm (structural formula (300) The comparative light-emitting element 10, which uses the EL element 10 as the light-emitting layer, has a good LT95 of 29 hours, but has a long-term deterioration. The slope of the curve was steeper than that of the organic compound according to one embodiment of the present invention. In one embodiment, the organic compounds 8BP-4mDBtPBfpm and 8mBP-4mDBtP Bfpm has a structure in which multiple arylene groups are linked to the 8-position of the benzofuropyrimidine skeleton. Preferably, this effect is due to the presence of a biphenyl group in which two identical phenyl groups are linked together. Therefore, the use of the organic compound according to one embodiment of the present invention improves the reliability of the light-emitting element. It can be said that it is useful in the above.

[0335] ≪Reference synthesis example 1≫ In this reference synthesis example, the comparative light-emitting element 6 of Example 5 and the comparative light-emitting element 10 of Example 6 were prepared. The organic compound represented by the following structural formula, 4-[3-(dibenzothiophen-4-yl)phenyl]propanol phenyl]-8-phenyl-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8Ph- A specific example of the synthesis of 4mDBtPBfpm) (structural formula (300)) will be given below.

[0336] [ka]

[0337] <Synthesis of 8Ph-4mDBtPBfpm> 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzophenone 3.00 g of 3,2-d-pyrimidine, 0.95 g of phenylboronic acid, and 0.5 g of potassium phosphate tribasic. Place 4.12 g of glycerol, 65 mL of diglyme, and 1.44 g of t-butanol in a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure and replaced with nitrogen. II) 42.7 mg, di(1-adamantyl)-n-butylphosphine 140 mg The mixture was stirred at 120°C for 15.5 hours.

[0338] To this reaction mixture, 45.2 mg of palladium (II) acetate, di(1-adamantyl)-n-butyl 140 mg of methylphosphine was added, and the mixture was stirred at 120°C for 6 hours, and then at 140°C for 3 hours. Water was added to the reaction mixture, which was then filtered under suction. The residue was washed with ethyl acetate and hexane. The residue was dissolved in hot toluene and packed in the order of celite, alumina, and celite. The resulting solution was concentrated to dryness and recrystallized from toluene to give the product. A white solid containing the target compound was obtained in a yield of 1.50 g.

[0339] The resulting white solid (1.50 g) was purified by train sublimation. The production conditions were a pressure of 3.48 Pa, argon gas flow rate of 15 mL / min, and 28 The solid was heated at 0°C. After purification by sublimation, the target product was obtained (white solid 1.02 g, recovery rate 68%). The synthesis scheme is shown in formula (d-1) below.

[0340] [ka]

[0341] The white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The analysis results by H-NMR are shown below. This shows that 8Ph-4mDBtPBfpm was obtained.

[0342] 1 H-NMR.δ(CDCl3):7.42(t,1H), 7.49-7.53(m,4 H), 7.64-7.66(m,2H), 7.71(d,2H), 7.79-7.82( m,2H), 7.87(d,1H), 7.97(t,2H), 8.23-8.25(m, 2H), 8.52(s,1H), 8.72(d,1H), 9.05(s,1H), 9.3 3(s,1H).

[0343] ≪Reference synthesis example 2≫ In this reference synthesis example, the organic compound represented by the following structural formula used in comparative light-emitting element 2 of Example 4 , 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-2-yl)phenyl 8βN-4mDBtPBfp A specific example of synthesis of m) (structural formula (301)) will be given below.

[0344] [ka]

[0345] <Synthesis of 8βN-4mDBtPBfpm> First, 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzyl 1.5 g of benzofuro[3,2-d]pyrimidine, 0.73 g of 2-naphthaleneboronic acid, Add 1.5 g of cesium fluoride and 32 mL of mesitylene to a 100 mL three-neck flask. Nitrogen-substituted 2'-(dicyclohexylphosphino)acetophenone ethylene ketal 7 0 mg and tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(db a) 89 mg of 3) was added, and the mixture was heated at 120°C for 5 hours under a nitrogen stream. Water was added to the mixture, followed by filtration, and the filter cake was washed with water and ethanol in that order.

[0346] This residue was dissolved in toluene and filtered through a filter aid packed with celite, alumina, and celite in that order. The solvent in the resulting solution was concentrated, and the target compound was obtained in a dilute form by recrystallization. A yellow solid was obtained in an amount of 1.5 g and a yield of 64%. The synthesis scheme is shown in formula (e-1) below.

[0347] [ka]

[0348] The resulting pale yellow solid (1.5 g) was purified by train sublimation. The purification conditions were a pressure of 2.0 Pa, argon gas flow rate of 10 mL / min, and The solid was heated at 90°C. After purification by sublimation, 0.60 g of the target yellow solid was obtained, with a recovery rate of 39%. Got it.

[0349] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by H-NMR are shown below. The results showed that 8βN-4mDBtPBfpm was obtained.

[0350] 1H-NMR.δ(TCE-d2):7.45-7.50(m,4H), 7.57-7. 62(m,2H), 7.72-7.93(m,8H), 8.03(d,1H), 8.10 (s,1H), 8.17(d,2H), 8.60(s,1H), 8.66(d,1H), 8.98(s,1H), 9.28(s,1H). [Example]

[0351] <Synthesis Example 4> In this example, an organic compound represented by structural formula (103) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1'-biphenyl-4-yl)-4-[3'-(dibenzothiophene- 4-yl)biphenyl-3-yl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation The synthesis method of 8BP-4mDBtBPBfpm is explained below. The structure of DBtBPBfpm is shown below.

[0352] [ka]

[0353] <Synthesis of 8BP-4mDBtBPBfpm> 8-chloro-4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]- [1] Benzofuro[3,2-d]pyrimidine 2.26g, 4-biphenylboronic acid 0.9g 15g, 1.27g of cesium fluoride, and 42mL of mesitylene were placed in a three-neck flask and The mixture was degassed by stirring and replaced with nitrogen. The mixture was heated to 60°C and tris(dibenzofuran) 2'-(dicyclohexylphosphine)dipalladium(0) 0.116g Add 90.2 mg of acetophenone ethylene ketal and heat at 100°C for 13.5 hours. The mixture was then stirred at 120°C for 7.5 hours. Dipalladium(0) 0.115g, 2'-(dicyclohexylphosphino)acetamide 90.3 mg of phenone ethylene ketal was added, and the mixture was stirred at 120°C for 28 hours. Water was added to the mixture, which was then subjected to suction filtration, and the residue was washed with water, ethanol, and toluene. The filter material was dissolved in hot toluene, and the filter aid was packed with Celite, alumina, and Celite in that order. The resulting solution was concentrated to dryness and recrystallized from toluene to obtain the target compound. A pale yellow solid was obtained in an amount of 1.93 g, a yield of 70%. The resultant was purified by train sublimation under the conditions of a pressure of 2.35 P. The solid was heated to 355°C while argon gas was flowing at a flow rate of 10 mL / min. After purification, 1.66 g of the target pale yellow solid was obtained with a recovery rate of 86%. This is shown in the following formula (f-1).

[0354] [ka]

[0355] The white solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results are shown below. 1 The H-NMR chart is shown in Figure 33. From these results, In the present invention, the organic compound represented by the structural formula (103) is 8BP- It was found that 4mDBtBPBfpm was obtained.

[0356] 1 H-NMR.δ(CDCl3):7.37-7.40(m,1H), 7.46-7.5 2(m,4H), 7.60-7.85(m,14H), 7.92-7.98(m,2H) , 8.19-8.23(m,3H), 8.57(m,1H), 8.64-8.66(m, 1H), 8.98-8.99(m,1H), 9.33(s,1H).

[0357] <Physical properties of 8BP-4mDBtBPBfpm> Next, the UV-visible absorption spectra of 8BP-4mDBtBPBfpm in toluene solution and solid thin film were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0358] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). A fluorometer (V550 type) was used to measure the emission spectrum in toluene solution. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption and emission spectra are shown in Figure 34. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity and and luminescence intensity.

[0359] As shown in Figure 34, the toluene solution of 8BP-4mDBtBPBfpm has a wavelength of 332 nm and 316 nm. The absorption peaks are observed around 281 nm and 406 nm (excitation wavelength 3). 18nm).

[0360] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and emission spectrum are shown in Figure 35. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. The values ​​represent the degree and luminescence intensity.

[0361] From Figure 35, the solid thin film of 8BP-4mDBtBPBfpm has 340nm and 310nm Absorption peaks were observed at 290 nm, 270 nm, and 245 nm, and 426 nm (excitation A peak in the emission wavelength was observed around 330 nm. [Example]

[0362] <Synthesis Example 5> In this example, an organic compound represented by structural formula (105) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-[(2,2'-binaphthalen)-6-yl]-4-[3'-(dibenzothiophene) (phenyl-4-yl)biphenyl-3-yl]-[1]benzofuro[3,2-d]pyrimidine The synthesis method of (abbreviation: 8(βN2)-4mDBtBPBfpm) will be explained. The structure of 8(βN2)-4mDBtBPBfpm) is shown below.

[0363] [ka]

[0364] <Synthesis of 8(βN2)-4mDBtBPBfpm> 8-chloro-4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]- [1] Benzofuro[3,2-d]pyrimidine 2.11g, [2,2'-binaphthalene]- 6-ylboronic acid 1.26 g, potassium phosphate tripotassium 2.55 g, diglyme 40 mL, t-butyl 2-methyl-2-propanol 0.93 g of ethanol was placed in a three-necked flask, and the contents of the flask were degassed by stirring under reduced pressure. The mixture was purged with nitrogen and heated to 60°C, and 27.0 mg of palladium (II) acetate and di 77.8 mg of (1-adamantyl)-n-butylphosphine was added, and the mixture was heated at 120°C for 14 hours. Stirred. Palladium (II) acetate 27.5 mg, di(1-adamantyl)-n-butyl 76.4 mg of phosphine was added, and the mixture was stirred at 120° C. for 16 hours. Palladium(II) 27.6 mg, Di(1-adamantyl)-n-butylphosphine 77 0.9 mg was added and the mixture was stirred at 120°C for 14.5 hours and then at 130°C for 6.5 hours.

[0365] Water was added to the reaction mixture, which was then subjected to suction filtration, and the resulting filter cake was washed with water and toluene. The filter material was dissolved in hot toluene, and the filter aid was filled with celite, alumina, and celite in that order. The resulting solution was concentrated to dryness and recrystallized from toluene to obtain the target product. A white solid was obtained in an amount of 1.56 g, yield 52%.

[0366] 1.15 g of this white solid was purified by train sublimation. The conditions were a pressure of 2.33 Pa, argon gas flow rate of 10 mL / min, and a temperature of 375 The solid was heated at ℃. After purification by sublimation, 1.06 g of the target pale yellow solid was obtained with a recovery rate of 92%. The synthesis scheme is shown in the following formula (g-1).

[0367] [ka]

[0368] The white solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results are shown below. 1 The H-NMR chart is shown in Figure 36. From these results, In the present invention, the organic compound represented by the structural formula (105) is an embodiment of the present invention. 2)-4mDBtBPBfpm was obtained.

[0369] 1 H-NMR.δ(CDCl3):7.46-7.57(m,4H), 7.62-7.6 3(m,2H), 7.70(t,1H), 7.75-7.87(m,5H), 7.90- 8.00(m,7H), 8.06-8.10(m,3H), 8.20-8.24(m,6 H), 8.66-8.68(m,2H), 9.00(s,1H), 9.34(s,1H) .

[0370] <Physical properties of 8(βN2)-4mDBtBPBfpm> Next, the UV-visible absorption spectrum of the solid thin film of 8(βN2)-4mDBtBPBfpm (hereafter The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0371] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and emission spectrum are shown in Figure 37. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. The values ​​represent the degree and luminescence intensity.

[0372] From Figure 37, the solid thin film of 8(βN2)-4mDBtBPBfpm has 328 nm and 29 Absorption peaks were observed around 446 nm (excitation wavelength 30 nm), 267 nm, and 246 nm. A peak in the emission wavelength was observed around 30 nm. [Example]

[0373] <Synthesis Example 6> In this example, an organic compound represented by structural formula (126) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1':3',1''-terphenyl-4-yl)-4-[3-(diphenyl (isothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation The synthesis method of 8pmTP-4mDBtPBfpm is explained below. The structure of P-4mDBtPBfpm is shown below.

[0374] [ka]

[0375] <Step 1: Synthesis of 4-bromo-1,1':3',1''-terphenyl> 3-biphenylboronic acid 0.50g, 1-bromo-4-iodobenzene 1.06g, carbonic acid Place 0.80 g of sodium, 17 mL of toluene, and 4 mL of ethanol in a side-arm flask. The flask was degassed by stirring under reduced pressure and replaced with nitrogen. Add 86.7 mg of (triphenylphosphine)palladium(0) and stir at 120°C for 26 hours. Water was added to the reaction mixture, which was then subjected to suction filtration, and the resulting filtrate was concentrated to give a brown solid. The solid was dissolved in a mixture of toluene and ethyl acetate, and silica gel was added to the resulting solution. The concentrate was purified by silica gel column chromatography using hexane as the developing solvent. The target product, a white solid, was obtained in 0.30 g and a yield of 39%. The synthesis scheme is shown in formula (h-1) below.

[0376] [ka]

[0377] Step 2: Synthesis of 1,1':3',1''-terphenyl-4-boronic acid 2.94 g of 4-bromo-1,1':3',1''-terphenyl synthesized in Step 1 The contents of the flask were replaced with nitrogen and 53 mL of dehydrated tetrahydrofuran was added. The mixture was cooled to -78°C. 8.9 mL of HCl was slowly added dropwise and stirred at -78°C for 1 hour. 1.6 mL of methyl methyl acetate was added dropwise, and the mixture was stirred at room temperature overnight. The resulting organic layer was washed with water and saturated brine, and dried over magnesium sulfate. This mixture was subjected to gravity filtration, and the filtrate was concentrated to obtain a solid. The obtained solid was dissolved in ethyl acetate. The target white solid was obtained in an amount of 1.57 g and a yield of 60%. This synthesis scheme is shown in formula (h-2) below.

[0378] [ka]

[0379] <Step 3: Synthesis of 8pmTP-4mDBtPBfpm> 1.12 g of 1,1':3',1''-terphenyl-4-boronic acid synthesized in Step 2 , 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzo Furo[3,2-d]pyrimidine 1.35g, cesium fluoride 1.70g, mesitylene 26 The resulting solution was placed in a three-neck flask, stirred under reduced pressure to degas the contents, and the atmosphere was replaced with nitrogen.

[0380] To this mixture, 343 mg of tris(dibenzylideneacetone)dipalladium(0), 343 mg of di(1 -adamantyl)-n-butylphosphine 127 mg, 2'-(dicyclohexylphosphine Add 126 mg of acetophenone ethylene ketal and stir at 120°C for 43.5 hours. Water was added to the reaction mixture and the mixture was filtered under suction. The residue obtained was diluted with water, ethanol, and toluene. After washing with toluene, dissolve in hot toluene and fill with celite, alumina and celite in that order. The mixture was passed through a filter aid containing toluene and ethanol as the solvent, and concentrated to dryness to separate into two phases. The target white solid was obtained in a yield of 702 mg by recrystallization using a diffusion method using ethanol. The yield was 37%.

[0381] In addition, hexane was added to the filtrate obtained by suction filtering the reaction product, and the precipitated solid was removed by suction. The mixture was filtered and purified by silica gel column chromatography (toluene: ethyl acetate = 50:1). The product was recrystallized from toluene / ethanol to obtain the target white solid in a yield of 0.18 g. These target substances were mixed, and 633 mg of a white solid was obtained. The sublimation purification was carried out under the conditions of a pressure of 2.52 Pa and an argon gas flow. The solid was heated to 330°C while flowing at a rate of 10 mL / min. 460 mg of a yellow solid was obtained with a recovery rate of 73%. The synthesis scheme is shown in the following formula (h-3). vinegar.

[0382] [ka]

[0383] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in Figure 38. From the results, In the above, the organic compound 8pm, which is one embodiment of the present invention, is represented by the structural formula (126). It was found that TP-4mDBtPBfpm was obtained.

[0384] 1 H-NMR.δ(CDCl3):7.40(t,1H), 7.47-7.70(m,1 1H), 7.79-7.89(m,8H), 7.98-8.04(m,2H), 8.24 -8.26(m,2H), 8.59(d,1H), 8.73(d,1H), 9.05(t ,1H), 9.34(s,1H).

[0385] <<Physical properties of 8pmTP-4mDBtPBfpm>> Next, the UV-visible absorption spectra of the toluene solution and solid thin film of 8pmTP-4mDBtPBfpm were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured.

[0386] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). A fluorometer (V550 type) was used to measure the emission spectrum in toluene solution. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption and emission spectra are shown in Figure 39. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity and and luminescence intensity.

[0387] As shown in Figure 39, the toluene solution of 8pmTP-4mDBtPBfpm exhibited a peak intensity of 315 nm and 282 nm. The absorption peak is observed around 406 nm, and the emission wavelength peak is 406 nm (excitation wavelength 310 nm). It was.

[0388] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared on a quartz substrate by vacuum deposition. The measurements were performed using a UV-visible spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The measurement results of the spectrum and emission spectrum are shown in Figure 40. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. The values ​​represent the degree and luminescence intensity.

[0389] From Figure 40, the solid thin film of 8BP-4mDBtBPBfpm has 340nm and 310nm Absorption peaks were observed at 288 nm, 270 nm, and 243 nm, and 426 nm (excitation A peak in the emission wavelength was observed around 330 nm. [Example]

[0390] <Synthesis Example 7> In this example, an organic compound represented by structural formula (128) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1':4',1''-terphenyl-3-yl)-4-[3-(diphenyl) (isothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation This section explains how to synthesize the 8mpTP-4mDBtPBfpm. The structure of P-4mDBtPBfpm is shown below.

[0391] [ka]

[0392] Step 1: 2-hydroxy-5-(1,1':4',1''-terphenyl-3-isopropyl) Synthesis of benzonitrile 5-Bromo-2-hydroxybenzonitrile 6.98g, β-[1,1':4',1'' -terphenyl]-3-ylboronic acid 10.9 g, potassium carbonate 11.0 g, toluene 3 Put 70 mL of ethanol, 40 mL of water, and 40 mL of ethanol into a three-neck flask and stir under reduced pressure. The mixture was degassed with 1000 kJ / ml and purged with nitrogen. 1.34 g of (-methylphenyl)phosphine was added, and the mixture was stirred at 80°C for 4.0 hours. Water was added to the reaction mixture and the mixture was filtered under suction. The resulting residue was diluted with water, ethanol, toluene, and ethyl acetate. The target gray solid was obtained in an amount of 12.0 g and a yield of 98%. The formula is shown in formula (i-1) below.

[0393] [ka]

[0394] Step 2: 3-amino-5-(1,1':4',1''-terphenyl-3-yl) Synthesis of ethyl benzo[b]furan-2-carboxylate Next, 2-hydroxy-5-(1,1':4',1''-terphenyl) (3-yl)benzonitrile 12.0 g, ethyl bromoacetate 7.05 g, potassium carbonate 9.64 g of dimethylformamide and 90 mL of dimethylformamide were placed in a three-neck flask. The reaction mixture was stirred at 00°C for 7.0 hours. Water was added to the reaction mixture, and the mixture was filtered under suction. The residue was dissolved in hot ethyl acetate and filtered under suction. The resulting solution was concentrated to give the target product, a gray solid, in an amount of 11.9 g and a yield of 79%. The scheme is shown in formula (i-2) below.

[0395] [ka]

[0396] Step 3: 8-(1,1':4',1''-terphenyl-3-yl)[1]benzo Synthesis of furo[3,2-d]pyrimidin-4(3H)-one Next, 3-amino-5-(1,1':4',1''-terphenyl) -3-yl)benzo[b]furan-2-carboxylate ethyl 11.9g, formamidine vinegar 5.81 g of the acid salt and 120 mL of formamide were placed in a three-neck flask. The reaction mixture was stirred at 0°C for 12.0 hours. Water was added to the reaction mixture, and the mixture was filtered under suction. The resulting residue was diluted with water and After washing with ethanol, the target brown solid was obtained in an amount of 10.6 g and a yield of 93%. The synthesis scheme is shown in formula (i-3) below.

[0397] [ka]

[0398] Step 4: 4-chloro-8-(1,1':4',1''-terphenyl-3-yl) [1] Synthesis of benzofuro[3,2-d]pyrimidine Next, 8-(1,1':4',1''-terphenyl-3-yl) [1] Benzofuro[3,2-d]pyrimidin-4(3H)-one 10.6g, phosphochloride 40 mL of ethanol and 0.02 mL of dimethylformamide were placed in a three-neck flask. The mixture was stirred at 90°C for 12.0 hours under a nitrogen stream. The resulting reaction mixture was poured into ice water, and the solution was The mixture was neutralized with sodium hydroxide and then saturated aqueous sodium bicarbonate, and stirred for 1 hour. The residue was filtered by suction, dissolved in hot toluene, and then separated into celite, alumina, and celite in this order. The resulting solution was concentrated and separated into two phases using toluene as the solvent. The product was recrystallized by the diffusion method using ethanol / ethanol to obtain the desired yellow solid in a yield of 8. The synthesis scheme is shown in formula (i-4) below.

[0399] [ka]

[0400] Step 5: 8-(1,1':4',1''-terphenyl-3-yl)-4-[3- (Dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidin Synthesis of Gin Next, 4-chloro-8-(1,1':4',1''-terphenyl) 1.98g, 3-(dibenzothiazole-3-yl)[1]benzofuro[3,2-d]pyrimidine (4-phenyl-4-yl)phenylboronic acid 1.69 g, potassium carbonate 1.64 g, toluene 45 mL, 5.0 mL of ethanol, and 5.0 mL of water were placed in a three-neck flask and stirred under reduced pressure. The mixture was degassed and replaced with nitrogen.

[0401] To this mixture, bis(triphenylphosphine)palladium(II) dichloride (abbreviation: P 407 mg of d(PPh3)2Cl2 was added and stirred at 90°C for 9.0 hours. Water was added to the reaction mixture, and the mixture was filtered under suction. The residue was washed with water, ethanol, and toluene. The solution was dissolved in hot toluene and passed through a filter aid filled with celite, alumina, and celite in that order. The resulting solution was concentrated to dryness and separated into two phases using toluene / ethanol as the solvent. The target product, a white solid, was obtained in an amount of 2.57 g and a yield of 8.0 g. Got it at 5%.

[0402] 2.30 g of this white solid was purified by train sublimation. The conditions were a pressure of 2.5 Pa, argon gas flow rate of 15 mL / min, and a temperature of 350°C. After sublimation purification, the target product, 8-(1,1':4',1''-terphenyl) (3-(dibenzothiophen-4-yl)phenyl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzyl The compound was obtained as a white solid in a yield of 1.69 g (74% recovery). The synthesis scheme is shown in formula (i-5) below.

[0403] [ka]

[0404] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in Figure 41. From the results, In the above, the organic compound represented by the structural formula (128) according to one embodiment of the present invention, 8mp It was found that TP-4mDBtPBfpm was obtained.

[0405] 1 H-NMR.δ(CDCl3):7.38(t,1H), 7.47-7.53(m,4 H), 7.59-7.74(m,9H), 7.77-7.88(m,5H), 7.97- 7.99(m,2H), 8.03-8.05(m,1H), 8.23-8.25(m,2 H), 8.61(d,1H), 8.73(d,1H), 9.05(t,1H), 9.34 (s,1H). [Example]

[0406] <Synthesis Example 8> In this example, an organic compound represented by structural formula (143) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1':3'1''-terphenyl-5'-yl)-4-[3-(diphenyl (isothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation This section explains how to synthesize 8mTP-4mDBtPBfpm. The structure of 4mDBtPBfpm is shown below.

[0407] [ka]

[0408] <Step 1: Synthesis of 8mTP-4mDBtPBfpm> 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzophenone 503mg of 3,2-d-pyrimidine, 92mg of (3,5-diphenylphenyl)boronic acid 3mg, tripotassium phosphate 1.23g, tert-butyl alcohol 700mg, diethyl 36 mL of ethylene glycol dimethyl ether was placed in a three-neck flask and stirred under reduced pressure. The mixture was degassed and replaced with nitrogen. To this mixture, 58.3 mg of palladium(II) acetate, 1-(2-methyl-1-propanol) 166 mg of damantyl-n-butylphosphine was added, and the mixture was stirred at 120°C for 7.5 hours. .

[0409] Water was added to the reaction mixture, which was then subjected to suction filtration, and the resulting filter cake was washed with water, ethanol, and toluene. The residue was dissolved in hot toluene and packed in the order of celite, alumina, and celite. The resulting solution was concentrated to dryness and separated into two phases using toluene as the solvent. By recrystallizing using the diffusion method using ethanol / ethanol, the target white solid was obtained. Obtained 302 mg, 25% yield.

[0410] 292 mg of this white solid was purified by train sublimation. The conditions were a pressure of 2.6 Pa, argon gas flow rate of 10 mL / min, and a temperature of 340°C. After sublimation purification, the target product, 8mTP-4mDBtPBfpm, was obtained. The compound was obtained in an amount of 161 mg (55% recovery, white solid). The synthesis scheme is shown in formula (j-1) below. show.

[0411] [ka]

[0412] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in Figure 42. From the results, In the above, the organic compound represented by the structural formula (143) according to one embodiment of the present invention, 8mT It was found that P-4mDBtPbfpm was obtained.

[0413] 1 H-NMR.δ(CDCl3):7.40-7.43(m,2H), 7.47-7.5 3(m,6H), 7.63-7.66(m,2H), 7.74-7.76(m,4H), 7.79-7.87(m,4H), 7.91(m,2H), 7.97-7.99(m,1 H), 8.08-8.09(m,1H), 8.22-8.26(m,2H), 8.66( m,1H), 8.72-8.73(m, 1H), 9.05-9.06(m, 1H), 9. 34(s, 1H). [Example]

[0414] <Synthesis Example 9> In this example, an organic compound represented by structural formula (144) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, 8-(1,1'-biphenyl-4-yl)-4-[3-(9H-carbazole-9 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4m The synthesis method of 8BP-4mCzPBfpm is explained below. The structure is shown below.

[0415] [ka]

[0416] The above 8BP-4mCzPBfpm can be synthesized according to the synthesis scheme shown in formula (k-1) below. Therefore, they can be synthesized.

[0417] [ka] [Example]

[0418] In this example, the light-emitting element of one embodiment of the present invention is 8(βN2) described in Example 8. -4mDBtBPBfpm (structural formula (105)), PCBBiF, and a guest material (phosphorus The light-emitting device was fabricated using the photoluminescent material as the light-emitting layer, and the results of measuring its characteristics are shown below. In this example, the guest material was [Ir(dmpqn)2(acac)] The light-emitting device 12 uses bis{4,6-dimethyl-2-[ 5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyridin Razinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptane Dionato-κO,O')iridium(III) (abbreviation: [Ir(dmdppr-mC P)2(dpm)] is referred to as light-emitting element 13.

[0419] The element structures of the light-emitting elements 12 and 13 fabricated in this example were the same as those shown in Example 4. The structure is the same as that shown in FIG. 14, but the specific configuration of each layer that constitutes the element structure is shown in Table 1. 7. The chemical formulas of the materials used in this example are shown below.

[0420] [Table 7]

[0421] [ka]

[0422] <Operating characteristics of each light-emitting element> The operating characteristics of the fabricated light-emitting elements 12 and 13 were measured. The experiment was carried out at room temperature (in an atmosphere maintained at 25°C).

[0423] The current density-luminance characteristics of each light-emitting element are shown in FIG. 43, the voltage-luminance characteristics in FIG. 44, and the luminance-current efficiency characteristics in FIG. The characteristics are shown in Figure 45 and the voltage-current characteristics are shown in Figure 46.

[0424] Also, 1000 cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 8 below. .

[0425] [Table 8]

[0426] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of 47. As shown in FIG. 47, the emission spectrum of the light-emitting element 12 is The peak is at [Ir(dmpqn)2(acac) It is suggested that the emission spectrum of the light-emitting element 13 is derived from the emission of 6 The peak is near 48 nm, and the [Ir(dmdppr- This suggests that the emission is due to the emission of β-glucan (m5CP)2(dpm).

[0427] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in Figure 48. In 8, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test was conducted at 75mA / cm 2 At a constant current density of A constant current drive test was carried out.

[0428] From the results of the reliability test, the organic compound according to one embodiment of the present invention, 8(βN2)-4mDBtB The light-emitting element 12 using PBfpm (structural formula (105)) in the light-emitting layer exhibited a 5% decrease in luminance from the initial luminance. The light-emitting element 13 has a LT95 of 62 hours. This is the organic compound 8(βN2)-4mDBtBPBfp, which is one embodiment of the present invention. m has a structure in which multiple naphthyl groups are linked to the 8-position of the benzofuropyrimidine skeleton. Therefore, the use of an organic compound according to one embodiment of the present invention can improve the reliability of a light-emitting element. This is useful for improving reliability. [Example]

[0429] In this example, the 8pmTP- 4mDBtPBfpm (structural formula (126)), PCCP, and [Ir(ppy)2(m dppy) as the light-emitting layer, and 8BP-4mDBtB described in Example 7. PBfpm (structural formula (103)), PCCP, and [Ir(ppy)2(mdppy) A light-emitting element 15 was fabricated using the above compound as a light-emitting layer, and the characteristics thereof were measured. The results are shown below.

[0430] The device structures of the light-emitting elements 14 and 15 fabricated in this example were the same as those shown in Example 4. The structure is the same as that shown in FIG. 14, but the specific configuration of each layer that constitutes the element structure is shown in Table 1. 9. The chemical formulas of the materials used in this example are shown below.

[0431] [Table 9]

[0432] [ka]

[0433] <Operating characteristics of each light-emitting element> The operating characteristics of the fabricated light-emitting elements 14 and 15 were measured. The experiment was carried out at room temperature (in an atmosphere maintained at 25°C).

[0434] The current density-luminance characteristics of each light-emitting element are shown in FIG. 49, the voltage-luminance characteristics in FIG. 50, and the luminance-current efficiency characteristics in FIG. The characteristics are shown in Figure 51 and the voltage-current characteristics are shown in Figure 52.

[0435] Also, 1000 cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 10 below. vinegar.

[0436] [Table 10]

[0437] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of , as shown in Figure 53. As shown in Figure 53, the emission spectrum of each light-emitting element has a peak at around 526 nm. The peak of [Ir(ppy)2(mdppy)] contained in the light-emitting layer 913 This suggests that it is due to luminescence.

[0438] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in Figure 54. In Figure 4, the vertical axis shows the normalized brightness (%) when the initial brightness is 100%, and the horizontal axis shows the The reliability test is conducted at 50mA / cm 2 At a constant current density of A constant current drive test was carried out.

[0439] From the results of the reliability test, the organic compound 8pmTP-4mDBtPB, which is one embodiment of the present invention, The light-emitting element 14 using fpm (structural formula (126)) in the light-emitting layer showed a 5% decrease in luminance from the initial value. The time to release (LT95) was approximately 30 hours, and 8BP-4mDBtBPBfpm (structural formula The light-emitting device 15 using the (103)) in the light-emitting layer had a LT95 of 21 hours. The organic compounds 8pmTP-4mDBtPBfpm and 8BP-4, which are an embodiment of the present invention, mDBtBPBfpm is a compound in which multiple arylene groups are linked to the 8-position of the benzofuropyrimidine skeleton. More preferably, it has a biphenyl group in which two identical phenyl groups are linked together. Therefore, the use of an organic compound according to one embodiment of the present invention improves the reliability of a light-emitting element. It can be said that this is useful for improving [Explanation of symbols]

[0440] 101: first electrode, 102: second electrode, 103: EL layer, 103a, 103b: EL Layers 104, 104a, 104b: charge generation layers; and layers 111, 111a, 111b: hole injection layers. Layers 112, 112a, 112b: hole transport layers 113, 113a, 113b, 113c : light-emitting layer, 114, 114a, 114b: electron transport layer, 115, 115a, 115b: electron Injection layer, 200R, 200G, 200B: optical path, 201: first substrate, 202: Transistors (FETs), 203R, 203G, 203B, 203W: light-emitting elements, 204: EL layer, 205: second substrate, 206R, 206G, 206B: color filters, 206 R', 206G', 206B': color filters, 207: first electrode, 208: second Electrode, 209: black layer (black matrix), 210R, 210G: conductive layer, 301 : first substrate, 302: pixel section, 303: driver circuit section (source line driver circuit), 304a, 304b: driving circuit section (gate line driving circuit), 305: sealing material, 306: second substrate, 307: Wiring, 308: FPC, 309: FET, 310: FET, 311: F ET, 312: FET, 313: first electrode, 314: insulator, 315: EL layer, 316 : second electrode, 317: light emitting element, 318: space, 900: substrate, 901: first electrode, 902: EL layer, 903: second electrode, 911: hole injection layer, 912: hole transport layer, 91 3: Light-emitting layer, 914: Electron transport layer, 915: Electron injection layer, 4000: Lighting device, 4001 : substrate, 4002: light emitting element, 4003: substrate, 4004: first electrode, 4005: EL layer, 4006: second electrode, 4007: electrode, 4008: electrode, 4009: auxiliary wiring, 4 010: insulating layer, 4011: sealing substrate, 4012: sealing material, 4013: desiccant, 420 0: lighting device, 4201: substrate, 4202: light-emitting element, 4204: first electrode, 4205 : EL layer, 4206: second electrode, 4207: electrode, 4208: electrode, 4209: auxiliary wiring Wire, 4210: insulating layer, 4211: sealing substrate, 4212: sealing material, 4213: barrier film , 4214: Flattening film, 5101: Light, 5102: Wheel, 5103: Door, 51 04: Display unit, 5105: Steering wheel, 5106: Shift lever, 5107: Seat, 5108: Inner rearview mirror, 7000: Housing, 7001: Display unit, 7002: Second display unit, 7003: Speaker, 7004: LED lamp, 7005: Operation keys, 70 06: Connection terminal, 7007: Sensor, 7008: Microphone, 7009: Switch, 7010: infrared port, 7011: recording medium reading unit, 7014: antenna, 7015: Shutter button, 7016: Image receiving unit, 7018: Stand, 7021: External connection unit, 7 022, 7023: Operation buttons, 7024: Connection terminal, 7025: Band, 7026: Microphone, 7027: Time icon, 7028: Other icons, 702 9: Sensor, 7030: Speaker, 7052, 7053, 7054: Information, 9310: Mobile Portable information terminal, 9311: display unit, 9312: display area, 9313: hinge, 9315: case body

Claims

1. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and a phosphorescent material; the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemical 1】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the aromatic hydrocarbon ring having 6 to 25 carbon atoms inclusive, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms, and represents a group to which one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 【Chemistry 2】 (In formula (1), Q represents oxygen or sulfur. １ and A ２ each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon, m represents any one of integers 0 to 4, and n represents any one of integers 1 to 4. １ ~R １２ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

2. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and a phosphorescent material; the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 3】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, and when the benzene ring or the naphthalene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Furthermore, m and n are each 0 or 1. Furthermore, A is a group having a total of 12 to 100 carbon atoms, and represents a group to which one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Furthermore, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 【Chemistry 4】 (In formula (1), Q represents oxygen or sulfur. １ and A ２ each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon, m represents any one of integers 0 to 4, and n represents any one of integers 1 to 4. １ ~R １２ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

3. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G1), a second organic compound, and a phosphorescent material, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 5】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted benzene ring, and when the benzene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Furthermore, m and n are each 0 or 1. Furthermore, A is a group having a total of 12 to 100 carbon atoms, and represents a group to which one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Furthermore, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

4. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G1), a second organic compound, and a phosphorescent material, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 6】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted naphthalene ring, and when the naphthalene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Furthermore, m and n are each 0 or 1. Furthermore, A is a group having a total of 12 to 100 carbon atoms, and represents a group to which one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Furthermore, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

5. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and a phosphorescent material; the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 7】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ represent the same substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 to 25, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Furthermore, m and n are each 0 or 1. Furthermore, A is a group having a total of 12 to 100 carbon atoms, and represents a group to which one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Furthermore, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 【Chemistry 8】 (In formula (1), Q represents oxygen or sulfur. １ and A ２ each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon, m represents any one of integers 0 to 4, and n represents any one of integers 1 to 4. １ ~R １２ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

6. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G2), a second organic compound, and a phosphorescent material, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 9】 (In formula (G2), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 to 25, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and m and n are each 0 or 1. α represents a substituted or unsubstituted phenylene group, and t represents an integer of 0 to 4. Ht ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

7. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G3), a second organic compound, and a phosphorescent material, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 10】 (In formula (G3), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the aromatic hydrocarbon ring has 6 to 25 carbon atoms, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and m and n are each 0 or 1. ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

8. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound represented by formula (G4), a second organic compound, and a phosphorescent material, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 11】 (In formula (G4), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the aromatic hydrocarbon ring has 6 to 25 carbon atoms, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and m and n are each 0 or 1. ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

9. In any one of claims 6 to 8, The Ht ｕｎｉ A light-emitting element represented by any one of formulas (Ht-1) to (Ht-26): 【Chemistry 12】 (In formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. ２ ~R ７１ Each of Ar represents 1 to 4 substituents, and each independently represents one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. ５ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

10. In any one of claims 6 to 9, Ar １ , Ar ２ , Ar ３ , and Ar ４ are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

11. In any one of claims 6 to 10, Ar １ , Ar ２ , Ar ３ , and Ar ４ The light-emitting element is identical.

12. In any one of claims 1 to 11, Ar １ , Ar ２ , Ar ３ , and Ar ４ is unsubstituted.

13. In any one of claims 1, 2, 5 to 11, A light-emitting element, wherein the following formula (G-X), which is a partial structure in the formulas (G1) to (G4), is represented by any one of the following formulas (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6). 【Chemistry 13】 【Chemistry 14】

14. A pair of electrodes and a light-emitting layer between the pair of electrodes, the light-emitting layer includes a first organic compound, a second organic compound, and a phosphorescent material; The first organic compound is a compound represented by any one of formulas (100) to (103), (105), (126), (128), (143), and (144), the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemistry 15】 【Chemistry 16】

15. In any one of claims 1 to 14, The phosphorescent material has an emission spectrum with a peak wavelength of 450 nm or more and 570 nm or less.

16. In any one of claims 1 to 14, The phosphorescent material has an emission spectrum with a peak wavelength of 495 nm or more and 590 nm or less.

17. In any one of claims 1 to 14, The phosphorescent material has an emission spectrum with a peak wavelength of 570 nm or more and 750 nm or less.

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