Organic compounds and methods of synthesis

Abstract

Provided is a novel organic compound. Also provided is a novel organic compound having hole-transporting properties. In addition, the invention provides a synthesis method of the 10-iodobenzo [b] naphtho [2, 1-d] furan.

Description

This application is a divisional application of the Chinese patent application titled “Organic compounds, light-emitting elements, light-emitting devices, electronic devices and lighting devices” with national application number 201880047589.7 after the PCT international application with international application number PCT / IB2018 / 055451 and international application date July 23, 2018 entered the Chinese stage. Technical Field

[0001] One embodiment of the present invention relates to a light-emitting element, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device. Note that one embodiment of the present invention is not limited to the above-mentioned technical field. The technical field of one embodiment of the invention disclosed in this specification and the like relates to an object, a method, or a manufacturing method. Alternatively, one embodiment of the present invention relates to a procedure (process), a machine (machine), a product (manufacture) or a composition (composition of matter). Therefore, more specifically, as examples of the technical field of one embodiment of the present invention disclosed in this specification, semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, camera devices, their driving methods, and their manufacturing methods can be cited. Background Art

[0002] The practical application of light-emitting elements (organic EL elements) using organic compounds and utilizing electroluminescence (EL) is very active. In the basic structure of these light-emitting elements, an organic compound layer (EL layer) containing a light-emitting material is sandwiched between a pair of electrodes. By applying voltage to the element, carriers are injected, and the recombination energy of the carriers is used to obtain light emission from the light-emitting material.

[0003] Because this light-emitting element is a self-luminous light-emitting element, it has advantages such as higher visibility and no need for backlight when used in pixels of a display compared to liquid crystal. Therefore, this light-emitting element is suitable for flat panel display elements. In addition, a display using this light-emitting element can be made thin and light, which is also a great advantage. Furthermore, very high-speed response is also one of the characteristics of this light-emitting element.

[0004] Since the light-emitting layer of such a light-emitting element can be continuously formed in two dimensions, surface light emission can be obtained. Since this is a feature that is difficult to obtain in point light sources represented by incandescent lamps or LEDs or line light sources represented by fluorescent lamps, the above-mentioned light-emitting element has high utilization value as a surface light source that can be applied to lighting, etc.

[0005] As described above, displays and lighting devices using light-emitting elements are applied to various electronic devices, and research and development of light-emitting elements having better efficiency and life are being actively pursued.

[0006] In such a light-emitting element, a hole injection layer is sometimes formed to facilitate the injection of holes into the EL layer, which is an organic compound. As one of the materials of the hole injection layer, there is an organic compound with acceptor properties. The organic compound with acceptor properties can be easily formed by vapor deposition, is suitable for mass production and is widely used. However, when there is a distance between the LUMO energy level of the organic compound with acceptor properties and the HOMO energy level of the organic compound constituting the hole transport layer, it is difficult to inject holes into the EL layer. Therefore, it is necessary to make the LUMO energy level of the organic compound with acceptor properties close to the HOMO energy level of the organic compound constituting the hole transport layer, but there is the following problem: when the HOMO energy level of the organic compound constituting the hole transport layer is made shallower, the difference between the HOMO energy level of the light-emitting layer and the HOMO energy level of the hole transport layer becomes larger. Although holes can be injected into the EL layer from the electrode, it is difficult to inject holes from the hole transport layer into the main material of the light-emitting layer.

[0007] Patent Document 1 discloses a structure in which a hole transport material having a HOMO level between the HOMO level of the first hole injection layer and the HOMO level of the host material is provided between a first hole transport layer in contact with a hole injection layer and a light emitting layer.

[0008] The characteristics of light-emitting elements have been significantly improved, but they are still not enough to cope with the high demands for various characteristics such as efficiency and durability. [Prior technical literature] [Patent Document]

[0009] [Patent Document 1] International Publication No. 2011 / 065136 Pamphlet Summary of the invention Technical problem to be solved by the invention

[0010] Therefore, in the present invention, an object of one embodiment of the present invention is to provide a novel organic compound. In addition, an object of one embodiment of the present invention is to provide a novel organic compound having hole transport properties. In addition, an object of one embodiment of the present invention is to provide a novel hole transport material. In addition, an object of one embodiment of the present invention is to provide a novel light-emitting element. In addition, an object of one embodiment of the present invention is to provide a light-emitting element with good life. In addition, an object of one embodiment of the present invention is to provide a light-emitting element with good luminous efficiency. In addition, an object of one embodiment of the present invention is to provide a light-emitting element with low driving voltage.

[0011] Another aspect of the present invention aims to provide a light emitting device, an electronic device, and a display device with high reliability. Another aspect of the present invention aims to provide a light emitting device, an electronic device, and a display device with low power consumption.

[0012] The present invention only needs to achieve any one of the above-mentioned objects. Solutions to technical problems

[0013] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0014] [Chemical formula 1]

[0015] In the general formula (G1), R 1 To R 10 One of them is a group represented by the following general formula (g1), and the others independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0016] [Chemical formula 2]

[0017] In the general formula (g1), Ar 3 ,Ar 4 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and any one of the groups represented by the following general formula (g2) to the following general formula (g4). 1 ,Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, n and m each independently represent an integer from 0 to 2, and in Ar 3 In the case of a group represented by the following general formula (g4), n is 1 or 2, and in Ar 4 In the case of a group represented by the following general formula (g4), m is 1 or 2. In the case of n being 2, two Ar 1 They may be different or the same. Similarly, when m is 2, the two Ar 2 They can be different or the same. 3 ,Ar 4When it is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is any one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms and a group represented by the following general formulae (g2) to (g4).

[0018] Note that the following structures are excluded: n and m are 0, Ar 3 and Ar 4 is a phenyl group, wherein the 2-position and 6-position of the phenyl group are substituted by aromatic hydrocarbon groups. In addition, n and m are independently 1 or 2 and are bonded to Ar 1 ,Ar 2 When the nitrogen skeleton is a benzene ring, that is, when it has an aniline skeleton, a structure in which the 2-position and 6-position of the aniline skeleton are substituted by aromatic hydrocarbon groups is excluded.

[0019] [Chemical formula 3]

[0020] Note that in general formula (g2), R 31 To R 40 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0021] In the general formula (g3), R 41 To R 50 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0022] In the general formula (g4), R 51 To R 60 One of them represents a single bond and is bonded to Ar in the above general formula (g1) 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0023] Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (g1) is bonded to R in the organic compound represented by the general formula (G1). 1 , R 8 and R 10 Any one of .

[0024] Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (g1) is bonded to R in the organic compound represented by the general formula (G1). 10 .

[0025] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0026] [Chemical formula 4]

[0027] In the general formula (G2), R 11 To R 20 One of them is a group represented by the following general formula (g1), and the others independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0028] [Chemical formula 5]

[0029] In the general formula (g1), Ar 3 ,Ar 4 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and any one of the groups represented by the following general formula (g2) to the following general formula (g4). 1 ,Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, n and m each independently represent an integer from 0 to 2, and in Ar 3 In the case of a group represented by the following general formula (g4), n is 1 or 2, and in Ar 4 In the case of a group represented by the following general formula (g4), m is 1 or 2. In the case of n being 2, two Ar 1 They may be different or the same. Similarly, when m is 2, the two Ar 2 They can be different or the same. 3 ,Ar 4When it is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is any one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms and a group represented by the following general formulae (g2) to (g4).

[0030] Note that the following structures are excluded: n and m are 0, Ar 3 and Ar 4 is a phenyl group, wherein the 2-position and 6-position of the phenyl group are substituted by aromatic hydrocarbon groups. In addition, n and m are independently 1 or 2 and are bonded to Ar 1 ,Ar 2 When the nitrogen skeleton is a benzene ring, that is, when it has an aniline skeleton, a structure in which the 2-position and 6-position of the aniline skeleton are substituted by aromatic hydrocarbon groups is excluded.

[0031] [Chemical formula 6]

[0032] Note that in general formula (g2), R 31 To R 40 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0033] In the general formula (g3), R 41 To R 50 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0034] In the general formula (g4), R 51 To R 60 One of them represents a single bond and is bonded to Ar in the above general formula (g1) 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0035] Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (g1) is bonded to R in the organic compound represented by the general formula (G2). 18 or R 20 .

[0036] Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (g1) is bonded to R in the organic compound represented by the general formula (G2). 20 .

[0037] In addition, another embodiment of the present invention is an organic compound having the above structure, wherein the Ar 1 And the Ar 2 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the Ar 3 and Ar 4 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0038] In addition, another embodiment of the present invention is an organic compound having the above structure, wherein the Ar 3 And the Ar 4 Each independently represents any of a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group.

[0039] In addition, another embodiment of the present invention is an organic compound having the above structure, wherein the Ar 1 And the Ar 2 Each independently represents any of a substituted or unsubstituted phenylene group and a substituted or unsubstituted naphthylene group.

[0040] In addition, another embodiment of the present invention is an organic compound having the above structure, wherein the Ar 3 And the Ar 4 It is phenyl.

[0041] In addition, another embodiment of the present invention is an organic compound having the above structure, wherein the Ar 1 And the Ar 2 It is a phenylene group.

[0042] Another embodiment of the present invention is an organic compound having the above structure, wherein the n and the m are 2.

[0043] Another embodiment of the present invention is an organic compound having the above structure, wherein both n and m are 1.

[0044] Another embodiment of the present invention is a light-emitting element including an anode, a cathode, and an EL layer, wherein the EL layer is located between the anode and the cathode, and the EL layer contains the above-mentioned organic compound.

[0045] Another embodiment of the present invention is a light-emitting element including an anode, a cathode, and an EL layer, wherein the EL layer is located between the anode and the cathode, and the EL layer includes a light-emitting layer, and the light-emitting layer contains the above-mentioned organic compound.

[0046] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein the light-emitting layer further contains a light-emitting material.

[0047] Another embodiment of the present invention is a light-emitting element having the above structure, wherein the light-emitting layer further includes a material having an electron-transporting property.

[0048] In addition, another embodiment of the present invention is a light-emitting element, which includes an anode, a cathode and an EL layer, wherein the EL layer is located between the anode and the cathode, the EL layer includes a light-emitting layer and a hole transport layer, the light-emitting layer contains a light-emitting material, the hole transport layer is located between the light-emitting layer and the anode, and the hole transport layer contains the above-mentioned organic compound.

[0049] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein the EL layer further includes a hole injection layer, the hole injection layer is arranged in contact with the anode and the hole transport layer, and the hole injection layer contains an organic compound with acceptor properties.

[0050] Another embodiment of the present invention is a light-emitting element having the above structure, wherein the compound having acceptor properties is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene.

[0051] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein the hole transport layer includes a first layer, a second layer and a third layer, the first layer is located between the hole injection layer and the second layer, the third layer is located between the second layer and the light-emitting layer, the first layer is in contact with the hole injection layer, the third layer is in contact with the light-emitting layer, the first layer contains a first hole transport material, the second layer contains the organic compound, the third layer contains a third hole transport material, the light-emitting layer contains a main material and a light-emitting material, the HOMO energy level of the organic compound is deeper than the HOMO energy level of the first hole transport material, the HOMO energy level of the main material is deeper than the HOMO energy level of the organic compound, and the difference between the HOMO energy level of the organic compound and the HOMO energy level of the third hole transport material is less than 0.3 eV.

[0052] Another embodiment of the present invention is a light-emitting element having the above structure, wherein the HOMO level of the first hole transport material is -5.4 eV or higher.

[0053] Another embodiment of the present invention is a light-emitting element having the above structure, wherein a difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound is 0.3 eV or less.

[0054] Another embodiment of the present invention is a light-emitting element having the above structure, wherein a difference between a HOMO level of the organic compound and a HOMO level of the third hole transport material is 0.2 eV or less.

[0055] Another embodiment of the present invention is a light-emitting element having the above structure, wherein a difference between a HOMO level of the first hole transport material and a HOMO level of the organic compound is 0.2 eV or less.

[0056] Still another embodiment of the present invention is a light-emitting element having the above structure, wherein a HOMO level of the light-emitting material is higher than a HOMO level of the host material.

[0057] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein a HOMO level of the third hole transport material is equal to or deeper than a HOMO level of the host material.

[0058] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein the light-emitting material is a fluorescent substance.

[0059] In addition, another embodiment of the present invention is a light-emitting element having the above structure, wherein the light emitted by the light-emitting material is blue fluorescent light.

[0060] Another embodiment of the present invention is a light-emitting element having the above structure, wherein the light-emitting material is a condensed aromatic diamine compound, and the amino group contained in the aromatic diamine compound contains a carbazole group.

[0061] Another embodiment of the present invention is a light-emitting element having the above structure, wherein the light-emitting material is a diaminopyrene compound, and the amino group included in the diaminopyrene compound includes a carbazole group.

[0062] In addition, in the above structure, another embodiment of the present invention is a light-emitting device including a transistor or a substrate.

[0063] In addition, another embodiment of the present invention is an electronic device including the above-mentioned light emitting device, and a sensor, an operation button, a speaker, or a microphone.

[0064] Another aspect of the present invention is a lighting device including the light emitting device having the above-mentioned structure and a housing.

[0065] In addition, the light-emitting device in this specification includes an image display device using a light-emitting element. In addition, the light-emitting device sometimes includes the following modules: a module in which a connector such as an anisotropic conductive film or TCP (Tape Carrier Package) is mounted on the light-emitting element; a module in which a printed circuit board is provided at the end of the TCP; a module in which an IC (integrated circuit) is directly mounted on the light-emitting element by COG (Chip On Glass). Furthermore, lighting fixtures and the like sometimes include light-emitting devices. Effects of the Invention

[0066] One embodiment of the present invention can provide a novel light-emitting element. In addition, one embodiment of the present invention can provide a light-emitting element with good life. In addition, one embodiment of the present invention can provide a light-emitting element with good luminous efficiency. In addition, one embodiment of the present invention can provide a light-emitting element with low driving voltage.

[0067] Another embodiment of the present invention can provide a light-emitting device, an electronic device, and a display device with high reliability. Another embodiment of the present invention can provide a light-emitting device, an electronic device, and a display device with low power consumption.

[0068] Note that the description of these effects does not prevent the existence of other effects. In addition, one mode of the present invention does not need to have all of the above effects. In addition, effects other than these effects are obvious from the description of the specification, drawings, claims, etc., so that effects other than these effects can be extracted from the description of the specification, drawings, claims, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0069] [Figure 1] Schematic diagram of a light-emitting element. [Fig. 2] A schematic diagram of an active matrix light-emitting device. [Fig. 3] A schematic diagram of an active matrix light-emitting device. [ Figure 4 ] Schematic diagram of an active matrix light-emitting device. [Fig. 5] A schematic diagram of a passive matrix light-emitting device. [Fig. 6] A diagram showing a lighting device. [Fig. 7] A diagram showing an electronic device. [Fig. 8] A diagram showing an electronic device. [ Fig. 9 ] shows a diagram of a lighting device. [ Fig.10 ] shows a diagram of a lighting device. [ Fig.11 ] shows a diagram of a vehicle-mounted display device and a lighting device. [Fig. 12] A diagram showing an electronic device. [Fig. 13] A diagram showing an electronic device. [Figure 14] 2-Chlorobenzo[b]naphtho[2,3-d]furan 1 H NMR spectrum. [Figure 15] N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)) 1 H NMR spectrum. [ Fig.16 ]BBABnf(II)(2))'s absorption and emission spectra in toluene solution. [ Fig.17 ]BBABnf(II)(2)) in thin film state. [Figure 18] 4-Chlorobenzo[b]naphtho[2,3-d]furan 1 H NMR spectrum. [Figure 19] N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)) 1 H NMR spectrum. [ Fig. 20]BBABnf(II)(4))'s absorption and emission spectra in toluene solution. [ Fig.21 ]BBABnf(II)(4)) in thin film state. [ Fig. 22 ]Brightness-current density characteristics of light-emitting element 1 and light-emitting element 2. [ Fig.23 ]Current efficiency-brightness characteristics of light-emitting element 1 and light-emitting element 2. [ Fig.24 ]Brightness-voltage characteristics of light-emitting element 1 and light-emitting element 2. [ Fig.25 ]Current-voltage characteristics of light-emitting element 1 and light-emitting element 2. [ Fig.26 ]External quantum efficiency-brightness characteristics of light-emitting element 1 and light-emitting element 2. [ Fig. 27 ]Emission spectra of light-emitting element 1 and light-emitting element 2. [ Fig.28 ]Normalized brightness-time variation characteristics of light-emitting element 1 and light-emitting element 2. [ Fig.29 ]Brightness-current density characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.30 ] Current efficiency-brightness characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.31 ]Brightness-voltage characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.32 ]Current-voltage characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.33 ]External quantum efficiency-brightness characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.34 ]Emission spectra of light-emitting element 3 and light-emitting element 4. [ Fig.35 ]Normalized brightness-time variation characteristics of light-emitting element 3 and light-emitting element 4. [ Fig.36 ]Brightness-current density characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.37 ] Current efficiency-brightness characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.38 ]Brightness-voltage characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.39 ] Current-voltage characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.40]External quantum efficiency-brightness characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.41 ]Emission spectra of light-emitting element 5 and light-emitting element 6. [ Fig.42 ]Normalized brightness-time variation characteristics of light-emitting element 5 and light-emitting element 6. [ Fig.43 ]Brightness-current density characteristics of light-emitting element 7. [ Fig.44 ]Current efficiency-brightness characteristics of light-emitting element 7. [ Fig.45 ]Brightness-voltage characteristics of light-emitting element 7. [ Fig.46 ]Current-voltage characteristics of light-emitting element 7. [ Fig.47 ]External quantum efficiency-brightness characteristics of light-emitting element 7. [ Fig.48 ]Emission spectrum of light-emitting element 7. [ Fig.49 ]Brightness-current density characteristics of light-emitting element 8. [ Fig.50 ]Current efficiency-brightness characteristics of light-emitting element 8. [ Fig.51 ]Brightness-voltage characteristics of light-emitting element 8. [ Fig.52 ]Current-voltage characteristics of light-emitting element 8. [ Fig.53 ]External quantum efficiency-brightness characteristics of light-emitting element 8. [ Fig.54 ]Emission spectrum of light-emitting element 8. [ Fig.55 ]Brightness-current density characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.56 ] Current efficiency-brightness characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.57 ]Brightness-voltage characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.58 ] Current-voltage characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.59 ]External quantum efficiency-brightness characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.60 ]Emission spectra of light-emitting element 9 and light-emitting element 10. [ Fig.61 ] Normalized brightness-time variation characteristics of light-emitting element 9 and light-emitting element 10. [ Fig.62 ]Brightness-current density characteristics of light-emitting element 11 and light-emitting element 12. [ Fig.63 ]Current efficiency-brightness characteristics of light-emitting element 11 and light-emitting element 12. [ Fig.64 ]Brightness-voltage characteristics of light-emitting element 11 and light-emitting element 12. [ Fig.65 ]The current-voltage characteristics of light-emitting element 11 and light-emitting element 12. [ Fig.66 ]External quantum efficiency-brightness characteristics of light-emitting element 11 and light-emitting element 12. [ Fig.67 ]Emission spectra of light-emitting element 11 and light-emitting element 12. [ Fig.68 ] Normalized brightness-time variation characteristics of light-emitting element 11 and light-emitting element 12. Modes for Carrying Out the Invention

[0070] Hereinafter, the embodiments of the present invention will be described in detail with reference to the accompanying drawings. However, the present invention is not limited to the following description, and a person skilled in the art can easily understand that the mode and details can be transformed into various forms without departing from the purpose and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the contents described in the embodiments shown below.

[0071] (Implementation Method 1) The organic compound according to one embodiment of the present invention is an organic compound represented by the following general formula (G1) or general formula (G2).

[0072] [Chemical formula 7]

[0073] In the general formula (G1), R 1 To R 10 One of them is a group represented by the following general formula (g1), and the others independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0074] [Chemical formula 8]

[0075] In the general formula (G2), R 11 To R 20One of them is a group represented by the following general formula (g1), and the others independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0076] [Chemical formula 9]

[0077] In the general formula (g1), Ar 3 ,Ar 4 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and any one of the groups represented by the following general formula (g2) to the following general formula (g4). 1 ,Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, n and m each independently represent an integer from 0 to 2, and in Ar 3 In the case of a group represented by the following general formula (g4), n is 1 or 2, and in Ar 4 In the case of a group represented by the following general formula (g4), m is 1 or 2. In the case of n being 2, two Ar 1 They may be different or the same. Similarly, when m is 2, the two Ar 2 They can be different or the same. 3 ,Ar 4 When it is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is any one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a haloalkyl group having 1 to 6 carbon atoms and a group represented by the following general formulae (g2) to (g4).

[0078] [Chemical formula 10]

[0079] Note that in general formula (g2), R 31 To R 40 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0080] In the general formula (g3), R 41 To R 50 One of them represents a single bond and is bonded to the nitrogen atom, Ar in the above general formula (g1). 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0081] In the general formula (g4), R 51 To R 60 One of them represents a single bond and is bonded to Ar in the above general formula (g1) 3 or Ar 4 The rest each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0082] In the above general formula (G1), R 1 , R 8 and R 10 Any one of the above is preferably an organic compound represented by the general formula (g1) because the number of steps required for the synthesis of the organic compound is small and the synthesis can be simple. In addition, a highly reliable element can be provided. In particular, R in the general formula (G1) is 10 The organic compound represented by the general formula (g1) has a high phosphorescence level and can therefore be suitably used in a phosphorescent element.

[0083] In addition, R in the above general formula (G2) 18 and R 20 Any one of the above is a base represented by the general formula (g1) because the number of steps required for the synthesis of the organic compound is small and the synthesis can be simple, so it is preferred. In addition, a light-emitting element using the organic compound can realize a light-emitting element with high reliability, so it is preferred. In particular, R in the general formula (G2) is 20 The organic compound represented by the general formula (g1) has a high phosphorescence level and can therefore be suitably used in a phosphorescent element.

[0084] As can be used for the above general formula R 1 To R 20 and R 31 To R 60Specifically, the substituents include substituents represented by the following structural formulae (1-1) to (1-37) or substituents represented by the following structural formulae (2-1) to (2-13). Note that there is no limitation on the substitution positions of the following structural formulae (2-1) to (2-13).

[0085] [Chemical formula 11]

[0086] [Chemical formula 12]

[0087] Ar 3 ,Ar 4 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and any one of the groups represented by the above general formula (g2) to the above general formula (g4). As the substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, specifically, groups represented by the following structural formulas (1-38) and (1-39) can be cited. Note that there is no limitation on their substitution positions. In addition, they may also have substituents.

[0088] [Chemical formula 13]

[0089] When Ar 3 ,Ar 4 When the aromatic hydrocarbon group has 6 to 10 carbon atoms and has a substituent, the substituent may be any one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a halogenated alkyl group having 1 to 6 carbon atoms, and a group represented by the above general formulae (g2) to (g4). Specific examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, and a halogenated alkyl group having 1 to 6 carbon atoms include substituents such as those in the following structural formulae (1-1) to (1-37). In addition, examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl, 1-naphthyl, and 2-naphthyl.

[0090] [Chemical formula 14]

[0091] As Ar 3 ,Ar 4 and Ar having a substituent 3 ,Ar 4As specific examples, groups represented by the following structural formulae (1-100) to (1-134) are preferred.

[0092] [Chemical formula 15]

[0093] In addition, Ar 1 and Ar 2 It is a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and typical examples thereof include the following. Note that there is no limitation on the substitution position thereof. In addition, they may also have a substituent.

[0094] [Chemical formula 16]

[0095] In addition, the following structural formulas (1-40) to (1-74) show that n is 2 and two Ar 1 Different from each other and m is 2 and two Ar 2 Different situations.

[0096] [Chemical formula 17]

[0097] In addition, in the organic compound having the above structure, in the above Ar 1 And the above Ar 2 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 10 carbon atoms, wherein the above Ar 3 and Ar 4 When the amine skeleton is independently substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, there is no bulky skeleton bonded to the amine skeleton, so a material with high hole transport property can be provided, so it is preferred. In addition, since it does not have a large condensed ring hydrocarbon, it is not easy to receive electrons, and when it is used in a device as a hole transport material, it exhibits high electron blocking property, so a device with high luminous efficiency can be provided, so it is preferred.

[0098] In addition, when n and m are 0, Ar 3 and Ar 4 In the case where n and m are each independently 1 or 2 and are bonded to Ar, the phenyl group is not considered to have high hole transport properties because the bulky substituents are bonded to the amine structure. 1 ,Ar 2 When the nitrogen skeleton is a benzene ring, that is, when it has an aniline skeleton, it is difficult to have high hole transport properties because the bulky substituents in the structure in which the 2- and 6-positions of the aniline skeleton are substituted by aromatic hydrocarbon groups are bonded to the amine structure, and therefore it is not regarded as an organic compound of the present invention.

[0099] In addition, in the organic compound having the above structure, in Ar 3 and Ar 4 When it is any one of a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group, an organic compound having both high heat resistance and high hole transport properties can be realized, and a transport layer with good film quality can be formed, so it is preferred. In addition, especially, when they are phenyl groups, they can have good film quality and exhibit good hole transport properties and high electron blocking properties, so they are more preferred.

[0100] In addition, in the organic compound having the above structure, Ar 1 ,Ar 2 The organic compound which is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group has high heat resistance, can form a transport layer with good film quality, and has good hole transport properties, so it is preferred. In addition, in particular, when they are phenylene groups, they can have good film quality and show good hole transport properties, so they are more preferred.

[0101] In addition, among the organic compounds having the above structure, an organic compound in which both n and m are 2 is preferred because it has both high hole transporting property and high heat resistance.

[0102] Among the organic compounds having the above structure, organic compounds in which both n and m are 1 have both high hole transport properties and high heat resistance and can be highly purified during the synthesis process, so they can be suitably used in organic EL devices and are therefore preferred.

[0103] Specific examples of the group represented by the above general formula (g1) are shown below.

[0104] [Chemical formula 18]

[0105] [Chemical formula 19]

[0106] [Chemical formula 20]

[0107] [Chemical formula 21]

[0108] [Chemical formula 22]

[0109] [Chemical formula 23]

[0110] [Chemical formula 24]

[0111] [Chemical formula 25]

[0112] Specific examples of the organic compound having the above structure are shown below.

[0113] [Chemical formula 26]

[0114] [Chemical formula 27]

[0115] [Chemical formula 28]

[0116] [Chemical formula 29]

[0117] [Chemical formula 30]

[0118] [Chemical formula 31]

[0119] [Chemical formula 32]

[0120] [Chemical formula 33]

[0121] [Chemical formula 34]

[0122] [Chemical formula 35]

[0123] [Chemical formula 36]

[0124] [Chemical formula 37]

[0125] The above organic compounds can be synthesized by the following synthesis scheme and the like.

[0126] Here, a method for synthesizing an organic compound represented by the following general formula (G1-a) is described. The organic compound is a compound represented by R in the general formula (G1). 10The compound wherein the group represented by the above general formula (g1) is 1 To R 9 In the case of other organic compounds of one embodiment of the present invention having various substituents, the synthesis described in the synthesis examples can be carried out by the same method by using starting materials having substituents corresponding to the corresponding substitution positions.

[0127] In addition, the substituent R in the following general formula (G1-a), reaction schemes (a-1) and (a-2) is 1 To R 9 , Substituent Ar 1 ,Ar 2 The substituent R described in the above general formula (G1) 1 To R 9 , Substituent Ar 1 ,Ar 2 The same, so the record is omitted.

[0128] Various reactions can be used as a method for synthesizing the organic compound represented by the general formula (G1-a). For example, the organic compound represented by the general formula (G1-a) can be synthesized by performing the synthesis reaction shown below.

[0129] [Chemical formula 38]

[0130] <Method for synthesizing organic compound represented by general formula (G1-a)> The organic compound represented by the general formula (G1-a) of the present invention can be synthesized through the following synthesis scheme (a-1) or (a-2).

[0131] First, scheme (a-1) is described. That is, a benzonaphthofuranylamine compound (G1-a) can be obtained by coupling a benzonaphthofuranylamine compound (Compound 1) with a diarylamine (Compound 2). The synthesis scheme (a-1) is shown below.

[0132] [Chemical formula 39]

[0133] Next, scheme (a-2) is described. That is, by coupling a benzonaphthofuran compound (compound 3) with an aryl compound (compound 4), a benzonaphthofuranylamine compound (compound 5) can be obtained, and then, by coupling compound 5 with an aryl compound (compound 6), the target benzonaphthofuranylamine compound (G1-a) can be obtained. The following is a synthesis scheme (a-2).

[0134] [Chemical formula 40]

[0135] In the above reaction schemes (a-1) and (a-2), X 1 and X 5 Each independently represents chlorine, bromine, iodine, or triflate, and X 2 represents hydrogen, organic tin group, etc., X 3 and X 4 Any one of represents an amino group or an amino group having an organotin group, X 3 and X 4 The other of represents chlorine, bromine, iodine or triflate.

[0136] When the Buchwald-Hartwig reaction using a palladium catalyst is performed in the synthesis schemes (a-1) and (a-2), palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium(0), allylpalladium(II) chloride dimer, tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(o-tolyl)phosphine, di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) and the like can be used as ligands. In this reaction, organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate and the like can be used. In this reaction, as a solvent, toluene, xylene, benzene, tetrahydrofuran, dioxane or the like can be used.

[0137] In addition, when the Ullmann reaction using copper or a copper compound is carried out in the synthesis schemes (a-1) and (a-2), X 1 and X 5 Each independently represents chlorine, bromine, iodine, or triflate, and X 2 represents hydrogen, organic tin group, etc., X 3 and X 4 Any one of X represents an amino group, 3 and X 4The other represents chlorine, bromine, iodine, or triflate. In the reaction, copper or a copper compound can be used. As the base used, inorganic bases such as potassium carbonate can be mentioned. As the solvent that can be used in the reaction, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidone (DMPU), toluene, xylene, benzene, etc. can be mentioned. In the Ullmann reaction, when the reaction temperature is above 100°C, the target product can be obtained in a shorter time and at a high yield, so it is preferred to use DMPU and xylene with a high boiling point. In addition, the reaction temperature is more preferably a high temperature of 150°C or more, so it is more preferred to use DMPU.

[0138] In R 1 To R 9 In the case of compounds having (g1) at the same place, the synthesis described in this synthesis example can be carried out by the same method. 10 The substitution position R 1 To R 9 When (G1) has an amino group such as the general formula (g1) or the general formula (g5) at any position in the compound, when (G1) is synthesized by (a-1), by using as a raw material a compound having X 1 The benzonaphthofuran compound of compound 1 can be obtained by 1 To R 9 On the other hand, when (G1) is synthesized by (a-2), by using as a raw material a compound equivalent to X 3 The benzonaphthofuran compound of compound 3 can be obtained by 1 To R 9 There is a target object (g1) at the location.

[0139] Next, a method for synthesizing an organic compound represented by the following general formula (G2-a) is described. The organic compound is R 20 The compound having the group represented by (g1). 11 To R 19 In the case of an organic compound of one embodiment of the present invention having various substituents represented by , the synthesis described in the synthesis examples can be carried out by the same method by using a raw material having a substituent corresponding to the corresponding substitution position.

[0140] In addition, the substituent R in the following general formula (G2-a), reaction schemes (b-1) and (b-2) 11 To R 19 , Substituent Ar 1 ,Ar 2 The substituent R described in the above general formula (G2) 11 To R19 , Substituent Ar 1 ,Ar 2 The same, so the record is omitted.

[0141] Various reactions can be used as a method for synthesizing the organic compound represented by the general formula (G2-a). For example, the organic compound represented by the general formula (G2-a) can be synthesized by performing the synthesis reaction shown below.

[0142] [Chemical formula 41]

[0143] <Method for synthesizing organic compounds represented by general formula (G2-a)> The organic compound represented by the general formula (G2-a) of the present invention can be synthesized through the following synthesis scheme (b-1) or (b-2).

[0144] First, scheme (b-1) is described. That is, a benzonaphthofuranylamine compound (G2-a) can be obtained by coupling a benzonaphthofuranylamine compound (Compound 7) with a diarylamine (Compound 2). The synthesis scheme (b-1) is shown below.

[0145] [Chemical formula 42]

[0146] Next, scheme (b-2) is described. That is, by coupling a benzonaphthofuran compound (compound 8) with an aryl compound (compound 4), a benzonaphthofuranylamine compound (compound 9) can be obtained, and then, by coupling compound 7 with an aryl compound (compound 6), the target benzonaphthofuranylamine compound (G2-a) can be obtained. The following is a synthesis scheme (b-2).

[0147] [Chemical formula 43]

[0148] X 5 and X 6 Each independently represents chlorine, bromine, iodine, or triflate, and X 2 represents hydrogen, organic tin group, etc., X 4 and X 7 Any one of represents an amino group or an amino group having an organotin group, X 4 and X 7 The other of represents chlorine, bromine, iodine or triflate.

[0149] When the Buchwald-Hartwig reaction using a palladium catalyst is performed in the synthesis schemes (b-1) to (b-2), palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium(0), allylpalladium(II) chloride dimer, tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(o-tolyl)phosphine, di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) and the like can be used. In this reaction, organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate and the like can be used. In this reaction, as a solvent, toluene, xylene, benzene, tetrahydrofuran, dioxane or the like can be used.

[0150] In addition, when the Ullmann reaction using copper or a copper compound is carried out in the synthesis schemes (b-1) and (b-2), X 5 and X 6 Each independently represents chlorine, bromine, iodine, or triflate, and X 2 represents hydrogen, organic tin group, etc., X 4 and X 7 Any one of X represents an amino group, 4 and X 7 The other represents chlorine, bromine, iodine, or triflate. In the reaction, copper or a copper compound can be used. As the base used, inorganic bases such as potassium carbonate can be mentioned. As the solvent that can be used in the reaction, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidone (DMPU), toluene, xylene, benzene, etc. can be mentioned. In the Ullmann reaction, when the reaction temperature is above 100°C, the target product can be obtained in a shorter time and at a high yield, so it is preferred to use DMPU and xylene with a high boiling point. In addition, the reaction temperature is more preferably a high temperature of 150°C or more, so it is more preferred to use DMPU.

[0151] In R 11 To R 19 In the compound having an amino group at a corresponding position, the synthesis described in this synthesis example can be carried out by the same method using a benzonaphthofuran compound having a chlorine, bromine, iodine, or trifluoromethanesulfonate group at a corresponding position. 20 The substitution position R 11 To R 19 In the case of (G2) having an amino group at any position in the reaction, when (G2) is synthesized by (b-1), by using as a raw material a compound having X 6The benzonaphthofuran compound of compound 7 can give R 11 To R 19 On the other hand, when (G2) is synthesized by (b-2), by using as a raw material a compound equivalent to X 7 The benzonaphthofuran compound 8 can be obtained by 11 To R 19 There is a target object (g1) at the location.

[0152] (Implementation Method 2)

[0153] 1 shows a light-emitting element according to one embodiment of the present invention. The light-emitting element according to one embodiment of the present invention includes a first electrode 101, a second electrode 102, and an EL layer 103. The EL layer uses the hole transport material containing the organic compound described above.

[0154] The EL layer 103 includes a light-emitting layer 113 and may further include a hole transport layer 112. The light-emitting layer 113 includes a light-emitting material and a host material, and the light-emitting element of one embodiment of the present invention obtains light from the light-emitting material. The hole transport material of one embodiment of the present invention may be included in the light-emitting layer 113, may be included in the hole transport layer 112, or may be included in both.

[0155] 1 illustrates the hole injection layer 111 , the electron transport layer 114 , and the electron injection layer 115 in addition to the above, but the structure of the light-emitting element is not limited thereto.

[0156] The hole transport material can be used as a host material. In addition, the hole transport material and the electron transport material can be co-evaporated to form an exciplex formed by the electron transport material and the hole transport material. By forming an exciplex with an appropriate emission wavelength, efficient energy transfer to the luminescent material can be achieved, thereby providing a light-emitting element with high efficiency and good lifespan.

[0157] In addition, the hole transport materials described above have good hole transport properties and are therefore suitable for the hole transport layer 112. This is particularly suitable when a hole injection layer 111 is provided between the hole transport layer 112 and the first electrode 101 and the hole injection layer 111 uses an organic compound that is an acceptor for holes that are easily injected from the electrode.

[0158] When hole injection is performed using an organic compound with acceptor properties, the compound contained in the hole transport layer 112 in contact with the hole injection layer 111 is preferably a hole transport material with a relatively shallow HOMO energy level, so that electrons can be extracted through the organic compound with acceptor properties. However, it is difficult for a hole transport material with a shallow HOMO energy level to inject holes into the light-emitting layer 113. When the hole transport layer 112 composed of the hole transport material with a shallow HOMO energy level is formed in contact with the light-emitting layer 113, carriers accumulate on its interface, which may lead to a decrease in the life and efficiency of the light-emitting element. Therefore, by providing a layer containing the organic compound described in Embodiment 1 between the hole transport material with a shallow HOMO energy level and the light-emitting layer 113, holes can be smoothly injected into the light-emitting layer, thereby improving the life and efficiency of the light-emitting element.

[0159] That is, the following light-emitting element can have good life and efficiency, so it is preferred, in which: the hole transport layer 112 includes a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side, the first hole transport layer contains a first hole transport material, and the second hole transport layer contains the organic compound described in Embodiment 1, and the HOMO energy level of the organic compound described in Embodiment 1 is deeper than the HOMO energy level of the first hole transport material. In addition, when the HOMO energy level of the first hole transport material is -5.4 eV or more, it is preferred because electrons can be easily extracted from the organic compound having an acceptor property.

[0160] In addition, when the difference between the HOMO energy level of the first hole transport material and the HOMO energy level of the organic compound described in Embodiment 1 is 0.3 eV or less, preferably 0.2 eV or less, holes can be easily injected from the first hole transport layer 112-1 to the second hole transport layer 112-2, which is preferred.

[0161] In addition, the hole transport layer 112 further includes a third hole transport layer 112-3 between the second hole transport layer 112-2 and the light emitting layer, and the third hole transport layer 112-3 may also include a third hole transport material. At this time, the HOMO energy level of the third hole transport material is preferably deeper than the HOMO energy level of the organic compound described in Embodiment 1 contained in the second hole transport layer 112-2, and the difference between the HOMO energy level of the third hole transport material and the HOMO energy level of the organic compound described in Embodiment 1 contained in the second hole transport layer 112-2 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.

[0162] In addition, the HOMO energy level of the third hole transport material is preferably the same as the HOMO energy level of the host material or the HOMO energy level of the third hole transport material is located at a deeper position, thereby allowing holes to be appropriately transported to the light-emitting layer and allowing the light-emitting element to have a good life and efficiency.

[0163] In addition, when the HOMO energy level of the light-emitting material is located at a shallower (higher) position than the HOMO energy level of the main material, the proportion of holes injected into the light-emitting material increases according to the position of the HOMO energy level of the hole transport layer. Moreover, the deviation of the light-emitting area due to the holes being captured by the light-emitting material sometimes leads to a decrease in life. In the above case, it is preferred to adopt the structure of the above-mentioned light-emitting element. As a light-emitting element that is easy to have the above-mentioned structure, a blue fluorescent element can be cited. It is particularly preferred to adopt the structure of the present invention for aromatic diamine compounds that emit good blue fluorescence, especially pyrene diamine compounds, thereby obtaining a light-emitting element with good life, efficiency and chromaticity.

[0164] Next, the detailed structure and material examples of the above-mentioned light-emitting element are described. As described above, the light-emitting element of one embodiment of the present invention includes an EL layer 103 composed of a plurality of layers between a pair of electrodes, namely, a first electrode 101 and a second electrode 102, and the EL layer 103 includes a hole injection layer 111, a hole transport layer 112, and a light-emitting layer 113 at least from the first electrode 101 side.

[0165] There is no particular limitation on other layers in the EL layer 103, and various layer structures such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier blocking layer, an exciton blocking layer, and a charge generation layer can be employed.

[0166] The first electrode 101 is preferably formed using a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. Although these conductive metal oxide films are usually formed by sputtering, they can also be formed by applying a sol-gel method. As an example of a formation method, a method of forming indium oxide-zinc oxide by sputtering using a target material having 1 wt% to 20 wt% of zinc oxide added to indium oxide can be cited. In addition, indium oxide (IWZO) containing tungsten oxide and zinc oxide can be formed by sputtering using a target material having 0.5 wt% to 5 wt% of tungsten oxide and 0.1 wt% to 1 wt% of zinc oxide added to indium oxide. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd) or a nitride of a metal material (for example, titanium nitride) can be cited. In addition, graphene can also be used. In addition, by using a composite material described later for the layer in contact with the first electrode 101 in the EL layer 103, it is possible to select an electrode material without taking the work function into consideration.

[0167] In this embodiment, the following two structures are described as the stacked-layer structure of the EL layer 103: Figure 1A As shown, a structure including a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114 and an electron injection layer 115 is adopted; Figure 1B As shown, a structure including a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116 is adopted. The materials constituting each layer are specifically shown below.

[0168] The hole injection layer 111 is a layer containing a substance having an acceptor property. It is more preferable to use the structure of one embodiment of the present invention in the case of using an organic compound having an acceptor property. As an organic compound having an acceptor property, a compound having an electron withdrawing group (halogen or cyano), 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), etc. can be used. As an organic compound having an acceptor property, a compound such as HAT-CN in which an electron withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms is thermally stable, so it is preferred. An organic compound having an acceptor property can extract electrons from an adjacent hole transport layer (or hole transport material) by applying an electric field.

[0169] When an organic compound having an acceptor property is not used for the hole injection layer 111, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used as the acceptor material. In addition, phthalocyanine compounds such as phthalocyanine (abbreviated as: H2Pc), copper phthalocyanine (abbreviated as: CuPC), etc.; aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as: DNTPD), etc.; or polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. can also be used to form the hole injection layer 111.

[0170] In addition, as the hole injection layer 111, a composite material containing an acceptor substance in a substance having hole transport properties can be used. Note that by using a composite material containing an acceptor substance in a substance having hole transport properties, it is not necessary to consider the work function of the electrode when selecting the material to form the electrode. In other words, as the first electrode 101, not only a material with a large work function can be used, but also a material with a small work function can be used. As the acceptor substance, organic compounds and transition metal oxides having acceptor properties such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as: F4-TCNQ), chloranil, 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as: F6-TCNNQ) can be cited. In addition, oxides of metals belonging to the fourth to eighth groups in the periodic table can be cited. As metal oxides belonging to the fourth to eighth groups in the periodic table, metal oxides with high electron acceptability such as vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferably used. Among them, molybdenum oxide is preferred because it is stable in the atmosphere and has low hygroscopicity and is easy to handle.

[0171] As hole transport materials for composite materials, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can be used. As materials with hole transport properties for composite materials, it is preferred to use a hole mobility of 10 -6 cm 2 / Vs or more. The following specifically lists organic compounds that can be used as the hole transport material in the composite material.

[0172] Examples of aromatic amine compounds that can be used for composite materials include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B). Specific examples of the carbazole derivatives include 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene. Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene (abbreviation: DMNA), and 2-tert-butyl-9,10-di(2-naphthyl)anthracene. Butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthracene, 10,10'-diphenyl-9,9'-bianthracene, 10,10'-bis(2-phenylphenyl)-9,9'-bianthracene, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthracene, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. In addition, pentacene, coronene, etc. can also be used. It may have a vinyl skeleton.As aromatic hydrocarbons having a vinyl group, for example, 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated as DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA) and the like can be cited. In addition, an organic compound of one embodiment of the present invention can also be used. In addition, at this time, F6-TCNNQ is preferably used as an acceptor substance.

[0173] In addition, high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used.

[0174] By forming the hole injection layer 111, hole injection properties can be improved, so that a light-emitting element with a low driving voltage can be obtained. In addition, an organic compound having an acceptor property can be easily formed by vapor deposition and is therefore an easy-to-use material.

[0175] The hole transport layer 112 is formed to contain a hole transport material. The hole transport material preferably has a 1×10 - 6 cm 2 The hole transport layer 112 preferably contains a hole transport material of one embodiment of the present invention. When the hole transport layer 112 contains the organic compound described in Embodiment 1, a light-emitting element with long life and good efficiency can be obtained.

[0176] In particular, when an organic compound with acceptor properties is used as the hole injection layer 111, by making the hole injection layer 111 have at least two layers, namely a first hole transport layer and a second hole transport layer, the first hole transport layer contains a first hole transport material with a relatively shallow HOMO energy level, and the second hole transport layer contains the organic compound described in embodiment 1, a light-emitting element with long life and good efficiency can be obtained.

[0177] The difference between the LUMO energy level of the organic compound with acceptor properties and the HOMO energy level of the first hole transport material changes according to the acceptor properties of the organic compound with acceptor properties, so there is no special restriction, as long as the difference in the energy level is about 1eV or less, holes can be injected. When HAT-CN is used as an organic compound with acceptor properties, the LUMO energy level of HAT-CN can be estimated to be -4.41eV using cyclic voltammetry measurement, so the HOMO energy level of the first hole transport material is preferably above -5.4eV. Note that if the HOMO energy level of the first hole transport material is too high, the hole injection property to the second hole transport material is reduced. In addition, the work function of the anode of ITO, etc. is about -5eV, so the situation where the HOMO energy level of the first hole transport material is higher than -5eV is also unfavorable. Therefore, the HOMO energy level of the first hole transport material is preferably below -5.0eV.

[0178] In addition, a third hole transport layer may be further formed between the second hole transport layer and the light emitting layer. The third hole transport layer includes a third hole transport material.

[0179] Since the first hole transport layer, the second hole transport layer and the third hole transport layer have been described in the above description, their repeated description is omitted. In addition, as for the hole transport material contained in the first hole transport layer, the second hole transport layer and the third hole transport layer, a material consistent with the relationship between the above layers can be selected from the above-mentioned materials having hole transport properties or other various materials having hole transport properties.

[0180] The light-emitting layer 113 is a layer containing a host material and a light-emitting material. The light-emitting material can be any one of a fluorescent light-emitting substance, a phosphorescent light-emitting substance, and a substance exhibiting thermally activated delayed fluorescence (TADF). In addition, it can be a single layer or can be composed of multiple layers containing different light-emitting materials. In one embodiment of the present invention, the light-emitting layer 113 is preferably used as a layer exhibiting fluorescent light, in particular, a layer exhibiting blue fluorescent light.

[0181] In the light-emitting layer 113, materials that can be used as the fluorescent substance include, for example, the following substances. In addition, other fluorescent substances can also be used.

[0182] For example, 5,6-bis[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthracenyl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N , N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl- 2-Anthracene) triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butyl perylene (abbreviation: TBP), 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N"-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene )bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviated as DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), N,N,N',N',N",N",N"',N"'-octaphenyldibenzo[g,p] (chrysene)-2,7,10,15-tetraamine (abbreviated as DBC1), coumarin 30, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), Abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenylnaphthacene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-ylidene)malononitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2, 3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)naphthocene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCJTI ), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malononitrile (abbreviated as: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as: BisDCJTM), N,N'-(pyrene-1,In particular, fused aromatic diamine compounds represented by pyrene diamine derivative compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferred because they have high hole-trapping properties and good luminous efficiency and reliability.

[0183] Materials that can be used as a phosphorescent substance in the light-emitting layer 113 include the following substances.

[0184] For example, organometallic iridium complexes having a 4H-triazole skeleton such as tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated as [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Mptz)3]), and tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(iPrptz-3b)3]) can be mentioned; tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III) (abbreviated as [I r(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Prptz1-Me)3]), etc. having an organometallic iridium complex with a 1H-triazole skeleton; fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated as [Ir(iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]), etc. having an imidazole skeleton; and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2 '] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviated as FIr6), bis [2-(4',6'-difluorophenyl) pyridinium-N,C 2 '] iridium (III) picolinate (abbreviated as FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2 '}iridium(III) picolinate (abbreviated as [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2'] Iridium (III) acetylacetonate (abbreviated as FIr(acac)) and other organic metal iridium complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands. The above substances are compounds that emit blue phosphorescence and have a peak emission wavelength of 440nm to 520nm.

[0185] In addition, tris(4-methyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonate)bis[5-methyl -6-(2-methylphenyl)-4-phenylpyrimidinyl]iridium(III) (abbreviated as [Ir(mpmppm)2(acac)]), (acetylacetonate)bis(4,6-diphenylpyrimidinyl)iridium(III) (abbreviated as [Ir(dppm)2(acac)]) and the like; (acetylacetonate)bis(3,5-dimethyl-2-phenylpyrazinyl)iridium(III) (abbreviated as [Ir(mppr-Me)2(acac)]), (acetylacetonate)bis(5-isopropyl-3-methyl-2-phenylpyrazinyl)iridium(III) (abbreviated as [Ir(mppr-iPr)2(acac)]) and the like; tris(2-phenylpyridinyl-N,C 2 ') iridium (III) (abbreviated as [Ir(ppy)3]), bis(2-phenylpyridinium-N,C 2 ') iridium(III) acetylacetonate (abbreviated as [Ir(ppy)2(acac)]), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviated as [Ir(bzq)2(acac)]), tris(benzo[h]quinoline)iridium(III) (abbreviated as [Ir(bzq)3]), tris(2-phenylquinoline-N,C 2 '] iridium (III) (abbreviated as [Ir(pq)3]), bis(2-phenylquinoline-N,C 2') iridium (III) acetylacetonate (abbreviated as [Ir(pq)2(acac)]) and other organic metal iridium complexes having a pyridine skeleton; and tris(acetylacetonate) (monophenanthroline) terbium (III) (abbreviated as [Tb(acac)3(Phen)] and other rare earth metal complexes. The above substances are compounds that mainly emit green phosphorescence and have a luminescence peak at 500nm to 600nm. In addition, since the organic metal iridium complexes having a pyrimidine skeleton have particularly excellent reliability and luminous efficiency, they are particularly preferred.

[0186] In addition, organic gold metals having a pyrimidine skeleton include: (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl)(dipivaloylmethanone)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinyl](dipivaloylmethanone)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]) and the like. Iridium complexes; (acetylacetonato)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dipivaloylmethano)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as [Ir(Fdpq)2(acac)]) and other organometallic iridium complexes with pyrazine skeletons; tris(1-phenylisoquinoline-N,C 2’ )iridium(III) (abbreviated as [Ir(piq)3]), bis(1-phenylisoquinoline-N,C 2’ ) iridium (III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and other organic metal iridium complexes having a pyridine skeleton; platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum (II) (abbreviation: PtOEP); and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedione (propanedionato))(monophenanthroline)europium (III) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium (III) (abbreviation: [Eu(TTA)3(Phen)]). The above substances are compounds that emit red phosphorescence and have a luminescence peak at 600nm to 700nm. In addition, organometallic iridium complexes with a pyrazine skeleton can obtain red light emission with good chromaticity.

[0187] In addition to the above-mentioned phosphorescent compounds, known phosphorescent materials may be selected and used.

[0188] As TADF materials, fullerene and its derivatives, acridine and its derivatives, and eosin derivatives can be used. In addition, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can also be mentioned. As the metal-containing porphyrin, for example, there can be mentioned protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), protoporphyrin-tin fluoride complex (SnF2(Etio I)) and octaethylporphyrin-platinum chloride complex (PtCl2OEP) etc. represented by the following structural formula.

[0189] [Chemical formula 44]

[0190] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindol[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), and 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) represented by the following structural formula can also be used. Heterocyclic compounds having both a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as 3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-oxanthene-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridinium)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracenes]-10'-one (abbreviation: ACRSA). In addition, the heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and its electron transport and hole transport properties are both high, so it is preferred. In the substance in which the π-electron-rich heteroaromatic ring and the π-electron-deficient heteroaromatic ring are directly bonded, the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-deficient heteroaromatic ring are both high, and the energy difference between the S1 energy level and the T1 energy level becomes small, and thermally activated delayed fluorescence can be obtained efficiently, so it is particularly preferred. In addition, an aromatic ring bonded with an electron-withdrawing group such as a cyano group can also be used instead of a π-electron-deficient heteroaromatic ring.

[0191] [Chemical formula 45]

[0192] As the host material of the light-emitting layer, various carrier transport materials such as a material having an electron transport property and a material having a hole transport property can be used.

[0193] In addition, examples of materials having hole transport properties include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl triphenylamine (PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (PCBAF ), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9-bifluorene-2-amine (abbreviated as PCBASF), etc.; 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), etc.; 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P -II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as: DBTFLP-IV) and other compounds having a thiophene skeleton; and 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviated as: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as: mmDBFFLBi-II) and other compounds having a furan skeleton. Among them, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton have good reliability and high hole transport properties and help to reduce the driving voltage, so they are preferred. In addition, the organic compounds shown in Implementation 1 can be appropriately used.

[0194] For example, as materials having electron transport properties, there are bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinolinolato)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl) phenol] zinc (II) (abbreviated as: ZnBTZ) and other metal complexes; 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as: PBD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as: OXD-7), 9-[4-(5 -phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviated as: CO11), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as: mDBTBIm-II) and other heterocyclic compounds having a polyazole skeleton; 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as: mDBTBIm-II); 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviated as: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and other heterocyclic compounds with a diazine skeleton; and 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tris[3-(3-pyridyl)-phenyl]benzene (abbreviation: TmPyPB) and other heterocyclic compounds with a pyridine skeleton. Among them, heterocyclic compounds with a diazine skeleton or heterocyclic compounds with a pyridine skeleton have good reliability, so they are preferred. In particular, heterocyclic compounds with a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties, which also helps to reduce the driving voltage.

[0195] In the case where a fluorescent substance is used as a light-emitting material, a material having an anthracene skeleton is preferably used as a host material. By using a substance having an anthracene skeleton as a host material of a fluorescent substance, a light-emitting layer having good luminous efficiency and durability can be achieved. Most materials having an anthracene skeleton have a deeper HOMO energy level, so one embodiment of the present invention can be appropriately used. Among the substances having an anthracene skeleton used as a host material, substances having a diphenylanthracene skeleton (especially a 9,10-diphenylanthracene skeleton) are chemically stable, so they are preferred. In addition, in the case where the host material has a carbazole skeleton, the injection / transport properties of holes are improved, so it is preferred. In particular, in the case of a benzocarbazole skeleton comprising a benzene ring fused to carbazole, its HOMO energy level is about 0.1eV shallower than carbazole, and holes are easily injected, so it is more preferred. In particular, in the case where the host material has a dibenzocarbazole skeleton, its HOMO energy level is about 0.1eV shallower than carbazole, and not only holes are easily injected, but also hole transport and heat resistance are improved, so it is preferred. Therefore, a more preferred host material is one having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). Note that from the viewpoint of the hole injection / transport property, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracenyl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), and 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4′-yl}-anthracene (abbreviation: FLPPA). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred because they exhibit very good properties.

[0196] The light-emitting element of one embodiment of the present invention is particularly preferably used for a light-emitting element that emits blue fluorescent light.

[0197] In addition, the host material may also be a material mixed with multiple substances. When a mixed host material is used, it is preferred to mix a material having electron transport properties and a material having hole transport properties. By mixing a material having electron transport properties and a material having hole transport properties, it is possible to make it easier to adjust the transport properties of the light-emitting layer 113, and it is also possible to more easily control the recombination area. The content ratio of the material having hole transport properties and the material having electron transport properties is 1:9 to 9:1.

[0198] In addition, these mixed materials can also be used to form an exciplex. By selecting the mixed material in a manner to form an exciplex that emits light with a wavelength overlapping the absorption band on the lowest energy side of the luminescent material, energy transfer can be smoothed, thereby efficiently obtaining luminescence, so it is preferred. In addition, by adopting this structure, the driving voltage can be reduced, so it is preferred.

[0199] The electron-transport layer 114 is a layer containing a substance having an electron-transport property. As the substance having an electron-transport property, the substances having an electron-transport property that can be used for the host material described above can be used.

[0200] An electron injection layer 115 containing an alkali metal, alkaline earth metal, or a compound thereof such as lithium fluoride (LiF), cesium fluoride (CsF), or calcium fluoride (CaF2) may be provided between the electron transport layer 114 and the second electrode 102. The electron injection layer 115 may be a layer containing an alkali metal, alkaline earth metal, or a compound thereof in a layer composed of a substance having electron transport properties or an electron compound (electride). Examples of the electron compound include a substance in which electrons are added to a mixed oxide of calcium and aluminum at a high concentration.

[0201] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (see Figure 1B ). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side of the layer, and inject electrons into the layer in contact with the anode side of the layer, by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the above-mentioned composite material that can constitute the hole injection layer 111. In addition, the P-type layer 117 can also be formed by stacking films that respectively contain the above-mentioned acceptor material and hole transport material as materials constituting the composite material. By applying a potential to the P-type layer 117, electrons and holes are respectively injected into the electron transport layer 114 and the second electrode 102 serving as the cathode, so that the light-emitting element works.

[0202] In addition, the charge generation layer 116 preferably includes one or both of an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117 .

[0203] The electron relay layer 118 contains at least a substance with electron transport properties, and can prevent the interaction between the electron injection buffer layer 119 and the P-type layer 117, and smoothly transfer electrons. The LUMO energy level of the substance with electron transport properties contained in the electron relay layer 118 is preferably set between the LUMO energy level of the acceptor substance in the P-type layer 117 and the LUMO energy level of the substance contained in the layer in the electron transport layer 114 that contacts the charge generation layer 116. Specifically, the LUMO energy level of the substance with electron transport properties in the electron relay layer 118 is preferably above -5.0 eV, and more preferably above -5.0 eV and below -3.0 eV. In addition, as the substance with electron transport properties in the electron relay layer 118, it is preferred to use a phthalocyanine material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0204] The electron injection buffer layer 119 can use substances with high electron injection properties such as alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)).

[0205] In addition, when the electron injection buffer layer 119 contains a substance having electron transport properties and a donor substance, as a donor substance, in addition to alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)), tetrathianaphthacene (abbreviated as: TTN), nickelocene, decamethylnickelocene and other organic compounds can also be used. In addition, as a substance having electron transport properties, the same material as the material for the electron transport layer 114 described above can be used.

[0206] As a material forming the second electrode 102, metals, alloys, conductive compounds and mixtures thereof with a small work function (specifically less than 3.8 eV) can be used. As a specific example of such a cathode material, elements belonging to Group 1 or Group 2 in the periodic table, alloys containing them (MgAg, AlLi), europium (Eu), rare earth metals such as ytterbium (Yb) and alloys containing them, etc. can be cited. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide can be used as the second electrode 102 regardless of the size of the work function. These conductive materials can be formed by dry methods such as vacuum evaporation and sputtering, inkjet, spin coating, etc. In addition, the electrode can be formed by a wet method such as a sol-gel method or a wet method using a paste of a metal material.

[0207] The EL layer 103 can be formed by any of a variety of methods, whether dry or wet, such as vacuum deposition, gravure printing, rotogravure printing, screen printing, inkjet printing, or spin coating.

[0208] In addition, each electrode or each layer described above may be formed by using a different film forming method.

[0209] Note that the structure of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above structure. However, it is preferable to adopt a structure in which a light-emitting region where holes and electrons recombine is provided at a portion away from the first electrode 101 and the second electrode 102 in order to suppress quenching caused by the proximity of the light-emitting region to a metal used for an electrode or a carrier injection layer.

[0210] In addition, in order to suppress the energy transfer from excitons generated in the light-emitting layer, the carrier transport layer and the electron transport layer in contact with the light-emitting layer 113, especially the carrier transport layer close to the recombination region in the light-emitting layer 113, are preferably composed of a substance having a band gap larger than the band gap of the light-emitting material constituting the light-emitting layer or the light-emitting material contained in the light-emitting layer.

[0211] Next, refer to Figure 1C A method of a light-emitting element having a structure in which a plurality of light-emitting units are stacked (hereinafter also referred to as a stacked element or a tandem element) is described. The light-emitting element is a light-emitting element having a plurality of light-emitting units between an anode and a cathode. Figure 1A The EL layer 103 shown in FIG. 1 has a substantially similar structure. That is, it can be said that Figure 1C The light emitting element shown is a light emitting element having a plurality of light emitting units. Figure 1Aor Figure 1B The light-emitting element shown is a light-emitting element having one light-emitting unit.

[0212] exist Figure 1C In the embodiment, a first light emitting unit 511 and a second light emitting unit 512 are stacked between the anode 501 and the cathode 502, and a charge generating layer 513 is provided between the first light emitting unit 511 and the second light emitting unit 512. The anode 501 and the cathode 502 are respectively equivalent to Figure 1A The first electrode 101 and the second electrode 102 in the embodiment of the present invention can be applied to Figure 1A In addition, the first light emitting unit 511 and the second light emitting unit 512 may have the same structure or different structures.

[0213] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied to the anode 501 and the cathode 502. Figure 1C When a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 may be a layer that injects electrons into the first light-emitting unit 511 and injects holes into the second light-emitting unit 512 .

[0214] The charge generation layer 513 preferably has Figure 1B The charge generation layer 116 shown in the figure has the same structure. Since the composite material of the organic compound and the metal oxide has good carrier injection and carrier transport properties, low voltage driving and low current driving can be achieved. Note that when the surface on the anode side of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can have the function of the hole injection layer of the light-emitting unit, so the hole injection layer may not be provided in the light-emitting unit.

[0215] When the electron injection buffer layer 119 is provided for the charge generation layer 513, since the electron injection buffer layer 119 has the function of an electron injection layer in the light-emitting unit on the anode side, an electron injection layer is not necessarily provided in the light-emitting unit on the anode side.

[0216] Although in Figure 1C , a light-emitting element having two light-emitting units is described, but a light-emitting element having three or more light-emitting units stacked can be applied in the same manner. As in the light-emitting element according to this embodiment, by separating and arranging a plurality of light-emitting units between a pair of electrodes using the charge generation layer 513, the element can achieve high-brightness light emission while maintaining a low current density, and can achieve an element with a long service life. In addition, a light-emitting device that can be driven at a low voltage and has low power consumption can be achieved.

[0217] In addition, by making the emission colors of each light-emitting unit different, the desired color of light can be obtained from the entire light-emitting element. For example, by obtaining red and green emission colors from the first light-emitting unit and blue emission color from the second light-emitting unit in a light-emitting element having two light-emitting units, a light-emitting element that emits white light can be obtained in the entire light-emitting element.

[0218] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, the charge generation layer and other layers and electrodes can be formed by, for example, evaporation (including vacuum evaporation), droplet jetting (also known as inkjet), coating, gravure printing, etc. In addition, they can also include low molecular weight materials, medium molecular weight materials (including oligomers, dendrimers) or high molecular weight materials.

[0219] (Implementation 3) In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 1 is described.

[0220] In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 is described with reference to FIG. 2. Note that Figure 2A is a top view showing a light emitting device, and Figure 2B is along Figure 2A 604 is a sealing substrate, 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

[0221] Note that the guide wiring 608 is a wiring for transmitting signals input to the source line driver circuit 601 and the gate line driver circuit 603, and receives a video signal, a clock signal, a start signal, a reset signal, etc. from an FPC (flexible printed circuit) 609 used as an external input terminal. Note that although only the FPC is shown here, the FPC can also be installed with a printed wiring board (PWB). The light-emitting device in this specification includes not only the light-emitting device body, but also the light-emitting device installed with an FPC or a PWB.

[0222] Below, refer to Figure 2B A cross-sectional structure is described. A driver circuit portion and a pixel portion are formed over an element substrate 610 , and here, a source line driver circuit 601 as a driver circuit portion and one pixel in a pixel portion 602 are shown.

[0223] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, or the like.

[0224] There is no particular restriction on the structure of the transistor used for the pixel or the driving circuit. For example, an inverted staggered transistor or a staggered transistor can be used. In addition, a top-gate transistor or a bottom-gate transistor can be used. There is no particular restriction on the semiconductor material used for the transistor, for example, silicon, germanium, silicon carbide, gallium nitride, etc. can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc such as an In-Ga-Zn metal oxide can be used.

[0225] There is no particular restriction on the crystallinity of the semiconductor material used for the transistor, and an amorphous semiconductor or a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part thereof) can be used. When a crystalline semiconductor is used, it is preferred because it can suppress the degradation of transistor characteristics.

[0226] Here, the oxide semiconductor is preferably used for semiconductor devices such as transistors provided in the above-mentioned pixel or driving circuit and transistors for touch sensors described later. It is particularly preferred to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor having a wider band gap than silicon, the off-state current of the transistor can be reduced.

[0227] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, the oxide semiconductor is more preferably an oxide semiconductor containing an oxide represented by an In-M-Zn oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf).

[0228] In particular, as the semiconductor layer, it is preferable to use an oxide semiconductor film having a plurality of crystal parts whose c axes are all oriented in a direction perpendicular to the formed surface of the semiconductor layer or the top surface of the semiconductor layer and having no grain boundaries between adjacent crystal parts.

[0229] By using the above-mentioned materials as the semiconductor layer, a highly reliable transistor with suppressed fluctuations in electric characteristics can be realized.

[0230] In addition, since the off-state current of the transistor having the semiconductor layer is low, the charge stored in the capacitor through the transistor can be maintained for a long period of time. By using such a transistor for a pixel, the driving circuit can be stopped while maintaining the grayscale of the image displayed in each display area. As a result, an electronic device with extremely low power consumption can be realized.

[0231] In order to achieve the stabilization of the characteristics of the transistor, etc., it is preferred to set a base film. As the base film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, an oxynitride silicon film, a silicon nitride oxide film, etc. can be used and manufactured in a single layer or a stacked layer. The base film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (plasma CVD method, thermal CVD method, MOCVD (Metal Organic CVD: Organic Metal Chemical Vapor Deposition) method, etc.) or an ALD (Atomic Layer Deposition) method, a coating method, a printing method, etc. Note that the base film may not be set if it is not necessary.

[0232] Note that FET623 shows one of the transistors formed in the driver circuit portion 601. In addition, the driver circuit can also be formed using various CMOS circuits, PMOS circuits, or NMOS circuits. In addition, although the driver integrated type in which the driver circuit is formed on the substrate is shown in this embodiment, this structure is not necessarily adopted, and the driver circuit can also be formed outside instead of being formed on the substrate.

[0233] In addition, the pixel portion 602 is formed by a plurality of pixels, each of which includes a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain of the current control FET 612, but is not limited to this, and a pixel portion combining three or more FETs and capacitors may also be used.

[0234] Note that the insulator 614 is formed to cover the end portion of the first electrode 613. Here, the insulator 614 can be formed using a positive photosensitive acrylic resin film.

[0235] In addition, the upper end or the lower end of the insulator 614 is formed into a curved surface having a curvature to obtain good coverage of the EL layer etc. formed later. For example, when a positive photosensitive acrylic resin is used as the material of the insulator 614, it is preferable to make only the upper end of the insulator 614 include a curved surface having a curvature radius (0.2 μm to 3 μm). As the insulator 614, a negative photosensitive resin or a positive photosensitive resin can be used.

[0236] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, as a material for the first electrode 613 used as an anode, a material having a large work function is preferably used. For example, in addition to a single-layer film such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 wt% to 20 wt% of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, a Pt film, etc., a stacked film composed of a titanium nitride film and a film containing aluminum as a main component, and a three-layer structure composed of a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film, etc. can be used. Note that if a stacked structure is used here, since the resistance value of the wiring is low, a good ohmic contact can be obtained, and in addition, it can be used as an anode.

[0237] The EL layer 616 is formed by various methods such as a vapor deposition method using a vapor deposition mask, an inkjet method, and a spin coating method. The EL layer 616 has the structure described in Embodiment 1. As other materials constituting the EL layer 616, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) can be used.

[0238] In addition, as a material for the second electrode 617 formed on the EL layer 616 and used as a cathode, a material having a small work function (Al, Mg, Li, Ca, or an alloy or compound thereof (MgAg, MgIn, AlLi, etc.) is preferably used. Note that when light generated in the EL layer 616 is allowed to pass through the second electrode 617, it is preferable to use a stacked layer composed of a metal thin film with a reduced thickness and a transparent conductive film (ITO, indium oxide containing 2wt% to 20wt% of zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0239] In addition, a light-emitting element is formed by a first electrode 613, an EL layer 616, and a second electrode 617. This light-emitting element is the light-emitting element described in Embodiment 1. In addition, the pixel portion is composed of a plurality of light-emitting elements, and the light-emitting device of this embodiment may include both the light-emitting element described in Embodiment 1 and a light-emitting element having another structure.

[0240] In addition, the sealing substrate 604 is attached to the element substrate 610 using the sealing material 605, and the light-emitting element 618 is provided in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. Note that the space 607 is filled with a filler, and as the filler, an inert gas (nitrogen, argon, etc.) can be used, and a sealing material can also be used. By forming a concave portion in the sealing substrate and providing a desiccant therein, deterioration due to moisture can be suppressed, which is preferable.

[0241] In addition, epoxy resin or glass powder is preferably used as the sealing material 605. In addition, these materials are preferably materials that do not allow water or oxygen to pass through as much as possible. In addition, as a material for the sealing substrate 604, in addition to a glass substrate or a quartz substrate, a plastic substrate composed of FRP (Fiber Reinforced Plastics; glass fiber reinforced plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, etc. can also be used.

[0242] Although not shown in FIG. 2 , a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. In addition, the protective film may be formed in a manner covering the exposed portion of the sealing material 605. In addition, the protective film may be provided to cover the surface and side surfaces of a pair of substrates, the exposed side surfaces of the sealing layer, the insulating layer, etc.

[0243] As the protective film, a material that does not easily permeate impurities such as water can be used. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0244] As a material constituting the protective film, oxides, nitrides, fluorides, sulfides, ternary compounds, metals or polymers can be used. For example, materials containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, etc., materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, nitride containing titanium and aluminum, oxide containing titanium and aluminum, oxide containing aluminum and zinc, sulfide containing manganese and zinc, sulfide containing cerium and strontium, oxide containing erbium and aluminum, oxide containing yttrium and zirconium, etc. can be used.

[0245] The protective film is preferably formed by a film forming method with good step coverage. One of such methods is the atomic layer deposition (ALD) method. It is preferred that a material that can be formed by the ALD method be used for the protective film. The ALD method can form a dense protective film with reduced defects such as cracks or pinholes or a uniform thickness. In addition, damage to the processed components when forming the protective film can be reduced.

[0246] For example, the ALD method can form a uniform protective film with few defects on a surface having a complex uneven shape or on the top, side, and back surface of a touch panel.

[0247] As described above, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 can be obtained.

[0248] Since the light-emitting device in this embodiment uses the light-emitting element described in Embodiment 1, it can have excellent characteristics. Specifically, the light-emitting element described in Embodiment 1 is a light-emitting element with a long life, so that a light-emitting device with good reliability can be realized. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has good luminous efficiency, thereby realizing a light-emitting device with low power consumption.

[0249] FIG. 3 shows an example of a light-emitting device that realizes full color by forming a light-emitting element that emits white light and providing a coloring layer (color filter) and the like. Figure 3A Shown are a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving circuit portion 1041, first electrodes 1024W, 1024R, 1024G, 1024B of the light-emitting element, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, a sealing substrate 1031, a sealing material 1032, and the like.

[0250] In addition, Figure 3A In the embodiment, the coloring layers (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B) are provided on the transparent substrate 1033. In addition, a black matrix 1035 may be provided. The transparent substrate 1033 provided with the coloring layers and the black matrix is ​​aligned and fixed to the substrate 1001. In addition, the coloring layers and the black matrix 1035 are covered by a protective layer 1036. In addition, Figure 3A A light-emitting layer is shown in which light is transmitted to the outside without passing through the coloring layer, and light is transmitted to the outside through the coloring layers of each color. The light that does not pass through the coloring layer becomes white light, and the light that passes through the coloring layer becomes red light, green light, and blue light, so that an image can be presented with pixels of four colors.

[0251] Figure 3B The example in which the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020 is shown. As described above, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0252] In the above description, a light-emitting device having a structure in which light is extracted from the substrate 1001 side where FET is formed (bottom emission type) is described. Alternatively, a light-emitting device having a structure in which light is extracted from the sealing substrate 1031 side (top emission type) may be used. Figure 41001 is a cross-sectional view of a top-emitting light-emitting device. In this case, a substrate that does not allow light to pass through can be used as the substrate 1001. The process up to the manufacture of the connection electrode for connecting the FET to the anode of the light-emitting element is performed in the same manner as the bottom-emitting light-emitting device. Then, a third interlayer insulating film 1037 is formed in a manner covering the electrode 1022. The third interlayer insulating film 1037 may also have a planarization function. The third interlayer insulating film 1037 may be formed using the same material as the second interlayer insulating film or other known materials.

[0253] Although the first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes, they may also be cathodes. Figure 4 In the case of a top emission type light-emitting device as shown, the first electrode is preferably a reflective electrode. The structure of the EL layer 1028 is the same as the structure of the EL layer 103 described in Embodiment 1, and employs an element structure capable of obtaining white light emission.

[0254] In adopting Figure 4 In the case of the top emission structure shown, a sealing substrate 1031 provided with a coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, and a blue coloring layer 1034B) can be used for sealing. The sealing substrate 1031 can also be provided with a black matrix 1035 located between pixels. The coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, and a blue coloring layer 1034B) and the black matrix 1035 can also be covered by a protective layer 1036. In addition, as the sealing substrate 1031, a light-transmitting substrate is used. In addition, although an example of full-color display in four colors of red, green, blue, and white is shown here, it is not limited to this. Full-color display can also be performed in four colors of red, yellow, green, and blue or in three colors of red, green, and blue.

[0255] In a top-emitting light-emitting device, a microcavity structure can be preferably applied. A reflective electrode is used as a first electrode and a semi-transmissive / semi-reflective electrode is used as a second electrode, thereby obtaining a light-emitting element having a microcavity structure. At least an EL layer is included between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer that becomes a light-emitting region is included.

[0256] Note that the reflective electrode has a visible light reflectivity of 40% to 100%, preferably 70% to 100%, and a resistivity of 1×10 -2 In addition, the visible light reflectance of the semi-transmissive and semi-reflective electrode is 20% to 80%, preferably 40% to 70%, and its resistivity is 1×10 -2 Ωcm or less.

[0257] Light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode, and resonates.

[0258] In this light-emitting element, the optical path between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed by changing the thickness of the transparent conductive film, the composite material, or the carrier transport material, etc. Thus, light of a resonant wavelength can be strengthened and light of a non-resonant wavelength can be attenuated between the reflective electrode and the semi-transmissive / semi-reflective electrode.

[0259] The light reflected by the reflective electrode (first reflected light) will cause great interference to the light directly incident from the light-emitting layer to the semi-transmissive and semi-reflective electrode (first incident light), so it is preferable to adjust the optical path between the reflective electrode and the light-emitting layer to (2n-1)λ / 4 (note that n is a natural number greater than 1, and λ is the wavelength of the light to be amplified). By adjusting this optical path, the phase of the first reflected light and the first incident light can be aligned, thereby further amplifying the light emitted from the light-emitting layer.

[0260] In the above structure, the EL layer may include a plurality of light-emitting layers or may include only one light-emitting layer. For example, the above structure may be combined with the structure of the above-mentioned tandem light-emitting element, in which a plurality of EL layers are provided in one light-emitting element with a charge generation layer sandwiched therebetween, and one or more light-emitting layers are formed in each EL layer.

[0261] By adopting a microcavity structure, the light emission intensity in the front direction of a specified wavelength can be enhanced, thereby achieving low power consumption. Note that in the case of a light-emitting device that displays an image using sub-pixels of four colors, red, yellow, green, and blue, since the brightness improvement effect due to yellow light emission can be obtained and a microcavity structure suitable for the wavelength of each color can be adopted in all sub-pixels, a light-emitting device with good characteristics can be realized.

[0262] Since the light-emitting device in this embodiment uses the light-emitting element described in Embodiment 1, it can have excellent characteristics. Specifically, the light-emitting element described in Embodiment 1 is a light-emitting element with a long life, so that a light-emitting device with good reliability can be realized. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has good luminous efficiency, thereby realizing a light-emitting device with low power consumption.

[0263] Although the active matrix light emitting device has been described so far, the passive matrix light emitting device will be described below. FIG5 shows a passive matrix light emitting device manufactured by using the present invention. Note that Figure 5A is a perspective view showing a light emitting device, and Figure 5B is along Figure 5A5 , an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. The end of the electrode 952 is covered by an insulating layer 953. An isolation layer 954 is provided on the insulating layer 953. The side wall of the isolation layer 954 has such an inclination that the distance between the two side walls is narrower as it approaches the substrate surface. In other words, the cross section of the isolation layer 954 in the short side direction is a trapezoid, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the top side (the side facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). In this way, by providing the isolation layer 954, defects of the light-emitting element caused by static electricity or the like can be prevented. In addition, in a passive matrix light-emitting device, by using the light-emitting element shown in Embodiment 1, a light-emitting device with good reliability or a light-emitting device with low power consumption can also be obtained.

[0264] The light emitting device described above can control each of a plurality of minute light emitting elements arranged in a matrix, and therefore can be suitably used as a display device that displays images.

[0265] In addition, this embodiment mode can be freely combined with other embodiment modes.

[0266] (Implementation 4) In this embodiment, an example in which the light-emitting element described in Embodiment 1 is used for a lighting device is described with reference to FIG. 6 . Figure 6B is a top view of the lighting device. Fig. 6A It is along Figure 6B Cross-sectional view of line ef.

[0267] In the lighting device of this embodiment, a first electrode 401 is formed on a light-transmitting substrate 400 serving as a support. The first electrode 401 corresponds to the first electrode 101 in Embodiment 1. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0268] In addition, a pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0269] An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 1 or a structure in which the light-emitting unit 511, the light-emitting unit 512, and the charge generation layer 513 are combined. Note that for these structures, refer to the respective descriptions.

[0270] The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 1. When light is extracted from the first electrode 401 side, the second electrode 404 is formed using a material with high reflectivity. The second electrode 404 is connected to the pad 412, so that a voltage is supplied to the second electrode 404.

[0271] As described above, the lighting device described in this embodiment includes a light-emitting element including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting element has high light emission efficiency, the lighting device of this embodiment can provide a lighting device with low power consumption.

[0272] The substrate 400 on which the light emitting element having the above structure is formed and the sealing substrate 407 are fixed and sealed using the sealing materials 405 and 406, thereby manufacturing a lighting device. Only one of the sealing materials 405 and 406 may be used. In addition, the inner sealing material 406 (at the Figure 6B The semiconductor device (not shown) is mixed with a desiccant, thereby absorbing moisture and improving reliability.

[0273] Furthermore, the pad 412 and part of the first electrode 401 can be used as an external input terminal by extending outside the sealing materials 405 and 406. Alternatively, an IC chip 420 or the like on which a converter or the like is mounted may be provided on the external input terminal.

[0274] The lighting device described in this embodiment uses the light-emitting element described in Embodiment 2 as an EL element, so that a light-emitting device with high reliability can be realized. In addition, a light-emitting device with low power consumption can be realized.

[0275] (Implementation method 5) In this embodiment, an example of an electronic device including a light-emitting element described in Embodiment 1 as a part thereof is described. The light-emitting element described in Embodiment 2 is a light-emitting element with a long life and good reliability. As a result, the electronic device described in this embodiment can realize an electronic device including a light-emitting portion with good reliability.

[0276] As electronic devices using the above-mentioned light-emitting elements, for example, television devices (also called televisions or television receivers), displays for computers, etc., digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones, mobile phone devices), portable game consoles, portable information terminals, sound reproduction devices, large-scale game consoles such as pinball machines, etc., can be cited. Specific examples of these electronic devices are shown below.

[0277] Fig. 7A100 shows an example of a television device. In the television device, a display portion 7103 is incorporated in a housing 7101. In addition, a structure in which the housing 7101 is supported by a bracket 7105 is shown. The display portion 7103 can display images, and is configured by arranging the light-emitting elements described in Embodiment 1 in a matrix.

[0278] The television device can be operated by using an operation switch provided in the housing 7101 or a remote controller 7110 provided separately. Channels and volume can be controlled by using operation keys 7109 provided in the remote controller 7110, thereby controlling the image displayed on the display portion 7103. The remote controller 7110 may be provided with a display portion 7107 for displaying information output from the remote controller 7110.

[0279] In addition, the television device is configured with a receiver, a modem, etc. The receiver can receive general television broadcasts. Furthermore, by connecting to a wired or wireless communication network via a modem, one-way (from a sender to a receiver) or two-way (between a sender and a receiver or between receivers, etc.) information communication can be performed.

[0280] Figure 7B1 7 shows a computer including a main body 7201 , a housing 7202 , a display portion 7203 , a keyboard 7204 , an external connection port 7205 , a pointing device 7206 , and the like. The computer is manufactured by arranging the light-emitting elements described in Embodiment 1 in a matrix and using the light-emitting elements for the display portion 7203 . Figure 7B1 The computer in can also be Figure 7B2 The method shown. Figure 7B2 The computer shown is provided with a second display unit 7210 instead of the keyboard 7204 and the pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating the input display displayed on the second display unit 7210 with a finger or a special pen. In addition, the second display unit 7210 can display not only the input display but also other images. In addition, the display unit 7203 can also be a touch panel. Because the two screens are connected by a hinge, problems such as damage to the screen and destruction during storage or transportation can be prevented.

[0281] Figure 7C 7400 includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. The mobile phone 7400 includes a display portion 7402 in which the light-emitting elements described in Embodiment 1 are arranged in a matrix.

[0282] Figure 7C The illustrated portable terminal may have a structure in which information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call or writing an e-mail can be performed by touching the display portion 7402 with a finger or the like.

[0283] The display portion 7402 mainly has three screen modes: a first display mode mainly for displaying images, a second input mode mainly for inputting information such as text, and a third display input mode that is a combination of the display mode and the input mode.

[0284] For example, when making a phone call or writing an e-mail, the text displayed on the screen can be input in a text input mode in which the display portion 7402 is mainly used to input text. In this case, it is preferred that a keyboard or number buttons are displayed in most parts of the screen of the display portion 7402.

[0285] Furthermore, by providing a detection device having a sensor for detecting inclination such as a gyroscope or an acceleration sensor inside the portable terminal, the orientation (portrait or landscape) of the portable terminal can be determined and the screen display of the display portion 7402 can be automatically switched.

[0286] The screen mode is switched by touching the display portion 7402 or operating the operation button 7403 of the housing 7401. Alternatively, the screen mode may be switched according to the type of image displayed on the display portion 7402. For example, when the image signal displayed on the display portion is data of a dynamic image, the screen mode is switched to the display mode, and when the image signal is text data, the screen mode is switched to the input mode.

[0287] In addition, when it is detected by detecting a signal detected by the optical sensor of the display portion 7402 in the input mode that there is no touch operation input to the display portion 7402 for a certain period of time, control may be performed to switch the screen mode from the input mode to the display mode.

[0288] The display portion 7402 can also be used as an image sensor. For example, by touching the display portion 7402 with a palm or a finger, palm prints, fingerprints, etc. can be photographed, thereby enabling personal identification. In addition, by using a backlight emitting near-infrared light or a sensing light source emitting near-infrared light in the display portion, finger veins, palm veins, etc. can also be photographed.

[0289] Note that the structure described in this embodiment can be used in combination with the structures described in Embodiments 1 to 4 as appropriate.

[0290] As described above, the light-emitting device including the light-emitting element described in Embodiment 1 has a very wide range of applications, and can be used for electronic devices in various fields. By using the light-emitting element described in Embodiment 1, a highly reliable electronic device can be obtained.

[0291] Fig. 8A is a schematic diagram showing an example of a cleaning robot.

[0292] The cleaning robot 5100 includes a display 5101 on the top surface and a plurality of cameras 5102, a brush 5103 and an operation button 5104 on the side. Although not shown, the bottom surface of the cleaning robot 5100 is provided with tires and a suction port, etc. In addition, the cleaning robot 5100 also includes various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezoelectric sensor, an optical sensor, and a gyroscope sensor. In addition, the cleaning robot 5100 includes a wireless communication unit.

[0293] The sweeping robot 5100 can walk automatically, detect garbage 5120, and suck the garbage from the suction port on the bottom.

[0294] In addition, the cleaning robot 5100 can determine the presence or absence of obstacles such as walls, furniture, or steps by analyzing the image captured by the camera 5102. In addition, when objects such as wiring that may be wrapped around the brush 5103 are detected through image analysis, the rotation of the brush 5103 can be stopped.

[0295] The remaining battery power and the amount of attracted garbage, etc. may be displayed on the display 5101. The walking path of the cleaning robot 5100 may be displayed on the display 5101. In addition, the display 5101 may be a touch panel, and the operation button 5104 may be displayed on the display 5101.

[0296] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smart phone. The image captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can also know the situation of the room when going out. In addition, the display content of the display 5101 can be confirmed using a portable electronic device such as a smart phone.

[0297] The light-emitting device of one embodiment of the present invention can be used for the display 5101.

[0298] Figure 8B The robot 2100 shown includes a computing device 2110 , an illumination sensor 2101 , a microphone 2102 , an upper camera 2103 , a speaker 2104 , a display 2105 , a lower camera 2106 , an obstacle sensor 2107 , and a moving mechanism 2108 .

[0299] The microphone 2102 has a function of detecting the user's voice and surrounding sounds, etc. In addition, the speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0300] The display 2105 has a function of displaying various information. The robot 2100 can display the information desired by the user on the display 2105. The display 2105 can be equipped with a touch panel. The display 2105 can be a detachable information terminal, and by setting the information terminal at a predetermined position of the robot 2100, charging and data transmission and reception can be performed.

[0301] The upper camera 2103 and the lower camera 2106 have the function of photographing the surrounding environment of the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of obstacles in front of the robot 2100 when the robot 2100 moves using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107 and move safely. The light emitting device of one embodiment of the present invention can be used for the display 2105.

[0302] Figure 8C 5 is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, an operation key 5005 (including a power switch or an operation switch), a connection terminal 5006, a sensor 5007 (which has a function of measuring the following factors: force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electricity, radiation, flow, humidity, inclination, vibration, smell or infrared), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc.

[0303] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the second display portion 5002 .

[0304] Fig. 9 An example in which the light-emitting element described in Embodiment 1 is used in a desk lamp as a lighting device will be described. Fig. 9 The table lamp shown includes a housing 2001 and a light source 2002 , and the lighting device described in Embodiment 3 is used as the light source 2002 .

[0305] Fig.10An example of using the light-emitting element described in Embodiment 1 for an indoor lighting device 3001 is shown. The light-emitting element described in Embodiment 1 is a light-emitting element with high reliability, and thus a lighting device with high reliability can be realized. In addition, since the light-emitting element described in Embodiment 2 can be realized in a large area, it can be used in a lighting device with a large area. In addition, since the light-emitting element described in Embodiment 1 is thin, a thin lighting device can be manufactured.

[0306] The light-emitting element described in Embodiment 2 can also be mounted on a windshield or an instrument panel of a car. Fig.11 This section describes one embodiment in which the light-emitting element described in Embodiment 2 is used for a windshield or an instrument panel of a car. Display areas 5200 to 5203 are displays provided using the light-emitting element described in Embodiment 2.

[0307] The display area 5200 and the display area 5201 are display devices provided on the windshield of a car and equipped with the light-emitting element shown in Embodiment 1. By using light-transmitting electrodes to manufacture the first electrode and the second electrode, the light-emitting element shown in Embodiment 2 can be formed into a so-called perspective display device that can see the scenery on the opposite side. If a perspective display is adopted, the field of vision is not obstructed even if it is provided on the windshield of a car. In addition, in the case of providing a transistor for driving, it is preferred to use a light-transmitting transistor, such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor.

[0308] Display area 5202 is a display device provided in the pillar part and equipped with the light-emitting element shown in Embodiment 1. By displaying the image from the imaging unit provided on the vehicle compartment on display area 5202, the field of vision blocked by the pillar can be supplemented. Similarly, display area 5203 provided on the instrument panel part can supplement the blind spot of the field of vision blocked by the vehicle compartment by displaying the image from the imaging unit provided on the outside of the vehicle, thereby improving safety. By displaying the image to supplement the part that cannot be seen, safety can be confirmed more naturally and simply.

[0309] Display area 5203 may also provide navigation information, speedometer, tachometer, driving distance, fuel level, gear status, air conditioning settings, and other information. The user may appropriately change the display content and layout. In addition, this information may also be displayed on display area 5200 to display area 5202. In addition, display area 5200 to display area 5203 may also be used as a lighting device.

[0310] Fig. 12A and Fig. 12BA foldable portable information terminal 5150 is shown. The foldable portable information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 5153. Fig. 12A The portable information terminal 5150 is shown in the unfolded state. Fig. 12B The portable information terminal 5150 is shown in a folded state. Although the portable information terminal 5150 has a large display area 5152, by folding the portable information terminal 5150, the portable information terminal 5150 becomes small and has good portability.

[0311] The display area 5152 can be folded in half by the curved portion 5153. The curved portion 5153 is composed of a retractable member and a plurality of supporting members, and the retractable member is stretched when folded. The folding is performed in such a manner that the curved portion 5153 has a curvature radius of 2 mm or more, preferably 3 mm or more.

[0312] The display area 5152 may be a touch panel (input / output device) on which a touch sensor (input device) is mounted. The light-emitting device of one embodiment of the present invention can be used for the display area 5152 .

[0313] also, FIG. 13A to FIG. 13C A foldable portable information terminal 9310 is shown. Fig.13A The portable information terminal 9310 is shown in the unfolded state. Fig. 13B The portable information terminal 9310 is shown in a state in the process of changing from one of the unfolded state and the folded state to the other state. Fig. 13C The portable information terminal 9310 is shown in a folded state. The portable information terminal 9310 is highly portable in the folded state, and has a large display area that is seamlessly connected and provides a high level of visibility in the unfolded state.

[0314] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display panel 9311 may also be a touch panel (input-output device) equipped with a touch sensor (input device). In addition, by bending the display panel 9311 at the hinge 9313 between the two housings 9315, the portable information terminal 9310 can be reversibly changed from an unfolded state to a folded state. The light-emitting device of one embodiment of the present invention can be used for the display panel 9311. [Example 1]

[0315] In this example, a method for synthesizing N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated as BBABnf(II)(2)), which is an organic compound of one embodiment of the present invention, is described in detail. The structural formula of BBABnf(II)(2) is shown below.

[0316] [Chemical formula 46]

[0317] <Step 1: Synthesis of 3-(5-chloro-2-fluorophenyl)-2-naphthol> 8.9 g (40 mmol) of 3-bromo-2-naphthol, 10 g (60 mmol) of 5-chloro-2-fluorophenylboric acid, 0.24 g (0.080 mmol) of tri(o-tolyl)phosphine, 40 mL of potassium carbonate aqueous solution (2.0 mmol / L), 120 mL of toluene, and 50 mL of ethanol were placed in a 300 mL three-necked flask and mixed. After the mixture was degassed under reduced pressure, the air in the flask was replaced with nitrogen. After the mixture was heated to 60°C, 90 mg (40 μmol) of palladium (II) acetate was added, and the mixture was stirred at 80°C for 8 hours. After stirring, 5.8 g (35 mmol) of 5-chloro-2-fluorophenylboric acid and 90 mg (40 μmol) of palladium (II) acetate were further added to the mixture, and the mixture was stirred at 80°C for 8 hours. After stirring, the mixture was cooled to room temperature, washed with water and saturated saline, the aqueous layer and the organic layer were separated, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, the filtrate was concentrated and dried. After drying, 7.6 g of a black solid was obtained. The synthesis scheme of step 1 is shown below.

[0318] [Chemical formula 47]

[0319] <Step 2: Synthesis of 2-chlorobenzo[b]naphtho[2,3-d]furan> 7.6 g of the black solid obtained in step 1, 7.6 g (55 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (abbreviated as: NMP) were placed in a 500 mL eggplant-shaped flask and stirred at 120°C for 7 hours. The obtained mixture was filtered to remove the potassium carbonate. 10 mL of 2 mol / L hydrochloric acid was added to the obtained filtrate to neutralize the filtrate to produce a white precipitate. The white precipitate was collected by suction filtration and washed with ethyl acetate, water and ethanol to obtain 3.5 g of a white solid with a total yield of 34% for steps 1 and 2. The synthesis scheme of step 2 is shown below.

[0320] [Chemical formula 48]

[0321] Fig.14A and Fig. 14B The obtained solid 1 H NMR data, numerical data are shown below. Note that Fig. 14B Is magnification Fig.14A The figure shows the range of 7.2 ppm to 8.3 ppm in 2-chlorobenzo[b]naphtho[2,3-d]furan.

[0322] 1 H NMR (chloroform-d, 500 MHz): δ = 8.39 (s, 1H), 8.04-8.03 (m, 2H), 7.97 (d, J = 8.0 Hz, 1H), 7.92 (s, 1H), 7.54 (t, J = 7.5 Hz, 1H), 7.52-7.45 (m, 3H)

[0323] <Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2))> 2.0 g (8.0 mmol) of 2-chlorobenzo[b]naphtho[2,3-d]furan, 2.6 g (8.0 mmol) of bis(4-biphenylyl)amine, 56 mg (0.16 mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP (registered trademark)), 1.5 g (16 mmol) of sodium tert-butoxide and 100 mL of toluene were placed in a 300 mL three-necked flask equipped with a reflux tube, the mixture was degassed under reduced pressure, the air in the flask was replaced with nitrogen, and then 46 mg (80 μmol) of bis(benzylideneacetone)palladium was added. The mixture was stirred at 110° C. for 13 hours. After stirring, water was added to the obtained mixture, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and dried with magnesium sulfate. The mixture was filtered and the obtained filtrate was concentrated to obtain 3.7 g of a brown solid at a yield of 86%. The synthesis scheme of step 3 is shown below.

[0324] [Chemical formula 49]

[0325] Fig.15A and Fig. 15B The obtained solid 1 H NMR data, numerical data are shown below. Note that Fig. 15B Is magnification Fig.15A This is a graph showing the range of 7.0 ppm to 8.1 ppm in . It is understood that in this synthesis example, BBABnf(II)(2), an organic compound of one embodiment of the present invention, was obtained.

[0326] 1H NMR (chloroform-d, 500 MHz): δ = 8.33 (s, 1H), 7.96 (d,J=10Hz,2H),7.92-7.91(m,2H),7.60(d,J=7.0Hz,4H),7.53-7.38(m,12H),7.32(t,J=7.5Hz,2H),7.24(d,J=7.0Hz,4H)

[0327] The obtained solid was purified by sublimation purification. The solid was heated to 275° C. under the conditions of an argon flow rate of 15 mL / min and a pressure of 2.6 Pa for sublimation purification. After sublimation purification, a yellow solid of the target compound was obtained with a yield of 2.6 g and a recovery rate of 70%.

[0328] then, Fig.16 The measurement results of the absorption spectrum and emission spectrum of the toluene solution of BBABnf(II)(2) are shown. Fig.17 The absorption spectrum and emission spectrum of the thin film of BBABnf(II)(2) are shown. The solid thin film was manufactured by vacuum evaporation on a quartz substrate. The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (V550 manufactured by JASCO Corporation), minus the spectrum measured by placing only toluene in a quartz dish. In the measurement of the absorption spectrum of the thin film, a spectrophotometer (spectrophotometer U4100 manufactured by Hitachi High-Technologies Corporation) was used. In the measurement of the emission spectrum, a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan) was used.

[0329] Depend on Fig.16 It can be seen that the absorption peaks of the toluene solution of BBABnf(II)(2) are observed near 402nm, 346nm, and 322nm, and the peak of the emission wavelength is at 435nm (excitation wavelength 385nm). Fig.17 It can be seen that the absorption peaks of the thin film of BBABnf(II)(2) were observed near 392nm, 350nm, 257nm, and 207nm, and the peak of the emission wavelength was observed near 452nm (excitation wavelength 350nm). From the above results, it was confirmed that BBABnf(II)(2)B emits blue light, and it can be used as a main body of a luminescent material or a main body of a fluorescent luminescent material in the visible region.

[0330] In addition, it was found that the thin film of BBABnf(II)(2) was not easily aggregated in the air, had little morphological change, and had good film quality.

[0331] Next, the results of calculating the HOMO level and LUMO level of BBABnf(II)(2) by cyclic voltammetry (CV) measurement are shown. The calculation method is shown below.

[0332] As a measuring device, an electrochemical analyzer (ALS model 600A or 600C manufactured by BAS Inc.) was used. The solution for CV measurement was prepared as follows: as a solvent, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used, tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as a supporting electrolyte was dissolved at a concentration of 100 mmol / L, and the measurement object was dissolved at a concentration of 2 mmol / L. A platinum electrode (manufactured by BAS Inc., PTE platinum electrode) was used as a working electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 (5 cm)) was used as an auxiliary electrode, and Ag / Ag was used as a reference electrode. + Electrode (manufactured by BAS Inc., RE7 non-aqueous solvent type reference electrode). Note that the measurement was performed at room temperature (20°C to 25°C). The scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea[V] and reduction potential Ec[V] relative to the reference electrode were measured. Ea is the middle potential between oxidation-reduction waves, and Ec is the middle potential between reduction-oxidation waves. Here, it is known that the potential energy of the reference electrode used in this embodiment relative to the vacuum energy level is -4.94[eV], so the HOMO energy level [eV] = -4.94-Ea, LUMO energy level [eV] = -4.94-Ec are used to calculate the HOMO energy level and the LUMO energy level, respectively.

[0333] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th measurement was compared with the oxidation-reduction wave in the first measurement to investigate the electrical stability of the compound.

[0334] The results show that the HOMO level of BBABnf(II)(2) is -5.45 eV and the LUMO level is -2.50 eV. In addition, by comparing the waveforms of the first and 100th measurements in the repeated measurement of the oxidation-reduction wave, it can be seen that 89% of the peak intensity is maintained in the oxidation potential Ea[V] measurement, which shows that BBABnf(II)(2) has very high oxidation resistance.

[0335] In addition, differential scanning calorimetry (DSC) of BBABnf(II)(2) was performed using a Pyris1DSC manufactured by PerkinElmer, Inc. In the differential scanning calorimetry, the following operation was performed twice in succession: the temperature was raised from -10°C to 310°C at a heating rate of 40°C / min, then the temperature was kept at the same temperature for 1 minute, then the temperature was cooled to -10°C at a cooling rate of 100°C / min, and the temperature was kept at -10°C for 5 minutes. From the DSC measurement results of the second cycle, it can be seen that the glass transition temperature of BBABnf(II)(2) is 106°C, that is, BBABnf(II)(2) is a substance with very high heat resistance.

[0336] In addition, thermogravimetry-differential thermal analysis (TG-DTA) was performed on BBABnf(II)(2). In the measurement, a high vacuum differential thermal balance (manufactured by Bruker AXS, TG-DTA 2410SA) was used. The measurement was performed under atmospheric pressure at a heating rate of 10°C / min and under a nitrogen flow (flow rate of 200 mL / min). From the thermogravimetry-differential thermal analysis, it can be seen that the temperature (decomposition temperature) at which the weight of BBABnf(II)(2) measured by thermogravimetry is -5% of the weight at the beginning of the measurement is above 440°C, which means that BBABnf(II)(2) is a substance with high heat resistance. [Example 2]

[0337] In this example, a method for synthesizing N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as BBABnf(II)(4)), which is an organic compound of one embodiment of the present invention, is described in detail. The structural formula of BBABnf(II)(4) is shown below.

[0338] [Chemical formula 50]

[0339] <Step 1: Synthesis of 3-(3-chloro-2-fluorophenyl)-2-naphthol> 7.5 g (34 mmol) of 3-bromo-2-naphthol, 5.9 g (34 mmol) of 3-chloro-2-fluorophenylboric acid, 0.21 g (67 μmol) of tri(o-tolyl)phosphine, 30 mL of potassium carbonate aqueous solution (2.0 mol / L), 110 mL of toluene and 30 mL of ethanol were placed in a 300 mL three-necked flask. After the mixture was degassed under reduced pressure, the air in the flask was replaced with nitrogen. After the mixture was heated to 60°C, 76 mg (34 μmol) of palladium (II) acetate was added, and the mixture was stirred at 80°C for 8 hours. After stirring, 3.0 g (17 mmol) of 3-chloro-2-fluorophenylboric acid and 36 mg (16 μmol) of palladium (II) acetate were further added, and the mixture was stirred at 80°C for 8 hours. After stirring, the mixture was cooled to room temperature, and the obtained mixture was washed with water and saturated saline, and the aqueous layer and the organic layer were separated, and then the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated and dried. After drying, 6.1 g of a black solid was obtained. The synthesis scheme of step 1 is shown below.

[0340] [Chemical formula 51]

[0341] <Step 2: Synthesis of 4-chlorobenzo[b]naphtho[2,3-d]furan> 6.1 g of the black solid obtained in step 1, 6.3 g (44 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (NMP) were placed in a 500 mL eggplant-shaped flask and stirred at 120 ° C for 7 hours. The obtained mixture was filtered to remove potassium carbonate. 10 mL of 2.0 mol / L hydrochloric acid was added to the obtained filtrate to neutralize it. Water was added to the mixture, the organic layer and the aqueous layer were separated, and then the aqueous layer was extracted with ethyl acetate. The obtained extract and the organic layer were combined, washed with water, saturated sodium bicarbonate aqueous solution, and saturated brine, and dried with magnesium sulfate. The mixture was gravity filtered and the obtained filtrate was concentrated to obtain 4.9 g of brown solid. The brown solid was purified by supercritical fluid chromatography (SFC) (mobile phase: liquid carbon dioxide: tetrahydrofuran = 7:3), and 2.2 g of the light yellow solid of the target was obtained with a total yield of 26% in steps 1 and 2. Below, the synthesis scheme of step 2 is shown.

[0342] [Chemical formula 52] Fig.18A and Fig.18B The obtained solid 1 H NMR data, numerical data are shown below. Note that Fig.18B Is magnification Fig.18A The figure shows the range of 7.2 ppm to 8.3 ppm in . It can be seen from this that 4-chlorobenzo[b]naphtho[2,3-d]furan was obtained.

[0343] 1 H NMR (chloroform-d, 500 MHz): δ = 8.42 (s, 1H), 8.04 (d,J=8.5Hz,1H),8.00-7.96(m,3H),7.57-7.49(m,3H),7.32(t,J=7.5Hz,1H)

[0344] <Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4))> 1.5 g (6.0 mmol) of 4-chlorobenzo[b]naphtho[2,3-d]furan, 1.9 g (6.0 mmol) of bis(4-biphenyl)amine, 42 mg (0.12 mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (cBRIDP (registered trademark)), 1.2 g (12 mmol) of sodium tert-butoxide and 90 mL of toluene were placed in a 300 mL three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen after degassing under reduced pressure. 34 mg (60 μmol) of bis(benzylideneacetone)palladium was added to the mixture, and the mixture was stirred at 110° C. for 6 hours. Water was added to the obtained mixture, and the aqueous layer and the organic layer were separated, and then the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and dried with magnesium sulfate. The mixture was gravity filtered and the obtained filtrate was concentrated to obtain 2.7 g of the target substance as a brown solid at a yield of 83%. The synthesis scheme of step 3 is shown below.

[0345] [Chemical formula 53]

[0346] Fig.19A and Fig.19B The obtained solid 1 H NMR data, numerical data are shown below. Note that Fig.19B Is magnification Fig.19A This is a graph showing the range of 7.0 ppm to 8.6 ppm in . It is understood that in this synthesis example, BBABnf(II)(4), an organic compound of one embodiment of the present invention, was obtained.

[0347] 1 H NMR (chloroform-d, 500 MHz): δ = 8.42 (s, 1H), 8.03 (d,J=10Hz,1H),7.91-7.87(m,2H),7.77(s,1H),7.60(d,J=8.0Hz,4H),7.53(d,J=8.0Hz,4H),7.50 -7.45(m,2H),7.42(t,J=7.5Hz,4H),7.38-7.34(m,2H),7.31(t,J=7.5Hz,2H),7.23(d,J=8.5Hz,4H)

[0348] The obtained solid was purified by sublimation purification. The solid was heated to 250° C. for sublimation purification under the conditions of an argon flow rate of 15 mL / min and a pressure of 3.7 Pa. After sublimation purification, a yellow solid of the target compound was obtained (yield: 450 mg, recovery rate: 17%).

[0349] then, Fig. 20 The measurement results of the absorption spectrum and emission spectrum of the toluene solution of BBABnf(II)(4) are shown. Fig.21 The absorption spectrum and emission spectrum of the thin film of BBABnf(II)(4) are shown. The measurement was performed in the same manner as in Example 1.

[0350] Depend on Fig. 20 It can be seen that the absorption peaks of the toluene solution of BBABnf(II)(4) are observed near 384nm, 345nm, and 327nm, and the peak of the emission wavelength is at 421nm (excitation wavelength 327nm). Fig.21 It can be seen that the absorption peaks of the thin film of BBABnf(II)(4) were observed near 374nm, 355nm, 325nm, 257nm, and 207nm, and the peak of the emission wavelength was observed near 439nm (excitation wavelength 350nm). From the above results, it was confirmed that BBABnf(II)(4)B emits blue light, and it can be used as a main body of a luminescent material or a main body of a fluorescent luminescent material in the visible region.

[0351] In addition, it was found that the thin film of BBABnf(II)(4) was not easily aggregated in the air, had little morphological change, and had good film quality.

[0352] Next, the results of calculating the HOMO level and LUMO level of BBABnf(II)(4) by cyclic voltammetry (CV) measurement are shown. The calculation method is the same as that in Example 1.

[0353] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th measurement was compared with the oxidation-reduction wave in the first measurement to investigate the electrical stability of the compound.

[0354] The results show that the HOMO level of BBABnf(II)(4) is -5.57 eV and the LUMO level is -2.48 eV. In addition, by comparing the waveforms of the first and 100th measurements in the repeated measurement of the oxidation-reduction wave, it can be seen that 85% of the peak intensity is maintained in the oxidation potential Ea[V] measurement, which shows that BBABnf(II)(4) has very high oxidation resistance.

[0355] In addition, differential scanning calorimetry of BBABnf(II)(4) was performed using the same apparatus as in Example 1. In the differential scanning calorimetry, the following operation was performed twice in succession: the temperature was raised from -10°C to 275°C at a heating rate of 40°C / min, then the temperature was kept at the same temperature for 1 minute, then the temperature was cooled to -10°C at a cooling rate of 100°C / min, and the temperature was kept at -10°C for 5 minutes. From the DSC measurement result of the second cycle, it was found that the glass transition temperature of BBABnf(II)(4) was 108°C, that is, BBABnf(II)(4) was a substance having very high heat resistance.

[0356] In addition, thermogravimetric-differential thermal analysis was performed on BBABnf(II)(4) in the same manner as in Example 1. The thermogravimetric-differential thermal analysis revealed that the temperature (decomposition temperature) at which the weight of BBABnf(II)(4) measured by thermogravimetry was -5% of the weight at the start of measurement was 410°C, which means that BBABnf(II)(4) is a substance having high heat resistance. [Example 3]

[0357] In this example, a method for synthesizing N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviation: BBAaBnf(10)), which is an organic compound of one embodiment of the present invention, is described in detail. The structural formula of BBAaBnf(10) is shown below.

[0358] [Chemical formula 54]

[0359] <Step 1: Synthesis of 2-bromophenyl-1-naphthyl ether> 2.9 g (20 mmol) of 1-naphthol and 13 g (40 mmol) of potassium carbonate were placed in a 200 mL three-necked flask, and the air in the flask was replaced with nitrogen. 110 mL of N-methylpyrrolidone (NMP) and 7.5 g (40 mmol) of 1-bromo-2-fluorobenzene were added to the mixture, and the mixture was stirred at 170 ° C for 4 hours. After stirring, 100 mL of 2 mol / L hydrochloric acid was added to the obtained mixture, and stirred at room temperature. After stirring, the organic layer of the mixture was washed twice with 100 mL of 2 mol / L hydrochloric acid, and the water layer was extracted twice with toluene. After combining the extract solution and the organic layer, 100 mL of 2 mol / L hydrochloric acid and saturated brine were used for washing, and magnesium sulfate was added to the obtained organic layer and dried. The mixture was gravity filtered, and the obtained filtrate was concentrated to obtain a brown compound. The compound was purified by silica gel column chromatography (developing solvent: toluene:hexane=1:1) to obtain 4.1 g of the target compound as a colorless transparent oil with a yield of 69%. The synthesis scheme of step 1 is shown below.

[0360] [Chemical formula 55]

[0361] <Step 2: Synthesis of benzo[b]naphtho[2,1-d]furan> 4.1 g (14 mmol) of 2-bromophenyl-1-naphthyl ether, 0.20 mg (0.40 mmol) of triphenylphosphine, and 10 g (30 mmol) of cesium carbonate were placed in a 500 mL eggplant-shaped flask, and the air in the flask was replaced with nitrogen. After adding 100 mL of NMP to the mixture, the mixture was degassed under reduced pressure. After adding 89 mg (0.40 mmol) of palladium (II) acetate to the mixture, it was stirred at 180 ° C for 3.5 hours under a nitrogen stream. After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract and organic layer were combined, washed with 2 mol / L hydrochloric acid, saturated sodium carbonate aqueous solution, and saturated brine, and then dried with magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to obtain 3.0 g of the target light brown solid with a yield of 99%. The synthesis scheme of step 2 is shown below.

[0362] [Chemical formula 56]

[0363] <Step 3: Synthesis of 10-iodobenzo[b]naphtho[2,1-d]furan> 3.0 g (14 mmol) of benzo[b]naphtho[2,1-d]furan was placed in a 200 mL three-necked flask, the air in the flask was replaced with nitrogen, and then 70 mL of tetrahydrofuran (THF) was added. After the solution was cooled to -75°C, 8.5 mL (14 mmol) of n-butyl lithium (1.64 mol / L n-hexane solution) was added dropwise to the solution. After the addition, the resulting solution was stirred at room temperature for 1 hour. After stirring, the solution was cooled to -75°C, and then a solution prepared by dissolving 3.6 g (14 mmol) of iodine in 10 mL of THF was added dropwise. After the addition, the resulting solution was stirred for 17 hours while returning to room temperature. After stirring, an aqueous sodium thiosulfate solution was added to the resulting solution and stirred for 1 hour, and then the organic layer of the mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract and the organic layer were combined, washed with saturated brine, and the resulting organic layer was dried with magnesium sulfate. After drying, the mixture was gravity filtered and the obtained solution was concentrated to obtain the target white solid in a yield of 4.4 g and a yield of 93%. The synthesis scheme of step 3 is shown below.

[0364] [Chemical formula 57]

[0365] The following shows the chloroform solution 1 H NMR measurement results. 1 H NMR (chloroform-d, 500 MHz): δ = 7.16 (t, J = 7.8 Hz, 1H), 7.59 (td,J1=7.5Hz,J2=1.5Hz,1H),7.67(td,J1=7.5Hz,J2=1.0Hz,1H),7.80(d,J=8.5Hz,1H),7.83 (dd,J1=8.0Hz,J2=1.5Hz,1H),7.94-7.96(m,2H),7.99(d,J=8.0Hz,1H),8.53(d,J=8.5Hz,1H)

[0366] <Step 4: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviation: BBAaBnf(10))> 2.0 g (6.0 mmol) of 10-iodobenzo[b]naphtho[2,1-d]furan, 1.9 g (6.0 mmol) of bis(4-biphenyl)amine, 42 mg (0.12 mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (cBRIDP (registered trademark)), 1.2 g (12 mmol) of sodium tert-butoxide and 70 mL of toluene were placed in a 200 mL three-necked flask equipped with a reflux tube. After the mixture was degassed under reduced pressure, the air in the flask was replaced with nitrogen. After adding 34 mg (0.060 mmol) of bis(benzylideneacetone)palladium, the mixture was stirred at 110°C for 10 hours. After stirring, water was added to the obtained mixture, and the aqueous layer was extracted with toluene. The organic layer and the obtained extract were combined, washed with water and saturated brine, and dried with magnesium sulfate. The mixture was gravity filtered and the obtained filtrate was concentrated. The obtained crude product was purified by silica gel column chromatography (mobile phase: hexane:toluene=5:1) to obtain 0.75 g of the target substance as a brown solid at a yield of 23%. The synthesis scheme of step 4 is shown below.

[0367] [Chemical formula 58]

[0368] The following shows the obtained solid 1 H NMR data. As can be seen from the above, in this synthesis example, BBAaBnf (10), an organic compound of one embodiment of the present invention, was obtained.

[0369] 1 H NMR (chloroform-d, 500 MHz): δ = 7.99 (d, J = 8.5 Hz, 1H), 7.93 (d,J=7.5Hz,1H),7.90(d,J=8.0Hz,1H),7.81(dd,J=5.0,4.0Hz,1H),7.76(d,J=8.5Hz,1H),7.60(d,J=8.5Hz,4H),7.54(d,J=8.5Hz,4H), 7.49(t,J=6.5Hz,1H),7.81(dd,J=8.0,1.5Hz,1H),7.42(t,J=8.0Hz,4H),7.38-7.37(m,2H),7.31(t,J=7.5Hz,2H),7.29(d,J=8.5Hz,4H)

[0370] The obtained solid was purified by sublimation purification. The solid was heated to 270°C for sublimation purification under the conditions of an argon flow rate of 15 mL / min and a pressure of 3.7 Pa. After sublimation purification, a glassy yellow solid of the target compound was obtained with a yield of 0.44 g and a recovery rate of 58%. [Example 4]

[0371] In this example, a description is given of the light-emitting element 1 and the light-emitting element 2 which are one embodiment of the present invention described in Embodiment 2. The structural formulas of the organic compounds used in the light-emitting element 1 and the light-emitting element 2 are shown below.

[0372] [Chemical formula 59]

[0373] (Method for Manufacturing Light Emitting Element 1) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0374] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0375] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4 Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0376] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN) represented by the above structural formula (i) is evaporated on the first electrode 101 in a thickness of 5 nm by an evaporation method utilizing resistance heating, thereby forming a hole injection layer 111.

[0377] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the above structural formula (ii) is evaporated to a thickness of 20 nm on the hole injection layer 111 to form a first hole transport layer 112-1, and N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as BBABnf(II)(4)) represented by the above structural formula (iii) is evaporated to a thickness of 10 nm on the first hole transport layer 112-1 to form a second hole transport layer 112-2.

[0378] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0379] Then, cgDBCzPA was evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated in a thickness of 10 nm to form the electron transport layer 114.

[0380] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115 , and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102 , thereby manufacturing the light emitting element 1 of this example.

[0381] (Method for Manufacturing Light Emitting Element 2) In the light-emitting element 2, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II) represented by the above structural formula (vii) was evaporated to a thickness of 15 nm, and then NBPhen was evaporated to a thickness of 10 nm to form an electron transport layer 114. The manufacturing process other than this was the same as that of the light-emitting element 1.

[0382] The following table shows the device structures of the light-emitting element 1 and the light-emitting element 2.

[0383] [Table 1]

[0384] In a glove box with a nitrogen atmosphere, the light emitting element 1 and the light emitting element 2 were sealed using a glass substrate in a manner that the light emitting element 1 and the light emitting element 2 were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at a temperature of 80°C for 1 hour), and then the initial characteristics and reliability of these light emitting elements were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25°C).

[0385] Fig. 22 The brightness-current density characteristics of the light-emitting element 1 and the light-emitting element 2 are shown. Fig.23 The current efficiency-brightness characteristics are shown. Fig.24 The brightness-voltage characteristics are shown. Fig.25 The current-voltage characteristics are shown. Fig.26 The external quantum efficiency-brightness characteristics are shown. Fig. 27 Table 2 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0386] [Table 2]

[0387] Depend on Figure 22 to Figure 27 As can be seen from Table 2, the light-emitting element 1 and the light-emitting element 2 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and luminous efficiency.

[0388] in addition, Fig.28 The current density is 50 mA / cm 2 The graph of the brightness change with respect to the driving time under the conditions of Fig.28 As shown, the light emitting element 1 and the light emitting element 2 of one embodiment of the present invention are light emitting elements with little luminance drop with cumulative driving time and good life. [Example 5]

[0389] In this example, description is given of the light-emitting element 3 and the light-emitting element 4 which are one embodiment of the present invention described in Embodiment 2. The structural formulas of the organic compounds used in the light-emitting element 3 and the light-emitting element 4 are shown below.

[0390] [Chemical formula 60]

[0391] (Method for Manufacturing Light Emitting Element 3) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0392] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0393] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4 Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0394] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as: BBABnf(II)(4)) represented by the above structural formula (iii) and molybdenum (VI) oxide are co-evaporated on the first electrode 101 in a thickness of 10 nm and a weight ratio of 4:2 (=BBABnf(II)(4):molybdenum oxide) by a resistance heating evaporation method to form a hole injection layer 111.

[0395] Next, BBABnf(II)(4) was deposited on the hole injection layer 111 to a thickness of 30 nm to form the hole transport layer 112 .

[0396] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0397] Then, cgDBCzPA was evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated in a thickness of 10 nm to form the electron transport layer 114.

[0398] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light emitting element 3 of this example.

[0399] (Method for Manufacturing Light Emitting Element 4) In the light-emitting element 4, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II) represented by the above structural formula (vii) was deposited at a thickness of 15 nm, and then NBPhen was deposited at a thickness of 10 nm to form an electron transport layer 114. The manufacturing process other than this was the same as that of the light-emitting element 3.

[0400] The following table shows the device structures of the light-emitting element 3 and the light-emitting element 4.

[0401] [Table 3]

[0402] In a glove box with a nitrogen atmosphere, the light emitting element 3 and the light emitting element 4 were sealed using a glass substrate in a manner that the light emitting element 3 and the light emitting element 4 were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at a temperature of 80°C for 1 hour), and then the initial characteristics and reliability of these light emitting elements were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25°C).

[0403] Fig.29 The brightness-current density characteristics of light-emitting element 3 and light-emitting element 4 are shown. Fig.30 The current efficiency-brightness characteristics are shown. Fig.31 The brightness-voltage characteristics are shown. Fig.32 The current-voltage characteristics are shown. Fig.33 The external quantum efficiency-brightness characteristics are shown. Fig.34 Table 4 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0404] [Table 4]

[0405] Depend on Figures 29 to 34 As can be seen from Table 4, the light-emitting element 3 and the light-emitting element 4 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and light-emitting efficiency.

[0406] in addition, Fig.35 The current density is 50 mA / cm 2 The graph of the brightness change with respect to the driving time under the conditions of Fig.35 As shown, the light emitting element 3 and the light emitting element 4 of one embodiment of the present invention are light emitting elements with little luminance drop with cumulative driving time and good life. [Example 6]

[0407] In this example, description is given of the light-emitting element 5 and the light-emitting element 6 which are one embodiment of the present invention described in Embodiment 2. The structural formulas of the organic compounds used in the light-emitting element 5 and the light-emitting element 6 are shown below.

[0408] [Chemical formula 61]

[0409] (Method for Manufacturing Light Emitting Element 5) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0410] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0411] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4 Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0412] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as: BBABnf(II)(4)) represented by the above structural formula (iii) and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinone dimethane (abbreviated as: F6-TCNNQ) are co-evaporated on the first electrode 101 by a resistance heating evaporation method in a thickness of 10 nm and a weight ratio of 1:0.5 (=BBABnf(II)(4):F6-TCNNQ), thereby forming a hole injection layer 111.

[0413] Next, BBABnf(II)(4) is vapor-deposited on the hole injection layer 111 in a thickness of 10 nm to form a first hole transport layer 112-1, and 3-〔4-(9-phenanthrenyl)-phenyl〕-9-phenyl-9H-carbazole (abbreviated as: PCPPn) represented by the above structural formula (ix) is vapor-deposited on the first hole transport layer 112-1 in a thickness of 20 nm to form a second hole transport layer 112-2, thereby forming a hole transport layer 112.

[0414] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0415] Then, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTBPDBq-II) represented by the above structural formula (vii) is evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as: NBPhen) represented by the above structural formula (vi) is evaporated in a thickness of 10 nm to form an electron transport layer 114.

[0416] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light-emitting element 5 of this example.

[0417] (Method for Manufacturing Light Emitting Element 6) In the light-emitting element 6 , PCPPn was vapor-deposited to a thickness of 30 nm to form the hole transport layer 112 , and the manufacturing process was otherwise the same as that of the light-emitting element 5 .

[0418] The following table shows the device structures of the light-emitting element 5 and the light-emitting element 6.

[0419] [Table 5]

[0420] In a glove box of nitrogen atmosphere, the light emitting element 5 and the light emitting element 6 were sealed using a glass substrate in a manner that the light emitting element 5 and the light emitting element 6 were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour), and then the initial characteristics and reliability of these light emitting elements were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25°C).

[0421] Fig.36 The brightness-current density characteristics of light-emitting element 5 and light-emitting element 6 are shown. Fig.37 The current efficiency-brightness characteristics are shown. Fig.38The brightness-voltage characteristics are shown. Fig.39 The current-voltage characteristics are shown. Fig.40 The external quantum efficiency-brightness characteristics are shown. Fig.41 Table 6 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0422] [Table 6]

[0423] Depend on Figure 36 to Figure 41 As can be seen from Table 6, the light-emitting element 5 and the light-emitting element 6 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and luminous efficiency.

[0424] in addition, Fig.42 The current density is 50 mA / cm 2 The graph of the brightness change with respect to the driving time under the conditions of Fig.42 As shown, it can be seen that the light emitting element 5 and the light emitting element 6 of the light emitting element of one embodiment of the present invention are light emitting elements with little luminance drop with cumulative driving time and good life. [Example 7]

[0425] In this example, a description is given of the light-emitting element 7 which is one embodiment of the present invention described in Embodiment 2. The structural formula of the organic compound used in the light-emitting element 7 is shown below.

[0426] [Chemical formula 62]

[0427] (Method for Manufacturing Light Emitting Element 7) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0428] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0429] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4 Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0430] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN) represented by the above structural formula (i) is evaporated on the first electrode 101 in a thickness of 5 nm by an evaporation method utilizing resistance heating, thereby forming a hole injection layer 111.

[0431] Next, a 20 nm thick layer of 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the above structural formula (ii) is evaporated on the hole injection layer 111 to form a first hole transport layer 112-1, and a 10 nm thick layer of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated as BBABnf(II)(2)) represented by the above structural formula (x) is evaporated on the first hole transport layer 112-1 to form a second hole transport layer 112-2.

[0432] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0433] Then, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTBPDBq-II) represented by the above structural formula (vii) is evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as: NBPhen) represented by the above structural formula (vi) is evaporated in a thickness of 10 nm to form an electron transport layer 114.

[0434] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light emitting element 7 of this example.

[0435] The following table shows the element structure of the light emitting element 7.

[0436] [Table 7]

[0437] In a glove box of nitrogen atmosphere, a sealing process was performed using a glass substrate in a manner that the light emitting element 7 was not exposed to the atmosphere (a sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at 80° C. for 1 hour), and then the initial characteristics and reliability of the light emitting element 7 were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25° C.).

[0438] Fig.43 The luminance-current density characteristics of the light-emitting element 7 are shown. Fig.44 The current efficiency-brightness characteristics are shown. Fig.45 The brightness-voltage characteristics are shown. Fig.46 The current-voltage characteristics are shown. Fig.47 The external quantum efficiency-brightness characteristics are shown. Fig.48 Table 8 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0439] [Table 8]

[0440] Depend on Figures 43 to 48 As can be seen from Table 8, the light-emitting element 7 of one embodiment of the present invention is a blue light-emitting element having excellent characteristics such as driving voltage and luminous efficiency. [Example 8]

[0441] In this example, a description is given of the light-emitting element 8 which is one embodiment of the present invention described in Embodiment 2. The structural formula of the organic compound used in the light-emitting element 8 is shown below.

[0442] [Chemical formula 63]

[0443] (Method for Manufacturing Light Emitting Element 8) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0444] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0445] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0446] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated as: BBABnf(II)(2)) represented by the above structural formula (x) and molybdenum (VI) oxide are co-evaporated on the first electrode 101 in a thickness of 10 nm and a weight ratio of 4:2 (=BBABnf(II)(2):molybdenum oxide) by a resistance heating evaporation method to form a hole injection layer 111.

[0447] Next, BBABnf(II)(2) was deposited on the hole injection layer 111 to a thickness of 30 nm to form the hole transport layer 112 .

[0448] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0449] Then, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTBPDBq-II) represented by the above structural formula (vii) is evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as: NBPhen) represented by the above structural formula (vi) is evaporated in a thickness of 10 nm to form an electron transport layer 114.

[0450] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light emitting element 8 of this example.

[0451] The following table shows the element structure of the light emitting element 8.

[0452] [Table 9]

[0453] In a glove box with a nitrogen atmosphere, a sealing process was performed using a glass substrate in a manner that the light emitting element 8 was not exposed to the atmosphere (a sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at a temperature of 80° C. for 1 hour), and then the initial characteristics and reliability of the light emitting element 8 were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25° C.).

[0454] Fig.49 The luminance-current density characteristics of the light-emitting element 8 are shown. Fig.50 The current efficiency-brightness characteristics are shown. Fig.51 The brightness-voltage characteristics are shown. Fig.52 The current-voltage characteristics are shown. Fig.53 The external quantum efficiency-brightness characteristics are shown. Fig.54 Table 10 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0455] [Table 10]

[0456] Depend on Figure 49 to Figure 54 As can be seen from Table 10, the light-emitting element 3 and the light-emitting element 4 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and luminous efficiency. [Example 9]

[0457] In this example, a description is given of the light-emitting element 9 and the light-emitting element 10 which are one embodiment of the present invention described in Embodiment 2. The structural formulas of the organic compounds used in the light-emitting element 9 and the light-emitting element 10 are shown below.

[0458] [Chemical formula 64]

[0459] (Method for Manufacturing Light Emitting Element 9) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0460] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0461] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0462] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN) represented by the above structural formula (i) is evaporated on the first electrode 101 in a thickness of 5 nm by an evaporation method utilizing resistance heating, thereby forming a hole injection layer 111.

[0463] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the above structural formula (ii) is evaporated on the hole injection layer 111 to form a first hole transport layer 112-1, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as BBABnf(II)(4)) represented by the above structural formula (iii) is evaporated on the first hole transport layer 112-1 to form a second hole transport layer 112-2, and 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviated as PCzN2) represented by the above structural formula (xi) is evaporated on the second hole transport layer 112-2 to form a third hole transport layer 112-3.

[0464] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0465] Then, cgDBCzPA was evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated in a thickness of 10 nm to form the electron transport layer 114.

[0466] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115 , and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102 , thereby manufacturing the light emitting element 1 of this example.

[0467] (Method for Manufacturing Light Emitting Element 10) In the light-emitting element 10, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II) represented by the above structural formula (vii) was evaporated to a thickness of 15 nm, and then NBPhen was evaporated to a thickness of 10 nm to form an electron transport layer 114. The manufacturing process other than this was the same as that of the light-emitting element 9.

[0468] The following table shows the device structures of the light-emitting device 9 and the light-emitting device 10.

[0469] [Table 11]

[0470] In a glove box of nitrogen atmosphere, the light emitting element 9 and the light emitting element 10 were sealed using a glass substrate in a manner that the light emitting element 9 and the light emitting element 10 were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at a temperature of 80° C. for 1 hour), and then the initial characteristics and reliability of these light emitting elements were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25° C.).

[0471] Fig.55 The brightness-current density characteristics of light-emitting element 9 and light-emitting element 10 are shown. Fig.56 The current efficiency-brightness characteristics are shown. Fig.57 The brightness-voltage characteristics are shown. Fig.58 The current-voltage characteristics are shown. Fig.59 The external quantum efficiency-brightness characteristics are shown. Fig.60 Table 12 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0472] [Table 12]

[0473] Depend on Figures 55 to 60 As can be seen from Table 12, the light-emitting element 9 and the light-emitting element 10 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and luminous efficiency.

[0474] in addition, Fig.61 The current density is 50 mA / cm 2The graph of the brightness change with respect to the driving time under the conditions of Fig.61 As shown, it can be seen that the light emitting element 9 and the light emitting element 10 of one embodiment of the light emitting element of the present invention are light emitting elements with little decrease in luminance with accumulation of driving time and good life. [Example 10]

[0475] In this example, the light-emitting element 11 and the light-emitting element 12 which are one embodiment of the present invention described in Embodiment 2 are described. The structural formulas of the organic compounds used in the light-emitting element 11 and the light-emitting element 12 are shown below.

[0476] [Chemical formula 65]

[0477] (Method for Manufacturing Light Emitting Element 11) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering, thereby forming the first electrode 101. The first electrode 101 had a thickness of 70 nm and an electrode area of ​​2 mm×2 mm.

[0478] Next, as pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds.

[0479] Then, the substrate is introduced into the chamber where the internal pressure is reduced to 10 -4 Pa in a vacuum deposition apparatus, and after vacuum baking at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, the substrate is cooled for about 30 minutes.

[0480] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and then 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN) represented by the above structural formula (i) is evaporated on the first electrode 101 in a thickness of 5 nm by an evaporation method utilizing resistance heating, thereby forming a hole injection layer 111.

[0481] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the above structural formula (ii) is evaporated to form a first hole transport layer 112-1 with a thickness of 10 nm, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated as BBABnf(II)(2)) represented by the above structural formula (iii) is evaporated to form a second hole transport layer 112-2 with a thickness of 10 nm, and 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviated as PCzN2) represented by the above structural formula (xi) is evaporated to form a third hole transport layer 112-3 with a thickness of 10 nm.

[0482] Next, 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-evaporated in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form a 25nm thick light-emitting layer 113.

[0483] Then, cgDBCzPA was evaporated on the light-emitting layer 113 in a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated in a thickness of 10 nm to form the electron transport layer 114.

[0484] After the electron transport layer 114 was formed, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light-emitting element 11 of this example.

[0485] (Method for Manufacturing Light Emitting Element 12) In the light-emitting element 12, 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II) represented by the above structural formula (vii) was evaporated to a thickness of 15 nm, and then NBPhen was evaporated to a thickness of 10 nm to form an electron transport layer 114. The manufacturing process other than this was the same as that of the light-emitting element 11.

[0486] The following table shows the device structures of the light emitting element 11 and the light emitting element 12.

[0487] [Table 13]

[0488] In a glove box of nitrogen atmosphere, the light emitting element 11 and the light emitting element 12 were sealed using a glass substrate in a manner that the light emitting element 11 and the light emitting element 12 were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour), and then the initial characteristics and reliability of these light emitting elements were measured. In addition, the measurement was performed at room temperature (an atmosphere maintained at 25°C).

[0489] Fig.62 The brightness-current density characteristics of the light-emitting element 11 and the light-emitting element 12 are shown. Fig.63 The current efficiency-brightness characteristics are shown. Fig.64 The brightness-voltage characteristics are shown. Fig.65 The current-voltage characteristics are shown. Fig.66 The external quantum efficiency-brightness characteristics are shown. Fig.67 Table 14 shows the emission spectrum of each light emitting element at 1000 cd / m 2 The main feature in the neighborhood.

[0490] [Table 14]

[0491] Depend on Figure 62 to Figure 67 As can be seen from Table 14, the light-emitting element 11 and the light-emitting element 12 according to one embodiment of the present invention are blue light-emitting elements having excellent characteristics such as driving voltage and luminous efficiency.

[0492] in addition, Fig.68 The current density is 50 mA / cm 2 The graph of the brightness change with respect to the driving time under the conditions of Fig.68 As shown, the light emitting element 11 and the light emitting element 12 of one embodiment of the present invention are light emitting elements with little luminance drop with cumulative driving time and good life. [Explanation of symbols]

[0493] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 112: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 112-3: third hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer, 116: charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection buffer layer, 400: substrate, 401: first electrode, 403: EL layer, 404: second electrode, 405: sealing material, 406: sealing material, 407: sealing substrate, 412: pad, 420: IC chip, 501: anode, 502: cathode, 511: First light-emitting unit, 512: second light-emitting unit, 513: charge generation layer, 601: drive circuit portion (source line drive circuit), 602: pixel portion, 603: drive circuit portion (gate line drive circuit), 604: sealing substrate, 605: sealing material, 607: space, 608: wiring, 609: FPC (flexible printed circuit), 610: element substrate, 611: switch FET, 612: current control FET, 613: first electrode, 614: insulator, 616: EL layer, 617: second electrode, 618: light-emitting element, 951: substrate, 952: electrode, 953: insulating layer, 954: partition wall layer, 955: EL layer, 956: electrode, 1001: substrate, 1002: base insulating film, 1003: gate insulating film, 1006: gate electrode, 1007: gate electrode, 1008: gate electrode, 1020: first interlayer insulating film, 1021: second interlayer insulating film, 1022: electrode, 1024W: anode, 1024R: anode, 1024G: anode, 1024B: anode, 1025: partition wall, 1028: EL layer, 1029: second electrode, 1031: sealing substrate, 1032: sealing material, 1033: transparent base material, 1034R: red coloring layer, 1034G: green coloring layer, 1034B: blue coloring layer, 1035: black matrix, 1036: protective layer, 1037: third interlayer insulating film, 1040: image Element, 1041: driving circuit part, 1042: peripheral part, 2001: casing, 2002: light source, 2100: robot, 2110: computing device, 2101: illumination sensor, 2102: microphone, 2103: upper camera, 2104: speaker, 2105: display, 2106: lower camera, 2107: obstacle sensor, 2108: moving mechanism, 3001: lighting device, 5000: casing, 5001: display part, 5002: second display part, 5003: speaker, 5004: LED light, 5005: operation key, 5006: connection terminal, 5007: sensor, 5008: microphone, 5012: support part, 5013: earphone,5100: sweeping robot, 5101: display, 5102: camera, 5103: brush, 5104: operation button, 5150: portable information terminal, 5151: housing, 5152: display area, 5153: bending part, 5120: garbage, 5200: display area, 5201: display area, 5202: display area, 5203: display area, 7101: housing, 7103: display part, 7105: bracket, 7107: display part, 7109: operation key, 7110 : Remote control machine, 7201: Main body, 7202: Housing, 7203: Display unit, 7204: Keyboard, 7205: External connection port, 7206: Pointing device, 7210: Second display unit, 7401: Housing, 7402: Display unit, 7403: Operation button, 7404: External connection port, 7405: Speaker, 7406: Microphone, 7400: Mobile phone, 9310: Portable information terminal, 9311: Display panel, 9313: Hinge unit, 9315: Housing,

Claims

1. An organic compound represented by the following general formula (G2): in: In the general formula (G2), R 18 and R 20 wherein one of them is a group represented by the following general formula (g1), and the other represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a halogenated alkyl group having 1 to 6 carbon atoms, and an unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and R 11 To R 17 , R 19 each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a fluorine group, a halogenated alkyl group having 1 to 6 carbon atoms, and an unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, In the general formula (g1), Ar 3 ,Ar 4 Each independently represents an unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms; in addition, Ar 1 ,Ar 2 Each independently represents an unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2.

2. The organic compound according to claim 1, wherein the group represented by the general formula (g1) is bonded to R in the organic compound represented by the general formula (G2) 20 .

3. The organic compound according to claim 1, wherein Ar 3 And the Ar 4 Each is independently an unsubstituted phenyl group and an unsubstituted naphthyl group.

4. The organic compound according to claim 1, wherein Ar 1 And the Ar 2 Each independently represents an unsubstituted phenylene group and an unsubstituted naphthylene group.

5. The organic compound according to claim 1, wherein Ar 3 And the Ar 4 It is phenyl.

6. The organic compound according to claim 1, wherein Ar 1 And the Ar 2 It is phenylene.

7. The organic compound according to claim 1, wherein said n and said m are 1.

8. An organic compound represented by the following formula: 。 9. A method for synthesizing 10-iodobenzo[b]naphtho[2,1-d]furan, in, Tetrahydrofuran is added to benzo[b]naphtho[2,1-d]furan, and a hexane solution containing n-butyl lithium is added thereto, followed by stirring. After stirring, a tetrahydrofuran solution in which iodine is dissolved is added thereto, followed by stirring.

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