Hole transport material

Abstract

To provide a novel light-emitting element. Another object of one embodiment of the present invention is to provide a light-emitting element with a long lifetime. Another object of one embodiment of the present invention is to provide a light-emitting element with high emission efficiency. Another object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide a novel organic compound having a hole-transport property. Another object of one embodiment of the present invention is to provide a novel hole-transport material.SOLUTION: A hole-transport material including an organic compound having a substituted or unsubstituted benzonaphthofuran skeleton and a substituted or unsubstituted amine skeleton is provided. A light-emitting element using the hole-transport material is provided. Another embodiment of the present invention provides an organic compound in which an amine skeleton including two aromatic hydrocarbon groups each having 6 to 60 carbon atoms is bonded to the 6-position or the 8-position of benzonaphthofuran.SELECTED DRAWING: None

Description

[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 element, a display module ... The present invention relates to an optical device, an electronic device, and a lighting device. The technical field of one embodiment of the invention disclosed in the present specification and the like is related to an object, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture It is about cha, or composition of matter. More specifically, the technical field of one embodiment of the present invention disclosed in this specification is a semiconductor device, a display, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and the like One example is a driving method or a manufacturing method thereof. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting elements (organic EL elements) that utilize these elements is progressing. The basic structure of a liquid crystal display is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material between them. A voltage is applied to this element to inject carriers, and the recombination energy of the carriers is By utilizing this, light can be emitted from the light-emitting material.

[0003] Since these light-emitting elements are self-luminous, when used as display pixels, they are more efficient than liquid crystals. It has the advantage of being highly visible and does not require a backlight, making it suitable for flat panel displays. Furthermore, displays using such light-emitting elements are thin and lightweight. Another major advantage is that it can be manufactured easily. Another feature is its extremely fast response time. be.

[0004] In addition, these light-emitting elements can have a light-emitting layer formed continuously in two dimensions, This is similar to point light sources such as incandescent bulbs and LEDs, or This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it can be used as a surface light source for lighting, etc. It is also highly useful.

[0005] Displays and lighting devices using such light-emitting elements are suitable for use in a variety of electronic devices. However, research and development is ongoing to develop light-emitting devices with better efficiency and life span.

[0006] As a material for the hole injection layer used to facilitate the injection of carriers, particularly holes, into the EL layer, There are organic compounds with acceptor properties. Organic compounds with acceptor properties can be formed by vapor deposition. Because it can be easily formed into a film, it is suitable for mass production and is widely used. The LUMO level of the organic compound constituting the hole transport layer is different from the HOMO level of the organic compound constituting the hole transport layer. If the distance is too far, it is difficult to inject holes into the EL layer. In order to bring the LUMO level of the compound close to the HOMO level of the organic compound that constitutes the hole transport layer, If the HOMO level of the organic compound that makes up the hole transport layer is made shallower, the HOMO level of the light-emitting layer will Even if holes can be injected into the EL layer, the difference between the However, there is a problem in that it becomes difficult to inject holes into the silicon material.

[0007] In Patent Document 1, a first hole injection layer is provided between a first hole transport layer in contact with the hole injection layer and a light emitting layer. Hole transport properties with a HOMO level between that of the interlayer and that of the host material A configuration for applying the material is disclosed.

[0008] The characteristics of light-emitting elements have improved dramatically, but there are still many issues regarding their efficiency, durability, and other characteristics. It must be said that this is still insufficient to meet the high level of demands that are being placed on the market. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] International Publication No. 2011 / 065136 Brochure Summary of the Invention [Problem to be solved by the invention]

[0010] In view of the above, an object of one embodiment of the present invention is to provide a novel light-emitting element. Another object of the present invention is to provide a light-emitting element having good luminous efficiency. Another object of the present invention is to provide a novel organic compound. Another embodiment of the present invention is to provide a novel organic compound having a hole-transporting property. Another object of the present invention is to provide a novel hole transport material. .

[0011] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. Another object of the present invention is to provide a light-emitting device with low power consumption. The present invention aims to provide a device, an electronic device, and a display device.

[0012] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0013] One aspect of the present invention is a compound having a substituted or unsubstituted benzonaphthofuran skeleton and a substituted or unsubstituted benzonaphthofuran skeleton. The hole transport material includes an organic compound having an amine skeleton.

[0014] Another embodiment of the present invention is a compound having a substituted or unsubstituted benzonaphthofuran skeleton and one substituted Alternatively, the hole transport material may include an organic compound having an unsubstituted amine skeleton.

[0015] Alternatively, another aspect of the present invention is a compound having the above-mentioned structure, wherein the amine skeleton is the benzonaphtho It is a hole transport material that is bonded to the 6th or 8th position of the furan skeleton.

[0016] Alternatively, another aspect of the present invention is a compound having the above structure, wherein the benzonaphthofuran skeleton and the amino group It is a hole transport material having an organic compound in which the nitrogen of the anthracene skeleton is directly bonded.

[0017] Alternatively, another embodiment of the present invention is a device having an anode, a cathode, and an EL layer, the EL layer being a light-emitting layer. the EL layer is located between the anode and the cathode, and the EL layer has any one of the above 1. A light-emitting element comprising the hole transport material according to claim 1.

[0018] Alternatively, another embodiment of the present invention is a light-emitting device having an anode, a cathode, and an EL layer, The EL layer is located between the electrode and the cathode, and the EL layer has a light-emitting layer and a hole-transporting layer, and the hole The transport layer is located between the light-emitting layer and the anode, and contains the hole transport material described above. The light emitting element is included in the transmission layer.

[0019] Alternatively, another embodiment of the present invention is a light-emitting layer having the above-described structure, wherein the light-emitting layer contains a light-emitting material and the hole and a transport material.

[0020] Alternatively, another embodiment of the present invention is a light-emitting layer having the above-described structure, wherein the light-emitting layer further contains an electron transport material The light emitting element includes:

[0021] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0022] [ka]

[0023] However, in general formula (G1), R 1 ~R 8 are each independently hydrogen, hydrocarbons 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 hydroxyl ... halogens, haloalkyl groups having 1 to 6 carbon atoms, and substituted or unsubstituted alkyl groups having 6 to 60 carbon atoms. A represents one of the aromatic hydrocarbon groups. In addition, either A or B is the following general a group represented by formula (g1), and the other is hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, a carbon a hydrocarbon group having 1 to 6 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms; Represents one of the two.

[0024] [ka]

[0025] However, in the general formula (g1), Ar 1 , Ar 2 are each independently the number of substituted or unsubstituted carbon atoms. 6 to 60 aromatic hydrocarbon groups or groups represented by the following general formula (g2): And Ar 1 , Ar 2is an aromatic hydrocarbon group having 6 to 60 carbon atoms and having a substituent The substituents include benzonaphthofuranyl and dinaphthofuranyl groups.

[0026] [ka]

[0027] However, in general formula (g2), R 11 ~R 18 are each independently hydrogen, carbon atoms having 1 to 6 carbon atoms, a hydroxyl group, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group , halogen, haloalkyl groups having 1 to 6 carbon atoms, and substituted or unsubstituted haloalkyl groups having 6 to 6 carbon atoms. 0. Also, Z 1 and Z 2 Either one of them In the general formula (g1), the other is hydrogen, a cyclic carbon atom having 3 to 6 carbon atoms, and a hydrogen atom, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen atom, a halo group having 1 to 6 carbon atoms alkyl groups, hydrocarbon groups having 1 to 6 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms; represents any one of aromatic hydrocarbon groups.

[0028] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the group represented by the general formula (g1) is The organic compound is a group represented by the general formula (g3).

[0029] [ka]

[0030] However, in the general formula (g3), Ar 3 , Ar 4 are each independently substituted or unsubstituted carbon atoms. Aromatic hydrocarbon groups having a prime number of 6 to 60, substituted or unsubstituted benzonaphthofuranyl groups and substituted or an unsubstituted dinaphthofuranyl group. 5 , Ar 6 are respectively each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms; n and m independently represents 0 to 2. 3 and Ar 5 The number of carbon atoms in Ar 4 and Ar 6 The sum of the carbon numbers of these is 60 or less.

[0031] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 3 and Ar 4 are respectively Independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted Organometallic compounds containing substituted anthracenyl groups and either substituted or unsubstituted pyrenyl groups It is a mixture.

[0032] Alternatively, another aspect of the present invention is the above-mentioned structure, 5 and the Ar 6 But each independently, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted a substituted or unsubstituted anthracenylene group and a substituted or unsubstituted pyrenylene group; It is an organic compound.

[0033] Alternatively, another aspect of the present invention is the above-mentioned structure, 3 and the Ar 4 Gafe It is an organic compound that is a hydroxyl group.

[0034] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 5 and Ar 6Phenyle It is an organic compound that is a fluorine-based compound.

[0035] Alternatively, another aspect of the present invention is a method for manufacturing a semiconductor device according to the above configuration, wherein one of the n and the m is 1. It is an organic compound in which one atom is zero and the other is zero.

[0036] Alternatively, another embodiment of the present invention is a light-emitting device having an anode, a cathode, and an EL layer, a light-emitting element located between the electrode and the cathode, wherein the EL layer contains the organic compound having the above-described structure. .

[0037] Alternatively, another embodiment of the present invention is a light-emitting device having an anode, a cathode, and an EL layer, the EL layer has a light-emitting layer, and the light-emitting layer is provided with an organic layer having the above-described structure. The light-emitting device includes a compound.

[0038] Alternatively, another embodiment of the present invention is a light-emitting device according to the above structure, wherein the light-emitting layer further contains a light-emitting material. It is a light-emitting element.

[0039] Alternatively, in the above structure, another embodiment of the present invention is a light-emitting layer having an electron transport property. The light-emitting element includes a material that

[0040] Alternatively, another embodiment of the present invention is a light-emitting device having an anode, a cathode, and an EL layer, the EL layer has a light-emitting layer and a hole-transporting layer, and the hole-transporting layer is located between the electrode and the cathode. The layer is located between the light-emitting layer and the anode, and the hole transport layer is an organic compound having the above-mentioned structure. The light-emitting device includes a compound.

[0041] Alternatively, another embodiment of the present invention is a device having the above structure, wherein the EL layer further includes a hole injection layer. The hole injection layer is provided in contact with the anode and the hole transport layer, and the hole injection layer The light-emitting element includes an organic compound having acceptor properties.

[0042] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the present invention, wherein the organic compound having an acceptor property is The substance is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexa The light-emitting element is a triphenylene.

[0043] Alternatively, another embodiment of the present invention is a semiconductor device having the above structure, wherein the hole transport layer is a first layer, a second layer, a a first layer and a third layer, the first layer being located between the hole injection layer and the second layer; The third layer is located between the second layer and the light-emitting layer, and the first layer is the hole-injecting layer. the third layer is in contact with the light-emitting layer, and the first layer is in contact with a first hole transport layer. the second layer comprises the organic compound, and the third layer comprises a third hole transport material. the light-emitting layer includes a host material and a light-emitting material, and the HOMO level of the organic compound is the HOMO level of the first hole transport material is deeper than the HOMO level of the first hole transport material, and the HOMO level of the host material is a third level deeper than the HOMO level of the organic compound, The difference in HOMO levels of the hole transport material is 0.3 eV or less.

[0044] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a hole transporting material having a HOMO The light-emitting element has an energy level of -5.4 eV or higher.

[0045] Alternatively, in the above-mentioned configuration, the present invention provides a method for manufacturing a hole transporting material having a HOMO quasi-atomic structure. The difference between the HOMO level of the organic compound and the HOMO level of the organic compound is 0.3 eV or less.

[0046] Alternatively, in the above structure, another embodiment of the present invention is a method for forming a HOMO level of the organic compound. The difference in HOMO level between the third hole transport material and the light emitting device is 0.2 eV or less.

[0047] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a hole transporting material having a HOMO The difference between the energy level of the organic compound and the HOMO energy level of the organic compound is 0.2 eV or less.

[0048] Alternatively, in the above structure, another embodiment of the present invention is a semiconductor device in which the HOMO level of the light-emitting material is This is a light-emitting device having a HOMO level higher than that of the host material.

[0049] Alternatively, in the above structure, another embodiment of the present invention is a method for manufacturing a hole-transporting material having a HOMO The level is the same as or deeper than the HOMO level of the host material.

[0050] Alternatively, another aspect of the present invention is the above-described structure, wherein the light-emitting material is a fluorescent material. It is a light-emitting element.

[0051] Alternatively, in the above-described structure, the light emitted by the light-emitting material may be blue fluorescent light. It is a light-emitting element that emits light.

[0052] Alternatively, in the above-described structure, the light-emitting material may be a condensed aromatic diamine. The light-emitting device is a silicon compound.

[0053] Alternatively, in the above-described structure, another aspect of the present invention is a light-emitting material comprising a diaminopyrenated The light-emitting element is a compound.

[0054] Another embodiment of the present invention is a light-emitting element having any of the above structures, a transistor, or a substrate. The light emitting device has:

[0055] Another embodiment of the present invention is a light-emitting device having the above structure, a sensor, an operation button, a switch, and a light-emitting element. It is an electronic device having a speaker or a microphone.

[0056] Another embodiment of the present invention is a lighting device including a light-emitting device having the above structure and a housing. It is a location.

[0057] In this specification, the term "light-emitting device" includes an image display device using a light-emitting element. In addition, a connector, such as an anisotropic conductive film or TCP (Tape Carrier), is attached to the light emitting element. The module has a printed wiring board at the end of the TCP. The COG (Chip On Glass) method is used for the module or light emitting element. A module on which an IC (integrated circuit) is directly mounted may also be included in the light emitting device. , lighting fixtures, etc. may include a light-emitting device. [Effects of the Invention]

[0058] According to one embodiment of the present invention, a novel light-emitting element can be provided. Alternatively, a light-emitting element having good luminous efficiency can be provided. Alternatively, the present invention can provide a novel organic compound. In this manner, a novel organic compound having hole transport properties can be provided. One aspect can provide a novel hole transport material.

[0059] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. In another embodiment of the present invention, a light-emitting device with low power consumption can be provided. An electronic device and a display device can each be provided.

[0060] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0061] [Figure 1] Schematic diagram of a light-emitting element. [Figure 2] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 3] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 4] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 5] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 6] FIG. [Figure 7] 1 is a diagram showing an electronic device. [Figure 8] FIG. [Figure 9] FIG. [Figure 10] FIG. [Figure 11] FIG. 2 is a diagram illustrating an in-vehicle display device and an illumination device. [Figure 12] 1 is a diagram showing an electronic device. [Figure 13] 1 is a diagram showing an electronic device. [Figure 14] 1H NMR chart of BnfABP. [Figure 15] Absorption and emission spectra of BnfABP solution. [Figure 16] Absorption and emission spectra of thin films of BnfABP. [Figure 17]1H NMR chart of BBABnf. [Figure 18] Absorption and emission spectra of BBABnf solutions. [Figure 19] Absorption and emission spectra of thin films of BBABnf. [Figure 20] FIG. 10 shows luminance-current density characteristics of Light-emitting Element 1. [Figure 21] FIG. 10 shows current efficiency vs. luminance characteristics of Light-emitting Element 1. [Figure 22] FIG. 10 is a graph showing luminance-voltage characteristics of the light-emitting element 1. [Figure 23] FIG. 2 is a graph showing current-voltage characteristics of the light-emitting element 1. [Figure 24] FIG. 10 is a graph showing external quantum efficiency vs. luminance characteristics of the light-emitting element 1. [Figure 25] FIG. 2 shows an emission spectrum of the light-emitting element 1. [Figure 26] FIG. 10 is a graph showing normalized luminance vs. time change characteristics of the light-emitting element 1. [Figure 27] FIG. 10 shows luminance-current density characteristics of Light-emitting Elements 2 and 3. [Figure 28] 10 is a graph showing current efficiency-luminance characteristics of Light-emitting Elements 2 and 3. FIG. [Figure 29] FIG. 10 shows luminance-voltage characteristics of Light-emitting Elements 2 and 3. [Figure 30] 10 is a graph showing current-voltage characteristics of Light-emitting Elements 2 and 3. FIG. [Figure 31] 10 is a graph showing external quantum efficiency-luminance characteristics of Light-emitting Elements 2 and 3. FIG. [Figure 32] 10 shows emission spectra of Light-Emitting Elements 2 and 3. FIG. [Figure 33] 10 is a graph showing normalized luminance versus time change characteristics of the light-emitting element 2 and the light-emitting element 3. FIG. [Figure 34] 1A to 1C are cross-sectional views illustrating a method for forming an EL layer. [Figure 35] FIG. 1 is a conceptual diagram illustrating a droplet ejection device. [Figure 36] 1H NMR chart of BBABnf(6). [Figure 37]Absorption and emission spectra of BBABnf(6) solution. [Figure 38] Absorption and emission spectra of thin films of BBABnf(6). [Figure 39] 1H NMR chart of BBABnf(8). [Figure 40] Absorption and emission spectra of BBABnf(8) solution. [Figure 41] Absorption and emission spectra of thin films of BBABnf(8). [Figure 42] FIG. 10 shows luminance-current density characteristics of Light-emitting Elements 4 and 5. [Figure 43] 10 is a graph showing current efficiency-luminance characteristics of Light-emitting Elements 4 and 5. FIG. [Figure 44] FIG. 10 shows luminance-voltage characteristics of Light-emitting Elements 4 and 5. [Figure 45] 10 is a graph showing current-voltage characteristics of Light-emitting Elements 4 and 5. FIG. [Figure 46] 10 is a graph showing external quantum efficiency-luminance characteristics of Light-emitting Elements 4 and 5. FIG. [Figure 47] FIG. 10 shows emission spectra of Light-emitting Elements 4 and 5. [Figure 48] FIG. 10 is a graph showing normalized luminance versus time change characteristics of the light-emitting elements 4 and 5. [Figure 49] FIG. 10 is a graph showing luminance-current density characteristics of Light-emitting Elements 6 and 7. [Figure 50] 10 is a graph showing current efficiency-luminance characteristics of Light-emitting Elements 6 and 7. FIG. [Figure 51] FIG. 10 is a graph showing luminance-voltage characteristics of the light-emitting elements 6 and 7. [Figure 52] 10 is a graph showing current-voltage characteristics of the light-emitting elements 6 and 7. FIG. [Figure 53] 10 is a graph showing external quantum efficiency-luminance characteristics of the light-emitting elements 6 and 7. FIG. [Figure 54] FIG. 10 shows emission spectra of the light-emitting elements 6 and 7. [Figure 55] FIG. 10 is a graph showing luminance-current density characteristics of the light-emitting element 8. [Figure 56]10 is a graph showing current efficiency vs. luminance characteristics of the light-emitting element 8. [Figure 57] FIG. 10 is a graph showing luminance-voltage characteristics of the light-emitting element 8. [Figure 58] 10 is a graph showing current-voltage characteristics of the light-emitting element 8. FIG. [Figure 59] 10 is a graph showing the external quantum efficiency vs. luminance characteristics of the light-emitting element 8. FIG. [Figure 60] FIG. 10 is a graph showing an emission spectrum of the light-emitting element 8. [Figure 61] 10 is a graph showing normalized luminance vs. time change characteristics of the light-emitting element 8. FIG. DETAILED DESCRIPTION OF THE INVENTION

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

[0063] (Embodiment 1) In the case of light-emitting elements that use organic materials, there are various factors that affect their lifespan. However, the properties of the hole transport material may have a particularly large effect. The transport properties of the transport material have a large effect, and the lifetime varies greatly depending on the type of hole transport material. come out.

[0064] Here, the present inventors have investigated the relationship between a substituted or unsubstituted benzonaphthofuran skeleton and a substituted or unsubstituted benzonaphthofuran skeleton. The hole transporting material containing an organic compound having a substituted amine skeleton has suitable transporting properties, and It has been found that the lifetime of a light-emitting device using a hole transport material is improved.

[0065] In particular, a substituted or unsubstituted amine skeleton is attached to a substituted or unsubstituted benzonaphthofuran skeleton. The hole transport material preferably contains an organic compound having one of the benzophenone groups. The naphthofuran skeleton of organic compounds with benzo[b]naphtho[1,2-d]furan skeleton is highly It is more preferable that the amine skeleton is benzo[b]na. Hole transport materials containing organic compounds bonded to the 6- or 8-position of the futo[1,2-d]furan skeleton The price is even more appropriate.

[0066] In addition, the nitrogen of the amine skeleton is directly bonded to the benzonaphthofuran skeleton without a substituent. The hole transport material containing the compound can provide a light-emitting device with high reliability, and the HOMO The hole transport material is preferably a hole transport material having an appropriate level. The organic compound contains a compound in which the nitrogen is directly bonded to the benzonaphthofuran skeleton without a substituent, resulting in high This is preferable because it can provide a hole transport material that exhibits good hole transport properties and can provide a light emitting device that operates at a low voltage. It's nice.

[0067] A light-emitting element using such a hole transport material in the EL layer has a long life. can be done.

[0068] FIG. 1 shows a diagram illustrating a light-emitting element according to one embodiment of the present invention. 101, a cathode 102, and an EL layer 103, and the EL layer contains the above-mentioned organic compound. Transport materials are used.

[0069] The EL layer 103 includes a light-emitting layer 113 and may include a hole-transporting layer 112. The light-emitting layer 113 contains a light-emitting material and a host material, and the light-emitting element of one embodiment of the present invention is The light-emitting layer 113 emits light. It does not matter whether the compound is contained in the hole transport layer 112 or in the hole transport layer 113.

[0070] In addition to these, FIG. 1 also shows a hole injection layer 111, an electron transport layer 114, and an electron injection layer 115. However, the configuration of the light emitting element is not limited to this.

[0071] The hole transport material can also be used as a host material. By co-evaporating the electron transport material with the hole transport material, an exciplex is formed. By forming an exciplex having an appropriate emission wavelength, the luminescence By realizing effective energy transfer to optical materials, we have been able to provide light-emitting devices with high efficiency and long life. It will be possible to provide

[0072] In addition, the hole transport material has good hole transport properties, so it can be used for the hole transport layer 112. In particular, the hole injection layer 111 is provided between the hole transport layer 112 and the anode 101. The hole injection layer 111 is provided with an organic compound having an acceptor property that facilitates hole injection from the electrode. This is preferable when a mixture is used.

[0073] When hole injection is performed using an organic compound having acceptor properties, the hole injection layer 111 is The compound contained in the hole transport layer 112 is an organic compound having an acceptor property. To facilitate electron extraction, the hole transport material is preferably one with a relatively shallow HOMO level. However, a hole transport material with a shallow HOMO level makes it difficult to inject holes into the light-emitting layer 113. Therefore, the hole transport layer 112 made of such a hole transport material with a shallow HOMO level is When the light emitting layer 113 is formed in contact with the semiconductor layer 111, carriers are accumulated at the interface, and the light emitting element Therefore, the layer containing the organic compound according to one embodiment of the present invention is between the hole transport material having a shallow HOMO level and the light emitting layer 113, This enables smooth hole injection, improving the lifespan and efficiency of light-emitting devices. .

[0074] That is, the hole transport layer 112 is formed from the hole injection layer 111 side to the first hole transport layer 112-1 and a second hole transport layer 112-2, the first hole transport layer comprising a first hole transport material the second hole transport layer contains the hole transport material according to one embodiment of the present invention; In one embodiment, the HOMO level of the hole transport material is deeper than the HOMO level of the first hole transport material. The optical element can be a light-emitting element having a long life and good efficiency. When the HOMO level of is -5.4 eV or higher, it is possible to obtain electrons from organic compounds with acceptor properties. This is a preferable configuration because electrons can be easily extracted.

[0075] In addition, the HOMO level of the first hole transport material and the HOMO level of the hole transport material of the present invention are The difference is preferably 0.3 eV or less, more preferably 0.2 eV or less, in the first hole transport layer. This is preferable because it facilitates the injection of holes from the first hole transport layer 112-1 to the second hole transport layer 112-2. It is a composition.

[0076] In addition, the hole transport layer 112 further includes a third hole transport layer 112-2 between the second hole transport layer 112-2 and the light emitting layer. The third hole transport layer 112-3 has a third hole transport In this case, the third hole transport material has a HOMO level is the HOMO quasi-atomic atom of the hole transport material of one embodiment of the present invention contained in the second hole transport layer 112-2. The difference is preferably 0.3 eV or less, more preferably 0.2 eV or less. It is preferable that:

[0077] The HOMO level of the third hole transporting material is the same as the HOMO level of the host material, or The deeper the third hole transport material is, the more holes are transported into the light-emitting layer. This results in a longer life and a better efficiency, making this a more preferable configuration.

[0078] In addition, the HOMO level of the light-emitting material is shallower (higher) than the HOMO level of the host material. In this case, depending on the position of the HOMO level of the hole transport layer, the proportion of holes injected into the light-emitting material may be high. Furthermore, holes are trapped in the light-emitting material, which shortens the lifespan due to the bias of the light-emitting region. In such a case, the configuration of the light-emitting device of the present invention is preferably applied. A blue fluorescent element is an example of a device that is likely to have this configuration. Aromatic diamine compounds, especially pyrenediamine compounds, which emit good blue fluorescence, are suitable. The configuration of the present invention can be particularly preferably applied to light-emitting devices having excellent lifespan, efficiency, and chromaticity. can be obtained.

[0079] Next, examples of the detailed structure and materials of the light-emitting element will be described. As described above, the optical element is an EL device having a plurality of layers between a pair of electrodes, an anode 101 and a cathode 102. The EL layer 103 has a hole injection layer 111 and a hole injection layer 112 at least from the anode 101 side. It includes a hole transport layer 112 and a light emitting layer 113 .

[0080] The other layers included in the EL layer 103 are not particularly limited, and may include a hole injection layer, a hole transport layer, and the like. layer, electron transport layer, electron injection layer, carrier blocking layer, exciton blocking layer, charge generation layer, etc. , various layer structures can be applied.

[0081] The anode 101 is made of a metal, alloy, or conductive compound having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a material such as a material containing fluorine, a compound ... Indium tin oxide (ITO), silicon or Indium oxide-tin oxide, indium oxide-zinc oxide, oxide containing silicon oxide Examples include indium oxide containing tungsten and zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they can also be formed by methods such as sol-gel deposition. As an example of the manufacturing method, indium oxide-zinc oxide Sputtering was performed using a target containing 1 to 20 wt% zinc oxide added to indium oxide. Also, there are methods for forming the film by the ring method. Indium oxide (IWZO) is a material that is made by mixing tungsten oxide with indium oxide at a ratio of 0.5 to 5. % by weight and zinc oxide 0.1-1 wt% by sputtering. Other materials include gold (Au), platinum (Pt), nickel (Ni), and titanium. W, chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co) , copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride), etc. Graphene can also be used. By using it as a layer in contact with the anode 101 in 3, the electrode material can be selected regardless of the work function. You will be able to do this.

[0082] In this embodiment, the stacked structure of the EL layer 103 is as shown in FIG. In addition to the injection layer 111, the hole transport layer 112, and the light emitting layer 113, an electron transport layer 114 and an electron injection layer 1B, the hole injection layer 111 and the hole transport layer 115 are formed. 112, the light-emitting layer 113, the electron transport layer 114, the electron injection layer 115, the charge generation layer 1 Two types of structures having 16 will be explained. The materials constituting each layer are as follows: Let me show you in detail.

[0083] The hole-injection layer 111 is a layer containing a substance having an acceptor property. In this case, the structure is more suitable for application when an organic compound having acceptor properties is used. Organic compounds with acceptor properties include those containing electron-withdrawing groups (halogen groups and cyano groups). Compounds having the formula 7,7,8,8-tetracyano-2,3,5,6 ... Trifluoroquinodimethane (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) can be used. As an organic compound having acceptor properties, HAT-C Compounds in which electron-withdrawing groups are bonded to condensed aromatic rings containing multiple heteroatoms such as N are thermally The organic compound having acceptor property is preferably a hole-transporting layer (or a Electrons can be extracted from the hole transport material by applying an electric field.

[0084] When an organic compound having acceptor properties is not used in the hole injection layer 111, Examples of materials that have this property include molybdenum oxide, vanadium oxide, ruthenium oxide, and tungsten oxide. Stenoxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviated as Phthalocyanine compounds such as phthalocyanine (H2Pc) and copper phthalocyanine (CuPC), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D Aromatic amine compounds such as NTPD, or poly(3,4-ethylenedioxythiophene) Hole injection is also possible using polymers such as PEDOT / PSS. An insulating layer 111 can be formed.

[0085] In addition, the hole-injecting layer 111 may be formed by adding an acceptor substance to a substance having a hole-transporting property. A composite material containing an acceptor substance can also be used. By using a composite material with this structure, it is possible to select a material for forming the electrode regardless of the work function. That is, the anode 101 can be made of not only a material with a large work function but also a material with a small work function. The acceptor material can also be used. Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ) , chloranil, 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodime Acceptor organic compounds such as tungstate (abbreviated as F6-TCNNQ) and transition metal oxides In addition, the oxidation of metals belonging to groups 4 to 8 in the periodic table can be mentioned. Oxides of metals belonging to groups 4 to 8 of the periodic table can also be used. Examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, and oxide. Tungsten oxide, manganese oxide, rhenium oxide, etc. are preferred because of their high electron-accepting properties. However, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. It's nice.

[0086] As hole transporting substances used in the composite material, aromatic amine compounds and carbazole derivatives are , aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. The following organic compounds can be used as hole transporting substances for the composite material: , 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. The organic compounds that can be used as hole transporting substances in the composite material are specifically listed below. Raise.

[0087] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl) )-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl Carbazole derivatives Specific examples of the compound include 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl]carbazol-3-yl ... Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol PCzPCA2 (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1 ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri bis[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenylanthracen-9-yl)phenyl]-9H-carbazole (abbreviation: CzP A), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetrafluoroethylene Examples of aromatic hydrocarbons that can be used include 2-tert-butylphenylbenzene. t-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 Helical anthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7 -Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) 10,10'-bis[(2,3,4,5,6-pentanthryl Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene , perylene, 2,5,8,11-tetra(tert-butyl)perylene, and the like. In addition, pentacene, coronene, etc. can also be used. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2, 2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2, 2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc. Note that the organic compound of one embodiment of the present invention can also be used. As the reactive substance, it is preferable to use F6-TCNNQ.

[0088] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl) PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine] N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. Cut.

[0089] By forming a hole injection layer, the hole injection property is improved, and light emission with a low driving voltage is possible. It is possible to obtain the element.

[0090] The hole injection layer is formed by using the above-mentioned acceptor material alone or by mixing it with other materials. In this case, the acceptor material extracts electrons from the hole transport layer and deposits holes in the hole transport layer. The acceptor material transports the extracted electrons to the anode.

[0091] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. Furthermore, organic compounds having acceptor properties can be easily vapor deposited. It is an easy material to use because it is easy to form a film.

[0092] The hole transport layer 112 is formed by containing a hole transport material. 0 -6 cm 2 It is preferable that the hole transport layer 112 has a hole mobility of 1 / Vs or more. It is preferable that the hole transport material of one aspect of the present invention is contained. By including a transport material in the hole transport layer 112, a light emitting element with a long life and good efficiency can be obtained. It is possible.

[0093] In particular, when an organic compound having acceptor properties is used as the hole injection layer 111, at least In both cases, the hole injection layer 111 is formed of two layers, a first hole transport layer and a second hole transport layer. The hole transport layer is made of a first hole transport material with a relatively shallow HOMO level, and the second hole transport layer is made of a By using a structure including a hole transport material according to one embodiment of the present invention, it is possible to achieve a long life and high efficiency. A light emitting element can be obtained.

[0094] The LUMO level of the organic compound with acceptor properties and the HOMO level of the first hole transport material The difference depends on the acceptor strength of the organic compound, so Although not limited thereto, holes can be injected if the difference in level is approximately 1 eV or less. When HAT-CN is used as an organic compound having acceptor properties, The LUMO level of is estimated to be -4.41 eV from cyclic voltammetry measurements. The HOMO level of the first hole transport material is preferably −5.4 eV or higher. However, if the HOMO level of the first hole transport material becomes too high, the second hole The hole injection into the transport material becomes poor. Also, the work function of the anode, such as ITO, is around -5 eV. Therefore, it is disadvantageous to use a first hole transport material with a higher HOMO level. Therefore, the HOMO level of the first hole transport material must be −5.0 eV or less. is preferred.

[0095] Furthermore, 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.

[0096] The first hole transport layer, the second hole transport layer, and the third hole transport layer have been described above. Therefore, repeated explanations will be omitted. The hole transporting material may be selected from the materials having hole transporting properties mentioned above or from various other materials having hole transporting properties. It is only necessary to select and use a material that matches the relationship between the layers from among the materials that can be used.

[0097] The light-emitting layer 113 is a layer containing a host material and a light-emitting material. Whether it is a phosphorescent material or a material that exhibits thermally activated delayed fluorescence (TADF), Furthermore, even if the layer is a single layer, different light-emitting materials may be included. Note that in one embodiment of the present invention, the light-emitting layer 113 may be a fluorescent layer. This is particularly suitable for use in a layer that emits blue fluorescent light. Cut.

[0098] In the light-emitting layer 113, materials that can be used as fluorescent materials include, for example: Examples include the following: Other fluorescent materials can also be used.

[0099] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene] N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPr n), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'- Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carba 4'-(10-phenyl-9-anthryl)triphenylamine ( Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-difluoromethyl) (phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo Perylene, 2,5,8,11-tetra-tert- -butylperylene (TBP), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA PA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4, 1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2 -anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA) , N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'- Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N', N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chryse N-(9,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, 10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3- Amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)] [N,9-diphenyl-9H-carbazol-3-amine (abbreviated as 2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine] :2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N '-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,1 0-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-t Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl] N,N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), ,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA) Coumarin 545 T,N,N'-Diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bi Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl 6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizidine] 4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitri (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetramethyl- tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi N,N'-diphenyl-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphthyl) 1,6BnfAPrn-03, etc. In particular, 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6Bn Condensed aromatic diamine compounds, such as pyrenediamine compounds like fAPrn-03 is preferable because it has a high hole trapping property, and is excellent in luminous efficiency and reliability.

[0100] In the light-emitting layer 113, materials that can be used as phosphorescent materials include, for example: The following are some examples:

[0101] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl Iridium(III) (abbreviation: [Ir(Mpt z)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3 b) Organometallic iridium complexes with a 4H-triazole skeleton, such as 3), and tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazol- Zolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1 -methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(PrptZ1-Me)3]) Organometallic iridium complexes with fac-tris[(1-2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimide Dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp and organometallic iridium complexes having an imidazole skeleton, such as impt-Me)3). Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4' ,6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) picolinate bis(2-[3',5'-bis(trifluoromethyl) fluoride] (abbreviation: FIrpic), Phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri[ Ginat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIraca c) Organometallic iridates with phenylpyridine derivatives having electron-withdrawing groups as ligands These are compounds that exhibit blue phosphorescence, with wavelengths from 440 nm to It is a compound that has an emission peak at 520 nm.

[0102] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm)3), (acetylacetonato)bis(Ir(tBuppm)3) (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl] [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm)2(acac)]) Organic metal iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Rupirazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Dinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzyl) Tribenzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetone Pyridine skeleton-containing compounds such as setonate (abbreviation: [Ir(pq)2(acac)]) In addition to organometallic iridium complexes, tris(acetylacetonato)(monophenanthroline)tetrahydrogen Rare earth metals such as rubium(III) (abbreviated as [Tb(acac)3(Phen)]) These are mainly compounds that exhibit green phosphorescence, with wavelengths ranging from 500 nm to 6 The emission peak is at 100 nm. The body is particularly preferred because it is remarkably excellent in reliability and luminous efficiency.

[0103] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organogold compounds with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] iridium complexes of the genus acetylacetonatobis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(tppr)2(dpm])]), (acetylacetonato)bis[2,3-bis(acetylacetonato) [Ir(F Organometallic iridium complexes having a pyrazine skeleton, such as dpq)2(acac)]), Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (I II) Pyrithiol, such as acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with an iridinium skeleton, 2,3,7,8,12,13,17,1 8-Octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monof (Phenanthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]) , tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monofena (Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence, and It has an emission peak between 00 nm and 700 nm. The iridium complex emits red light with good chromaticity.

[0104] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting materials may be selected and used. stomach.

[0105] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium, etc. can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. Examples of the metal-containing porphyrin include: For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiop Porphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -platinum chloride complex (PtCl2OEP) and the like.

[0106] [ka]

[0107] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4-phenyl-4-methyl-4-phenyl ... (phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl phenyl]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT zn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-difluoro Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1, 2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-azabicyclo[4.2.1.2]phenyl) cridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[ 4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9 π-electron-rich heteroaromatic rings such as '-anthracene]-10'-one (abbreviation: ACRSA) A heterocyclic compound having both a π-electron-deficient heteroaromatic ring and a π-electron-deficient heteroaromatic ring can also be used. The compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, and therefore has electron transport properties. The π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring are preferable. The substance in which the heteroaromatic ring is directly bonded exhibits the donor property of the π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring. The acceptor properties of the heteroaromatic rings become stronger, and the energy difference between the S1 and T1 levels becomes smaller. Therefore, it is particularly preferable since thermally activated delayed fluorescence can be efficiently obtained. Instead of the toe-shaped heteroaromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used. stomach.

[0108] [ka]

[0109] The host material of the light-emitting layer may be a material having electron transport properties or a material having hole transport properties. A variety of carrier transport materials can be used.

[0110] As a material having hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-phenyl] N,N'-bis(3-methylphenyl)-N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylalanine 4-phenyl-4'-(9-phenylfluorene)biphenyl (abbreviation: BSPB), -9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- (phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-fluoren-9-yl Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine ( PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-chlor PCBBi1BP, 4-(1-naphtho-3-yl)triphenylamine (9-phenyl-9H-carbazol-3-yl)-4'-triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9 H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-di Methyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] N-phenyl-N-[4-( 9-phenyl-9H-carbazol-3-yl)phenyl]-spiro-9,9'-bifluor Compounds with aromatic amine skeletons such as PCBASF (dichlorobenzofuran), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)bis(3,6-diphenylbenzoyl)biphenyl (abbreviation: CBP) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H -carbazole (abbreviated as PCCP), and ',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene phenyl-9-yl)dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds with a thiophene skeleton, such as thiophene (abbreviated as DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)fluorene phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan skeletons Among the above, compounds having an aromatic amine skeleton and Compounds having a rubazole skeleton have good reliability, high hole transport properties, and are easy to drive. This is preferable because it also contributes to voltage reduction.

[0111] Examples of materials having electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nat)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato) )(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8- Quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) phenolato]zinc(II) (abbreviation: ZnBTZ) and other metal complexes, (4-tert-butylphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation :PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) phenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5 -benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TP BI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H -benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl 4,6-[(2-yl)-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq) -Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation Heterocyclic compounds with diazine skeletons such as 3,5 -Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCz PPy), 1,3,5-tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: Tm PyPB) and other heterocyclic compounds having a pyridine skeleton. Heterocyclic compounds with an azine skeleton and heterocyclic compounds with a pyridine skeleton have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are The electron transport property is high, and this contributes to reducing the driving voltage.

[0112] When a fluorescent substance is used as the light-emitting material, the host material is a compound having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used in this way, it is possible to realize a light-emitting layer having good luminous efficiency and durability. Many materials having a Csene skeleton have a deep HOMO level, and therefore, one embodiment of the present invention is preferably applied to The substance having an anthracene skeleton used as the host material can be Substances with a phenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, It is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, This is preferable because it improves the hole injection and transport properties, but the benzene ring is further condensed to the carbazole. When the benzocarbazole skeleton is included, the HOMO is shallower than that of carbazole by about 0.1 eV. This is particularly preferable since the host material is dibenzocarbazoline. When a carbazole skeleton is included, the HOMO is shallower than that of carbazole by about 0.1 eV, and holes can enter. This is preferable because it makes it easier to attach the film, has excellent hole transport properties, and has high heat resistance. Further, preferred host materials include those having a 9,10-diphenylanthracene skeleton and Carbazole skeleton (or benzocarbazole skeleton or dibenzocarbazole skeleton) From the viewpoint of the hole injection and transport properties mentioned above, it is desirable to use a carbazole skeleton. Alternatively, a benzofluorene skeleton or a dibenzofluorene skeleton may be used. Examples of substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] 3-[4-(1-naphthyl)-phenyl]-9H-carbazole (abbreviation: PCzPA), 9-[4-(10-phenyl)-9H-carbazole (abbreviation: PCPN), (9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7- [4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbamate BAZOLE (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracene) (aryl)phenyl)-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA ), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl {4'-yl}anthracene (abbreviation: FLPPA), etc. In particular, CzPA , cgDBCzPA, 2mBnfPPA, and PCzPA show very good properties and are therefore preferred. This is a good choice.

[0113] Note that the light-emitting element of one embodiment of the present invention is particularly applicable to a light-emitting element that emits blue fluorescent light. It is preferable that:

[0114] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transport property with a material having a hole transport property. Therefore, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The ratio of the content of the material having hole transport properties to the content of the material having electron transport properties can be The ratio of the material having electron transport properties to the material having electron transport properties may be 1:9 to 9:1.

[0115] Furthermore, these mixed materials may form an exciplex. The exciplex is formed to emit light that overlaps with the wavelength of the lowest energy absorption band of By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage is reduced.

[0116] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the electron-transporting material include those listed as the materials having electron-transporting properties that can be used as the host material. can be used.

[0117] Between the electron transport layer 114 and the cathode 102, an electron injection layer 115 containing lithium fluoride (Li Alkali such as iF, cesium fluoride (CsF), calcium fluoride (CaF2), etc. A layer containing a metal, an alkaline earth metal, or a compound thereof may be provided. 5 is a layer made of a substance having an electron transporting property, in which an alkali metal or alkaline earth metal or A material containing these compounds or an electride may also be used. For example, a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum is Examples include:

[0118] In addition, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and electrons are generated in the layer in contact with the anode side. The charge generation layer 116 is a layer that can inject electrons into the layer adjacent to it. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer 1 using the composite material mentioned above as a material that can be used. 17 is a film containing the above-mentioned acceptor material and a hole transport material as materials constituting a composite material. By applying a potential to the P-type layer 117, electrons Electrons are injected into the transport layer 114 and holes are injected into the cathode 102, which is the negative electrode, and the light-emitting element operates.

[0119] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117. Preferably, one or both of layers 119 are provided.

[0120] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO level in the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0121] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate) Alkaline earth metal compounds (including carbonates such as titanium and cesium carbonate), alkaline earth metal compounds (oxides, halogens compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties, such as SiO 2 .

[0122] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. When the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates) In addition to tetrathianaphthacene (abbreviated as TTN), nickelocene, decamethicone, An organic compound such as nickelocene can also be used. The electron transport layer 114 may be formed using the same material as that used for forming the electron transport layer 114 described above. This can be done.

[0123] The material for forming the cathode 102 is gold, which has a small work function (specifically, 3.8 eV or less). Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). , and elements such as magnesium (Mg), calcium (Ca), and strontium (Sr) Elements belonging to Group 1 or 2 of the periodic table and alloys containing these elements (MgAg, AlL i), europium (Eu), ytterbium (Yb), and other rare earth metals, and However, an electron injection layer may be provided between the cathode 102 and the electron transport layer. By providing this, regardless of the magnitude of the work function, Al, Ag, ITO, silicon or oxide Various conductive materials such as silicon dioxide-containing indium oxide-tin oxide can be used as the cathode 102. You can be there. These conductive materials can be applied by dry methods such as vacuum deposition and sputtering, inkjet printing, It is possible to form the film using a spin coating method, etc. Also, it is possible to form the film using a wet sol-gel method. Alternatively, the metal layer may be formed by a wet method using a paste of a metal material.

[0124] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method, or the like may also be used.

[0125] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0126] The structure of the layer provided between the anode 101 and the cathode 102 is not limited to the above. However, the proximity of the light-emitting region to the metals used in the electrodes and carrier injection layer In order to suppress quenching caused by the hole It is preferable to provide a light-emitting region where the electrons recombine with the cathode.

[0127] Furthermore, recombination in the hole transport layer or electron transport layer in contact with the light-emitting layer 113, particularly in the light-emitting layer 113 The carrier transport layer close to the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material that constitutes the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material be made of a substance having a band gap larger than the band gap of the material. I wish.

[0128] Next, we will introduce light-emitting devices (such as stacked devices and tandem devices) that have a structure in which multiple light-emitting units are stacked. The embodiment of the light-emitting element (also referred to as a "light-emitting element") will be described with reference to FIG. 1(C). The light-emitting element has a plurality of light-emitting units between them. 1(C) has a structure similar to that of the EL layer 103 shown in FIG. The element is a light-emitting element having a plurality of light-emitting units, and is the light-emitting element shown in FIG. 1(A) or FIG. 1(B). An optical element can be said to be a light-emitting element having one light-emitting unit.

[0129] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between the anode 501 and the cathode 502. The second light-emitting unit 512 is stacked, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the anode 101 and the cathode 102 in FIG. 1(A), respectively, and are described in the explanation of FIG. 1(A). The same as that used for the first light-emitting unit 511 and the second light-emitting unit 512 can be applied. The optical units 512 may be of the same or different construction.

[0130] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting The electron-injecting unit has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. In 1(C), when a voltage is applied so that the anode potential is higher than the cathode potential, In this case, the charge generating layer 513 injects electrons into the first light-emitting unit 511 and Any material capable of injecting holes into the gate 512 may be used.

[0131] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1B. The composite material of an organic compound and a metal oxide has the properties of carrier injection, carrier transport, and the like. It has excellent electrical properties, making it possible to achieve low voltage and low current driving. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 is the light emitting unit. Since it can also function as a hole injection layer for the light-emitting unit, the light-emitting unit does not need to have a hole injection layer. Both are good.

[0132] In addition, when the electron injection buffer layer 119 is provided, the electron injection buffer layer 119 is Since it plays the role of an electron injection layer in the light-emitting unit of the anode side, There is no need to form an electron injection layer.

[0133] Although the light-emitting element having two light-emitting units has been described in FIG. 1C, a light-emitting element having three or more light-emitting units may be used. The present invention can be similarly applied to a light-emitting element in which light-emitting units are stacked. As in the case of the light-emitting element according to the embodiment, a plurality of light-emitting units are disposed between a pair of electrodes, and a charge generating layer 513 By separating the layers, high brightness light emission is possible while keeping the current density low. It is possible to realize a long-life element. It is also possible to realize a light-emitting device that can be driven at a low voltage and consumes little power. It is possible.

[0134] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole For example, a light-emitting element having two light-emitting units can be In this case, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. This makes it possible to obtain a light-emitting element that emits white light as a whole.

[0135] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer and the electrodes can be formed by, for example, a vapor deposition method (including a vacuum deposition method), a droplet discharge method (including an ink jet method), or the like. It can be formed by using methods such as ink jet printing, coating, and gravure printing. They can be used in a variety of applications, including low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and or polymeric material.

[0136] Here, a method for forming the EL layer 786 by droplet discharge will be described with reference to FIG. 34A to 34D are cross-sectional views illustrating a method for manufacturing the EL layer 786. do.

[0137] First, a conductive film 772 is formed over a planarization insulating film 770. An insulating film 730 is formed on the insulating film 730 (see FIG. 34(A)).

[0138] Next, droplets are discharged from a droplet discharge device 783 onto the exposed portions of the conductive film 772, which are openings in the insulating film 730. The droplets 784 are ejected to form a layer 785 containing the composition. The conductive film 772 is attached to the conductive film 772 (see FIG. 34B).

[0139] The step of discharging the droplets 784 may be performed under reduced pressure.

[0140] Next, the solvent is removed from the layer 785 containing the composition, and the layer is solidified to form an EL layer 786. (See Figure 34(C)).

[0141] The solvent may be removed by a drying step or a heating step.

[0142] Next, a conductive film 788 is formed on the EL layer 786 to form a light-emitting element 782 (FIG. 34(D) )reference).

[0143] In this way, when the EL layer 786 is formed by the droplet discharge method, the composition can be selectively discharged. This reduces material waste. Since no additional steps are required, the process can be simplified and costs can be reduced.

[0144] The droplet discharge method described above is a method using a nozzle having a discharge port for discharging the composition, or one or more This is a general term for anything that has a means for ejecting droplets, such as a head with multiple nozzles.

[0145] Next, a droplet discharge device used in the droplet discharge method will be described with reference to FIG. FIG. 14 is a conceptual diagram illustrating a droplet ejection device 1400.

[0146] The droplet discharge device 1400 has a droplet discharge means 1403. has a head 1405 , a head 1412 , and a head 1416 .

[0147] The head 1405, the head 1412, and the head 1416 are connected to a control means 1407, It is controlled by the computer 1410 to produce a pre-programmed pattern. Can be drawn.

[0148] The timing of drawing may be, for example, the timing of the marker 14 formed on the substrate 1402. Alternatively, the reference point may be determined based on the outer edge of the substrate 1402. Here, the marker 1411 is detected by the imaging means 1404, and the image processing means 14 The signal converted to a digital signal by 09 is recognized by computer 1410 and a control signal is generated. and sends it to the control means 1407.

[0149] The imaging means 1404 may be a charge coupled device (CCD) or a complementary metal oxide semiconductor (CMO An image sensor using a photodiode (S) can be used. The information on the pattern to be processed is stored in the storage medium 1408. and sends a control signal to the control means 1407, and controls the individual heads 1405 of the droplet discharging means 1403. The head 1412 and the head 1416 can be controlled individually. The material supply source 1413, the material supply source 1414, and the material supply source 1415 are supplied to the head 1 through piping. 405, head 1412, and head 1416, respectively.

[0150] The inside of the head 1405 is a space filled with a liquid material as shown by the dotted line 1406, and a discharge space. Although not shown, the head 1412 and the head 14 The head 1405 and the head 1412 have the same internal structure. By providing different sizes of nozzles, different materials can be imaged at different widths simultaneously. A single head can eject and print multiple types of luminescent materials, allowing for wide-area printing. When drawing on a large area, the same material is ejected simultaneously from multiple nozzles to improve throughput. When a large substrate is used, the head 1405, the head 1412, The head 1416 freely scans the substrate in the directions of the X, Y, and Z arrows shown in FIG. 35, and draws. The area to be marked can be freely set, and the same pattern can be drawn multiple times on one board. can be done.

[0151] The step of discharging the composition may be carried out under reduced pressure. After the composition is discharged, one or both of the steps of drying and baking are carried out. The steps of drying and baking are Both processes involve heat treatment, but the purpose, temperature and time are different. The firing process is carried out under normal pressure or reduced pressure by laser light irradiation, instantaneous thermal annealing, or heating furnace. The timing and number of times of the heat treatment are not particularly limited. In order to perform the drying and baking processes well, the temperature at that time must be adjusted depending on the material and composition of the substrate. It depends on the nature of the thing.

[0152] As described above, the EL layer 786 can be manufactured using a droplet discharge apparatus.

[0153] When the EL layer 786 is produced using a droplet discharge device, the hole transport material of the present invention is used. When the hole transport layer is formed by a wet process using a composition dissolved in a solvent, various organic solvents are used. The organic solvent that can be used in the composition can be used to prepare a coating composition. Examples include benzene, toluene, xylene, mesitylene, tetrahydrofuran, dioxane, ethanol, methanol, n-propanol, isopropanol, n-butanol, t-butanol, acetonitrile, dimethyl sulfoxide, dimethylformamide, chloroform chloroform, methylene chloride, carbon tetrachloride, ethyl acetate, hexane, cyclohexane, etc. Various organic solvents can be used, particularly benzene, toluene, xylene, mesityle, By using a low polarity benzene derivative such as benzene, a solution of suitable concentration can be prepared. In addition, the hole transport material of the present invention contained in the ink can be prevented from deteriorating due to oxidation or the like. In addition, when the uniformity of the film after formation and the uniformity of the film thickness are taken into consideration, it is preferable to use a film having a boiling point of 10 A temperature of 0° C. or higher is preferred, and toluene, xylene, and mesitylene are more preferred.

[0154] The above configuration may be appropriately combined with other embodiments or other configurations in this embodiment. is possible.

[0155] (Embodiment 2) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0156] Some of the organic compounds that can be used for the second hole transport material described in the first embodiment are new. Since these organic compounds are novel compounds, they are also an embodiment of the present invention. The compounds are described below.

[0157] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0158] [ka]

[0159] However, in general formula (G1), R 1 ~R 8 are each independently hydrogen, hydrocarbons 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 hydroxyl ... halogens, haloalkyl groups having 1 to 6 carbon atoms, and substituted or unsubstituted alkyl groups having 6 to 60 carbon atoms. represents any one of aromatic hydrocarbon groups.

[0160] R in the above general formula (G1) 1 ~R 8 Specific examples of the formula (1-1) are shown below. ) to (1-40). 1 ~R 8 Substituted or unsubstituted carbon atoms of 6 or more In the case of an aromatic hydrocarbon group having a substituent group of 60 to 60, the aromatic hydrocarbon forming the skeleton of the substituent group The following formulas (2-1) to (2-13) are given. 13) There is no limitation on the substitution position of the aromatic hydrocarbons represented by the formula (13), and multiple aromatic hydrocarbons may have a skeleton formed by linking the following.

[0161] [ka]

[0162] [ka]

[0163] In addition, R 1 ~R 8 When is an aromatic hydrocarbon group having a substituent, the substituent may be a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an aryl group having 1 to 6 carbon atoms, Alkoxy group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted an aromatic hydrocarbon group having 6 to 60 carbon atoms, a dibenzofuranyl group, a dibenzothiophenyl group , benzonaphthofuranyl group, and benzonaphthothiophenyl group. 1 ~R 8 is an aromatic hydrocarbon group having a substituent, the substituent is a hydrocarbon group having 1 to 6 carbon atoms a group, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halo group, Specific examples of the structure of the alkyl group and the haloalkyl group having 1 to 6 carbon atoms are shown in the above R 1 No To R 8 These are the same as the formulas (1-1) to (1-40) shown as specific examples.

[0164] Also, R 1 ~R 8 When is an aromatic hydrocarbon group having a substituent, the substituent may be substituted or unsubstituted. or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms, dibenzofuranyl groups, dibenzothio Specific examples of phenyl, benzonaphthofuranyl, and benzonaphthothiophenyl groups include Typical examples include groups represented by the following formulae (1-41) to (1-81). The substituents represented by the formulae (1-41) to (1-81) are not limited in their positions. .

[0165] [ka]

[0166] [ka]

[0167] In addition, one of A and B is a group represented by the following general formula (g1), and the other is Hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a hydroxyl group, halogens, haloalkyl groups having 1 to 6 carbon atoms, hydrocarbon groups having 1 to 6 carbon atoms, and substituted or unsubstituted It represents any one of substituted aromatic hydrocarbon groups having 6 to 60 carbon atoms. Specific examples thereof include substituent R 1 ~R 8 is the same as

[0168] [ka]

[0169] However, in the general formula (g1), Ar 1 , Ar 2 are each independently a substituted or unsubstituted carbon atom. an aromatic hydrocarbon group having 6 to 60 carbon atoms or a group represented by the following general formula (g2): Represents Ar 1 , Ar 2 is an aromatic hydrocarbon group having 6 to 60 carbon atoms and having a substituent, In this case, the substituents include benzonaphthofuranyl and dinaphthofuranyl groups.

[0170] [ka]

[0171] However, in general formula (g2), R 11 ~R 18 are each independently hydrogen, carbon atoms having 1 to 6 carbon atoms, a hydroxyl group, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group , halogen, haloalkyl groups having 1 to 6 carbon atoms, and substituted or unsubstituted haloalkyl groups having 6 to 6 carbon atoms. 0. Also, Z1 and Z 2 Either one of them In the general formula (g1), the other is hydrogen, a cyclic carbon atom having 3 to 6 carbon atoms, and a hydrogen atom, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen atom, a halo group having 1 to 6 carbon atoms alkyl groups, hydrocarbon groups having 1 to 6 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms; In the group represented by the general formula (g2), R 1 1 ~R 18 Specific examples of R in the organic compound represented by the general formula (G1) are 1 No To R 8 It is the same as Z. 1 or Z 2 The nitrogen atom of the group represented by general formula (g1) is bonded to the nitrogen atom of the group represented by general formula (g1) A specific example of the compound that does not match A or B in the organic compound represented by general formula (G1) is In the formula (g1), the group is the same as the group that is not represented by the general formula (g1). 1 and Z 2 The group not bonded to the nitrogen atom of the group represented by general formula (g1) is a hydrogen atom, a carbon atom, or a a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a carbon atom, haloalkyl groups having 1 to 6 prime numbers, hydrocarbon groups having 1 to 6 carbon atoms, and substituted or unsubstituted carbon It is any one of aromatic hydrocarbon groups having a number of 6 to 60. Specific examples thereof are as described above. Substituent R 1 ~R 8 is the same as

[0172] Ar in the above general formula (g1) 1 , Ar 2 Aromatic polyolefins having 6 to 60 carbon atoms that can be used for Specific examples of the aromatic hydrocarbon group skeleton include those represented by the following structural formulas (2-1) to (2-13). The skeleton may be any of the following skeletons, regardless of the substitution position. good.

[0173] [ka]

[0174] In general formula (g1), Ar 1 , Ar 2 is a "substituted" aromatic hydrocarbon group In some cases, the substituent may be a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, or a hydrogen atom, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen atom, a halo group having 1 to 6 carbon atoms Alkyl groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms, dibenzofuran dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl Ar 1 , Ar 2 is a "substituted" aromatic hydrocarbon group, The substituent is a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, a cyclic hydrocarbon group having 1 carbon atom, a alkoxy groups having 1 to 6 carbon atoms, cyano groups, halogens, and haloalkyl groups having 1 to 6 carbon atoms. In this case, examples of specific structures include R 1 ~R 8 As a specific example, These are the same as the formulas (1-1) to (1-40) shown above.

[0175] In addition, in the general formula (g1), Ar 1 , Ar 2 is a "substituted" aromatic hydrocarbon group When the substituent is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, benzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, and benzonaphtho Specific examples of the thiophenyl group include the following formulae (1-41) to (1-13) 5) The substituents represented by the following formulae (1-41) to (1-135) are also included. There are no limitations on the substitution positions of the groups.

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181] Specific examples of the substituent represented by (g2) include the following: do.

[0182] [ka]

[0183] [ka]

[0184] [ka]

[0185] In another embodiment of the organic compound of the present invention, the group represented by the general formula (g1) is It is an organic compound that is a group represented by formula (g3).

[0186] [ka]

[0187] However, in the general formula (g3), Ar 3 , Ar 4 are each independently substituted or unsubstituted carbon atoms. Aromatic hydrocarbon groups having a prime number of 6 to 60, substituted or unsubstituted benzonaphthofuranyl groups and substituted or an unsubstituted dinaphthofuranyl group. 3 , Ar 4 is the above general formula (g 1) Ar 1 ,Ar 2 However, Ar 3 and Ar 5 The number of carbon atoms added together And, Ar 4 and Ar 6 The sum of the carbon numbers of these is 60 or less.

[0188] Also, Ar 5 , Ar 6 each independently represents a substituted or unsubstituted divalent aromatic group having 6 to 54 carbon atoms. represents an aromatic hydrocarbon group, and n and m independently represent 0 to 2. 3 and Ar 5 Charcoal The sum of prime numbers and Ar 4 and Ar 6 The sum of the carbon numbers of each of these is 60 or less. Ar 5 , Ar 6 Specific examples include those represented by the following structural formulas (2-1) to (2-13): Examples of such a divalent group include a divalent group having a skeleton such as

[0189] [ka]

[0190] In the organic compound having the above structure, Ar 3 and Ar 4 substituted or unsubstituted a phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and and either a substituted or unsubstituted pyrenyl group, the resulting polymer has high heat resistance and good film quality. These are particularly preferred because they can form a transport layer and have good hole transport properties. A phenyl group is a more preferred structure because it exhibits good film-forming properties and hole transport properties.

[0191] In the organic compound having the above structure, Ar 5 and Ar 6 is substituted or unsubstituted Phenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted anthracenylene group The use of a substituted or unsubstituted pyrenylene group provides a transport layer with high heat resistance and good film quality. In addition, these are preferred because they have good hole transport properties. The aryl group is a more preferred structure because it exhibits good film-forming properties and hole transport properties.

[0192] In the organic compound having the above structure, one of n and m is 1 and the other is 0. When present, a good film can be formed and good hole transport properties are exhibited, which is particularly preferable.

[0193] Specific examples of organic compounds having the above structure are shown below.

[0194] [ka]

[0195]

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[0196]

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[0197]

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[0198]

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[0199]

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[0200]

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[0201]

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[0202]

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[0203]

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[0204]

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[0205]

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[0206]

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[0207]

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[0208]

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[0209]

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[0210]

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[0211]

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[0212]

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[0213]

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[0214]

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[0215]

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[0216] [ka]

[0217] The above organic compounds can be synthesized by the following synthesis schemes (a-1), (a-2), (b-1) and (b-2). It can be synthesized by (b-2).

[0218] A method for synthesizing an organic compound represented by the following general formula (G1) will be described. Medium, R 1 ~R 8 are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a hydrocarbon group having 3 to 6 carbon atoms, a cyclic hydrocarbon group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen atom, a 6 haloalkyl groups and substituted or unsubstituted aromatic hydrocarbon groups having 6 to 60 carbon atoms. In addition, either A or B is represented by the following general formula (g1): group, and the other is hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms, hydrocarbon having 1 to 6 carbon atoms group and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0219] [ka]

[0220] However, in the general formula (g1), Ar 1 , Ar 2 are each independently the number of substituted or unsubstituted carbon atoms. represents an aromatic hydrocarbon group having a carbon number of 6 to 60; Ar 1 , Ar 2 When has a substituent, the substituent is Includes benzonaphthofuranyl and dinaphthofuranyl groups.

[0221] [ka]

[0222] Therefore, general formula (G1) can be represented by the following general formula (G1-a) or (G1-b). As a method for synthesizing the organic compounds represented by the general formulas (G1-a) and (G1-b), various reactions are available. The reaction can be applied to the compounds represented by general formulae (G1-a) and (G1 The synthesis method of the organic compound represented by -b) is not limited to the following synthesis method.

[0223] [ka]

[0224] [ka]

[0225] <Method for synthesizing organic compounds represented by general formula (G1-a)> The organic compound represented by general formula (G1-a), which is an embodiment of the present invention, is represented by the following formula: The compound can be synthesized as shown in the synthesis scheme (a-1) or (a-2).

[0226] That is, a benzonaphthofuran compound (compound 1) and a diarylamine (compound 2), to obtain the benzonaphthofuranylamino compound (G1-a). Alternatively, benzonaphthofuranylamine (compound 3) and a benzonaphthofuranylamine having an aryl skeleton can be synthesized. Benzonaphthofuranyl amination is carried out by coupling with compound (compound 4). Compound (G1-a) can be obtained. The synthesis schemes (a-1) and (a-2) are shown below. Shows.

[0227] [ka]

[0228] [ka]

[0229] In the synthesis schemes (a-1) and (a-2), R 1 ~R 8 are each independently hydrogen, hydrocarbon groups having 1 to 6 carbon atoms, cyclic hydrocarbon groups having 3 to 6 carbon atoms, aralkyl groups having 1 to 6 carbon atoms, oxy group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms and substituted or unsubstituted A represents any one of hydrogen, carbon atoms having 3 to 60 carbon atoms, 6 cyclic hydrocarbon groups, alkoxy groups having 1 to 6 carbon atoms, cyano groups, halogens, haloalkyl groups having from 1 to 6 carbon atoms, hydrocarbon groups having from 1 to 6 carbon atoms, and substituted or unsubstituted hydrocarbon groups having from 6 to 6 carbon atoms. 60 aromatic hydrocarbon groups, Ar 1 , Ar 2 are each independently substituted or or an unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms; Ar 1 , Ar 2 has a substituent In the latter case, the substituents include benzonaphthofuranyl and dinaphthofuranyl groups, and the substituents include It does not contain amino groups.

[0230] X 1 and X 4 each independently represents chlorine, bromine, iodine, or a triflate group, and X 2 and X 3 each independently represents hydrogen, an organotin group, or the like.

[0231] In the synthesis schemes (a-1) and (a-2), a palladium-catalyzed Buchwald reaction is carried out. For the Hartwig reaction, bis(dibenzylideneacetone)palladium(0) Palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), Palladium compounds such as arylpalladium(II) chloride (dimer) and tri(tert -butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine Di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino -2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, (S)-( 6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine ) (abbreviation: cBRIDP (registered trademark)) or other ligands can be used. Organic bases such as sodium tert-butoxide, potassium carbonate, cesium carbonate, An inorganic base such as sodium can be used. In this reaction, toluene is used as a solvent. , xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. The reagents that can be used in the reaction are not limited to those mentioned above.

[0232] In the synthesis schemes (a-1), (a-2) and (b-1), copper or a copper compound When performing the Ullmann reaction using X 1 and X 4 are independently chlorine, bromine, and iodine Represents X 2 ~X 3 represents hydrogen. Copper or copper compounds can be used in this reaction. The base used may be an inorganic base such as potassium carbonate. The solvent that can be used is 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H ) pyrimidinone (DMPU), toluene, xylene, benzene, etc. Ullmann In the reaction, the target product can be obtained in a shorter time and with a higher yield when the reaction temperature is 100°C or higher. It is preferable to use DMPU or xylene, which have high boiling points. Since a higher temperature than the above is more preferable, DMPU is more preferably used. Reagents that can be used in the reaction are not limited to the above-mentioned reagents.

[0233] <Method for synthesizing organic compounds represented by general formula (G1-b)> The organic compound represented by the general formula (G1-b) of the present invention can be synthesized by the following synthesis scheme (b-1) or can be synthesized as shown in (b-2).

[0234] That is, a benzonaphthofuran compound (compound 5) and a diarylamine (compound 6), to obtain the benzonaphthofuranylamino compound (G1-b). Alternatively, benzonaphthofuranylamine (compound 7) and a benzonaphthofuranylamine having an aryl skeleton can be synthesized. Benzonaphthofuranyl amination is carried out by coupling compound (compound 8) with Compound (G1-b) can be obtained. The synthesis schemes (b-1) and (b-2) are shown below. Shows.

[0235] [ka]

[0236] [ka]

[0237] In the synthesis schemes (b-1) and (b-2), R 1 ~R 8 are each independently hydrogen, hydrocarbon groups having 1 to 6 carbon atoms, cyclic hydrocarbon groups having 3 to 6 carbon atoms, aralkyl groups having 1 to 6 carbon atoms, oxy group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms and substituted or unsubstituted A represents any one of hydrogen, carbon atoms having 3 to 60 carbon atoms, 6 cyclic hydrocarbon groups, alkoxy groups having 1 to 6 carbon atoms, cyano groups, halogens, haloalkyl groups having from 1 to 6 carbon atoms, hydrocarbon groups having from 1 to 6 carbon atoms, and substituted or unsubstituted hydrocarbon groups having from 6 to 6 carbon atoms. 60 aromatic hydrocarbon groups, Ar 1 , Ar 2 are each independently substituted or or an unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms; Ar 1 , Ar 2 has a substituent In the latter case, the substituents include benzonaphthofuranyl and dinaphthofuranyl groups, and the substituents include It does not contain amino groups.

[0238] X 1 and X 4 each independently represents chlorine, bromine, iodine, or a triflate group, and X 2 and X 3 each independently represents hydrogen, an organotin group, or the like.

[0239] In the synthesis schemes (b-1) and (b-2), a palladium-catalyzed Buchwald reaction For the Hartwig reaction, bis(dibenzylideneacetone)palladium(0) Palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), Palladium compounds such as arylpalladium(II) chloride (dimer) and tri(tert -butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine Di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino -2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, (S)-( 6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) ) (abbreviation: cBRIDP (registered trademark)) or other ligands can be used. Organic bases such as sodium tert-butoxide, potassium carbonate, cesium carbonate, Inorganic bases such as sodium can be used. In this reaction, toluene is used as a solvent. , xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. The reagents that can be used in the reaction are not limited to those mentioned above.

[0240] In the synthesis schemes (b-1) and (b-2), copper or a copper compound is used to prepare a urethane resin. When performing the Mann reaction, X 1 and X 4 each independently represents chlorine, bromine, or iodine, and X 2 Reach and X 3 represents hydrogen. Copper or a copper compound can be used in this reaction. Examples of the base that can be used in this reaction include inorganic bases such as potassium carbonate. The solvent is 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidino Examples of suitable solvents include dimethyl ether (DMPU), toluene, xylene, and benzene. A reaction temperature of 100°C or higher allows the target product to be obtained in a shorter time and with a higher yield, so It is preferable to use DMPU and xylene. The reaction temperature is higher than 150°C. is more preferable, and therefore, DMPU is more preferably used. The reagents that can be used are not limited to those mentioned above.

[0241] (Embodiment 3) In this embodiment mode, a light-emitting device using the light-emitting element described in Embodiment 1 will be described.

[0242] In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 will be described. The description will be made with reference to FIG. 2. Note that FIG. 2(A) is a top view showing a light-emitting device, and FIG. 2(B) is a top view showing a light-emitting device. (A) is a cross-sectional view taken along the lines AB and CD. The drive circuit section (source line drive circuit) 601 shown by the dotted line controls the pixel section 602 includes a driving circuit section (gate line driving circuit) 603. Also, 604 is a sealing substrate. , 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space 607. .

[0243] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0244] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. , one pixel in the pixel section 602 is shown.

[0245] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of, for example, fluoride, polyester, or acrylic. That's fine.

[0246] The structure of the transistors used in the pixels and driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium or the like can be used. Alternatively, in-type metal oxides such as In-Ga-Zn-based metal oxides can be used. An oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0247] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a partially crystalline region) When a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0248] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be This can reduce the current in the

[0249] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (metal such as La, Ce or Hf). More preferable.

[0250] In particular, the semiconductor layer has a plurality of crystal portions, and the c-axes of the crystal portions are aligned with the surface on which the semiconductor layer is formed, Alternatively, the oxide is oriented perpendicular to the upper surface of the semiconductor layer and has no grain boundary between adjacent crystal portions. It is preferable to use a nitride semiconductor film.

[0251] By using such materials for the semiconductor layer, fluctuations in electrical characteristics are suppressed, resulting in high reliability. This makes it possible to realize a low-power transistor.

[0252] Furthermore, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to retain the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0253] For stabilizing the characteristics of the transistor, it is preferable to provide an underlayer film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed as a single layer or a laminated layer. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film need not be provided if it is not necessary.

[0254] The FET 623 indicates one of the transistors formed in the driving circuit section 601. The drive circuit is made up of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driving circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally rather than on the substrate. .

[0255] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including an anode 613 electrically connected to the drain. However, the present invention is not limited to this, and the pixel section may be a combination of three or more FETs and a capacitance element.

[0256] An insulator 614 is formed to cover the end of the anode 613. It can be formed by using a photosensitive acrylic resin film.

[0257] In order to improve the coverage of the EL layer and the like to be formed later, the insulating material 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic is used, the radius of curvature (0. It is preferable that the insulating material 614 has a curved surface with a thickness of 2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0258] An EL layer 616 and a cathode 617 are formed on the anode 613. It is desirable to use a material with a large work function for the anode 613. For example, ITO film, or silicon-containing indium tin oxide film, 2 to 20 wt% oxide Zinc-containing indium oxide film, titanium nitride film, chromium film, tungsten film, Zn film, Pt In addition to single layer films such as titanium nitride films, laminated films with aluminum as the main component, titanium nitride films, A three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and the like can be used. Furthermore, the multilayer structure provides low resistance as wiring and good ohmic contact. It can be taken.

[0259] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods such as the above. Other materials that make up the EL layer 616 include low molecular weight compounds, may be a polymer compound (including an oligomer or a dendrimer).

[0260] Furthermore, the material used for the cathode 617 formed on the EL layer 616 is a material having a small work function. Materials with low resistance (Al, Mg, Li, Ca) or their alloys or compounds (MgAg, MgIn, It is preferable to use AlLi, etc. When light is transmitted through the cathode 617, a thin metal film and a transparent conductive film (I TO, indium oxide containing 2-20 wt% zinc oxide, indium tin containing silicon It is preferable to use a laminate of an oxide, zinc oxide (ZnO, etc.).

[0261] The anode 613, the EL layer 616, and the cathode 617 form a light-emitting element. The light-emitting element is the light-emitting element described in Embodiment 1. Note that the pixel portion is formed of a plurality of light-emitting elements. In the light emitting device of this embodiment, the light emitting element described in the first embodiment is The light-emitting element may include both a light-emitting element and a light-emitting element having other configurations.

[0262] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light emitting element is disposed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. 618 is provided. The space 607 is filled with a filler. In addition to being filled with inert gas (nitrogen, argon, etc.), it can also be filled with sealing material. A recess is formed in the sealing substrate, and a desiccant is placed there to prevent deterioration due to the influence of moisture. This is a preferable configuration because it can control the

[0263] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic can be used.

[0264] Although not shown in Figure 2, a protective film may be provided on the cathode. The insulating film may be formed. In addition, a protective film may be formed to cover the exposed portion of the sealing material 605. The protective film may be formed on the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, It can be provided to cover the exposed side surfaces of the above.

[0265] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively prevent impurities such as these from diffusing from the outside to the inside.

[0266] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium Lanthanum 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 or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing erbium and strontium, oxides containing erbium and aluminum, yttrium Materials containing oxides containing lithium and zirconium can be used.

[0267] The protective film can be formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). The ALD method can be used to form protective materials. It is preferable to use it for films. By using the ALD method, it is possible to eliminate cracks, pinholes, etc. It is possible to form a protective film with reduced defects or with a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0268] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex irregularities or a surface with a touch panel. A uniform protective film with few defects can be formed on the top, sides and back of the panel. .

[0269] In this manner, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 can be obtained. This can be done.

[0270] The light-emitting device in this embodiment mode uses the light-emitting element described in Embodiment 1; Specifically, the light-emitting device described in Embodiment 1 can be obtained. Since the element is a light-emitting element with a long life, a highly reliable light-emitting device can be obtained. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has high emission efficiency, and therefore consumes less power. It is possible to make a light emitting device with a small size.

[0271] In FIG. 3, a light emitting element that emits white light is formed, and a colored layer (color filter) or the like is provided. 3A shows an example of a full-color light-emitting device. film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, first An interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving operating circuit section 1041, anodes 1024W, 1024R, 1024G, 1024B of the light-emitting elements, Partition wall 1025, EL layer 1028, cathode 1029 of light-emitting element, sealing substrate 1031, sealing material 1032 and the like are shown.

[0272] In addition, in FIG. 3(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. A transparent substrate 1 on which a colored layer and a black matrix are provided may be further provided. The colored layer and the black matrix are aligned and fixed to the substrate 1001. The dust 1035 is covered with an overcoat layer 1036. The light-emitting layer is where light does not pass through the colored layers and goes out, and the light passes through the colored layers of each color and goes out. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This allows images to be expressed using four color pixels.

[0273] In FIG. 3(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020 As shown in the figure, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0274] In the light emitting device described above, light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure. A cross-sectional view of the light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light is used as the substrate 1001. Until the connection electrode that connects the FET and the anode of the light-emitting element is fabricated, the bottom electrode is The third interlayer insulating film 1037 is then formed on the electrode 1. This insulating film may also serve as a planarizing layer. The insulating film 1037 may be formed using the same material as the second interlayer insulating film, or other known materials. This can be done.

[0275] The anodes 1024W, 1024R, 1024G, and 1024B of the light-emitting elements are referred to as anodes here. However, it may be a cathode. Also, in the case of a top emission type light emitting device as shown in FIG. In this case, it is preferable that the anode is a reflective electrode. The EL layer 103 has the same structure as that described above, and white light is emitted. The element structure is as follows.

[0276] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1034G, The blue colored layer 1034B) and the black matrix are covered by the overcoat layer 1036. The sealing substrate 1031 may be covered. Note that a light-transmitting substrate is used. Although an example of full-color display using four colors, red, green, blue, and white, is shown here, there is no particular limitation. Alternatively, full color display may be performed using four colors of red, yellow, green, and blue, or three colors of red, green, and blue.

[0277] In a top-emission type light-emitting device, the microcavity structure can be suitably applied. The light-emitting device with a microcavity structure uses the anode as a reflective electrode and the cathode as a semi-transparent / semi-reflective electrode. At least an EL layer is placed between the reflective electrode and the semi-transmissive / semi-reflective electrode. The light-emitting element has at least one light-emitting layer that serves as a light-emitting region.

[0278] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0279] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The sound is reflected and resonates.

[0280] The light-emitting element can be fabricated by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. This allows the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode to be changed. Between the reflective electrode and the semi-transparent / semi-reflective electrode, the light of the resonating wavelength is strengthened and the light of the non-resonating wavelength is strengthened. It is possible to attenuate light of wavelengths.

[0281] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that directly enters the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength of the first light. By matching the phase of the reflected light with the phase of the first incident light, the light emitted from the light-emitting layer can be further amplified. do.

[0282] In the above configuration, even if the EL layer has a plurality of light-emitting layers, a single light-emitting For example, it may be combined with the configuration of the tandem light emitting device described above. In this case, a plurality of EL layers are provided on one light-emitting element with a charge generating layer sandwiched therebetween, and each EL layer is provided with a single Alternatively, it may be applied to a configuration in which a plurality of light-emitting layers are formed.

[0283] The microcavity structure makes it possible to enhance the front-direction emission intensity of specific wavelengths. This allows for lower power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure tailored to the wavelength of each color can be applied, it is possible to achieve light-emitting devices with excellent characteristics. It can be placed.

[0284] The light-emitting device in this embodiment mode uses the light-emitting element described in Embodiment 1; Specifically, the light-emitting device described in Embodiment 1 can be obtained. Since the element is a light-emitting element with a long life, a highly reliable light-emitting device can be obtained. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has high emission efficiency, and therefore consumes less power. It is possible to make a light emitting device with a small size.

[0285] Up to this point, we have explained about active matrix light emitting devices, but from now on we will be talking about passive light emitting devices. A passive matrix light-emitting device will be described. 5A is a perspective view showing the light emitting device, and FIG. 5B) is a cross-sectional view of FIG. 5A cut along XY. In FIG. 5, on a substrate 951, An EL layer 955 is provided between the electrode 952 and the electrode 956. The ends of the electrode 952 are It is covered with an insulating layer 953. A partition wall layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 become thicker between one sidewall and the other sidewall as they approach the substrate surface. That is, the cross section of the partition wall layer 954 in the short side direction has a slope such that the gap between the partition walls becomes narrower. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). In this way, by providing the partition layer 954, the length of the light-emitting element caused by static electricity or the like can be reduced. In addition, in the passive matrix type light emitting device, the present invention can be applied to the embodiment. A light-emitting device with high reliability or a light-emitting device with low power consumption using the light-emitting element according to Embodiment 1. It may be an optical device.

[0286] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix. Since it is possible to control the light emission, it can be suitably used as a display device for displaying images. It is a device.

[0287] This embodiment mode can be freely combined with other embodiment modes.

[0288] (Fourth embodiment) In this embodiment mode, an example in which the light-emitting element described in Embodiment 1 is used as a lighting device will be described with reference to FIG. 6. 6(B) is a top view of the lighting device, and FIG. 6(A) is a diagram of the lighting device in FIG. 6(B). ef cross-sectional view.

[0289] The lighting device of this embodiment has an anode 4 on a light-transmitting substrate 400 serving as a support. The anode 401 corresponds to the anode 101 in the first embodiment. When light is extracted from the anode 401 side, the anode 401 is formed from a light-transmitting material.

[0290] A pad 412 for supplying a voltage to the cathode 404 is formed on the substrate 400 .

[0291] An EL layer 403 is formed on the anode 401. The EL layer 403 is the same as that in the first embodiment. The configuration of the EL layer 103, or the combination of the light-emitting units 511, 512 and the charge-generating layer 513 For details about these configurations, please refer to the relevant descriptions.

[0292] A cathode 404 is formed to cover the EL layer 403. The cathode 404 is the same as the cathode 1 in the first embodiment. When light is extracted from the anode 401 side, the cathode 404 is made of a material with high reflectivity. The cathode 404 is connected to a pad 412, and a voltage is applied to the cathode 404. can be.

[0293] As described above, a light-emitting element having the anode 401, the EL layer 403, and the cathode 404 is shown in this embodiment mode. Since the light emitting element has high luminous efficiency, the lighting device of this embodiment The lighting device in this embodiment can be a lighting device with low power consumption.

[0294] The substrate 400 on which the light emitting element having the above structure is formed and the sealing substrate 407 are sealed with a sealing material 4. The lighting device is completed by fixing and sealing using the sealant 40. Either one of the seal material 5 and 406 may be used. (not shown) can also be mixed with a desiccant, which can absorb moisture. This leads to improved reliability.

[0295] In addition, a part of the pad 412 and the anode 401 is provided so as to extend outside the sealing materials 405 and 406. By doing so, it can be used as an external input terminal. An IC chip 420 or the like may be provided.

[0296] As described above, the lighting device described in this embodiment uses the light-emitting element described in Embodiment 1 as the EL element. In addition, the light emitting device can be made to have low power consumption. It can be placed.

[0297] (Embodiment 5) In this embodiment mode, examples of electronic devices each including the light-emitting element described in Embodiment 1 will be described. The light-emitting element described in Embodiment 1 has a long life and is a highly reliable light-emitting element. As a result, the electronic device described in this embodiment has a light-emitting portion with good reliability. It may be an electronic device.

[0298] As an electronic device to which the light-emitting element is applied, for example, a television set (television or television) (also called revision receivers), monitors for computers, digital cameras, digital Video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) ), portable game machines, personal digital assistants, audio playback devices, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are listed below.

[0299] 7A shows an example of a television device. The television device includes a housing 710 A display unit 7103 is built into the housing 1. In this case, a stand 7105 is used to hold the housing The display unit 7103 can display images. The display portion 7103 has the light-emitting elements described in Embodiment 1 arranged in matrix. It is composed of:

[0300] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0301] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0302] FIG. 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. Note that this computer is configured by arranging the light-emitting elements described in Embodiment 1 in a matrix. The display portion 7203 is used for the computer shown in FIG. The computer shown in FIG. 7(B2) may have a keyboard 720. 4. A second display unit 7210 is provided instead of the pointing device 7206. The second display portion 7210 is a touch panel type, and the contents displayed on the second display portion 7210 can be displayed. Input can be made by operating the input display with a finger or a special pen. In addition, the second display portion 7210 can display not only an input display but also other images. The display unit 7203 may also be a touch panel. Two screens are connected by a hinge. This may cause problems such as scratches or breakage on the screen when storing or transporting the device. The occurrence of bubbles can also be prevented.

[0303] FIG. 7C shows a portable gaming machine, which is composed of two housings, a housing 7301 and a housing 7302. The housing 7301 is connected by a connecting portion 7303 so as to be openable and closable. A display portion 7304 formed by arranging the light-emitting elements according to Embodiment 1 in a matrix is ​​incorporated. A display portion 7305 is incorporated in the housing 7302. The gaming machine also includes a speaker unit 7306, a recording medium insertion unit 7307, an LED lamp 73 08, input means (operation keys 7309, connection terminals 7310, sensors 7311 (force, displacement, position Position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time , hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell or infrared rays It is equipped with a microphone (7312) and a portable The configuration of the belt-type gaming machine is not limited to the above, and at least the display unit 7304 and the display unit 7 The light-emitting elements described in Embodiment 1 are arranged in a matrix on either one of the substrates 305. It is sufficient to use a display unit manufactured by the manufacturer, and other accessories may be provided as appropriate. The portable gaming machine shown in FIG. 7(C) can be used to play a program or data recorded on a recording medium. It has the function of reading data and displaying it on the display, and communicating information wirelessly with other portable gaming machines. The functions of the portable gaming machine shown in FIG. 7(C) are not limited to these. It can have a variety of functions.

[0304] FIG. 7D shows an example of a mobile terminal. A mobile phone 7400 is incorporated in a housing 7401. In addition to the built-in display 7402, operation buttons 7403, external connection port 7404, speaker The mobile phone 7400 is provided with a camera 7405, a microphone 7406, and the like. The display portion 7402 has the light-emitting elements described in Embodiment 1 arranged in a matrix. .

[0305] The mobile terminal shown in FIG. 7D allows users to input information by touching the display portion 7402 with a finger or the like. In this case, it is possible to make a call or create an email. Operations such as turning on / off the camera can be performed by touching the display portion 7402 with a finger or the like.

[0306] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0307] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0308] In addition, the mobile terminal may include a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a device, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0309] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0310] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0311] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0312] Note that the structure described in this embodiment mode may be combined with any of the structures described in Embodiment Modes 1 to 4 as appropriate. They can be used in combination.

[0313] As described above, the light-emitting device including the light-emitting element described in Embodiment 1 has a very wide range of application. The light emitting device described in Embodiment 1 can be applied to electronic devices in a variety of fields. By using the light-emitting element, a highly reliable electronic device can be obtained.

[0314] FIG. 8 shows an example of a liquid crystal display device in which the light-emitting element according to the first embodiment is used as a backlight. The liquid crystal display device shown in FIG. 8 includes a housing 901, a liquid crystal layer 902, a backlight unit The liquid crystal layer 902 is connected to a driver IC 905. In addition, the backlight unit 903 uses the light-emitting element described in Embodiment 1. Terminal 906 provides the electrical current.

[0315] By applying the light-emitting element described in Embodiment 1 to a backlight of a liquid crystal display device, A backlight with reduced power consumption can be obtained. This allows the creation of a surface-emitting lighting device, and also makes it possible to increase the area. This makes it possible to increase the area of ​​the backlight, and also the area of ​​the liquid crystal display device. The light emitting device to which the light emitting element according to the first embodiment is applied can be made thinner than conventional devices. This also makes it possible to make the display device thinner.

[0316] FIG. 9 shows an example in which the light-emitting element described in Embodiment 1 is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002. Alternatively, the lighting device described in the fourth embodiment may be used.

[0317] FIG. 10 shows an example in which the light-emitting element described in Embodiment 1 is used as an indoor lighting device 3001. Since the light-emitting element described in Embodiment 1 is a highly reliable light-emitting element, In addition, the light-emitting element described in Embodiment 1 can be made large in area. Therefore, the light emitting device can be used as a large-area lighting device. The optical element is thin and can therefore be used as a thin illumination device.

[0318] The light-emitting element described in the first embodiment can be mounted on the windshield or dashboard of an automobile. FIG. 11 shows a case where the light-emitting element described in Embodiment 1 is applied to a windshield or a door of an automobile. The display area 5000 to the display area 5005 are used in the embodiment. 1 is a display provided using the light-emitting element according to embodiment 1.

[0319] In this embodiment, the display area 5000 and the display area 5001 are provided on the windshield of a car. 1 is a display device equipped with the light-emitting device according to embodiment 1. The light-emitting device according to embodiment 1 has an anode By making the cathode and cathode electrodes transparent, the other side can be seen through. It can be a see-through display device. If it is a see-through display, it can be used in automobiles. Even if it is installed on the windshield, it can be installed without obstructing the view. In addition, when transistors for driving are provided, organic transistors made of organic semiconductor materials are used. A light-transmitting transistor such as a transistor using an oxide semiconductor is It is good to use.

[0320] The display region 5002 is a display region including the light-emitting element described in Embodiment 1 provided in the pillar portion. The display area 5002 displays an image captured by an imaging means provided on the vehicle body. This can compensate for the visibility obstructed by the pillars. The display area 5003 provided on the board allows the view outside the car to be hidden by the car body. By projecting images from the imaging means installed in the By projecting images that complement the invisible parts, it becomes more natural and less awkward. Safety can be checked without any sense of discomfort.

[0321] The display area 5004 and the display area 5005 display navigation information, a speedometer, a tachometer, and a mileage. , fuel, gear status, air conditioning settings, and much more. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in the display areas 5000 to 5003. The display areas 5000 to 5005 can also be used as lighting devices.

[0322] 12(A) and 12(B) show an example of a foldable tablet terminal. (A) shows the tablet terminal in an open state. The tablet terminal includes a housing 9630, a display unit 9631a, Display unit 9631b, display mode changeover switch 9034, power switch 9035, power saving A force mode changeover switch 9036, a fastener 9033, and an operation switch 9038 are provided. The tablet terminal displays a light-emitting device including the light-emitting element described in Embodiment 1. The insulating film is fabricated by using it in one or both of the portion 9631a and the display portion 9631b.

[0323] A part of the display unit 9631a can be used as a touch panel area 9632a. Data can be input by touching the operation keys 9637. In a, for example, half of the area has a display function only, and the other half has a Although a configuration having a touch panel function is shown, the present invention is not limited to this configuration. The entire area of ​​the display unit 963 may have a touch panel function. The entire surface of the display 9631a is used as a touch panel by displaying keyboard buttons, and the display 9631b is used as a display screen. It can be used as a surface.

[0324] In addition, in the display unit 9631b, as in the display unit 9631a, a part of the display unit 9631b The area can be used as a touch panel area 9632b. The display can be changed by touching the area where the display switch button 9639 is displayed with your finger or a stylus. A keyboard button can be displayed on the display unit 9631b.

[0325] In addition, when the touch panel area 9632a and the touch panel area 9632b are touched simultaneously, You can also input it.

[0326] The display mode switch 9034 is used to change the display orientation, such as portrait or landscape. You can switch between black and white and color display. The Switch 9036 detects external light during use using a light sensor built into the tablet device. The tablet device can optimize the display brightness according to the amount of light in the room. In addition to sensors, other detection devices such as gyros and acceleration sensors that detect tilt are also included. It may be built-in.

[0327] FIG. 12A shows an example in which the display area of ​​the display portion 9631b is the same as that of the display portion 9631a. However, there is no particular limitation, and one size may be different from the other, and the display For example, one display panel may be capable of displaying images with higher resolution than the other. It may also be possible to use the following.

[0328] FIG. 12(B) shows the tablet terminal in the closed state. 9630, solar cell 9633, charge / discharge control circuit 9634, battery 9635, DCDC 12B shows an example in which a converter 9636 is provided. As an example, a configuration having a battery 9635 and a DC-DC converter 9636 is shown. is doing.

[0329] In addition, since the tablet device can be folded in half, the housing 9630 can be folded when not in use. Therefore, the display portions 9631a and 9631b can be protected, and thus the display portions 9631a and 9631b can be withstood. This makes it possible to provide a tablet terminal that is highly durable and reliable even from the perspective of long-term use.

[0330] In addition, the tablet terminals shown in Figs. 12(A) and 12(B) can also store various information. Functions that display information (still images, videos, text images, etc.), calendars, dates, or times, etc. The function to display the information on the display unit, and the function to operate or edit the information displayed on the display unit by touch input. It has the function of controlling the processing by various software (programs), etc. This can be done.

[0331] The solar cell 9633 attached to the surface of the tablet terminal supplies power to the touch panel, The solar cell 9633 can be supplied to a display unit, a video signal processor, or the like. When installed on one or both sides of the housing 9630, it allows for efficient charging of the battery 9635. This is preferable because it can be configured to perform the above.

[0332] The configuration and operation of the charge / discharge control circuit 9634 shown in FIG. 12(B) will be described with reference to FIG. ) shows a block diagram and explains. In FIG. 12(C), a solar cell 9633, a battery 96 35, DC-DC converter 9636, converter 9638, switches SW1 to SW3, The display unit 9631 is shown, along with the battery 9635 and the DC-DC converter 9636. The converter 9638 and the switches SW1 to SW3 constitute the charge / discharge control circuit shown in FIG. This corresponds to road 9634.

[0333] First, an example of operation when power is generated by the solar cell 9633 using external light will be described. The power generated by the solar cell is converted to a voltage to charge the Battery 9635. The voltage is increased or decreased by the C converter 9636. When power charged by the solar battery 9633 is used, switch SW1 is turned on and the converter The voltage is increased or decreased by a voltage controller 9638 to the voltage required for the display unit 9631. When not displaying on the display unit 9631, turn SW1 off and SW2 on to turn on the back It is sufficient to configure it to charge the Terry 9635.

[0334] Although the solar cell 9633 is shown as an example of a power generating means, the power generating means is not particularly limited. It is not limited to this, and other power generation methods such as piezoelectric elements and thermoelectric conversion elements (Peltier elements) are also used. The battery 9635 may be charged by the stage. It is possible to combine a wireless power transmission module that transmits and receives electrical current to charge the battery, or other charging methods. The power generating means may not be provided.

[0335] Furthermore, if the display unit 9631 is provided, the tablet terminal shown in FIG. Not limited.

[0336] 13(A) to 13(C) show a foldable mobile information terminal 9310. 13(A) shows the mobile information terminal 9310 in an unfolded state. The mobile information terminal 9310 is shown in a state in which it is changing from one folded state to the other. FIG. 13C shows the portable information terminal 9310 in a folded state. The foldable design offers excellent portability and a seamless, large viewing area when unfolded. This provides excellent visibility of the display.

[0337] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for a display panel 9311. A display area 931 in the display panel 9311 2 is a display area located on the side of the portable information terminal 9310 in the folded state. Area 9312 contains information icons and shortcuts to frequently used apps and programs. You can display the information and launch apps smoothly. do.

[0338] The substituted or unsubstituted benzonaphthofuran skeleton according to one embodiment of the present invention may further include a substituted or unsubstituted benzonaphthofuran skeleton. Organic compounds with one unsubstituted amine skeleton can be used in organic thin-film solar cells. More specifically, because of its carrier transport properties, it is used in carrier transport layers and carrier injection layers. In addition, by using a mixed film with an acceptor material, it is possible to use In addition, since it is photoexcited, it can be used as a power generation layer. [Example]

[0339] <Synthesis Example 1> In this synthesis example, the active ingredient of one aspect of the present invention represented by structural formula (142) in the embodiment is Organic compound, N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2- d] A specific example of the synthesis of furan-8-amine (abbreviation: BnfABP) is given below. The structural formula of BP is shown below.

[0340] [ka]

[0341] <Step 1: Synthesis of 6-iodobenzo[b]naphtho[1,2-d]furan> In a 500 mL three-neck flask, add 8.5 g (39 mmol) of benzo[b]naphtho[1,2- d]Furan was added, and the atmosphere in the flask was replaced with nitrogen. Then, 195 mL of tetrahydrofuran (T HF) was added. The solution was cooled to -75°C, and then 25 mL (40 mmol) of HCl was added to the solution. l) n-butyllithium (1.59 mol / L n-hexane solution) was added dropwise. After the dropwise addition, the resulting solution was stirred at room temperature for 1 hour. After a predetermined time had elapsed, the solution was heated to -75°C. After cooling, add dropwise a solution of 10 g (40 mmol) of iodine in 40 mL of THF. After the dropwise addition, the resulting solution was stirred for 17 hours while being returned to room temperature. Aqueous sodium thiosulfate solution was added to the mixture, and after stirring for 1 hour, the organic layer of the mixture was extracted with water. The organic layer was dried over magnesium sulfate. After drying, the mixture was gravity filtered. The resulting solution was diluted with Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-052 65), through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305). The filtrate was concentrated to give a solid, which was then recrystallized from toluene. The desired white powder was obtained in an amount of 6.0 g (18 mmol) and a yield of 45%. The synthesis scheme is shown in the following formula (a-1).

[0342] [ka]

[0343] Step 2: Synthesis of 6-phenylbenzo[b]naphtho[1,2-d]furan In a 200 mL three-neck flask, add the 6-iodobenzo[b]naphtho[1,2 -d]furan (6.0 g, 18 mmol) and 2.4 g (19 mmol) of phenylboron phosphate, 70 mL of toluene, 20 mL of ethanol, and 22 mL of aqueous potassium carbonate. The mixture was degassed by stirring under reduced pressure. After degassing, the flask was purged with nitrogen, and 480 mg (0.42 mmol) of tetrakis(2,4-dichloro-2,4-dichloro-1 ... (Triphenylphosphine)palladium(0) was added, and the mixture was heated at 90 After a predetermined time had elapsed, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with water, and then dried over magnesium sulfate. This mixture was gravity filtered, and the resulting filtrate was concentrated to give a solid, which was dissolved in toluene. The resulting solution was filtered through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-168 55), Florisil (Wako Pure Chemical Industries, Ltd., Catalog No.: 540-00135), The filtrate was concentrated and the resulting solid was reconstituted with toluene. Crystallization was performed and the desired white solid was obtained in an amount of 4.9 g (17 mmol) and a yield of 93%. The synthesis scheme of step 2 is shown in formula (b-1) below.

[0344] [ka]

[0345] Step 3: Synthesis of 8-iodo-6-phenylbenzo[b]naphtho[1,2-d]furan > In a 300 mL three-neck flask, add the 6-phenylbenzo[b]naphtho[1 ,2-d]furan (4.9 g, 17 mmol) was added to the flask, and the atmosphere in the flask was replaced with nitrogen. mL of tetrahydrofuran (THF) was added. The solution was cooled to -75°C and then To the solution, 11 mL (18 mmol) of n-butyllithium (1.59 mol / L n-butyllithium) was added. After the dropwise addition, the resulting solution was stirred at room temperature for 1 hour. After a period of time had passed, the solution was cooled to -75°C, and 4.6 g (18 mmol) of iodine was added to the solution. The solution dissolved in 18 mL of F was added dropwise. The resulting solution was allowed to return to room temperature for 17 hours. After stirring, an aqueous solution of sodium thiosulfate was added to the mixture, and the mixture was stirred for 1 hour. The organic layer of this mixture was washed with water and dried over magnesium sulfate. The filtrate obtained by gravity filtration was filtered through Celite (Wako Pure Chemical Industries, Ltd., Catalog No. 53 1-16855), Florisil (Wako Pure Chemical Industries, Ltd., Catalog number: 540-00 The filtrate was concentrated and the resulting solid was dissolved in toluene. The desired white solid was obtained in a yield of 3.7 g (8.8 mmol). The synthesis scheme of step 3 is shown in formula (c-1) below.

[0346] [ka]

[0347] Step 4: 6,N-Diphenylbenzo[b]naphtho[1,2-d]furan-8-amine Synthesis of amine In a 200 mL three-neck flask, add 5.0 g (12 mmol) of the 8-iodobenzoate synthesized in Step 3. do-6-phenylbenzo[b]naphtho[1,2-d]furan and 2.9 g (30 mmol ) sodium tert-butoxide was added, and the atmosphere in the flask was replaced with nitrogen. of toluene, 1.4 g (13 mmol) of aniline, and 0.4 mL of tri(tert- A 10 wt% hexane solution of (butyl)phosphine was added. After degassing the mixture under reduced pressure, After heating to 60°C under a nitrogen stream, 60 mg (0.1 mmol) of bis(dibenzylidene amine) was added. Palladium(0) acetate was added and the mixture was stirred at 60°C for 40 minutes. The resulting mixture was washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. After removing the magnesium sulfate by filtration, the obtained filtrate was concentrated to obtain a white solid. The solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:2 ) to obtain 3.5 g of the desired white solid in 77% yield. The synthesis scheme is shown in the following formula (d-1).

[0348] [ka]

[0349] The resulting white solid 1 The H NMR is shown below. 1 H NMR (chloroform-d, 500 MHz): δ = 6.23 (s, 1H), 7.0 4(t, J=7.5Hz, 1H), 7.24-7.26(m, 2H), 7.34-7.4 1(m, 4H), 7.47(t, J=8.0Hz, 1H), 7.54-7.60(m, 3 H), 7.74(t, J=7.5Hz, 1H), 7.95(d, J=6.5Hz, 2H) , 7.99(dd, J1=1.5Hz, J2=7.0Hz, 1H), 8.03(s, 1H ), 8.08(d, J=8.0Hz, 1H), 8.66(d, J=9.0Hz, 1H)

[0350] Step 5: N-4-biphenyl-6,N-diphenylbenzo[b]naphtho[1,2- d] Synthesis of furan-8-amine> In a 200 mL three-neck flask, add 1.3 g (5.0 mmol) of 4-bromobiphenyl and 6,N-Diphenylbenzo[b]naphtho[1,2-d]furan-8- synthesized in Step 4 1.9 g (5.0 mmol) of amine and 0.14 g (0.30 mmol) of 2-dicyclohexyl 2',4',6'-triisopropylbiphenyl (abbreviation: X- Phos) and 1.5g (15mmol) of sodium tert-butoxide were added. After replacing the atmosphere in the flask with nitrogen, 25 mL of toluene was added. The mixture was degassed under reduced pressure. After that, the temperature was raised to 60°C under a nitrogen stream, and 61 mg (0.10 mmol) of bis(dibenzyl) (Decayneacetone)palladium(0) was added and the mixture was stirred at 80°C for 3 hours. The resulting mixture was washed with water and saturated saline, and the organic layer was washed with magnesium sulfate. After removing the magnesium sulfate by natural filtration, the obtained filtrate was concentrated to give a brown solid. This solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 3 7), the target pale yellow solid was obtained in an amount of 2.0 g in a yield of 67%. The synthesis scheme of the compound 5 is shown in the following formula (e-1).

[0351] [ka]

[0352] The obtained pale yellow solid 1 The H NMR is shown below. 1 H NMR chart 14(B) shows the difference between 7.00 ppm and 9.00 ppm in FIG. 14(A). 1 is a chart showing an expanded range of m. This shows that the organic compound according to one embodiment of the present invention It was found that a certain BnfABP was obtained.

[0353] 1 H NMR (dichloromethane-d2, 500 MHz): δ = 7.11 (t, J = 7.0 Hz, 1H), 7.16(t, J=7.0Hz, 4H), 7.22-7.33(m, 7H ), 7.39-7.47(m, 5H), 7.53-7.60(m, 5H), 7.74(t , J=7.0Hz, 1H), 8.02(s, 1H), 8.06(d, J=8.0Hz, 1 H), 8.23(d, J=8.0Hz, 1H), 8.66(d, J=8.0Hz, 1H)

[0354] The resulting 1.5 g of pale yellow solid was purified by train sublimation. The sublimation purification was carried out under a pressure of 3.6 Pa with argon flowing at a rate of 15 mL / min. The purification was carried out by heating from 35°C to 250°C for 16 hours. After purification by sublimation, the target pale yellow solid was obtained. 4g was obtained with a recovery rate of 90%.

[0355] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of BnfABP (hereinafter simply referred to as The solid thin film was formed on a quartz substrate. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer. The spectrophotometer (V550 model, manufactured by JASCO Corporation) was used to measure the toluene content in a quartz cell. The absorption spectrum of the thin film was measured using a spectrophotometer (Nihon Co., Ltd.). A spectrophotometer (U4100, manufactured by Ritsumeikan High Technologies) was used. A fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for the measurement. The absorption and emission spectra of the fluorine solution are shown in Figure 15. The measurement results of the emission spectrum are shown in FIG.

[0356] As shown in Figure 15, the toluene solution of BnfABP has wavelengths around 376 nm, 340 nm, and 321 nm. The absorption peak was observed at 417 nm (excitation wavelength 370 nm). .

[0357] Also, from Figure 16, the BnfABP thin film exhibited the following wavelengths: 387 nm, 346 nm, 326 nm, and 294 nm. The absorption peaks are observed at around 262 nm and 440 nm (excitation wavelength). The wavelength is 360 nm.

[0358] In addition, the HOMO and LUMO levels of BnfABP were measured by cyclic voltammetry ( The calculation method is shown below.

[0359] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 05-6) was used, and the supporting electrolyte was tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. The working electrode was a platinum electrode (PT, manufactured by BAS Co., Ltd.). E platinum electrode), and as an auxiliary electrode, a platinum electrode (B.A.S. Co., Ltd., VC-3 P The counter electrode (5 cm) was used as the reference electrode, and Ag / Ag + Electrode (B.A.E. The measurements were carried out at room temperature (20 to 32°C). The scan rate during CV measurement was standardized to 0.1 V / sec. The oxidation potential Ea [V] and reduction potential Ec [V] were measured against the reference electrode. The potential of the reduction wave is defined as the midpoint potential of the reduction wave, and Ec is defined as the midpoint potential of the reduction-oxidation wave. The potential energy of the reference electrode relative to the vacuum level is -4.94 eV. Since it is known that the HOMO level [eV] = -4.94-Ea, the LUMO level [eV ]=-4.94-Ec, calculate the HOMO and LUMO levels. In addition, CV measurement was repeated 100 times, and the acid in the 100th cycle measurement was The electrical stability of the compound was investigated by comparing the oxidation-reduction wave of the first cycle with the oxidation-reduction wave of the second cycle. .

[0360] As a result, the HOMO level of BnfABP is -5.59 eV and the LUMO level is -2.53 e V. In addition, the oxidation-reduction wave after 100 cycles was the same as that of the first cycle. The peak intensity of the oxidized-reduced wave was 83% of that of the oxidized-reduced wave, indicating that the oxidized BnfABP It was confirmed that BnfABP has very good resistance to oxidative stress. Differential thermal analysis (TG-DTA:Thermogravimetry-Differentia The measurement was carried out using a high vacuum differential thermobalance ( A Bruker AXS TG-DTA2410SA was used. Measurements were taken under conditions of a temperature rise rate of 10°C / min and a nitrogen gas flow (flow rate: 200 mL / min). From the relationship between weight and temperature (thermogravimetry), the 5% weight loss temperature of BnfABP is approximately 370 This indicates that BnfABP has good heat resistance. Differential scanning calorimetry (DSC) was performed using a PerkinElmer Pyris1 DSC. The differential scanning calorimetry was performed at a temperature rise rate of 40°C / min from -10°C to 300°C. After heating to 10℃, keep the temperature at that temperature for 1 minute and then cool to -10℃ at a rate of 40℃ / min. The DSC measurement showed that the glass transition temperature of BnfABP was 97°C. It was revealed that the compound has high heat resistance. [Example]

[0361] <Synthesis Example 2> In this synthesis example, the active ingredient of one aspect of the present invention represented by structural formula (146) in the embodiment is Organic compound, N,N-bis(biphenyl-4-yl)-6-phenylbenzo[b]naphtho[ A specific example of the synthesis of 1,2-d]furan-8-amine (abbreviation: BBABnf) will be given below. The structural formula of BBABnf is shown below.

[0362] [ka]

[0363] <Step 1: Synthesis of 6-iodobenzo[b]naphtho[1,2-d]furan> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0364] Step 2: Synthesis of 6-phenylbenzo[b]naphtho[1,2-d]furan The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0365] Step 3: Synthesis of 8-iodo-6-phenylbenzo[b]naphtho[1,2-d]furan > The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 1.

[0366] Step 4: (9,9-dimethyl-9H-fluorene-2,7-diyl)bis(6,N Synthesis of -diphenylbenzo[b]naphtho[1,2-d]furan-8-amine In a 200 mL three-neck flask, 8-iodo-6-phenyl 2.1 g (5.0 mmol) of benzo[b]naphtho[1,2-d]furan and 1.6 g ( 5.0 mmol) of di(1,1'-biphenyl-4-yl)amine and 0.17 g (0. 40mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1' -biphenyl (abbreviation: S-Phos) and 0.97 g (10 mmol) of sodium t Add ert-butoxide, replace the atmosphere in the flask with nitrogen, then add 25 mL of xylene. After degassing the mixture under reduced pressure, it was heated to 80°C under a nitrogen stream, and then 0.12 g (0.2 0 mmol) bis(dibenzylideneacetone)palladium(0) was added and the mixture was The mixture was stirred at 80° C. for 5.5 hours and then at 100° C. for 5 hours. The organic layer was washed with magnesium sulfate and then with water and saturated saline. After removing magnesium, the obtained filtrate was concentrated to give a brown solid. Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305) The resulting filtrate was concentrated to give 2.0 g of the desired yellow solid in a yield of 1.0 g. The synthesis scheme of step 4 is shown in formula (d-2) below.

[0367] [ka]

[0368] The obtained yellow solid 1 The H NMR is shown below. 1 H NMR chart FIG. 17(B) shows the range from 7.00 ppm to 9.00 ppm in FIG. 17(A). 1 is a chart showing an enlarged range of the organic compound of one embodiment of the present invention. It was found that BBABnf was obtained. 1H NMR (dichloromethane-d2, 500 MHz): δ = 7.14-7.19 (m, 3H), 7.22(d, J=8.5Hz, 4H), 7.29-7.33(m, 3H), 7 .41(t, J=8.0Hz, 4H), 7.44-7.49(m, 3H), 7.55-7 .58(m, 5H), 7.61(d, J=8.0Hz, 4H), 7.74(t, J=8. 0Hz, 1H), 8.02(s, 1H), 8.06(d, J=8.0Hz, 1H), 8. 26(d, 1H), 8.67(d, J=8.0Hz, 1H)

[0369] The resulting yellow solid (2.0 g) was purified by train sublimation. The sublimation purification was carried out under a pressure of 3.8 Pa with argon flowing at a rate of 15 mL / min. After sublimation purification, 1.7 g of the target yellow solid was obtained, with a recovery rate of 81%. Obtained in %.

[0370] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of BBABnf (hereinafter simply referred to as The absorption spectrum and emission spectrum of BnfABP were measured. The measurement was carried out using the same equipment and method as in the previous measurement. The measurement results of the spectrum are shown in Figure 18. The measurement results of the absorption spectrum and emission spectrum of the thin film are shown in Figure 19. is shown in Figure 19.

[0371] As shown in Figure 18, the toluene solution of BBABnf exhibits an absorption peak around 343 nm, and an emission peak The peak wavelength was 420 nm (excitation wavelength 340 nm).

[0372] Also, from Figure 19, the BBABnf thin film has wavelengths around 344 nm, 325 nm, and 257 nm. An absorption peak is observed at 439 nm (excitation wavelength 361 nm), and the emission wavelength peak is at 439 nm (excitation wavelength 361 nm).

[0373] In addition, the HOMO and LUMO levels of BBABnf were measured by cyclic voltammetry ( The calculation method was the same as that described in Example 1.

[0374] As a result, the HOMO level of BBABnf is -5.56 eV and the LUMO level is -2.51 e V. In addition, the oxidation-reduction wave after 100 cycles was the same as that of the first cycle. The peak intensity of the BBABnf oxidation was 90% of that of the reduction-oxidation wave. It was confirmed that BBABnf has very good resistance to steroids. The determination and DSC measurement were carried out in the same manner as for BnfABP. The temperature was raised to 330°C. From the TG-DTA measurement, the 5% weight loss temperature was about 410°C. ° C. This indicates that BBABnf has good heat resistance. DSC measurement revealed that the glass transition temperature of BBABnf is 117°C. It was revealed that this compound has excellent heat resistance. [Example]

[0375] In this example, the light-emitting element 1 according to one embodiment of the present invention, which is described in Embodiment 1, will be described. The structural formula of the organic compound used in the light-emitting element 1 is shown below.

[0376] [ka]

[0377] (Method for fabricating light-emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 2 mm x 2 mm.

[0378] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0379] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0380] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. By this method, 2,3,6,7,10,11-hexacyano-1,2-dione represented by the above structural formula (i) ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0381] Next, N-(1,1'-biphenyl) represented by the above structural formula (ii) was deposited on the hole injection layer 111. 4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9H-fluoren-2-amine (abbreviation: PCBBiF) After vapor deposition to a thickness of 1000 μm, N,N-bis(biphenyl) represented by the above structural formula (iii) was (phenyl-4-yl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine A hole transport layer 112 was formed by depositing a 5 nm thick film of BBABnf. .

[0382] Next, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N'-bis(3-methylphenyl)-N,N'-bis[3- (9-phenyl-9H-fluoren-9-yl)phenyl)-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCzP A: 1,6mMemFLPAPrn) was co-evaporated to form a 25 nm light-emitting layer 113. Successful.

[0383] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (vi) was The electron transport layer 114 was formed by vapor deposition so that the thickness of the film became m.

[0384] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The cathode 102 was formed by vapor deposition to fabricate the light-emitting device 1 of this example.

[0385] The device structure of the light-emitting device 1 is summarized in the table below.

[0386] [Table 1]

[0387] The light emitting element 1 is placed in a glove box with a nitrogen atmosphere so that the light emitting element is not exposed to the atmosphere. The process of sealing the device with a glass substrate (applying a sealant around the device and applying UV light during sealing) After the test, the initial characteristics and reliability of these light-emitting devices were evaluated. The measurements were carried out in an atmosphere maintained at 25°C.

[0388] FIG. 20 shows the luminance-current density characteristics of Light-emitting Element 1, FIG. 21 shows the current efficiency-luminance characteristics, and FIG. The voltage characteristics are shown in Fig. 22, the current-voltage characteristics in Fig. 23, the external quantum efficiency-luminance characteristics in Fig. 24, and the The optical spectrum is shown in FIG. 25. The luminance of the light-emitting element 1 is 1000 cd / m 2 Major in the vicinity The characteristics are shown in Table 2.

[0389] [Table 2]

[0390] 20 to 25 and Table 2, it can be seen that the light-emitting element 1 of one embodiment of the present invention has a low driving voltage. It was found to be a blue light-emitting device with good efficiency.

[0391] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. As shown in Figure 26, the decrease in brightness due to the accumulation of driving time is small. It was found that the light-emitting element had a long life. [Example]

[0392] In this example, the light-emitting element 2 and the light-emitting element 3 according to one embodiment of the present invention described in Embodiment 1 The structural formulae of the organic compounds used in the light-emitting elements 2 and 3 are shown below.

[0393] [ka]

[0394] (Method for manufacturing light-emitting element 2) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 2 mm x 2 mm.

[0395] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0396] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0397] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. By this method, 2,3,6,7,10,11-hexacyano-1,2-dione represented by the above structural formula (i) ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0398] Next, N-(1,1'-biphenyl) represented by the above structural formula (ii) was deposited on the hole injection layer 111. 4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9H-fluoren-2-amine (abbreviation: PCBBiF) The first hole transport layer 112-1 is formed by vapor deposition to a thickness of 1000 nm. N,N-bis(biphenyl-4-yl) represented by the above structural formula (iii) was added to 112-1. -6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBAB nf) was evaporated to a thickness of 5 nm to form a second hole transport layer 112-2, and On the hole transport layer 112-2, 3-[4-(9-phenanthroline)-(4-methylphenanthroline)-(9- ... PCPPn) was applied to a 5 mm thick film. The third hole transport layer 112-3 was formed by vapor deposition to a thickness of 100 nm.

[0399] Next, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N'-bis(3-methylphenyl)-N,N'-bis[3- (9-phenyl-9H-fluoren-9-yl)phenyl)-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCzP A: 1,6mMemFLPAPrn) was co-evaporated to form a 25 nm light-emitting layer 113. Successful.

[0400] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (vi) was The electron transport layer 114 was formed by vapor deposition so that the thickness of the film became m.

[0401] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The cathode 102 was formed by vapor deposition to fabricate the light-emitting device 2 of this example.

[0402] (Method for manufacturing light-emitting element 3) The light-emitting element 3 has the same structure as the light-emitting element 2 except that the second hole transport layer 112-2 is made of BBABnf instead of BBABnf. N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]fura The light-emitting element was fabricated in the same manner as for Light-emitting element 2, except that it was formed using benzyl-8-amine (abbreviation: BnfABP). Ta.

[0403] The device structures of the light-emitting elements 2 and 3 are summarized in the table below.

[0404] [Table 3]

[0405] The light emitting element 2 and the light emitting element 3 are placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics and The measurements were carried out at room temperature (an atmosphere maintained at 25°C). .

[0406] The luminance-current density characteristics of the light-emitting elements 2 and 3 are shown in FIG. 27, and the current efficiency-luminance characteristics are shown in FIG. 8, the brightness-voltage characteristics are shown in Figure 29, the current-voltage characteristics are shown in Figure 30, and the external quantum efficiency-brightness characteristics are shown in Figure 31. The emission spectrum is shown in Figure 31 and the luminescence spectrum is shown in Figure 32. 2 With The main characteristics of the current model are shown in Table 4.

[0407] [Table 4]

[0408] 27 to 32 and Table 4, the light-emitting elements 2 and 3 of one embodiment of the present invention have the following characteristics: It was found that the blue light emitting device had a low operating voltage and good efficiency.

[0409] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. As shown in FIG. 33, the light-emitting element 2 and the light-emitting element 3 are After a short period of operation, the brightness remains at 94% or more of the initial brightness, and there is very little decrease in brightness due to the accumulation of operating time. It was found that the light emitting element was always small and had a long life. [Example]

[0410] <Synthesis Example 3> In this synthesis example, the active ingredient of one embodiment of the present invention represented by structural formula (229) in the embodiment is Organic compound, N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan A specific example of the synthesis of 6-amine (abbreviation: BBABnf(6)) is given below. The structural formula of 6) is shown below.

[0411] [ka]

[0412] <Step 1: Synthesis of 6-iodobenzo[b]naphtho[1,2-d]furan> 6-iodobenzo[b]naphtho[1,2-d]furan was synthesized using the same synthesis method as in Synthesis Example 1 of Example 1. It was synthesized in the same manner as in Step 1.

[0413] <Step 2: Synthesis of BBABnf(6)> In a 200 mL three-neck flask, add the 6-iodobenzo[b]naphtho[1, 2-d]furan (2.7 g, 8.0 mmol) and 2.6 g (8.0 mmol) of bis( 1,1'-biphenyl-4-yl)amine and 0.19 g (0.40 mmol) of 2-diphenyl Cyclohexylphosphino-2',4',6'-triisopropylbiphenyl (abbreviation: X -Phos) and 1.5g (15mmol) of sodium tert-butoxide. After replacing the atmosphere in the flask with nitrogen, 40 mL of xylene was further added. After degassing, the temperature was raised to 80°C under a nitrogen stream, and 0.11 g (0.20 mmol) of bis( Dibenzylideneacetone)palladium(0) was added and the mixture was stirred at 120°C for 3 hours. After stirring, the resulting mixture was diluted with water, saturated saline, and The organic layer was dried over magnesium sulfate. After removing the solvent, the obtained filtrate was concentrated to give a brown solid. When purified by filtration (mobile phase: chloroform), 3.4 g of the target pale yellow solid was obtained. The synthesis scheme of step 2 is shown in formula (d-3) below.

[0414] [ka]

[0415] The obtained pale yellow solid 1 The H NMR is shown below. 1 H NMR chart 36(B) shows the range from 7.00 ppm to 9.00 ppm in FIG. 36(A). 1 is a chart showing an enlarged range of the compound of the present invention. It was found that the organic compound BBABnf(6) was obtained. 1H NMR (chloroform-d, 500 MHz): δ = 7.25 (d, J = 8.5 Hz , 4H), 7.31(t, J=7.5Hz, 2H), 7.41-7.48(m, 6H), 7.51-7.54(m, 6H), 7.60(d, J=8.0Hz, 4H), 7.67( t, J=7.5Hz, 1H), 7.73(s, 1H), 7.88(d, J=8.0Hz, 1H), 8.42(d, J=7.0Hz, 1H), 6.83(d, J=8.0Hz, 1H )

[0416] The resulting pale yellow solid (3.4 g) was purified by train sublimation. The sublimation purification was carried out under a pressure of 3.8 Pa with argon flowing at a rate of 15 mL / min. The mixture was heated at 75°C for 15 hours. After purification by sublimation, 3.0 g of the target yellow solid was obtained, with a recovery rate of 8. Got it at 7%.

[0417] Next, the UV-visible absorption spectra of BBABnf(6) in toluene solution and solid thin film were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurement was carried out using the same equipment and method as in the previous measurement. The measurement results of the optical spectrum are shown in Figure 37, and the measurement results of the absorption spectrum and emission spectrum of the thin film are shown in Figure 38. The results are shown in Figure 38.

[0418] As shown in Figure 37, the toluene solution of BBABnf(6) has a main absorption peak around 382 nm. was observed, and the peak emission wavelength was 429 nm (excitation wavelength 337 nm).

[0419] Also, from Figure 38, the thin film of BBABnf(6) has a main absorption peak around 390 nm. The peak emission wavelength is 453 nm (excitation wavelength 390 nm). [Example]

[0420] <Synthesis Example 4> In this synthesis example, the active ingredient of one aspect of the present invention represented by structural formula (189) in the embodiment is Organic compound, N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan A specific example of the synthesis of 8-amine (abbreviation: BBABnf(8)) is given below. The structural formula of 8) is shown below.

[0421] [ka]

[0422] <Step 1: Synthesis of BBABnf(8)> In a 200 mL three-neck flask, add 2. 0 g (8.0 mmol) and 2.6 g (8.0 mmol) of bis(1,1'-biphenyl) -4-yl)amine and 0.19 g (0.40 mmol) of 2-dicyclohexylphosphine 1. Add 5 g (15 mmol) of sodium tert-butoxide and place the flask under nitrogen. After the mixture was degassed under reduced pressure, 40 mL of xylene was added. After cooling to 0°C, 0.11 g (0.20 mmol) of bis(dibenzylideneacetone) Radium(0) was added and the mixture was stirred at 120°C for 3 hours, then further stirred at 140°C for 6 hours. The mixture was stirred for 5 hours. After stirring, the resulting mixture was heated at 120°C and then poured onto a pad of Celite (Wako Pure Chemical Industries, Ltd., Catalog No.: 537-02305), Florisil (Wako Pure Chemical Industries, Ltd. Co., Ltd., Catalog No.: 066-05265), and filtered through alumina. The filtrate was concentrated to give a light brown solid. When purified with chloroform (mobile phase), 2.9 g of the target pale yellow solid was obtained. The synthesis scheme of step 1 is shown in formula (d-4) below.

[0423] [ka]

[0424] The obtained pale yellow solid 1 The H NMR is shown below. 1 H NMR chart In addition, FIG. 39(B) shows the range from 7.00 ppm to 9.00 ppm in FIG. 39(A). 1 is a chart showing an enlarged range of the compound of the present invention. It was found that the organic compound BBABnf(8) was obtained. 1 H NMR (chloroform-d, 500 MHz): δ = 7.23 (d, J = 8.5 Hz , 4H), 7.31(t, J=7.5Hz, 2H), 7.36(d, J=8.0Hz, 1 H), 7.42(t, J=8.0Hz, 4H), 7.47(d, J=8.0Hz, 1H) , 7.52(d, J=9.0Hz, 4H), 7.56(t, J=7.5Hz, 1H), 7 .59-7.61(m, 5H), 7.74(t, J=8.5Hz, 1H), 7.87(d , J=8.0Hz, 1H), 8.01(d, J=8.0Hz, 1H), 8.25(d, J =8.0Hz, 1H), 8.65(d, J=8.0Hz, 1H)

[0425] The resulting pale yellow solid (3.9 g) was purified by train sublimation. The sublimation purification was carried out under a pressure of 3.8 Pa with argon flowing at a rate of 15 mL / min. The mixture was heated at 75°C for 15 hours. After sublimation purification, 2.1 g of the target yellow solid was obtained, with a recovery rate of 7. Got it at 2%

[0426] Next, the UV-visible absorption spectra of BBABnf(8) in toluene solution and solid thin film were measured. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurement was carried out using the same equipment and method as in the previous measurement. The measurement results of the optical spectrum are shown in Figure 40, and the measurement results of the absorption spectrum and emission spectrum of the thin film are shown in Figure 41. The results are shown in Figure 41.

[0427] As shown in Figure 40, the toluene solution of BBABnf(8) has a main absorption peak around 337 nm. was observed, and the peak emission wavelength was 410 nm (excitation wavelength 337 nm).

[0428] Also, from Figure 41, the thin film of BBABnf(8) has a main absorption peak around 370 nm. The peak emission wavelength is 431 nm (excitation wavelength 358 nm). [Example]

[0429] In this example, the light-emitting elements 4 and 5 of one embodiment of the present invention described in Embodiment 1 The structural formulae of the organic compounds used in the light-emitting elements 4 and 5 are shown below.

[0430] [ka]

[0431] (Method for manufacturing light-emitting element 4) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 2 mm x 2 mm.

[0432] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0433] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0434] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. By this method, 2,3,6,7,10,11-hexacyano-1,2-dione represented by the above structural formula (i) ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0435] Next, on the hole injection layer 111, 4,4'-bis[N-(1- naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm The first hole transport layer 112-1 is formed by vapor deposition in the manner described above, and then a layer of N,N-di(4-bis(2-methyl-2-methyl-2-phenyl)-2-propanol) is an organic compound of one embodiment of the present invention represented by the structural formula (229). (phenyl)benzo[b]naphtho[1,2-d]furan-6-amine) (abbreviation: BBABn f(6)) is evaporated to a thickness of 10 nm to form a second hole transport layer 112-2, On the second hole transport layer 112-2, 3,6-bis[4-(2- naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: βNP2PC) The third hole transport layer 112-3 was formed by vapor deposition to a thickness of 10 nm.

[0436] Next, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N'-bis(3-methylphenyl)-N,N'-bis[3- (9-phenyl-9H-fluoren-9-yl)phenyl)-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCzP A: 1,6mMemFLPAPrn) was co-evaporated to form a 25 nm light-emitting layer 113. Successful.

[0437] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (vi) was The electron transport layer 114 was formed by vapor deposition so that the thickness of the film became m.

[0438] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The cathode 102 was formed by vapor deposition to fabricate the light emitting device 4 of this example.

[0439] (Method for manufacturing light-emitting element 5) The light-emitting element 5 is the same as the light-emitting element 4 except that the second hole transport layer 112-2 is made of BBABnf(6). Instead, N,N-di(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8- The light-emitting element was fabricated in the same manner as in Light-emitting element 4, except that it was formed using amine (abbreviation: BBABnf(8)). .

[0440] The device structures of the light-emitting elements 4 and 5 are summarized in the table below.

[0441] [Table 5]

[0442] The light emitting elements 4 and 5 are placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics and The measurements were carried out at room temperature (an atmosphere maintained at 25°C). .

[0443] The luminance-current density characteristics of the light-emitting elements 4 and 5 are shown in FIG. 42, and the current efficiency-luminance characteristics are shown in FIG. 3, the brightness-voltage characteristics are shown in Figure 44, the current-voltage characteristics are shown in Figure 45, and the external quantum efficiency-brightness characteristics are shown in Figure 46. The emission spectrum is shown in Figure 46 and the luminescence spectrum is shown in Figure 47. 2 With The main characteristics of the current model are shown in Table 6.

[0444] [Table 6]

[0445] 42 to 46 and Table 6, the light-emitting elements 4 and 5 of one embodiment of the present invention have the following characteristics: It was found that the blue light emitting device had a low operating voltage and good efficiency.

[0446] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. As shown in FIG. 48, the light-emitting element 4 and the light-emitting element 5 are Even after 24-hour operation, the brightness remains at 85% or more of the initial brightness, and there is no decrease in brightness due to the accumulation of operation time. It was found that the light emitting element had a very small capacitance and a long life. [Example]

[0447] In this example, the light-emitting elements 6 and 7 of one embodiment of the present invention described in Embodiment 1 The structural formulae of the organic compounds used in the light-emitting elements 6 and 7 are shown below.

[0448] [ka]

[0449] (Method for manufacturing light-emitting element 6) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 2 mm x 2 mm.

[0450] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0451] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0452] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. By this method, 2,3,6,7,10,11-hexacyano-1,2-dione represented by the above structural formula (i) ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0453] Next, on the hole injection layer 111, 4,4'-bis[N-(1- naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 20 nm The first hole transport layer 112-1 is formed by vapor deposition in the manner described above, and then a layer of N,N-di(4-bis(2-methyl-2-methyl-2-phenyl)-2-propanol) is an organic compound of one embodiment of the present invention represented by the structural formula (229). (phenyl)benzo[b]naphtho[1,2-d]furan-6-amine) (abbreviation: BBABn f(6)) was evaporated to a thickness of 10 nm to form a second hole transport layer 112-2. .

[0454] Next, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N'-bis(3-methylphenyl)-N,N'-bis[3- (9-phenyl-9H-fluoren-9-yl)phenyl)-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCzP A: 1,6mMemFLPAPrn) was co-evaporated to form a 25 nm light-emitting layer 113. Successful.

[0455] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (vi) was The electron transport layer 114 was formed by vapor deposition so that the thickness of the film became m.

[0456] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The cathode 102 was formed by vapor deposition to fabricate the light emitting device 6 of this example.

[0457] (Method for manufacturing light-emitting element 7) The light-emitting element 7 has the same structure as the light-emitting element 6 except that the second hole transport layer 112-2 is made of BBABnf(6). Instead, N,N-di(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8- The light-emitting element was fabricated in the same manner as in Light-emitting element 6, except that it was formed using amine (abbreviation: BBABnf(8)). .

[0458] The device structures of the light-emitting elements 6 and 7 are summarized in the table below.

[0459] [Table 7]

[0460] The light emitting elements 6 and 7 are placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics and The measurements were carried out at room temperature (an atmosphere maintained at 25°C). .

[0461] The luminance-current density characteristics of the light-emitting elements 6 and 7 are shown in FIG. 49, and the current efficiency-luminance characteristics are shown in FIG. 0, brightness-voltage characteristics are shown in Figure 51, current-voltage characteristics are shown in Figure 52, and external quantum efficiency-brightness characteristics are shown in Figure 53. The emission spectrum is shown in Figure 53 and the luminescence spectrum is shown in Figure 54. 2 With The main characteristics of the current model are shown in Table 8.

[0462] [Table 8]

[0463] 49 to 54 and Table 8, the light-emitting elements 6 and 7 of one embodiment of the present invention have the following characteristics: It was found that the blue light emitting device had a low operating voltage and good efficiency. [Example]

[0464] In this example, the light-emitting element 8 of one embodiment of the present invention described in Embodiment 1 will be described. The structural formula of the organic compound used in the light-emitting element 8 is shown below.

[0465] [ka]

[0466] (Method for manufacturing light-emitting element 8) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 2 mm x 2 mm.

[0467] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0468] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0469] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The N,N- organic compound of one embodiment of the present invention represented by the above structural formula (146) can be obtained by the evaporation method. Bis(biphenyl-4-yl)-6-phenylbenzo[b]naphtho[1,2-d]furan -8-amine (abbreviation: BBABnf) and 1,3,4,5- ,7,8-Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ ) were co-evaporated to a weight ratio of 2:1 (=BBABnf:F6-TCNNQ) to 10 nm. The hole injection layer 111 was formed by deposition.

[0470] Next, BBABnf was deposited on the hole injection layer 111 to a thickness of 10 nm. The hole transport layer 112-1 is formed by disposing a compound represented by the structural formula (vii) on the first hole transport layer 112-1. ) represented by 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H- Rubazole (abbreviation: PCPPn) was evaporated to a thickness of 20 nm to form a second hole transport layer. Formed 112-2.

[0471] Next, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N'-bis(3-methylphenyl)-N,N'-bis[3- (9-phenyl-9H-fluoren-9-yl)phenyl)-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCzP A: 1,6mMemFLPAPrn) was co-evaporated to form a 25 nm light-emitting layer 113. Successful.

[0472] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiazolinone)-1-(2-methyl-2-propanol]-1-one represented by the above structural formula (xii) was [4-(4-phenyl-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II) was evaporated to a thickness of 10 nm, and then the above structural formula (x iii) 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1, 10-phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 15 nm, and A molecule transport layer 114 was formed.

[0473] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The cathode 102 was formed by vapor deposition to fabricate the light emitting device 8 of this example.

[0474] The device structure of the light-emitting device 8 is summarized in the table below.

[0475] [Table 9]

[0476] The light emitting element 8 is placed in a glove box with a nitrogen atmosphere so that the light emitting element is not exposed to the atmosphere. The process of sealing the device with a glass substrate (applying a sealant around the device and applying UV light during sealing) After the device was subjected to a thermal treatment at 80°C for 1 hour, the initial characteristics and reliability were measured. The measurements were carried out at room temperature (an atmosphere maintained at 25°C).

[0477] The luminance-current density characteristics of the light-emitting element 8 are shown in FIG. 55, the current efficiency-luminance characteristics in FIG. 56, and the luminance-current The voltage characteristics are shown in Figure 57, the current-voltage characteristics in Figure 58, the external quantum efficiency-luminance characteristics in Figure 59, and the The optical spectrum is shown in Figure 60. The light emitting element 8 has a luminance of 1000 cd / m 2 Major nearby The characteristics are shown in Table 10.

[0478] [Table 10]

[0479] 55 to 60 and Table 10, it can be seen that the light-emitting element 8 of one embodiment of the present invention has a low driving voltage. It was also found to be a blue light-emitting device with good efficiency.

[0480] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. As shown in FIG. 61, the light-emitting element 8 remained unchanged even after 100 hours of operation. It maintains 90% or more of its initial brightness, and the decrease in brightness due to accumulated operating time is very small. It was found that the light-emitting element had a long life. [Explanation of symbols]

[0481] 101 Anode 102 Cathode 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 Electronic Relay Layer 119 Electron injection buffer layer 400 boards 401 Anode 403 EL layer 404 Cathode 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 Driver circuit section (source line driver circuit) 602 Pixel section 603 Drive circuit section (gate line drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching FET 612 Current control FET 613 Anode 614 Insulators 616 EL layer 617 Cathode 618 Light-emitting element 730 insulating film 770 Planarization insulating film 772 Conductive film 782 Light-emitting element 783 Droplet discharge device 784 Droplet 785 layers 786 EL layer 788 Conductive Film 901 Case 902 Liquid crystal layer 903 Backlight Unit 904 Case 905 Driver IC 906 terminal 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024W anode 1024R Anode 1024G anode 1024B Anode 1025 Bulkhead 1028 EL layer 1029 Cathode 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black Matrix 1036 Overcoat layer 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 1400 Droplet discharge device 1402 PCB 1403 Droplet discharge means 1404 Imaging means 1405 Head 1406 dotted line 1407 Control means 1408 Storage medium 1409 Image processing means 1410 Computer 1411 Marker 1412 head 1413 Material Source 1414 Material Source 1415 Material Source 1416 Head 2001 Case 2002 light source 3001 Lighting equipment 5000 display area 5001 Display area 5002 Display area 5003 Display area 5004 Display area 5005 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7210 Second display unit 7301 Housing 7302 Housing 7303 Connection section 7304 Display section 7305 Display section 7306 Speaker section 7307 Recording medium insertion section 7308 LED Lamp 7309 Operation Key 7310 Connection terminal 7311 Sensor 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 7400 mobile phone 9033 Fasteners 9034 Switch 9035 Power Switch 9036 Switch 9038 Operation switch 9310 Mobile Information Terminal 9311 Display Panel 9312 Display area 9313 Hinge 9315 Housing 9630 chassis 9631 Display section 9631a Display section 9631b Display section 9632a Touch panel area 9632b Touch panel area 9633 Solar Cells 9634 Charge / Discharge Control Circuit 9635 Battery 9636 DC / DC Converter 9637 Operation Key 9638 Converter 9639 Button

Claims

[Claim 1] A hole transport material comprising an organic compound having a substituted or unsubstituted benzonaphthofuran skeleton and a substituted or unsubstituted amine skeleton.

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