KR102629300B1 - Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices - Google Patents

Abstract

Provides new organic compounds. Alternatively, a novel organic compound having hole transport properties is provided. Alternatively, a new hole transport material is provided. A new light emitting device is provided. Alternatively, a light emitting device with a good lifespan is provided. Alternatively, a light-emitting device with good luminous efficiency is provided. An organic compound having a benzo[b]naphtho[2,1-d]furanyl group or benzo[b]naphtho[2,3-d]furanyl group and a diarylamine skeleton is provided. Alternatively, a light emitting device using the organic compound is provided.

Description

Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices

One aspect of the present invention relates to light-emitting elements, display modules, lighting modules, display devices, light-emitting devices, electronic devices, and lighting devices. Additionally, one embodiment of the present invention is not limited to the above technical field. The technical field of one form of the invention disclosed in this specification and the like relates to products, methods, or manufacturing methods. Alternatively, one form of the invention relates to a process, machine, manufacture, or composition of matter. Therefore, more specifically, the technical field of one form of the present invention disclosed in this specification includes semiconductor devices, display devices, liquid crystal display devices, light emitting devices, lighting devices, power storage devices, memory devices, imaging devices, and driving methods thereof, Or these manufacturing methods can be cited as examples.

The commercialization of light-emitting devices (organic EL devices) using electroluminescence (EL) using organic compounds is in progress. The basic structure of these light-emitting devices is that an organic compound layer (EL layer) containing a light-emitting material is sandwiched between a pair of electrodes. By applying a voltage to this element, injecting carriers, and using the recombination energy of the carriers, light emission from the light-emitting material can be obtained.

Since such a light-emitting device is self-emitting, when used as a pixel of a display, it has advantages such as higher visibility compared to liquid crystal and no need for a backlight, making it suitable as a flat panel display device. Additionally, a major advantage of displays using such light-emitting elements is that they can be manufactured in a thin and lightweight manner. Another feature is that the response speed is very fast.

Additionally, these light-emitting devices can emit light in a two-dimensional manner because the light-emitting layer can be formed continuously in two dimensions. Since this is a characteristic that is difficult to obtain with point light sources such as incandescent bulbs or LEDs, or line light sources such as fluorescent lamps, it also has high usability as a surface light source that can be applied to lighting, etc.

Displays and lighting devices using light-emitting devices like this can be suitably applied to various electronic devices, but research and development is in progress for light-emitting devices with better efficiency and lifespan.

In such light-emitting devices, a hole injection layer to facilitate hole injection is sometimes formed in the EL layer, which is an organic compound. However, one of the materials for the hole injection layer is an organic compound with acceptor properties. Organic compounds with acceptor properties can be easily formed by vapor deposition, making them suitable for mass production, and their use is spreading. However, the LUMO level of organic compounds with acceptor properties and the HOMO level of organic compounds constituting the hole transport layer are different. If separated, hole injection into the EL layer is difficult. Therefore, it is necessary to bring the LUMO level of the organic compound having acceptor properties close to the HOMO level of the organic compound constituting the hole transport layer. However, if the HOMO level of the organic compound constituting the hole transport layer is shallow, the HOMO level of the emitting layer becomes closer to the HOMO level of the organic compound constituting the hole transport layer. Since the difference in the HOMO level of the hole transport layer increases, there is a problem that even if holes can be injected from the electrode into the EL layer, it becomes difficult to inject holes from the hole transport layer into the host material of the light emitting layer.

Patent Document 1 discloses a configuration for providing a hole-transporting material having a HOMO level between the HOMO level of the first hole-injecting layer and the HOMO level of the host material between the first hole-transporting layer and the light-emitting layer in contact with the hole-injecting layer. .

Although the characteristics of light-emitting devices have improved significantly, they are still insufficient to meet the high demands for various characteristics, including efficiency and durability.

International Publication No. WO2011/065136

Therefore, in one form of the present invention, the purpose of the present invention is to provide a novel organic compound. Alternatively, one embodiment of the present invention aims to provide a novel organic compound having hole transport properties. Alternatively, one embodiment of the present invention aims to provide a novel hole transport material. Alternatively, the task is to provide a new light-emitting device. Alternatively, the object is to provide a light-emitting element with a good lifespan. Alternatively, the object is to provide a light-emitting device with good luminous efficiency. Alternatively, the object is to provide a light-emitting device with a low driving voltage.

Alternatively, another aspect of the present invention aims to provide highly reliable light-emitting devices, electronic devices, and display devices, respectively. Alternatively, another aspect of the present invention aims to provide a light-emitting device, an electronic device, and a display device with low power consumption, respectively.

The present invention is intended to solve any one of the problems described above.

One form of the present invention is an organic compound represented by the following general formula (G1).

[Formula 1]

However, in the general formula (G1), one of R ¹ to R ¹⁰ is a group represented by the general formula (g1) below, and the rest are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, or a cyclic group with 3 to 6 carbon atoms. It represents any one of a hydrocarbon group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[Formula 2]

In addition, in the general formula (g1), Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the general formula (g2) to (g4) below. represents one or the other. Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2, but Ar ³ has the following general formula (g4 ), n is 1 or 2, and when Ar ⁴ is a group represented by the following general formula (g4), m is 1 or 2. Additionally, when n is 2, the two Ar ¹ 's may be different or the same, and similarly, when m is 2, the two Ar ² 's may be different or the same. In addition, when Ar ³ and Ar ⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms and have a substituent, the substituent group may be an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, or a cyclic hydrocarbon group having 3 to 6 carbon atoms. , an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to the following general formulas (g4).

In addition, configurations in which n and m are 0, Ar ³ and Ar ⁴ are phenyl groups, and the 2nd and 6th positions of the phenyl group are substituted with aromatic hydrocarbon groups are excluded, and n and m are each independently 1 or 2. , Ar ¹ , Ar ² When the skeleton bonded to the nitrogen is a benzene ring, that is, when it has an aniline skeleton, configurations in which the 2nd and 6th positions of the aniline skeleton are substituted with aromatic hydrocarbon groups are excluded.

[Formula 3]

However, in general formula (g2), one of R ³¹ to R ⁴⁰ represents a single bond and is bonded to the nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g3), one of R ⁴¹ to R ⁵⁰ represents a single bond and is bonded to a nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g4), one of R ⁵¹ to R ⁶⁰ represents a single bond and is bonded to Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

In another embodiment of the present invention, in the above configuration, the group represented by the general formula (g1) is bonded to any one of R ¹ , R ⁸ , and R ¹⁰ in the organic compound represented by the general formula (G1). It is an organic compound.

Alternatively, another aspect of the present invention is an organic compound in which the group represented by the general formula (g1) in the above structure is bonded to R ¹⁰ in the organic compound represented by the general formula (G1).

Alternatively, another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[Formula 4]

However, in the general formula (G2), one of R ¹¹ to R ²⁰ is a group represented by the general formula (g1) below, and the rest are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, or a cyclic group with 3 to 6 carbon atoms. It represents any one of a hydrocarbon group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[Formula 5]

However, in the general formula (g1), Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the general formula (g2) to (g4) below. represents one or the other. In addition, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2, but Ar ³ is represented by the following general formula ( In the case of a group represented by g4), n is 1 or 2, and in the case that Ar ⁴ is a group represented by the general formula (g4) below, m is 1 or 2. Additionally, when n is 2, the two Ar ¹ 's may be different or the same, and similarly, when m is 2, the two Ar ² 's may be different or the same. In addition, when Ar ³ and Ar ⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms and have a substituent, the substituent group may be an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, or a cyclic hydrocarbon group having 3 to 6 carbon atoms. , an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to the following general formulas (g4).

In addition, configurations in which n and m are 0, Ar ³ and Ar ⁴ are phenyl groups, and the 2nd and 6th positions of the phenyl group are substituted with aromatic hydrocarbon groups are excluded, and n and m are each independently 1 or 2. , Ar ¹ , Ar ² When the skeleton bonded to the nitrogen is a benzene ring, that is, when it has an aniline skeleton, configurations in which the 2nd and 6th positions of the aniline skeleton are substituted with aromatic hydrocarbon groups are excluded.

[Formula 6]

However, in general formula (g2), one of R ³¹ to R ⁴⁰ represents a single bond and is bonded to the nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g3), one of R ⁴¹ to R ⁵⁰ represents a single bond and is bonded to a nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g4), one of R ⁵¹ to R ⁶⁰ represents a single bond and is bonded to Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Another embodiment of the present invention is an organic compound in which the group represented by the general formula (g1) is bonded to R ¹⁸ or R ²⁰ in the organic compound represented by the general formula (G2).

Another embodiment of the present invention is an organic compound in which the group represented by the general formula (g1) is bonded to R ²⁰ in the organic compound represented by the general formula (G2).

In another embodiment of the present invention, in the above configuration, Ar ¹ and Ar ² are each independently substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, and Ar ³ and Ar ⁴ are each independently substituted or unsubstituted. It is an organic compound that is a ringed aromatic hydrocarbon group having 6 to 10 carbon atoms.

Another embodiment of the present invention is an organic compound in which Ar ³ and Ar ⁴ are each independently any one of a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Another embodiment of the present invention is an organic compound in which Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

Alternatively, another embodiment of the present invention is an organic compound in which Ar ³ and Ar ⁴ are phenyl groups.

Alternatively, another form of the present invention is an organic compound in which Ar ¹ and Ar ² in the above configuration are phenylene groups.

Alternatively, another form of the present invention is an organic compound in which n and m are 2 in the above configuration.

Alternatively, another form of the present invention is an organic compound in which both n and m are 1 in the above configuration.

Alternatively, another aspect of the present invention is a light emitting device having an anode, a cathode, and an EL layer, the EL layer being located between the anode and the cathode, and the EL layer containing the organic compound.

Alternatively, another aspect of the present invention has an anode, a cathode, and an EL layer, the EL layer is located between the anode and the cathode, the EL layer has a light-emitting layer, and the light-emitting layer includes the organic compound. It is small.

Alternatively, another aspect of the present invention is a light emitting device in which the light emitting layer further includes a light emitting material in the above configuration.

Alternatively, another aspect of the present invention is a light-emitting device in which the light-emitting layer further includes a material having electron transport properties.

Alternatively, another aspect of the present invention has an anode, a cathode, and an EL layer, the EL layer is located between the anode and the cathode, the EL layer has a light-emitting layer and a hole transport layer, and the light-emitting layer has a light-emitting material. , the hole transport layer is located between the light emitting layer and the anode, and is a light emitting device including the organic compound in the hole transport layer.

Alternatively, in another aspect of the present invention, in the above configuration, the EL layer further has 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 is an organic compound having an acceptor property. It is a light emitting device containing a.

Alternatively, in another form of the present invention, in the above configuration, the compound having the acceptor property is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaza It is a light emitting device made of triphenylene.

Alternatively, another aspect of the present invention is that in the above configuration, the hole transport layer has a first layer, a second layer, and a third layer, and the first layer is located between the hole injection layer and the second layer, and a third layer is positioned between the second layer and the emissive layer, the first layer is in contact with the hole injection layer, the third layer is in contact with the emissive layer, and the first layer includes a first hole transport material; , the second layer includes the organic compound, the third layer includes 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 first hole transport material. It is deeper than the HOMO level of the transport material, the HOMO level of the host material is deeper than the HOMO level of the organic compound, and the difference between the HOMO level of the organic compound and the HOMO level of the third hole transport material is 0.3 eV or less. It is a light emitting device.

Alternatively, another aspect of the present invention is a light-emitting device in which the HOMO level of the first hole transport material is -5.4 eV or higher in the above configuration.

Alternatively, another aspect of the present invention is a light emitting device in which, in the above configuration, the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound is 0.3 eV or less.

Alternatively, another aspect of the present invention is a light emitting device in which, in the above configuration, the difference between the HOMO level of the organic compound and the HOMO level of the third hole transport material is 0.2 eV or less.

Alternatively, another aspect of the present invention is a light emitting device in which, in the above configuration, the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound is 0.2 eV or less.

Alternatively, another aspect of the present invention is a light-emitting device in the above configuration in which the HOMO level of the light-emitting material is higher than the HOMO level of the host material.

Alternatively, another aspect of the present invention is a light emitting device in which, in the above configuration, the HOMO level of the third hole transport material is equal to or deeper than the HOMO level of the host material.

Alternatively, another aspect of the present invention is a light-emitting device in the above configuration wherein the light-emitting material is a fluorescent light-emitting material.

Alternatively, another aspect of the present invention is a light-emitting device in which the light emitted by the light-emitting material in the above configuration is blue fluorescent light.

Alternatively, another aspect of the present invention is a light emitting device in the above configuration wherein the light emitting material is a condensed aromatic diamine compound. Additionally, the amino group of the aromatic diamine compound includes a carbazolyl group.

Alternatively, another aspect of the present invention is a light-emitting device in the above-described configuration wherein the light-emitting material is a diaminopyrene compound. In addition, the amino group of the diaminopyrene compound shall include a carbazolyl group.

Alternatively, another form of the present invention is a light emitting device having the transistor or substrate in the above configuration.

Alternatively, another aspect of the present invention is an electronic device having the above light-emitting device, a sensor, an operation button, a speaker, or a microphone.

Alternatively, another aspect of the present invention is a lighting device having a light emitting device having the above structure and a housing.

Additionally, the light-emitting device in this specification includes an image display device using a light-emitting element. Additionally, the light-emitting element may be equipped with a connector, for example, an anisotropic conductive film or TCP (Tape Carrier Package), a module provided with a printed circuit board at the end of the TCP, or the light-emitting element may be equipped with an IC (integrated circuit) in a COG (Chip On Glass) manner. A directly mounted module may have a light emitting device. Additionally, lighting fixtures and the like may have a light emitting device.

One embodiment of the present invention can provide a novel light-emitting device. Alternatively, a light emitting device with a good lifespan can be provided. Alternatively, a light-emitting device with good luminous efficiency can be provided. Alternatively, a light emitting device with a low driving voltage can be provided.

Alternatively, another aspect of the present invention can provide highly reliable light emitting devices, electronic devices, and display devices, respectively. Alternatively, another aspect of the present invention can provide a light emitting device, an electronic device, and a display device with low power consumption, respectively.

Additionally, the description of these effects does not preclude the existence of other effects. Additionally, one embodiment of the present invention does not necessarily have all of these effects. Additionally, effects other than these will naturally become apparent from descriptions such as specifications, drawings, claims, etc., and effects other than these can be extracted from descriptions such as specifications, drawings, claims, etc.

1 is a schematic diagram of a light emitting device.
Figure 2 is a conceptual diagram of an active matrix type light emitting device.
3 is a conceptual diagram of an active matrix type light emitting device.
4 is a conceptual diagram of an active matrix type light emitting device.
5 is a conceptual diagram of a passive matrix type light emitting device.
Figure 6 is a diagram showing a lighting device.
7 is a diagram showing an electronic device.
8 is a diagram showing an electronic device.
Figure 9 is a diagram showing a lighting device.
Figure 10 is a diagram showing a lighting device.
Fig. 11 is a diagram showing an in-vehicle display device and lighting device.
12 is a diagram showing an electronic device.
13 is a diagram showing an electronic device.
Figure 14 is a ¹ H NMR chart of 2-chlorobenzo[b]naphtho[2,3-d]furan.
Figure 15 is ^{a 1} H NMR chart of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)(2)).
Figure 16 shows the absorption spectrum and emission spectrum of BBABnf(II)(2)) in toluene solution.
Figure 17 shows the absorption spectrum and emission spectrum of BBABnf(II)(2)) in a thin film state.
Figure 18 is a ¹ H NMR chart of 4-chlorobenzo[b]naphtho[2,3-d]furan.
Figure 19 is a ¹ H NMR chart of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)(4)).
Figure 20 shows the absorption spectrum and emission spectrum of BBABnf(II)(4)) in toluene solution.
Figure 21 shows the absorption spectrum and emission spectrum of BBABnf(II)(4)) in a thin film state.
22 shows luminance-current density characteristics of light-emitting device 1 and light-emitting device 2.
23 shows current efficiency-luminance characteristics of light-emitting device 1 and light-emitting device 2.
24 shows the luminance-voltage characteristics of light-emitting device 1 and light-emitting device 2.
25 shows current-voltage characteristics of light-emitting device 1 and light-emitting device 2.
26 shows external quantum efficiency-luminance characteristics of light-emitting device 1 and light-emitting device 2.
Figure 27 shows the emission spectra of light-emitting element 1 and light-emitting element 2.
28 shows normalized luminance-time change characteristics of light-emitting device 1 and light-emitting device 2.
Figure 29 shows the luminance-current density characteristics of light-emitting element 3 and light-emitting element 4.
30 shows the current efficiency-luminance characteristics of light-emitting element 3 and light-emitting element 4.
31 shows the luminance-voltage characteristics of light-emitting device 3 and light-emitting device 4.
32 shows current-voltage characteristics of light-emitting device 3 and light-emitting device 4.
33 shows external quantum efficiency-luminance characteristics of light-emitting device 3 and light-emitting device 4.
Figure 34 shows the emission spectra of light-emitting element 3 and light-emitting element 4.
35 shows normalized luminance-time change characteristics of light-emitting device 3 and light-emitting device 4.
36 shows the luminance-current density characteristics of light-emitting device 5 and light-emitting device 6.
37 shows the current efficiency-luminance characteristics of light-emitting element 5 and light-emitting element 6.
38 shows the luminance-voltage characteristics of light-emitting element 5 and light-emitting element 6.
39 shows current-voltage characteristics of light-emitting device 5 and light-emitting device 6.
Figure 40 shows external quantum efficiency-luminance characteristics of light-emitting device 5 and light-emitting device 6.
Figure 41 shows the emission spectra of light-emitting element 5 and light-emitting element 6.
42 shows normalized luminance-time change characteristics of light-emitting device 5 and light-emitting device 6.
Figure 43 shows the luminance-current density characteristics of light-emitting device 7.
Figure 44 shows the current efficiency-luminance characteristics of light emitting element 7.
Figure 45 shows the luminance-voltage characteristics of light-emitting device 7.
Figure 46 shows the current-voltage characteristics of light-emitting device 7.
Figure 47 shows external quantum efficiency-brightness characteristics of light-emitting device 7.
Figure 48 shows the emission spectrum of light-emitting element 7.
Figure 49 shows the luminance-current density characteristics of light-emitting device 8.
Figure 50 shows the current efficiency-luminance characteristics of light emitting element 8.
Figure 51 shows the luminance-voltage characteristics of light-emitting element 8.
Figure 52 shows the current-voltage characteristics of light-emitting element 8.
Figure 53 shows external quantum efficiency-brightness characteristics of light-emitting device 8.
Figure 54 shows the emission spectrum of light-emitting element 8.
Figure 55 shows the luminance-current density characteristics of light-emitting element 9 and light-emitting element 10.
Figure 56 shows the current efficiency-luminance characteristics of light-emitting element 9 and light-emitting element 10.
Figure 57 shows the luminance-voltage characteristics of light-emitting element 9 and light-emitting element 10.
Figure 58 shows the current-voltage characteristics of light-emitting element 9 and light-emitting element 10.
Figure 59 shows external quantum efficiency-luminance characteristics of light-emitting element 9 and light-emitting element 10.
Figure 60 shows the emission spectra of light-emitting element 9 and light-emitting element 10.
61 shows normalized luminance-time change characteristics of light-emitting device 9 and light-emitting device 10.
Figure 62 shows the luminance-current density characteristics of light-emitting element 11 and light-emitting element 12.
Figure 63 shows the current efficiency-luminance characteristics of light-emitting element 11 and light-emitting element 12.
Figure 64 shows the luminance-voltage characteristics of light-emitting element 11 and light-emitting element 12.
Figure 65 shows the current-voltage characteristics of light-emitting element 11 and light-emitting element 12.
Figure 66 shows external quantum efficiency-luminance characteristics of light-emitting element 11 and light-emitting element 12.
Figure 67 shows emission spectra of light-emitting elements 11 and 12.
Figure 68 shows normalized luminance-time change characteristics of light-emitting device 11 and light-emitting device 12.

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and those skilled in the art can easily understand that the form and details can be changed in various ways without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as limited to the description of the embodiments shown below.

(Embodiment 1)

One type of organic compound of the present invention is an organic compound represented by the following general formula (G1) or (G2).

[Formula 7]

However, in the general formula (G1), one of R ¹ to R ¹⁰ is a group represented by the general formula (g1) below, and the rest are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, or a cyclic group with 3 to 6 carbon atoms. It represents any one of a hydrocarbon group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[Formula 8]

In addition, in the general formula (G2), one of R ¹¹ to R ²⁰ is a group represented by the general formula (g1) below, and the rest are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, or a cyclic group with 3 to 6 carbon atoms. It represents any one of a hydrocarbon group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[Formula 9]

In the general formula (g1), Ar ³ and Ar ⁴ are each independently any of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4) represents one. In addition, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2, but Ar ³ is represented by the following general formula ( In the case of a group represented by g4), n is 1 or 2, and in the case that Ar ⁴ is a group represented by the general formula (g4) below, m is 1 or 2. Additionally, when n is 2, the two Ar ¹ 's may be different or the same, and similarly, when m is 2, the two Ar ² 's may be different or the same. In addition, when Ar ³ and Ar ⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms and have a substituent, the substituent group may be an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, or a cyclic hydrocarbon group having 3 to 6 carbon atoms. , an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to the following general formulas (g4).

[Formula 10]

In general formula (g2), one of R ³¹ to R ⁴⁰ represents a single bond and is bonded to a nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g3), one of R ⁴¹ to R ⁵⁰ represents a single bond and is bonded to a nitrogen atom, Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

Additionally, in general formula (g4), one of R ⁵¹ to R ⁶⁰ represents a single bond and is bonded to Ar ³ or Ar ⁴ in general formula (g1). The remainder each independently represents any one of hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cyano group, a halogen, and a haloalkyl group with 1 to 6 carbon atoms. represents one.

In addition, the organic compound in which any of R ¹ , R ⁸ , and R ¹⁰ in the general formula (G1) is represented by the general formula (g1) can be easily synthesized with a small number of steps required for synthesis, and provides a highly reliable device. It is desirable because it can be provided. In particular, an organic compound in which R ¹⁰ in the general formula (G1) is a group represented by the general formula (g1) has a high phosphorescence rank and can be suitably used in a phosphorescent device.

In addition, an organic compound in which any of R ¹⁸ and R ²⁰ in the general formula (G2) is a group represented by the general formula (g1) is preferable because the number of steps required for synthesis is small and it can be easily synthesized. Additionally, a light-emitting device using the organic compound is preferable because it can be used as a highly reliable light-emitting device. In particular, the organic compound in which R ²⁰ in the general formula (G2) is a group represented by the general formula (g1) has a high phosphorescence rank and can be suitably used in a phosphorescent device.

As a substituent applicable to the general formulas R ¹ to R ²⁰ and R ³¹ to R ⁶⁰ , specifically, a substituent represented by the following structural formula (1-1) to the following structural formula (1-37) or the following structural formula (2- Substituents represented by 1) to the following structural formulas (2-13), etc. may be mentioned. Additionally, the substitution position in the following structural formulas (2-1) to (2-13) is not limited.

[Formula 11]

[Formula 12]

Ar ³ and Ar ⁴ each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms or a group represented by the general formulas (g2) to (g4). Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms include groups represented by the following structural formulas (1-38) and (1-39). In addition, for these, the position of substitution does not matter. Additionally, they may have substituents.

[Formula 13]

When Ar ³ and Ar ⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms and also have a substituent, the substituents include aromatic hydrocarbon groups having 6 to 10 carbon atoms, hydrocarbon groups having 1 to 6 carbon atoms, and cyclic hydrocarbon groups having 3 to 6 carbon atoms. , an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the general formulas (g2) to (g4). However, aromatic hydrocarbon group with 6 to 10 carbon atoms, hydrocarbon group with 1 to 6 carbon atoms, cyclic hydrocarbon group with 3 to 6 carbon atoms, alkoxy group with 1 to 6 carbon atoms, cyano group, fluorine, halo group with 1 to 6 carbon atoms Specific examples of alkyl groups include those shown in the following structural formulas (1-1) to (1-37). Additionally, aromatic hydrocarbon groups having 6 to 10 carbon atoms include phenyl group, 1-naphthyl group, and 2-naphthyl group.

[Formula 14]

Specific examples of Ar ³ , Ar ⁴ , and Ar ³ and Ar ⁴ having substituents are preferably groups represented by the following structural formulas (1-100) to (1-134).

[Formula 15]

Additionally, Ar ¹ and Ar ² are divalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and representative examples include the following. In addition, for these, the position of substitution does not matter. Additionally, it may have a substituent.

[Formula 16]

In addition, examples of the case where n is 2 and the two Ar ¹ are different from each other and the case where m is 2 and the two Ar ² are different are shown in the following structural formulas (1-40) to (1-74).

[Formula 17]

In addition, in the organic compound having the above structure, Ar ¹ and Ar ² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, and Ar ³ and Ar ⁴ are each independently substituted or unsubstituted. An aromatic hydrocarbon group having 6 to 10 carbon atoms is preferable because no bulky skeleton is bonded to the amine skeleton and a material with high hole transport properties can be provided. In addition, since it does not have a large condensed ring hydrocarbon, it is difficult to receive electrons, and when used as a hole transport material in a device, it exhibits high electron blocking properties, so it is desirable because it can provide a device with high luminous efficiency.

In addition, the configuration in which n and m are 0, Ar ³ and Ar ⁴ are phenyl groups, and the 2nd and 6th positions of the phenyl group are substituted with aromatic hydrocarbon groups have high hole transport properties because the bulky substituent is bonded to the amine structure. Since it is difficult to have, it is excluded as an organic compound of the present invention. In addition, when n and m are each independently 1 or 2, and the skeleton bonded to the nitrogen of Ar ¹ and Ar ² is a benzene ring, that is, when it has an aniline skeleton, the 2nd and 6th positions of the aniline skeleton are aromatic hydrocarbon groups. Since the substituted structure has a bulky substituent bonded to the amine structure, it is difficult to have high hole transport properties, so it is excluded as an organic compound of the present invention.

In addition, in the organic compound having the above structure, if Ar ³ and Ar ⁴ are either a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, the organic compound has both high heat resistance and high hole transport properties and has good film quality. It is preferable because it can form a transport layer. In particular, if these are phenyl groups, the film quality is good and good hole transport properties and high electron blocking properties are shown, so it is a more preferable configuration.

In addition, in the organic compound having the above structure, Ar ¹ and Ar ² are a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group, the organic compound has high heat resistance, can form a transport layer with good film quality, and has good hole It is preferable because it has transportability. In particular, if these are phenylene groups, the film quality is good and good hole transport properties are shown, so it is a more preferable structure.

In addition, among the organic compounds having the above structure, an organic compound in which both n and m are 2 is a preferable structure because it has both high hole transport properties and heat resistance.

In addition, among the organic compounds having the above structure, an organic compound in which both n and m are 1 has high hole transport and heat resistance, and can be highly purified in the synthesis process, so it can be suitably used in an organic EL device, so it is a preferable structure.

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

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

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

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

The above organic compounds can be synthesized using the following synthesis scheme.

Here, a synthetic method will be described for an organic compound represented by the following general formula (G1-a), which is a compound in which the group represented by R ¹⁰ in the general formula (G1) has a group represented by the general formula (g1). . In this synthesis example, other organic compounds of the present invention having various substituents at R ¹ to R ⁹ can be synthesized by the same method by using raw materials having substituents corresponding to the corresponding substitution positions.

In addition, with regard to the substituents R ¹ to R ⁹ and the substituents Ar ¹ and Ar 2 in the following general formula (G1-a), reaction scheme (a-1), and reaction scheme (a- ²⁾ , in the general formula (G1) Since it is the same as described, the description is omitted.

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

[Formula 38]

<Method for synthesizing organic compounds represented by formula (G1-a)>

The organic compound represented by general formula (G1-a) of the present invention can be synthesized according to the following synthesis scheme (a-1) or the following synthesis scheme (a-2).

First, the scheme (a-1) will be explained. That is, by coupling a benzonaphthofuran compound (Compound 1) and diarylamine (Compound 2), a benzonaphthofuranylamino compound (G1-a) can be obtained. The synthesis scheme (a-1) is shown below.

[Formula 39]

Next, the scheme (a-2) will be explained. That is, by coupling a benzonaphthofuran compound (Compound 3) and an aryl compound (Compound 4), a benzonaphthofuranylamino compound (Compound 5) can be obtained, and then Compound 5 and an aryl compound (Compound 6) can be obtained. By coupling, the target benzonaphthofuranylamino compound (G1-a) can be obtained. The synthesis scheme (a-2) is shown below.

[Formula 40]

In the reaction scheme (a-1) and ^the reaction scheme (a-2), X ¹ and X ⁵ each independently represent chlorine, bromine, iodine, triflate group, and , one of X ³ and X ⁴ represents an amino group having an amino group or an organic tin group, and the other of X ³ and X ⁴ represents a chlorine, bromine, iodine, or triflate group.

In the synthesis scheme (a-1) and synthesis scheme (a-2), when performing the Buchwald-Hartwig reaction using a palladium catalyst, bis(dibenzylideneacetone)palladium (0), acetic acid Palladium(II), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), allylpalladium(II) chloride (dimer), etc. Palladium compound, tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphine -2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviated name: cBRIDP (registered trademark) )), etc., can be used. In the above reaction, an organic base such as sodium tert-butoxide or an inorganic base such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In the above reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used as solvents.

Additionally, in the synthesis scheme (a-1) and synthesis scheme (a-2), when performing the Ullman reaction using copper or a copper compound, X ¹ and X ⁵ are each independently chlorine, bromine, iodine, triflate group, X ² represents hydrogen, an organic tin group, etc., one of ^{X 3} and X ⁴ represents an amino group, and the other of X ³ and Copper or a copper compound can be used in the above reaction. Examples of the base to be used include inorganic bases such as potassium carbonate. Solvents that can be used in the above reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, it is preferable to use DMPU and xylene with high boiling points because the target product can be obtained in a shorter time and with higher yield when the reaction temperature is 100°C or higher. In addition, since the reaction temperature is more preferably 150°C or higher, DMPU is more preferably used.

In this synthesis example, compounds having (g1) in R ¹ to R ⁹ can be synthesized in the same manner. For example, when synthesizing (G1) having an amino group such as general formula (g1) or general formula (g5) at any position among R ¹ to R ⁹ , which is a substitution position different from R ¹⁰ , (a-1) When synthesizing (G1) according to ( ^G1 ), benzonaphthofuran compound corresponding to compound ¹ having When a naphthofuran compound is used as a raw material, the target product having (g1) in R ¹ to R ⁹ can be obtained.

Next, a synthetic method will be described for an organic compound represented by the following general formula (G2-a), which is a compound in which R ²⁰ in the general formula (G2) has a group represented by (g1). In this synthesis example, one type of organic compound of the present invention having various substituents represented by R ¹¹ to R ¹⁹ can be synthesized by the same method by using raw materials having substituents corresponding to the corresponding substitution positions.

In addition, with regard to the substituents R ¹¹ to R ¹⁹ and the substituents Ar ¹ and Ar 2 in the general formula (G2-a), reaction scheme (b-1), and reaction scheme (b- ²⁾ , in the general formula (G2) Since it is the same as described, the description is omitted.

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

[Formula 41]

<Method for synthesizing organic compounds represented by chemical formula (G2-a)>

The organic compound represented by general formula (G2-a) of the present invention can be synthesized according to the following synthesis scheme (b-1) or the following synthesis scheme (b-2).

First, the scheme (b-1) will be explained. That is, by coupling a benzonaphthofuran compound (compound 7) and diarylamine (compound 2), a benzonaphthofuranylamino compound (G2-a) can be obtained. The synthesis scheme (b-1) is shown below.

[Formula 42]

Next, the scheme (b-2) will be explained. That is, by coupling a benzonaphthofuran compound (Compound 8) and an aryl compound (Compound 4), a benzonaphthofuranylamino compound (Compound 9) can be obtained, and then compound 7 and an aryl compound (Compound 6) By coupling, the target benzonaphthofuranylamino compound (G2-a) can be obtained. The synthesis scheme (b-2) is shown below.

[Formula 43]

X ⁵ and X ⁶ each independently represent chlorine ^, bromine, ^iodine , or triflate, X ² represents hydrogen, an organic tin group, etc., and , and the other of X ⁴ and X ⁷ represents a chlorine, bromine, iodine, or triflate group.

In the synthesis scheme (b-1) and synthesis scheme (b-2), when performing the Burkewald-Hartwig reaction using a palladium catalyst, bis(dibenzylideneacetone)palladium (0), palladium (II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium compounds such as palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), allylpalladium(II) chloride (dimer), and tri (tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphine-2',6 Ligands such as '-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviated name: cBRIDP (registered trademark)), etc. can be used. In the above reaction, an organic base such as sodium tert-butoxide or an inorganic base such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In the above reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used as solvents.

Additionally, in the synthesis scheme (b-1) and synthesis scheme (b-2), when performing the Ullman reaction using copper or a copper compound, X ⁵ and X ⁶ are each independently chlorine, bromine, iodine, triflate group, X ² represents hydrogen, an organic tin group, etc., one of ^{X 4} and X ⁷ represents an amino group, and the other of X ^{4 and} Copper or a copper compound can be used in the above reaction. Examples of the base to be used include inorganic bases such as potassium carbonate. Solvents that can be used in the above reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, it is preferable to use DMPU and xylene with high boiling points because the target product can be obtained in a shorter time and with higher yield when the reaction temperature is 100°C or higher. In addition, since the reaction temperature is more preferably 150°C or higher, DMPU is more preferably used.

In this synthesis example, compounds having an amino group at R ¹¹ to R ¹⁹ can be synthesized in the same manner using a benzonaphthofuran compound having a chlorine, bromine, iodine, or triflate group at the corresponding position. For example, when synthesizing (G2) having an amino group at any of R ¹¹ to R ¹⁹ , which are substitution positions different from R ²⁰ , when synthesizing (G2) according to (b-1), having X ⁶ When the benzonaphthofuran compound corresponding to compound 7 is used as a raw material and (G2) is synthesized according to (b-2), the benzonaphthofuran compound corresponding to compound ⁸ having , the target product having (g1) in R ¹¹ to R ¹⁹ can be obtained.

(Embodiment 2)

Figure 1 shows a diagram showing a light-emitting device of one form of the present invention. A light emitting device of one embodiment of the present invention has a first electrode 101, a second electrode 102, and an EL layer 103, and a hole transport material containing the above-described organic compound is used for the EL layer.

The EL layer 103 may have a light-emitting layer 113 and a hole transport layer 112. The light-emitting layer 113 contains a light-emitting material and a host material, and the light-emitting device of one embodiment of the present invention emits light from the light-emitting material. The hole transport material of one embodiment of the present invention may be included in either the light-emitting layer 113 or the hole transport layer 112.

In addition, FIG. 1 shows a hole injection layer 111, an electron transport layer 114, and an electron injection layer 115, but the configuration of the light emitting device is not limited thereto.

The hole transport material can also be used as a host material. Additionally, it may be configured to form an excited complex using the electron transport material and the hole transport material by co-depositing it with the electron transport material. By forming an excited complex with an appropriate emission wavelength, effective energy transfer to the light-emitting material can be realized, and a light-emitting device with high efficiency and good lifespan can be provided.

Additionally, since the hole transport material has good hole transport properties, it is effective for use in the hole transport layer 112. In particular, a hole injection layer 111 is provided between the hole transport layer 112 and the first electrode 101, and an acceptor organic compound that facilitates hole injection from the electrode is used in the hole injection layer 111. It is suitable in cases where

When performing hole injection using an organic compound having acceptor properties, the compound included in the hole transport layer 112 in contact with the hole injection layer 111 facilitates electron extraction by the organic compound having acceptor properties. For this purpose, it is desirable to use a hole transport material with a relatively shallow HOMO level. However, since it is difficult to inject holes into the light-emitting layer 113 with a hole transport material having a shallow HOMO level, when the hole transport layer 112 and the light-emitting layer 113 made of a hole transport material with a shallow HOMO level are formed in contact with each other, the interface is formed. Carrier accumulation may occur, which may cause a decrease in the lifespan or efficiency of the light emitting device. Here, by providing a layer containing the organic compound described in Embodiment 1 between the hole transport material with a shallow HOMO level and the light emitting layer 113, it becomes possible to perform smooth hole injection into the light emitting layer, thereby reducing the lifespan and efficiency of the light emitting device. Improvement is realized.

That is, the hole transport layer 112 has a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side, and the first hole transport layer has a first hole transport material. and the second hole transport layer contains the organic compound described in Embodiment 1 above, and the HOMO level of the organic compound described in Embodiment 1 is deeper than the HOMO level of the first hole transport material. The light emitting device has good lifespan and efficiency. This is a desirable configuration because it can be used as a light-emitting device. Additionally, if the HOMO level of the first hole transport material is -5.4 eV or higher, it is a preferable configuration because electron extraction from an organic compound having acceptor properties is easy.

In addition, if the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound described in Embodiment 1 is 0.3 eV or less, more preferably 0.2 eV or less, the second hole transport layer from the first hole transport layer 112-1 This is a desirable configuration because hole injection into (112-2) becomes easy.

In addition, the hole transport layer 112 further has a third hole transport layer 112-3 between the second hole transport layer 112-2 and the light-emitting layer, and the third hole transport layer 112-3 includes a third hole transport material. It may be included. In this case, it is preferable that the HOMO level of the third hole transport material is deeper than the HOMO level of the organic compound described in Embodiment 1 included in the second hole transport layer 112-2. In addition, the difference between the HOMO level of the third hole transport material and the HOMO level of the organic compound described in Embodiment 1 included in the second hole transport layer 112-2 is preferably 0.3 eV or less, and more preferably 0.2 eV or less. .

In addition, if the HOMO level of the third hole transport material and the HOMO level of the host material are the same or the third hole transport material is located at a deeper position, holes are appropriately transported in the light emitting layer, thereby improving lifespan and efficiency, which is a more preferable configuration. It can be said that

Additionally, when the HOMO level of the light-emitting material is shallower (higher) than the HOMO level of the host material, the hole injection ratio to the light-emitting material increases depending on the HOMO level position in the hole transport layer, and holes are trapped in the light-emitting material. There are cases where the lifespan is reduced due to bias in the light emitting area. In such cases, the configuration application of the light emitting element is suitable. An example of one that can easily achieve this configuration is a blue fluorescent element. The structure of the present invention can be particularly preferably applied to aromatic diamine compounds that emit good blue fluorescence, especially pyrenediamine compounds, and a light-emitting device with good lifespan, efficiency, and chromaticity can be obtained.

Next, detailed structures and examples of materials of the above-described light-emitting devices will be described. As described above, the light emitting device of one embodiment of the present invention has an EL layer 103 made of a plurality of layers between a pair of electrodes, the first electrode 101 and the second electrode 102, and the EL layer ( 103) includes a hole injection layer 111, a hole transport layer 112, and a light emitting layer 113, at least from the first electrode 101 side.

There is no particular limitation on the remaining layers included in the EL layer 103, and various layer structures such as hole injection layer, hole transport layer, electron transport layer, electron injection layer, carrier block layer, exciton block layer, and charge generation layer can be applied. there is.

The first electrode 101 is preferably formed using a metal, alloy, conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide with silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide and indium oxide (IWZO) with zinc oxide. etc. can be mentioned. These conductive metal oxide films are generally formed by a sputtering method, but may also be produced by applying a sol-gel method or the like. Examples of the production method include a method of forming indium oxide-zinc oxide by a sputtering method using a target to which 1 wt% to 20 wt% of zinc oxide is added relative to indium oxide. In addition, indium oxide (IWZO) containing tungsten oxide and zinc oxide is formed by a sputtering method using a target containing 0.5 wt% to 5 wt% of tungsten oxide and 0.1 wt% to 1 wt% of zinc oxide relative to indium oxide. You may. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), Palladium (Pd), or nitride of a metal material (for example, titanium nitride), etc. are mentioned. Graphene can also be used. Additionally, by using the composite material described later in the layer in contact with the first electrode 101 in the EL layer 103, it becomes possible to select the electrode material regardless of the work function.

Regarding the stacked structure of the EL layer 103, in this embodiment, as shown in FIG. 1 (A), in addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, an electron transport layer 114 ) and an electron injection layer 115, and as shown in Figure 1 (B), in addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, the electron transport layer 114 and two types of configurations including an electron injection layer 115 and a charge generation layer 116. The materials constituting each layer are shown in detail below.

The hole injection layer 111 is a layer containing a material having acceptor properties. The configuration of one embodiment of the present invention is more suitable for application when an organic compound having acceptor properties is used. As an organic compound having acceptor properties, a compound having an electron-withdrawing group (halogen group or cyano group) can be used, such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoro. Quinodimethane (abbreviated name: 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 (abbreviated name: HAT-CN), etc. can be used. As organic compounds having acceptor properties, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of complex atoms, such as HAT-CN, are preferable because they are thermally stable. Organic compounds having acceptor properties can extract electrons from an adjacent hole transport layer (or hole transport material) by applying an electric field.

When an organic compound having acceptor properties is not used in the hole injection layer 111, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used as an acceptor material. . In addition, phthalocyanine-based compounds such as phthalocyanine (abbreviated name: H ₂ Pc) and copper phthalocyanine (CuPC), 4,4'-bis[N-(4-diphenylaminophenyl)- N-phenylamino]biphenyl (abbreviated name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl )-4,4'-diamine (abbreviated name: DNTPD), aromatic amine compounds, or poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS), etc. The hole injection layer 111 can also be formed.

Additionally, as the hole injection layer 111, a composite material containing an acceptor material and a hole transport material may be used. Additionally, by using a composite material containing a hole-transporting material and an acceptor material, a material forming the electrode can be selected without depending on the work function. In other words, not only materials with a large work function but also materials with a small work function can be used as the first electrode 101. Examples of the acceptor substances include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated name: F4-TCNQ), chloranil, 1,3,4 , 5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated name: F6-TCNNQ), organic compounds having acceptor properties, and transition metal oxides. Additionally, oxides of metals belonging to groups 4 to 8 of the periodic table of elements can also be used. As oxides of metals belonging to groups 4 to 8 in the periodic table of elements, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide have high electron acceptance properties. desirable. Among these, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle.

As the hole transport material used in the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and high molecular compounds (oligomers, dendrimers, polymers, etc.) can be used. Additionally, the hole transporting material used in the composite material is preferably a material having a hole mobility of 10 ^-6 cm ² /Vs or more. Below, organic compounds that can be used as hole-transporting materials in composite materials are specifically listed.

As aromatic amine compounds that can be used in composite materials, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated name: DTDPPA), 4,4'-bis[ N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'- Diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated name: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviated name: DPA3B), etc. can be mentioned. Specific examples of carbazole derivatives include 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated name: PCzPCA1), 3,6-bis[N-( 9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated name: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3 -yl)amino]-9-phenylcarbazole (abbreviated name: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviated name: CBP), 1,3,5-tris[4-(N- Carbazolyl)phenyl]benzene (abbreviated name: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated name: CzPA), 1,4-bis[4-(N -Carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. can be used. Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated name: t-BuDNA) and 2-tert-butyl-9,10-di(1-naphthyl). Anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated name: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviated name: t-BuDBA), 9 , 10-di(2-naphthyl)anthracene (abbreviated name: DNA), 9,10-diphenylanthracene (abbreviated name: DPAnth), 2-tert-butylanthracene (abbreviated name: t-BuAnth), 9,10-bis( 4-methyl-1-naphthyl)anthracene (abbreviated name: DMNA), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1) -naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2) -Naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'- Bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2, 5,8,11-tetra(tert-butyl)perylene, etc. can be mentioned. Additionally, pentacene, coronene, etc. can also be used. It may also have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated name: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl) ) phenyl] anthracene (abbreviated name: DPVPA), etc. Additionally, one type of organic compound of the present invention can also be used. Also, in this case, it is preferable to use F6-TCNNQ as the acceptor substance.

Also, poly(N-vinylcarbazole) (abbreviated name: PVK), poly(4-vinyltriphenylamine) (abbreviated name: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino) )phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine]( Polymer compounds such as (abbreviated name: Poly-TPD) can also be used.

By forming the hole injection layer 111, hole injection properties are improved, and a light emitting device with a low driving voltage can be obtained. In addition, organic compounds with acceptor properties are easy to deposit and form into films, making them easy to use materials.

The hole transport layer 112 is formed including a hole transport material. As a hole transport material, it is preferable to have a hole mobility of 1×10 ^-6 cm ² /Vs or more. The hole transport layer 112 preferably includes one type of hole transport material of the present invention. By including the organic compound described in Embodiment 1 in the hole transport layer 112, a light emitting device with a long life and good efficiency can be obtained.

In particular, when an organic compound having acceptor properties is used as the hole injection layer 111, the hole injection layer 111 is formed of at least two layers, a first hole transport layer and a second hole transport layer, and the first hole transport layer includes By comprising a first hole transport material with a relatively shallow HOMO level and the organic compound described in Embodiment 1 in the second hole transport layer, a light emitting device with a long life and good efficiency can be obtained.

The difference between the LUMO level of the organic compound having acceptor properties and the HOMO level of the first hole transport material is not particularly limited as it changes depending on the strength of the acceptor property of the organic compound having acceptor properties, but the difference in levels is approximately 1 eV. Holes can be injected at levels below this level. When HAT-CN is used as an organic compound having acceptor properties, the LUMO level of HAT-CN is estimated to be -4.41 eV in cyclic voltammetry measurement, so the HOMO level of the first hole transport material is -5.4 eV or more. It is desirable. However, if the HOMO level of the first hole transport material becomes too high, the hole injection property into the second hole transport material deteriorates. Additionally, since the work function of an anode such as ITO is around -5 eV, it is disadvantageous to use a first hole transport material with a higher HOMO level than that. Therefore, it is preferable that the HOMO level of the first hole transport material is -5.0 eV or less.

Additionally, 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.

Since the first hole transport layer, the second hole transport layer, and the third hole transport layer have been described above, repeated descriptions will be omitted. In addition, regarding the hole transport material contained in each, a material that matches the relationship between the above layers may be selected and used from among the materials having the above-mentioned hole transport properties or from materials with various hole transport properties.

The light-emitting layer 113 is a layer containing a host material and a light-emitting material. The light-emitting material may be a fluorescent material, a phosphorescent material, a material exhibiting thermally activated delayed fluorescence (TADF), or other light-emitting material. Additionally, it may be a single layer or may be composed of multiple layers containing different light-emitting materials. Additionally, one embodiment of the present invention can be more suitably applied when the light-emitting layer 113 is a layer that emits fluorescence, particularly a layer that emits blue fluorescence.

Examples of materials that can be used as a fluorescent light-emitting material in the light-emitting layer 113 include the following. Additionally, fluorescent materials other than these can also be used.

5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviated name: PAP2BPy), 5,6-bis[4'-(10-phenyl-9- Anthryl) biphenyl-4-yl] -2,2'-bipyridine (abbreviated name: PAPP2BPy), N, N'-diphenyl-N, N'-bis [4-(9-phenyl-9H-fluorene -9-yl)phenyl]pyrene-1,6-diamine (abbreviated name: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H -Fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviated name: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N, N'-diphenylstilbene-4,4'-diamine (abbreviated name: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated name: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviated name: 2YGAPPA), N,9-diphenyl -N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated name: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl) Perylene (abbreviated name: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated name: PCBAPA), N,N ''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviated name) : DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated name: 2PCAPPA), N-[4 -(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated name: 2DPAPPA), N,N,N',N ',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviated name: DBC1), coumarin 30 , N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviated name: 2PCAPA), N-[9,10-bis(1,1 '-Biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviated name: 2PCABPhA), N-(9,10-diphenyl-2-anthryl) Tril)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated name: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)- 2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated name: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)- N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated name: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated name: DPhAPhA) Coumarin 545T, N,N'-diphenylquinacridone (abbreviated name: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene ( Abbreviated name: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviated name: DCM1) , 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4 -ylidene}propanedinitrile (abbreviated name: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated name: p-mPhTD), 7 ,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated name: p-mPhAFD) , 2-{2-isopropyl-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 (abbreviated name: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviated name) : DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviated name: BisDCM), 2 -{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine- 9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviated name: BisDCJTM), N,N'-(pyrene-1,6-diyl)bis[(6,N- and diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviated name: 1,6BnfAPrn-03). In particular, condensed aromatic diamine compounds such as pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferred because they have high hole trapping properties and are excellent in luminous efficiency and reliability.

Examples of materials that can be used as a phosphorescent material in the light-emitting layer 113 include the following.

Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III)( Abbreviated name: [Ir(mpptz-dmp) ₃ ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazoleto)iridium(III) (abbreviated name: [Ir(Mptz) ₃ ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazoleto]iridium(III) (abbreviated name: [Ir(iPrptz-3b) ₃ ]), an organometallic iridium complex having a 4H-triazole skeleton, or tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazoleto]iridium ( III) (abbreviated name: [Ir(Mptz1-mp) ₃ ]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazoleto)iridium(III) (abbreviated name: [ Organometallic iridium complexes having a 1H-triazole skeleton such as Ir(Prptz1-Me) ₃ ]) or fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole] Iridium(III) (abbreviated name: [Ir(iPrpmi) ₃ ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium ( III) (abbreviated name: [Ir(dmpimpt-Me) ₃ ]), an organometallic iridium complex having an imidazole skeleton, or bis[2-(4',6'-difluorophenyl)pyridinato-N ,C ^2' ]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated name: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ^2' ]Iridium(III)picolinate (abbreviated name: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C ^2' }iridium(III)pi Collinate (abbreviated name: [Ir(CF ₃ ppy) ₂ (pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ^2' ]iridium(III) Examples include organometallic iridium complexes that use a phenylpyridine derivative having an electron-withdrawing group such as acetylacetonate (abbreviated name: FIr(acac)) as a ligand. These are compounds that exhibit blue phosphorescent light emission and have a light emission peak at 440 nm to 520 nm.

In addition, tris(4-methyl-6-phenylpyrimidineto)iridium(III) (abbreviated name: [Ir(mppm) ₃ ]), tris(4-t-butyl-6-phenylpyrimidineto)iridium(III) ) (abbreviated name: [Ir(tBuppm) ₃ ]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidineto)iridium(III) (abbreviated name: [Ir(mppm) ₂ (acac)] ), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidineto)iridium(III) (abbreviated name: [Ir(tBuppm) ₂ (acac)]), (acetylacetonato)bis [6-(2-norbornyl)-4-phenylpyrimidineto]iridium(III) (abbreviated name: [Ir(nbppm) ₂ (acac)]), (acetylacetonato)bis[5-methyl-6 -(2-methylphenyl)-4-phenylpyrimidine]iridium(III) (abbreviated name: [Ir(mpmppm) ₂ (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidine) Naito)iridium(III) (abbreviated name: [Ir(dppm) ₂ (acac)]), an organometallic iridium complex having a pyrimidine skeleton such as (acetylacetonato)bis(3,5-dimethyl-2) -Phenylpyrazinato)iridium(III) (abbreviated name: [Ir(mppr-Me) ₂ (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato) ) Iridium (III) (abbreviated name: [Ir(mppr-iPr) ₂ (acac)]), an organometallic iridium complex having a pyrazine skeleton, or tris(2-phenylpyridinato-N,C ^2' ) iridium. (III) (abbreviated name: [Ir(ppy) ₃ ]), bis(2-phenylpyridinato-N,C ^2' ) iridium(III) acetylacetonate (abbreviated name: [Ir(ppy) ₂ (acac)) ]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviated name: [Ir(bzq) ₂ (acac)]), tris(benzo[h]quinolinato)iridium(III) ) (abbreviated name: [Ir(bzq) ₃ ]), tris(2-phenylquinolinato-N,C ^2' )iridium(III) (abbreviated name: [Ir(pq) ₃ ]), bis(2-phenyl In addition to organometallic iridium complexes having a pyridine skeleton such as quinolinato-N,C ^2' )iridium(III) acetylacetonate (abbreviated name: [Ir(pq) ₂ (acac)]), tris(acetylacetonate) )(monophenanthroline)terbium(III) (abbreviated name: [Tb(acac) ₃ (Phen)]). These are compounds that mainly exhibit green phosphorescence emission and have a peak emission at 500 nm to 600 nm. Additionally, an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because it has excellent reliability and luminous efficiency.

In addition, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviated name: [Ir(5mdppm) ₂ (dibm)]), bis[4, 6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviated name: [Ir(5mdppm) ₂ (dpm)]), bis[4,6-di(naphthalene) -1-yl) pyrimidine] (dipivaloyl methanato) iridium (III) (abbreviated name: [Ir (d1npm) ₂ (dpm)]), an organometallic iridium complex having a pyrimidine skeleton such as, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviated name: [Ir(tppr) ₂ (acac)]), bis(2,3,5-triphenylpyrazinato) Zineto)(dipivaloylmethanato)iridium(III) (abbreviated name: [Ir(tppr) ₂ (dpm])]), (acetylacetonato)bis[2,3-bis(4-fluoro) Phenyl)quinoxalinato]iridium(III) (abbreviated name: [Ir(Fdpq) ₂ (acac)]), an organometallic iridium complex having a pyrazine skeleton such as tris(1-phenylisoquinolinato-N, C ^2' )iridium(III) (abbreviated name: [Ir(piq) ₃ ]), bis(1-phenylisoquinolinato-N,C ^2' )iridium(III) acetylacetonate (abbreviated name: [Ir( In addition to organometallic iridium complexes having a pyridine skeleton such as [piq) ₂ (acac)]), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviated name) : Platinum complex such as PtOEP) or tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated name: [Eu(DBM) ₃ (Phen) ]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated name: [Eu(TTA) ₃ (Phen)] ) and rare earth metal complexes such as these. These are compounds that emit red phosphorescence and have an emission peak at 600 nm to 700 nm. Additionally, an organometallic iridium complex having a pyrazine skeleton emits red light with good chromaticity.

Additionally, in addition to the phosphorescent compounds described above, known phosphorescent materials may be selected and used.

As TADF materials, fullerene and its derivatives, acridine and its derivatives, eosin derivatives, etc. can be used. Additionally, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be included. Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complex (SnF ₂ (Proto IX)), mesoporphyrin-tin fluoride complex (SnF ₂ (Meso IX)), and hematoporphyrin represented by the following structural formula: - Tin fluoride complex (SnF ₂ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF ₂ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF ₂ (OEP) ), ethioporphyrin-tin fluoride complex (SnF ₂ (Etio I)), and octaethylporphyrin-platinum chloride complex (PtCl ₂ OEP).

[Formula 44]

Also, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5- represented by the structural formula below: Triazine (abbreviated name: PIC-TRZ) or 9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9'-phenyl-9H,9'H-3,3' -Bicarbazol (abbreviated name: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-di Phenyl-1,3,5-triazine (abbreviated name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine ( Abbreviated name: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated name) : PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviated name: ACRXTN), bis[4-(9,9- Dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviated name: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10 Heterocyclic compounds having both a π-electron-excessive heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as '-one (abbreviated name: ACRSA), can also be used. Since the heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, it is preferable because both electron transport and hole transport properties are high. In addition, in a material in which a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring are directly bonded, both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-deficient heteroaromatic ring become stronger, and S Since the energy difference between _{the 1} level and the T ₁ level is small, thermally activated delayed fluorescence can be obtained efficiently, which is particularly desirable. Additionally, instead of the π-electron-deficient heteroaromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used.

[Formula 45]

As the host material for the light-emitting layer, various carrier transport materials such as materials with electron transport properties and materials with hole transport properties can be used.

Materials having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated name: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene -2-yl)-N--phenylamino]biphenyl (abbreviated name: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated name: BPAFLP), 4-phenyl -3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated name: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated name: : PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated name: PCBBi1BP), 4-(1-naphthyl)-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated name: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole -3-yl) triphenylamine (abbreviated name: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene-2 -Amine (abbreviated name: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviated name) : Compounds with an aromatic amine skeleton such as PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviated name: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated name: CBP) , 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated name: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated name: PCCP), etc. A compound having a carbazole skeleton, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated name: DBT3P-II), 2,8-diphenyl -4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated name: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviated name: DBTFLP-IV), a compound having a thiophene skeleton, or 4,4',4''-(benzene-1,3,5-triyl) ) Tri(dibenzofuran) (abbreviated name: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl} dibenzofuran (abbreviated name: mmDBFFLBi-II) ) and other compounds having a furan skeleton. Among the above-mentioned compounds, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferable because they have good reliability, have high hole transport properties, and also contribute to reducing the driving voltage. Additionally, the organic compound described in Embodiment 1 can also be suitably used.

Materials having electron transport properties include, for example, bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviated name: BeBq ₂ ), bis(2-methyl-8-quinolinoleto) ( 4-phenylphenolate)aluminum(III) (abbreviated name: BAlq), bis(8-quinolinoleto)zinc(II) (abbreviated name: Znq), bis[2-(2-benzoxazolyl)phenolate]zinc Metal complexes such as (II) (abbreviated name: ZnPBO), bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviated name: ZnBTZ), 2-(4-biphenylyl)-5 -(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated name: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)- 1,2,4-triazole (abbreviated name: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated name: OXD) -7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviated name: CO11), 2,2',2''- (1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated name: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl -Heterocyclic compounds with a polyazole skeleton such as 1H-benzimidazole (abbreviated name: mDBTBIm-II), or 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinox Saline (abbreviated name: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated name: 2mDBTBPDBq-II), 2 -[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated name: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9) -Diazine skeletons such as -yl)phenyl]pyrimidine (abbreviated name: 4,6mPnP2Pm) and 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviated name: 4,6mDBTP2Pm-II) A heterocyclic compound having, 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviated name: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl) Heterocyclic compounds having a pyridine skeleton, such as -phenyl]benzene (abbreviated name: TmPyPB), can be mentioned. Among the above-mentioned compounds, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a pyridine skeleton are preferred because they have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and contribute to reducing driving voltage.

When a fluorescent substance is used as a light-emitting material, a material having an anthracene skeleton is suitable as a host material. If a material having an anthracene skeleton is used as a host material for a fluorescent material, a light-emitting layer with good luminous efficiency and durability can be realized. Since many materials having an anthracene skeleton have a deep HOMO level, one form of the present invention can be suitably applied. As a substance having an anthracene skeleton used as a host material, a substance having a diphenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, it is preferable because the hole injection and transport properties increase, but when the host material contains a benzocarbazole skeleton in which the benzene ring is further condensed to carbazole, the HOMO becomes shallower by about 0.1 eV than that of carbazole. This is more preferable because it becomes easier for holes to enter. In particular, when the host material contains a dibenzocarbazole skeleton, it is suitable because not only does the HOMO become shallower by about 0.1 eV than that of carbazole, making it easier for holes to enter, but also excellent hole transport properties and increased heat resistance. Therefore, a more preferable host material is a material that simultaneously has a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). In addition, from the viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated name: PCzPA), 3-[4-(1-naphthyl)- Phenyl]-9-phenyl-9H-carbazole (abbreviated name: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated name: CzPA), 7-[4- (10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl] -benzo[b]naphtho[1,2-d]furan (abbreviated name: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'- Examples include anthracene (abbreviated name: FLPPA). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are desirable choices because they exhibit very good properties.

In addition, the light-emitting device of one embodiment of the present invention is preferably applied to a light-emitting device that emits blue fluorescence.

Additionally, the host material may be a mixture of multiple types of substances, and when a mixed host material is used, it is preferable to mix a material with electron transport properties and a material with hole transport properties. By mixing a material with electron transport properties and a material with hole transport properties, the transport properties of the light emitting layer 113 can be easily adjusted, and the recombination region can also be easily controlled. The content ratio of the material having hole transport properties and the material having electron transport properties may be set to material having hole transport properties: material having electron transport properties = 1:9 to 9:1.

Additionally, an excited complex may be formed from these mixed materials. The excited complex is preferably selected as a combination that forms an excited complex that emits light that overlaps the wavelength of the absorption band on the lowest energy side of the light-emitting material, as energy transfer becomes smooth and light emission can be obtained efficiently. Additionally, by using the above configuration, the driving voltage also decreases, so it is a preferable configuration.

The electron transport layer 114 is a layer containing a material having electron transport properties. As the substance having electron transport properties, those listed as substances having electron transport properties that can be used in the above host material can be used.

The electron injection layer 115 between the electron transport layer 114 and the second electrode 102 is an alkali metal or alkaline earth metal such as lithium fluoride (LiF), cesium fluoride (CsF), or calcium fluoride (CaF ₂ ), or A layer containing these compounds may be provided. The electron injection layer 115 is a layer made of a material having electron transport properties and contains an alkali metal or an alkaline earth metal, or a compound thereof, or an electride may be used. Examples of electrified materials include materials obtained by adding electrons at a high concentration to mixed oxides of calcium and aluminum.

Additionally, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 refers to a layer that can inject holes into a layer in contact with the cathode side of the layer and electrons into a layer in contact with the anode side by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the composite materials listed as materials that can form the hole injection layer 111 described above. Additionally, the P-type layer 117 is a material constituting a composite material and may be formed by laminating a film containing the above-described acceptor material and a film containing a hole transport material. By applying a potential to the P-type layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light emitting device operates.

Additionally, the charge generation layer 116 is preferably provided with one or both of an electronic relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117.

The electronic relay layer 118 contains at least a material having electron transport properties and has a function of smoothly transferring electrons by preventing interaction between the electron injection buffer layer 119 and the P-type layer 117. The LUMO level of the material having electron transport properties included in the electronic relay layer 118 is the LUMO level of the acceptor material in the P-type layer 117 and the layer in contact with the charge generation layer 116 in the electron transport layer 114. It is preferable that it is between the LUMO levels of the substances included in . The specific energy level of the LUMO level in the electron transporting material used in the electronic relay layer 118 is preferably -5.0 eV or more, preferably -5.0 eV or more or -3.0 eV or less. Additionally, as the material having electron transport properties used in the electronic relay layer 118, it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

The electron injection buffer layer 119 contains alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metals, etc. Materials with high electron injection properties, such as compounds (including oxides, halides, and carbonates) or compounds of rare earth metals (including oxides, halides, and carbonates), can be used.

In addition, when the electron injection buffer layer 119 is formed including a material having electron transport properties and a donor material, the donor material may include an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (alkali metal compound (lithium oxide, etc.) oxides, halides, and carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, and carbonates), or rare earth metal compounds (including oxides, halides, and carbonates) In addition), organic compounds such as tetracyanaphthacene (abbreviated name: TTN), nickelocene, and decamethylnickelocene can also be used. Additionally, the material having electron transport properties can be formed using the same material as the material constituting the electron transport layer 114 described above.

As the material forming the second electrode 102, metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less) can be used. Specific examples of such negative electrode materials include alkali metals such as lithium (Li) and cesium (Cs), elements belonging to group 1 or 2 of the periodic table of elements such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, silicon, or indium oxide-tin oxide including silicon oxide can be used regardless of the size of the work function. It can be used as the second electrode 102. These conductive materials can be formed into a film using dry methods such as vacuum deposition or sputtering, inkjet methods, spin coating methods, etc. Additionally, it may be formed by a wet method using a sol-gel method, or it may be formed by a wet method using a paste of a metal material.

Additionally, as a method of forming the EL layer 103, various methods can be used, regardless of whether they are a dry method or a wet method. For example, vacuum deposition, gravure printing, offset printing, screen printing, inkjet, or spin coating may be used.

Additionally, each electrode or each layer described above may be formed using a different film formation method.

Additionally, the configuration of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, to suppress quenching that occurs due to the proximity of the light emitting area to the metal used in the electrode or carrier injection layer, a light emitting area where holes and electrons recombine is provided at a distance from the first electrode 101 and the second electrode 102. The configuration is desirable.

In addition, the hole transport layer or electron transport layer in contact with the light-emitting layer 113, especially the carrier transport layer close to the recombination region in the light-emitting layer 113, is a light-emitting material or light-emitting layer constituting the light-emitting layer in order to suppress energy transfer from excitons generated in the light-emitting layer. It is desirable to make the material with a band gap larger than the band gap of the light emitting material included in .

Next, the form of a light-emitting device (also referred to as a stacked device or tandem device) composed of a plurality of light-emitting units stacked will be described with reference to (C) of FIG. 1. This light-emitting device is a light-emitting device that has a plurality of light-emitting units between an anode and a cathode. One light emitting unit has almost the same structure as the EL layer 103 shown in FIG. 1(A). That is, the light-emitting device shown in (C) of FIG. 1 is a light-emitting device having a plurality of light-emitting units, and the light-emitting device shown in (A) or (B) of FIG. 1 can be said to be a light-emitting device having one light-emitting unit. You can.

In Figure 1 (C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between the anode 501 and the cathode 502, and the first light-emitting unit 511 and the second light-emitting unit 512 A charge generation layer 513 is provided between the units 512. The anode 501 and the cathode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1 (A), respectively, and are the same as those mentioned in the description of FIG. 1 (A). It can be applied. Additionally, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same or different structures.

The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit when a voltage is applied to the anode 501 and the cathode 502. That is, in Figure 1 (C), when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 injects electrons into the first light-emitting unit 511 and the second light-emitting unit ( 512), it is good if holes are injected.

The charge generation layer 513 is preferably formed in the same configuration as the charge generation layer 116 described in (B) of FIG. 1. Since composite materials of organic compounds and metal oxides have excellent carrier injection and carrier transport properties, low voltage and low current driving can be realized. Additionally, when the anode side surface of the light emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can also serve as a hole injection layer of the light emitting unit, so the light emitting unit is not provided with a hole injection layer. You don't have to.

Additionally, when the electron injection buffer layer 119 is provided on the charge generation layer 513, since the electron injection buffer layer 119 functions as an electron injection layer in the light emitting unit on the anode side, electrons are stored in the light emitting unit on the anode side. It is not necessarily necessary to form an injection layer.

In Figure 1(C), a light-emitting device having two light-emitting units has been described, but the same can be applied to a light-emitting device in which three or more light-emitting units are stacked. Like the light-emitting device according to this embodiment, a plurality of light-emitting units are separated by a charge generation layer 513 and arranged between a pair of electrodes, thereby enabling high-brightness light emission while maintaining low current density and a longer lifespan. can be realized. Additionally, a light-emitting device that can be driven at low voltage and consumes low power can be realized.

Additionally, by varying the emission color of each light-emitting unit, it is possible to obtain light emission of a desired color from the entire light-emitting device. For example, in a light-emitting device having two light-emitting units, by obtaining red and green light-emitting colors from the first light-emitting unit and blue light-emitting colors from the second light-emitting unit, a light-emitting device that emits white light as a whole can be obtained. .

In addition, each layer or electrode, such as the above-mentioned EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the charge generation layer, can be formed, for example, by vapor deposition (including vacuum deposition) or droplet discharge. It can be formed using methods such as printing (also called inkjet), coating, and gravure printing. Additionally, they may include low molecular materials, medium molecular materials (including oligomers and dendrimers), or high molecular materials.

(Embodiment 3)

In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 1 will be described.

In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 will be described using FIG. 2. Additionally, FIG. 2(A) is a top view showing a light emitting device, and FIG. 2(B) is a cross-sectional view of FIG. 2(A) cut along A-B and C-D. This light-emitting device controls the light emission of the light-emitting element and includes a driving circuit portion (source line driving circuit) 601, a pixel portion 602, and a driving circuit portion (gate line driving circuit) 603 shown in dotted lines. Additionally, 604 is a sealing substrate, 605 is an entity, and the inside surrounded by the entity 605 is a space 607.

In addition, the lead wire 608 is a wire for transmitting signals input to the source line driving circuit 601 and the gate line driving circuit 603, and a video signal from the FPC (flexible printed circuit) 609, which is an external input terminal. , it receives clock signals, start signals, reset signals, etc. Additionally, although only the FPC is shown here, a printed wiring board (PWB) may be mounted on this FPC. The light emitting device in this specification includes not only the light emitting device main body but also a state in which an FPC or PWB is mounted thereon.

Next, the cross-sectional structure will be explained using FIG. 2(B). A driving circuit part and a pixel part are formed on the device substrate 610, but here, the source line driving circuit 601, which is the driving circuit part, and one pixel of the pixel part 602 are shown.

The device substrate 610 includes a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic, in addition to a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc. It is good to use when making.

The structure of the transistor used in the pixel or driving circuit is not particularly limited. For example, an inverted staggered transistor may be used, or a staggered transistor may be used. Additionally, it may be a top gate type transistor or a bottom gate type transistor. The semiconductor material used in the transistor is not particularly limited, and for example, silicon, germanium, silicon carbonide, gallium nitride, etc. can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn metal oxide, may be used.

The crystallinity of the semiconductor material used in the transistor is not particularly limited, and either an amorphous semiconductor or a crystalline semiconductor (microcrystalline semiconductor, polycrystalline semiconductor, single crystalline semiconductor, or semiconductor with a partial crystalline region) may be used. It is preferable to use a semiconductor having crystallinity because deterioration of transistor characteristics can be suppressed.

Here, in addition to the transistors provided in the pixels and driving circuits, it is preferable to use oxide semiconductors in semiconductor devices such as transistors used in touch sensors, etc., which will be described later. In particular, it is desirable to use an oxide semiconductor with a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the current in the off state of the transistor can be reduced.

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

In particular, the semiconductor layer uses an oxide semiconductor film having a plurality of crystal parts, the c-axis of the crystal parts being oriented perpendicular to the formation surface of the semiconductor layer or the upper surface of the semiconductor layer, and having no grain boundaries between adjacent crystal parts. It is desirable to do so.

By using such a material as the semiconductor layer, variations in electrical characteristics are suppressed, making it possible to realize a highly reliable transistor.

Additionally, since the transistor having the above-described semiconductor layer has a low off-state current, the charge accumulated in the capacitive element through the transistor can be maintained for a long period of time. By applying such a transistor to a pixel, it becomes possible to stop the driving circuit while maintaining the gradation of the image displayed in each display area. As a result, electronic devices with greatly reduced power consumption can be realized.

In order to stabilize the characteristics of the transistor, etc., it is desirable to provide an underlayer. As the base film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film can be used, and can be produced in a single layer or by stacking them. The base film can be formed using sputtering method, CVD (Chemical Vapor Deposition) method (plasma CVD method, thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD (Atomic Layer Deposition) method, coating method, printing method, etc. You can. Additionally, the undercoat does not need to be provided if it is unnecessary.

Additionally, the FET 623 illustrates one of the transistors formed in the driving circuit unit 601. Additionally, the driving circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. Additionally, in this embodiment, an integrated driver type in which the driving circuit is formed on the substrate is exemplified, but this is not necessarily the case, and the driving circuit may be formed externally rather than on the substrate.

In addition, the pixel portion 602 is formed of a plurality of pixels including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain, but is not limited to this. The pixel portion may be a combination of three or more FETs and a capacitor element.

Additionally, an insulating material 614 is formed to cover the end of the first electrode 613. Here, it can be formed using a positive type photosensitive acrylic resin film.

Additionally, in order to improve the covering properties of the EL layer to be formed later, a curved surface having a curvature is formed at the upper or lower end of the insulating material 614. For example, when positive photosensitive acrylic is used as the material of the insulating material 614, it is desirable to have a curved surface with a radius of curvature (0.2 μm to 3 μm) only at the upper end of the insulating material 614. Additionally, as the insulator 614, either a negative photosensitive resin or a positive photosensitive resin may be used.

An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, it is desirable to use a material with a large work function as the material used for the first electrode 613 functioning as the anode. For example, in addition to monolayer films such as ITO film, indium tin oxide film containing silicon, indium oxide film containing 2 wt% to 20 wt% zinc oxide, titanium nitride film, chromium film, tungsten film, Zn film, Pt film, etc. , a lamination of a titanium nitride film and a film mainly containing aluminum, a three-layer structure of a titanium nitride film, a film mainly containing aluminum, and a titanium nitride film, etc. can be used. Additionally, with a laminated structure, the resistance as a wiring is low, good ohmic contact is obtained, and it can function as an anode.

Additionally, the EL layer 616 is formed by various methods such as deposition using a deposition mask, inkjet, and spin coating. The EL layer 616 includes the same configuration as described in Embodiment 1. Additionally, other materials constituting the EL layer 616 may be low molecular compounds or high molecular compounds (including oligomers and dendrimers).

Additionally, as the material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode, materials with a small work function (Al, Mg, Li, Ca, or alloys or compounds thereof (MgAg, MgIn, It is preferable to use AlLi, etc.). In addition, when the light generated in the EL layer 616 transmits the second electrode 617, the second electrode 617 is composed of a thin metal film and a transparent conductive film (ITO, 2 wt% to 20 wt%). It is preferable to use a laminate of indium oxide containing zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.).

Additionally, a light emitting element is formed from the first electrode 613, the EL layer 616, and the second electrode 617. This light-emitting element is the light-emitting element described in Embodiment 1. Additionally, a plurality of light-emitting elements are formed in the pixel portion, but the light-emitting device of this embodiment may include both the light-emitting elements described in Embodiment 1 and light-emitting elements having other structures.

Additionally, by bonding the sealing substrate 604 and the element substrate 610 with the seal 605, the light emitting element 618 is formed in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the seal 605. The structure is provided. Additionally, the space 607 is filled with a filler, and in addition to the case where it is filled with an inert gas (nitrogen, argon, etc.), there are also cases where it is actually filled. It is preferable to form a concave portion in the sealing substrate and provide a desiccant thereto because deterioration due to the influence of moisture can be suppressed.

Additionally, it is preferable to use epoxy resin or glass frit for the material 605. Additionally, it is desirable that these materials do not transmit moisture or oxygen as much as possible. Additionally, as a material used for the sealing substrate 604, in addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic can be used.

Although not shown in FIG. 2, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. Additionally, a protective film may be formed to cover the exposed portion of the substance 605. Additionally, a protective film may be provided to cover the exposed sides of the pair of substrates, such as the surface and sides, sealing layer, and insulating layer.

For the protective film, a material that makes it difficult for impurities such as water to pass through can be used. Therefore, diffusion of impurities such as water from the outside to the inside can be effectively suppressed.

As the material constituting the protective film, oxides, nitrides, fluorides, sulfides, ternary compounds, metals, or polymers can be used, for example, aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, and 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, aluminum nitride, hafnium nitride, etc. , materials including silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, nitrides including titanium and aluminum, oxides including titanium and aluminum, aluminum and zinc, etc. Materials containing oxides, sulfides including manganese and zinc, sulfides including cerium and strontium, oxides including erbium and aluminum, oxides including yttrium and zirconium, etc. can be used.

It is desirable to form the protective film using a film formation method that has good step coverage. One of these methods is Atomic Layer Deposition (ALD). It is desirable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a protective film that is dense, has reduced defects such as cracks and pinholes, or has a uniform thickness. Additionally, damage inflicted to the processed member when forming a protective film can be reduced.

For example, by using the ALD method, it is possible to form a protective film that is uniform and has few defects even on surfaces with complex uneven shapes or on the top, side, and back surfaces of a touch panel.

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

Since the light-emitting element described in Embodiment 1 is used in the light-emitting device of this embodiment, a light-emitting device with good characteristics can be obtained. Specifically, since the light emitting element described in Embodiment 1 is a light emitting element with a long life, it can be used as a highly reliable light emitting device. Additionally, since the light-emitting device using the light-emitting element described in Embodiment 1 has good luminous efficiency, it can be used as a light-emitting device with low power consumption.

Figure 3 shows an example of a light-emitting device in which a light-emitting element emitting white light is formed and a color layer (color filter) is provided to provide full color. 3(A) includes a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, Peripheral portion 1042, pixel portion 1040, driving circuit portion 1041, first electrode of light emitting element (1024W, 1024R, 1024G, 1024B), partition 1025, EL layer 1028, second electrode of light emitting element 1029, sealing substrate 1031, substance 1032, etc. are shown.

Additionally, in Figure 3 (A), the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are provided on a transparent substrate 1033. Additionally, a black matrix 1035 may be further provided. A transparent substrate 1033 provided with a colored layer and a black matrix is aligned and fixed to the substrate 1001. Additionally, the colored layer and black matrix 1035 are covered with an overcoat layer 1036. In addition, in Figure 3 (A), there is a light-emitting layer in which light goes out without passing through the colored layer, and a light-emitting layer in which light goes out through the colored layer of each color, and the light that does not pass through the colored layer is white and colored. Since the light that passes through the layer becomes red, green, and blue, images can be expressed with four-color pixels.

In Figure 3 (B), an example of forming a colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. is shown. In this way, the colored layer may be provided between the substrate 1001 and the sealing substrate 1031.

In addition, the above-mentioned light emitting device is a light emitting device with a structure (bottom emission type) that extracts light toward the substrate 1001 on which the FET is formed, but is a light emitting device with a structure (top emission type) that extracts light toward the sealing substrate 1031. You can also do this. A cross-sectional view of the top emission type light emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light can be used as the substrate 1001. It is formed in the same manner as the bottom emission type light emitting device until the connection electrode connecting the FET and the anode of the light emitting element is fabricated. After that, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may have a flattening role. The third interlayer insulating film 1037 can be formed using other known materials in addition to the same material as the second interlayer insulating film.

The first electrodes (1024W, 1024R, 1024G, 1024B) of the light emitting element are used as anodes here, but may also be cathodes. Additionally, in the case of a top emission type light emitting device as shown in FIG. 4, it is preferable that the first electrode is a reflective electrode. The configuration of the EL layer 1028 is the same as that described for the EL layer 103 in Embodiment 1, and is also set to have an element structure that produces white light emission.

In the top emission type structure as shown in FIG. 4, sealing can be performed by the sealing substrate 1031 provided with colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B). . The sealing substrate 1031 may be provided with a black matrix 1035 positioned between pixels. The colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) and the black matrix may be covered with the overcoat layer 1036. Additionally, a light-transmitting substrate is used as the sealing substrate 1031. In addition, although an example of full color display using four colors of red, green, blue, and white is presented here, it is not particularly limited to this, and can be used in four colors of red, yellow, green, and blue, or three colors of red, green, and blue. You may use to perform full color display.

A microcavity structure is suitably applied in a top emission type light emitting device. A light-emitting device having a microcavity structure can be obtained by using the first electrode as a reflective electrode and the second electrode as a semi-transmissive/semi-reflective electrode. It has at least an EL layer between the reflective electrode and the semi-transmissive/semi-reflective electrode, and has at least a light emitting layer serving as a light emitting area.

Additionally, the reflective electrode is assumed to be a film having a reflectance of visible light of 40% to 100%, preferably 70% to 100%, and a resistivity of 1Х10 ^-2 Ωcm or less. In addition, the semi-transmissive/semi-reflective electrode shall be a film having a reflectance of visible light of 20% to 80%, preferably 40% to 70%, and a resistivity of 1Х10 ^-2 Ωcm or less.

The light emitted from the light emitting layer included in the EL layer is reflected and resonated by the reflective electrode and the semi-transmissive/semi-reflective electrode.

The light-emitting device can change the optical distance between the reflective electrode and the semi-transmissive/semi-reflective electrode by changing the thickness of the transparent conductive film, the above-mentioned composite material, or the carrier transport material. As a result, light of a resonant wavelength can be strengthened and light of a non-resonant wavelength can be attenuated between the reflective electrode and the semi-transmissive/semi-reflective electrode.

In addition, the light reflected and returned by the reflective electrode (first reflected light) causes significant interference with the light (first incident light) directly incident from the light emitting layer to the semi-transparent/semi-reflective electrode, so the optical distance between the reflective electrode and the light emitting layer is (2n) -One) /4 (however, n is a natural number greater than 1, is preferably adjusted to the wavelength of light emission to be amplified. By adjusting the optical distance, the phase of the first reflected light and the first incident light can be aligned to further amplify the light emission from the light emitting layer.

In addition, in the above-described configuration, the EL layer may have a structure having a plurality of light-emitting layers, or may have a structure having one light-emitting layer. For example, in combination with the structure of the tandem type light-emitting device described above, a plurality of charge generation layers sandwiching the charge generation layer may be used. A configuration in which an EL layer is provided in one light-emitting element and one or a plurality of light-emitting layers are formed in each EL layer may be applied.

By having a microcavity structure, the intensity of light emission in the front direction at a specific wavelength can be increased, thereby reducing power consumption. In addition, in the case of a light emitting device that displays images with four color subpixels of red, yellow, green, and blue, in addition to the luminance improvement effect by yellow light emission, a microcavity structure tailored to the wavelength of each color can be applied to all subpixels. Therefore, a light emitting device with good characteristics can be obtained.

Since the light emitting device in this embodiment uses the light emitting element described in Embodiment 1, a light emitting device with good characteristics can be obtained. Specifically, since the light emitting element described in Embodiment 1 is a light emitting element with a long life, it can be used as a highly reliable light emitting device. Additionally, since the light emitting device using the light emitting element described in Embodiment 1 has good luminous efficiency, it can be used as a light emitting device with low power consumption.

Up to this point, the active matrix type light emitting device has been described, but hereinafter, the passive matrix type light emitting device will be described. Figure 5 shows a passive matrix type light emitting device manufactured by applying the present invention. Additionally, Figure 5(A) is a perspective view showing a light emitting device, and Figure 5(B) is a cross-sectional view of Figure 5(A) taken along X-Y. In Fig. 5, on the substrate 951, an EL layer 955 is provided between the electrodes 952 and 956. The end of the electrode 952 is covered with an insulating layer 953. And, a partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have an inclination in which the gap between one side wall and the other side wall narrows as it approaches the substrate surface. That is, the cross section of the short side of the partition layer 954 is trapezoidal, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is the upper side (the side that is in contact with the insulating layer 953). It faces the same direction as the surface direction of and is shorter than the side that is not in contact with the insulating layer 953). By providing the barrier layer 954 in this way, it is possible to prevent defects in the light emitting element due to static electricity, etc. Also, in a passive matrix type light emitting device, since the light emitting element described in Embodiment 1 is used, a light emitting device with good reliability or a light emitting device with low power consumption can be obtained.

The above-described light-emitting device is a light-emitting device that can be suitably used as a display device for expressing images because it is possible to individually control a large number of minute light-emitting elements arranged in a matrix.

Additionally, this embodiment can be freely combined with other embodiments.

(Embodiment 4)

In this embodiment, an example of using the light-emitting element described in Embodiment 1 as a lighting device will be described with reference to FIG. 6. Figure 6(B) is a top view of the lighting device, and Figure 6(A) is a cross-sectional view taken along line e-f in Figure 6(B).

In the lighting device of this embodiment, the first electrode 401 is formed on a light-transmitting substrate 400, which serves as a support. The first electrode 401 corresponds to the first electrode 101 of Embodiment 1. When extracting light emission from the first electrode 401 side, the first electrode 401 is formed of a light-transmitting material.

A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to the configuration of the EL layer 103 in Embodiment 1, or to a configuration combining the light emitting units 511 and 512 and the charge generation layer 513. Also, please refer to the above description for these configurations.

A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 1. When light emission is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. The second electrode 404 is connected to the pad 412 to supply voltage.

As described above, the lighting device described in this embodiment has a light emitting element having the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting element has high luminous efficiency, the lighting device of this embodiment can be used as a lighting device with low power consumption.

The lighting device is completed by fixing and sealing the substrate 400 and the sealing substrate 407 on which the light emitting element having the above structure is formed using the seal 405 and the seal 406. Reality (405, 406) can be either one or the other. Additionally, a desiccant can be mixed into the inner seal 406 (not shown in (B) of FIG. 6), which allows moisture to be adsorbed, leading to improved reliability.

In addition, a portion of the pad 412 and the first electrode 401 can be provided to extend outside the materials 405 and 406 to serve as external input terminals. Additionally, an IC chip 420 or the like with a converter mounted thereon may be provided.

In the lighting device described in this embodiment, the light emitting element described in Embodiment 2 is used as the EL element, and a light emitting device with good reliability can be obtained. Additionally, it can be used as a light-emitting device with low power consumption.

(Embodiment 5)

In this embodiment, an example of an electronic device including a part of the light emitting element described in Embodiment 1 will be described. The light emitting element described in Embodiment 2 is a light emitting element that has a good lifespan and good reliability. As a result, the electronic device described in this embodiment can be an electronic device having a highly reliable light emitting portion.

Electronic devices to which the above light-emitting elements are applied include, for example, television devices (also called televisions or television receivers), computer monitors, digital cameras, digital video cameras, digital picture frames, and mobile phones (also called mobile phones and mobile phone devices). ), portable game machines, portable information terminals, sound reproduction devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are described below.

Figure 7(A) shows an example of a television device. The television device is provided with a display portion 7103 in a housing 7101. Also, here, a configuration in which the housing 7101 is supported by the stand 7105 is shown. An image can be displayed on the display unit 7103, and the display unit 7103 is configured by arranging the light emitting elements described in Embodiment 1 in a matrix.

The television device can be operated using an operation switch provided in the housing 7101 or a separate remote controller 7110. Channels and volume can be controlled using the operation keys 7109 included in the remote controller 7110, and images displayed on the display unit 7103 can be controlled. Additionally, the remote controller 7110 may be provided with a display unit 7107 that displays information output from the remote controller 7110.

Additionally, the television device is configured to include a receiver, modem, etc. The receiver can receive general television broadcasting, and by connecting to a wired or wireless communication network through a modem, one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) communication of information is possible. It may be possible.

(B1) in FIG. 7 is a computer and includes a main body 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, and a pointing device 7206. Additionally, this computer is manufactured by arranging the light emitting elements described in Embodiment 1 in a matrix and using them in the display portion 7203. The computer in (B1) of FIG. 7 may have the same form as (B2) in FIG. 7. The computer in Figure 7 (B2) is provided with a second display unit 7210 instead of the keyboard 7204 and the pointing device 7206. Since the second display unit 7210 is a touch panel type, input can be performed by manipulating the input display displayed on the second display unit 7210 with a finger or a dedicated pen. Additionally, the second display unit 7210 can display not only an input display but also other images. Additionally, the display unit 7203 may also be a touch panel. By connecting the two screens with a hinge, it is possible to prevent problems such as damaging or damaging the screen when storing or transporting it.

Figure 7(C) shows an example of a portable terminal. In addition to the display unit 7402 provided in the housing 7401, the portable terminal 7400 has an operation button 7403, an external connection port 7404, a speaker 7405, a microphone 7406, etc. Additionally, the portable terminal 7400 has a display portion 7402 manufactured by arranging the light emitting elements described in Embodiment 1 in a matrix.

The portable terminal shown in (C) of FIG. 7 may be configured to allow information to be input by touching the display unit 7402 with a finger or the like. In this case, operations such as making a phone call or writing an email can be performed by touching the display unit 7402 with a finger or the like.

The screen of the display unit 7402 mainly has three modes. The first mode is a display mode that mainly displays images, and the second mode is an input mode that mainly inputs information such as text. The third mode is display + input mode, which is a mixture of two modes, display mode and input mode.

For example, when making a phone call or writing an email, the display unit 7402 may be set to a text input mode in which text is mainly input, and input operations for text displayed on the screen may be performed. In this case, it is desirable to display a keyboard or number buttons on most of the screen of the display unit 7402.

In addition, by providing a detection device with a sensor for detecting tilt, such as a gyroscope or an acceleration sensor, inside the mobile terminal, the orientation of the mobile terminal (vertical or horizontal) is determined and the screen display of the display unit 7402 is automatically switched. can do.

Additionally, switching the screen mode is performed by touching the display unit 7402 or operating the operation button 7403 on the housing 7401. Additionally, it can be switched depending on the type of image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is video data, the display mode is switched, and if the image signal displayed on the display unit is text data, it is switched to the input mode.

In addition, in the input mode, a signal detected by the optical sensor of the display unit 7402 is detected, and when there is no input by touch operation of the display unit 7402 for a certain period of time, the screen mode is controlled to switch from the input mode to the display mode. It's also good.

The display unit 7402 may function as an image sensor. For example, identity authentication can be performed by touching the display unit 7402 with the palm or finger to capture a palm print or fingerprint. Additionally, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light on the display, it is possible to image finger veins, palm veins, etc.

Additionally, the configuration described in this embodiment can be used by appropriately combining the configurations described in Embodiment 1 to Embodiment 4.

As described above, the application range of the light-emitting device including the light-emitting element described in Embodiment 1 is very wide, and this light-emitting device can be applied to electronic devices in various fields. By using the light emitting element described in Embodiment 1, a highly reliable electronic device can be obtained.

Figure 8 (A) is a schematic diagram showing an example of a cleaning robot.

The cleaning robot 5100 has a display 5101 disposed on the upper surface, a plurality of cameras 5102 disposed on the side, a brush 5103, and an operation button 5104. Additionally, although not shown, wheels, suction ports, etc. are provided on the bottom of the cleaning robot 5100. The cleaning robot 5100 is also equipped with various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, an optical sensor, and a gyro sensor. Additionally, the cleaning robot 5100 is equipped with a wireless communication means.

The cleaning robot 5100 can move by magnetic force, detect trash 5120, and suck the trash through a suction port provided on the lower surface.

Additionally, the cleaning robot 5100 can analyze the image captured by the camera 5102 to determine the presence or absence of obstacles such as walls, furniture, or steps. Additionally, when an object that is likely to become entangled in the brush 5103, such as a wire, is detected through image analysis, the rotation of the brush 5103 can be stopped.

The display 5101 can display the remaining battery capacity or the amount of garbage sucked in. The path traveled by the cleaning robot 5100 may be displayed on the display 5101. Additionally, the display 5101 may be a touch panel, and operation buttons 5104 may be provided on the display 5101.

The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the situation of the room even when outside. Additionally, the display on the display 5101 can be checked using a portable electronic device such as a smartphone.

One form of light emitting device of the present invention can be used in the display 5101.

The robot 2100 shown in (B) of FIG. 8 includes an arithmetic device 2110, an illumination sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, and a lower camera ( 2106), an obstacle sensor 2107, and a movement mechanism 2108.

The microphone 2102 has the function of detecting the user's voice and environmental sounds. Additionally, the speaker 2104 has the function of emitting voice. The robot 2100 can communicate with the user using a microphone 2102 and a speaker 2104.

The display 2105 has the function of displaying various types of information. The robot 2100 can display information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. Additionally, the display 2105 may be a detachable information terminal, and can be installed in a fixed position on the robot 2100 to enable charging and data transfer.

The upper camera 2103 and lower camera 2106 have the function of capturing images of the surroundings of the robot 2100. Additionally, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the direction in which the robot 2100 moves forward using the movement mechanism 2108. The robot 2100 can move safely by recognizing the surrounding environment using the upper camera 2103, lower camera 2106, and obstacle sensor 2107. One form of light emitting device of the present invention can be used in the display 2105.

Figure 8 (C) is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, an operation key 5005 (including a power switch or an operation switch), and a connection terminal 5006. , Sensor 5007 (force, displacement, position, speed, acceleration, angular velocity, rotation, distance, light, liquid, magnetism, temperature, chemical, voice, time, longitude, electric field, current, voltage, power, radiation, (including functions to measure flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc.

The light emitting device of one embodiment of the present invention can be used in the display portion 5001 and the second display portion 5002.

Fig. 9 is an example in which the light emitting element described in Embodiment 1 is used in an electric stand that is a lighting device. The electric stand shown in FIG. 9 has a housing 2001 and a light source 2002, and the lighting device described in Embodiment 3 may be used as the light source 2002.

Fig. 10 is an example of using the light emitting element described in Embodiment 1 as an indoor lighting device 3001. Since the light emitting device described in Embodiment 1 is a highly reliable light emitting device, it can be used as a highly reliable lighting device. Additionally, since the light emitting element described in Embodiment 2 can be expanded to a large area, it can be used as a large area lighting device. Additionally, since the light emitting element described in Embodiment 1 is thin, it can be used as a thinner lighting device.

The light emitting element described in Embodiment 2 can also be mounted on the windshield or dashboard of a car. Fig. 11 shows one form in which the light emitting element described in Embodiment 2 is used on a windshield or dashboard of a car. Display areas 5200 to 5203 are displays provided using the light emitting element described in Embodiment 2.

The display area 5200 and the display area 5201 are provided on the windshield of an automobile and are display devices equipped with the light emitting element described in Embodiment 1. The light emitting element described in Embodiment 2 can be used as a so-called see-through display device in which the opposite side is visible by making the first and second electrodes transparent. If the display is in a see-through state, it can be installed without blocking the view even when installed on the windshield of a car. Additionally, when providing a transistor for driving, etc., it is good to use a transistor with light transparency, such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor.

The display area 5202 is provided in the pillar portion and is a display device equipped with the light emitting element described in Embodiment 1. The display area 5202 can supplement the view obscured by the filler by displaying an image from an imaging means provided on the vehicle body. Likewise, the display area 5203 provided on the dashboard portion can display an image from an imaging means provided on the outside of the vehicle in a view obscured by the vehicle body, thereby improving safety by compensating for blind spots. By displaying images to complement invisible parts, safety can be confirmed more naturally and without discomfort.

Additionally, the display area 5203 can provide various other information, such as navigation information, speedometer or tachometer, mileage, fuel, gear status, and air conditioner settings. The display items and layout can be changed appropriately to suit the user's taste. Additionally, this information can also be provided to the display area 5200 to 5202. Additionally, the display areas 5200 to 5203 can also be used as a lighting device.

Additionally, a foldable portable information terminal 5150 is shown in Figures 12 (A) and (B). The foldable portable information terminal 5150 has a housing 5151, a display area 5152, and a bent portion 5153. Figure 12(A) shows the portable information terminal 5150 in an unfolded state. Figure 12(B) shows the portable information terminal in a folded state. Although the portable information terminal 5150 has a large display area 5152, it is compact when folded and has excellent portability.

The display area 5152 can be folded in half by the bent portion 5153. The bent portion 5153 is composed of an elastic member and a plurality of support members, and the elastic member expands when folded. The bent portion 5153 is folded to have a radius of curvature of 2 mm or more, preferably 3 mm or more.

Additionally, the display area 5152 may be a touch panel (input/output device) equipped with a touch sensor (input device). A light emitting device of one form of the present invention can be used in the display area 5152.

Additionally, a foldable portable information terminal 9310 is shown in Figures 13 (A) to (C). Figure 13(A) shows the portable information terminal 9310 in an unfolded state. Figure 13(B) shows the portable information terminal 9310 in the middle of changing from one of the unfolded and folded states to the other. Figure 13(C) shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 has excellent portability in the folded state, and has excellent display visibility in the unfolded state due to the seamless and wide display area.

The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Additionally, the display panel 9311 may be a touch panel (input/output device) equipped with a touch sensor (input device). Additionally, the display panel 9311 can reversibly transform the portable information terminal 9310 from an unfolded state to a folded state by bending between the two housings 9315 using the hinge 9313. A light emitting device of one embodiment of the present invention can be used in the display panel 9311.

(Example 1)

In this example, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)), which is a type of organic compound of the present invention. (2)) The synthesis method is explained in detail. The structural formula of BBABnf(II)(2) is shown below.

[Formula 46]

<Step 1: Synthesis of 3-(5-chloro-2-fluorophenyl)-2-naphthol>

In a 300 mL three-necked flask, 8.9 g (40 mmol) 3-bromo-2-naphthol, 10 g (60 mmol) 5-chloro-2-fluorophenylboronic acid, and 0.24 g (0.080 mmol) tri(ortho-tolyl). ) Phosphine, 40 mL of potassium carbonate aqueous solution (2.0 mmol/L), 120 mL of toluene, and 50 mL of ethanol were added and mixed. After degassing this mixture under reduced pressure, the inside of the flask was replaced with nitrogen. This mixture was heated to 60°C, then 90 mg (40 μmol) of palladium(II) acetate was added and stirred at 80°C for 8 hours. After stirring, 5.8 g (35 mmol) of 5-chloro-2-fluorophenylboronic acid and 90 mg (40 μmol) of palladium(II) acetate were further added to the mixture, and the mixture was stirred at 80°C for 8 hours. After stirring, the mixture was cooled to room temperature, the resulting mixture was washed with water and saturated saline solution, the aqueous layer and the organic layer were separated, and the organic layer was dried over magnesium sulfate. The mixture was filtered naturally, and the filtrate was concentrated and dried. After drying, 7.6 g of black solid was obtained. The synthesis scheme for Step 1 is shown below.

[Formula 47]

<Step 2: Synthesis of 2-chlorobenzo[b]naphtho[2,3-d]furan>

In a 500 mL eggplant-shaped flask, add 7.6 g of black solid obtained in Step 1, 7.6 g (55 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (abbreviated name: NMP), and stir at 120°C for 7 days. It was stirred for some time. The obtained mixture was suction filtered to remove potassium carbonate. 10 mL of 2 mol/L hydrochloric acid was added to the obtained filtrate to neutralize it, and a white precipitate was formed. This white precipitate was recovered by suction filtration and washed with ethyl acetate, water, and ethanol, and 3.5 g of white solid was obtained at a 34% yield based on the combined yield of steps 1 and 2. The synthesis scheme for step 2 is shown below.

[Formula 48]

^1H NMR data of the obtained solid are shown in Figures 14 (A) and (B), and numerical data are shown below. Additionally, Figure 14 (B) is an enlarged view showing the range of 7.2 ppm to 8.3 ppm in Figure 14 (A). As a result, it was confirmed that 2-chlorobenzo[b]naphtho[2,3-d]furan was obtained.

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

<Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)(2))>

In a 300 mL three-necked flask provided with a reflux tube, 2.0 g (8.0 mmol) of 2-chlorobenzo[b]naphtho[2,3-d]furan and 2.6 g (8.0 mmol) of bis(4-biphenylyl) were added. )amine, 56 mg (0.16 mmol) di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP (registered trademark)), 1.5 g (16 mmol) sodium tert-butoc Side and 100 mL of toluene were added, the mixture was degassed under reduced pressure, the inside of the flask was replaced with nitrogen, and then 46 mg (80 μmol) of bis(benzylideneacetone)palladium was added. This mixture was stirred at 110°C for 13 hours. After stirring, water was added to the resulting mixture, the aqueous layer and the organic layer were separated, and the aqueous layer was subjected to extraction with toluene. The obtained extract and the organic layer were combined, washed with water and saturated saline solution, and dried over magnesium sulfate. This mixture was filtered and the resulting filtrate was concentrated to obtain 3.7 g of brown solid with a yield of 86%. The synthesis scheme for step 3 is shown below.

[Formula 49]

¹ H NMR data of the obtained solid are shown in Figures 15 (A) and (B), and numerical data are shown below. In addition, Figure 15 (B) is an enlarged view showing the range of 7.0 ppm to 8.1 ppm in Figure 15 (A). As a result, it was found that BBABnf(II)(2), a type of organic compound of the present invention, was obtained in this synthesis example.

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

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

Next, the results of measuring the absorption spectrum and emission spectrum of the toluene solution of BBABnf(II)(2) are shown in Figure 16. Additionally, the absorption spectrum and emission spectrum of the thin film are shown in Figure 17. The solid thin film was produced by vacuum deposition on a quartz substrate. To measure the absorption spectrum of the toluene solution, an ultraviolet-visible spectrophotometer (V550 type, manufactured by JASCO Corporation) was used, and only toluene was placed in a quartz cell, and the measured spectrum was subtracted. Additionally, a spectrophotometer (Spectrophotometer U4100 manufactured by Hitachi High-Technologies Corporation) was used to measure the absorption spectrum of the thin film. Additionally, a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.) was used to measure the emission spectrum.

From Figure 16, the toluene solution of BBABnf(II)(2) had absorption peaks observed around 402 nm, 346 nm, and 322 nm, and the peak emission wavelength was 435 nm (excitation wavelength 385 nm). Additionally, from Figure 17, the thin film of BBABnf(II)(2) had absorption peaks observed around 392 nm, 350 nm, 257 nm, and 207 nm, and a peak emission wavelength was observed around 452 nm (excitation wavelength 350 nm). From these results, it was confirmed that BBABnf(II)(2)B emits blue light, and it was found that it can also be used as a host for a luminescent material or a fluorescent material in the visible region.

In addition, it was found that the thin film of BBABnf(II)(2) was difficult to aggregate even under air, had little change in shape, and had good film quality.

Next, the results of calculating the HOMO level and LUMO level of BBABnf(II)(2) based on cyclic voltammetry (CV) measurements are shown. The calculation method is shown below.

As a measuring device, an electrochemical analyzer (manufactured by BAS Inc., model number: ALS model 600A or 600C) was used. The solution in the CV measurement used dehydrated dimethylformamide (DMF) (manufactured by Sigma-Aldrich Inc., 99.8%, catalog number; 22705-6) as a solvent, and tetra-n-butylammonium perchlorate (n) as a supporting electrolyte. -Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number; T0836) was dissolved to a concentration of 100 mmol/L, and the measurement target was dissolved to a concentration of 2 mmol/L. Additionally, a platinum electrode (manufactured by BAS Inc., PTE platinum electrode) was used as a working electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode (5 cm) for VC-3) was used as an auxiliary electrode, and Ag was used as a reference electrode. /Ag+ electrode (manufactured by BAS Inc., RE7 non-aqueous solvent-based reference electrode) was used. Additionally, measurements were performed at room temperature (20°C to 25°C). In addition, the scan speed during CV measurement was standardized to 0.1 V/sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was set as the middle potential of the oxidation-reduction wave, and Ec was set as the middle potential of the reduction-oxidation wave. Here, since it is known that the potential energy with respect to the vacuum level of the reference electrode used in this example is -4.94 [eV], HOMO level [eV] = -4.94-Ea, LUMO level [eV] = -4.94-Ec The HOMO level and LUMO level can be obtained respectively using the equation.

The CV measurement was repeated 100 times, and the electrical stability of the compound was investigated by comparing the oxidation-reduction wave in the 100th cycle measurement with the oxidation-reduction wave in the first cycle.

As a result, it was found that the HOMO level of BBABnf(II)(2) was -5.45 eV and the LUMO level was -2.50 eV. In addition, as a result of comparing the waveforms after the first cycle and the 100th cycle in repeated measurements of oxidation-reduction waves, BBABnf(II)(2) maintained a peak intensity of 89% in the oxidation potential Ea[V] measurement. It was confirmed that resistance to oxidation was very good.

Additionally, differential scanning calorimetry (DSC) of BBABnf(II)(2) was measured using Pyris1DSC manufactured by PerkinElmer. Differential scanning calorimetry involves raising the temperature from -10℃ to 310℃ at a heating rate of 40℃/min, holding the same temperature for 1 minute, and then cooling to -10℃ at a cooling rate of 100℃/min, and - The operation of maintaining at 10°C for 5 minutes was performed twice in succession. From the DSC measurement results of the second cycle, the glass transition point of BBABnf(II)(2) was found to be 106°C, suggesting that it is a material with very high heat resistance.

Additionally, thermogravimetry-differential thermal analysis (TG-DTA) of BBABnf(II)(2) was performed. A high-vacuum differential differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS K.K.) was used for the measurement. Measurements were performed at atmospheric pressure, a temperature increase rate of 10°C/min, and a nitrogen stream (flow rate of 200 mL/min). From thermogravimetry-differential thermal analysis, it can be seen that BBABnf(II)(2) has a temperature (decomposition temperature) above 440°C at which the weight obtained by thermogravimetry becomes -5% of the starting point of measurement, and has high heat resistance. It was suggested that it was a substance.

(Example 2)

In this example, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)), which is a type of organic compound of the present invention. (4)) The synthesis method is explained in detail. The structural formula of BBABnf(II)(4) is shown below.

[Formula 50]

<Step 1: Synthesis of 3-(3-chloro-2-fluorophenyl)-2-naphthol>

In a 300 mL three-necked flask, 7.5 g (34 mmol) 3-bromo-2-naphthol, 5.9 g (34 mmol) 3-chloro-2-fluorophenylboronic acid, 0.21 g (67 μmol) tri(ortho-tolyl) ) Phosphine, 30 mL of potassium carbonate aqueous solution (2.0 mol/L), 110 mL of toluene, and 30 mL of ethanol were added, the mixture was degassed under reduced pressure, and the inside of the flask was replaced with nitrogen. After heating this mixture to 60°C, 76 mg (34 μmol) of palladium(II) acetate was added and stirred at 80°C for 8 hours. After stirring, 3.0 g (17 mmol) of 3-chloro-2-fluorophenylboronic acid and 36 mg (16 μmol) of palladium(II) acetate were further added, and stirred at 80°C for 8 hours. After stirring, the mixture was cooled to room temperature, the resulting mixture was washed with water and saturated saline solution, the aqueous layer and the organic layer were separated, and the organic layer was dried over magnesium sulfate. The mixture was filtered naturally, and the filtrate was concentrated and dried. After drying, 6.1 g of black solid was obtained. The synthesis scheme for Step 1 is shown below.

[Formula 51]

<Step 2: Synthesis of 4-chlorobenzo[b]naphtho[2,3-d]furan>

In a 500 mL eggplant flask, 6.1 g of the black solid obtained in Step 1, 6.3 g (44 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (NMP) were added, and stirred at 120°C for 7 hours. . The obtained mixture was suction filtered to remove potassium carbonate. 10 mL of 2.0 mol/L hydrochloric acid was added to the obtained filtrate to neutralize it. Water was added to this mixture, the organic layer and the aqueous layer were separated, and the aqueous layer was subjected to extraction with ethyl acetate. The obtained extract and the organic layer were combined, washed with water, saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution, and dried over magnesium sulfate. This mixture was naturally filtered, and the resulting filtrate was concentrated to obtain 4.9 g of a brown solid. As a result of purifying this brown solid by supercritical fluid chromatography (SFC) (mobile phase: liquid carbon dioxide: tetrahydrofuran = 7:3), 2.2 g of light yellow solid of the target product was obtained, with a yield of 26 by combining steps 1 and 2. Obtained in %. The synthesis scheme for step 2 is shown below.

[Formula 52]

¹ H NMR data of the obtained solid are shown in Figures 18 (A) and (B), and numerical data are shown below. Additionally, Figure 18 (B) is an enlarged view showing the range of 7.2 ppm to 8.3 ppm in Figure 18 (A). As a result, it was confirmed that 4-chlorobenzo[b]naphtho[2,3-d]furan was obtained.

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

<Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)(4))>

In a 300 mL three-necked flask provided with a reflux tube, 1.5 g (6.0 mmol) of 4-chlorobenzo[b]naphtho[2,3-d]furan and 1.9 g (6.0 mmol) of bis(4-biphenylyl) were added. )amine, 42 mg (0.12 mmol) di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (cBRIDP (registered trademark)), 1.2 g (12 mmol) sodium tert-butoxide, and 90 mL of toluene were added, degassed under reduced pressure, and the inside of the flask was replaced with nitrogen. 34 mg (60 μmol) of bis(benzylideneacetone)palladium was added to this mixture and stirred at 110°C for 6 hours. Water was added to the resulting mixture, the aqueous layer and the organic layer were separated, and then the aqueous layer was subjected to extraction with toluene. The obtained extract and the organic layer were combined, washed with water and saturated saline solution, and dried over magnesium sulfate. This mixture was naturally filtered, and the resulting filtrate was concentrated to obtain 2.7 g of brown solid of the target product with a yield of 83%. The synthesis scheme for step 3 is shown below.

[Formula 53]

^1H NMR data of the obtained solid are shown in Figures 19 (A) and (B), and numerical data are shown below. In addition, Figure 19 (B) is an enlarged view showing the range of 7.0 ppm to 8.6 ppm in Figure 19 (A). As a result, it was found that BBABnf(II)(4), a type of organic compound of the present invention, was obtained in this synthesis example.

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

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

Next, the results of measuring the absorption spectrum and emission spectrum of the toluene solution of BBABnf(II) (4) are shown in Figure 20. Additionally, the absorption spectrum and emission spectrum of the thin film are shown in Figure 21. Measurements were performed similarly to Example 1.

From Figure 20, the toluene solution of BBABnf(II)(4) had absorption peaks observed around 384 nm, 345 nm, and 327 nm, and the peak emission wavelength was 421 nm (excitation wavelength 327 nm). Additionally, from Figure 21, the thin film of BBABnf(II)(4) had absorption peaks observed around 374 nm, 355 nm, 325 nm, 257 nm, and 207 nm, and a peak emission wavelength was observed around 439 nm (excitation wavelength 350 nm). From these results, it was confirmed that BBABnf(II)(4)B emits blue light, and it was found that it can also be used as a host for a luminescent material or a fluorescent material in the visible region.

In addition, it was found that the thin film of BBABnf(II)(4) was difficult to aggregate even under air, had little change in shape, and had good film quality.

Next, the results of calculating the HOMO level and LUMO level of BBABnf(II)(4) based on cyclic voltammetry (CV) measurements are shown. The calculation method is the same as Example 1.

The CV measurement was repeated 100 times, and the electrical stability of the compound was investigated by comparing the oxidation-reduction wave in the 100th cycle measurement with the oxidation-reduction wave in the first cycle.

As a result, it was found that the HOMO level of BBABnf(II)(4) was -5.57 eV and the LUMO level was -2.48 eV. In addition, as a result of comparing the waveforms after the first cycle and the 100th cycle in repeated measurements of oxidation-reduction waves, it was found that 85% of the peak intensity was maintained in the oxidation potential Ea[V] measurement, BBABnf(II)(4) It was confirmed that resistance to oxidation was very good.

Additionally, differential scanning calorimetry of BBABnf(II)(4) was performed using the same device as in Example 1. Differential scanning calorimetry involves raising the temperature from -10℃ to 275℃ at a heating rate of 40℃/min, holding it at the same temperature for 1 minute, cooling to -10℃ at a cooling rate of 100℃/min, and The operation held for 5 minutes was performed twice in succession. From the DSC measurement results of the second cycle, the glass transition point of BBABnf(II)(4) was found to be 108°C, suggesting that it is a material with very high heat resistance.

Additionally, thermogravimetric-differential thermal analysis of BBABnf(II)(4) was performed in the same manner as in Example 1. From thermogravimetry-differential thermal analysis, it can be seen that BBABnf(II)(4) has a temperature of 410°C (decomposition temperature) at which the weight obtained by thermogravimetry becomes -5% of the starting point of measurement, and has high heat resistance. It was suggested that it was a substance.

(Example 3)

In this example, N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviated name: BBAaBnf(10)) is one type of organic compound of the present invention. ) The synthesis method is explained in detail. The structural formula of BBAaBnf(10) is shown below.

[Formula 54]

<Step 1: Synthesis of 2-bromophenyl-1-naphthyl ether>

In a 200 mL three-necked flask, 2.9 g (20 mmol) of 1-naphthol and 13 g (40 mmol) of potassium carbonate were added, and the inside of the flask was replaced with nitrogen. To this mixture, 110 mL of N-methylpyrrolidone (NMP) and 7.5 g (40 mmol) of 1-bromo-2-fluorobenzene were added, and the mixture was stirred at 170°C for 4 hours. After stirring, 100 mL of 2 mol/L hydrochloric acid was added to the resulting mixture and stirred at room temperature. After stirring, the organic layer of this mixture was washed twice with 100 mL of 2 mol/L hydrochloric acid, and the aqueous layer was extracted with toluene twice. The extraction solution and the organic layer were combined, washed with 100 mL of 2 mol/L hydrochloric acid and saturated saline solution, and magnesium sulfate was added to the obtained organic layer and dried. This mixture was naturally filtered, and the obtained filtrate was concentrated to obtain a brown compound. This compound was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:1), and 4.1 g of the target substance, a colorless and transparent oil, was obtained in a yield of 69%. The synthesis scheme of Step 1 is shown below.

[Formula 55]

<Step 2: Synthesis of benzo[b]naphtho[2,1-d]furan>

In a 500 mL eggplant flask, 4.1 g (14 mmol) of 2-bromophenyl-1-naphthyl ether, 0.20 mg (0.40 mmol) of triphenylphosphine, and 10 g (30 mmol) of cesium carbonate were added to the flask. The inside was replaced with nitrogen. After adding 100 mL of NMP to this mixture, the mixture was degassed under reduced pressure. After adding 89 mg (0.40 mmol) of palladium(II) acetate to this mixture, it was stirred at 180°C for 3 and a half hours under a nitrogen stream. After stirring, water was added to this mixture, and extraction with toluene was performed on the aqueous layer. The obtained extract and the organic layer were combined, washed with 2 mol/L hydrochloric acid, saturated aqueous sodium carbonate solution, and saturated saline solution, and then dried over magnesium sulfate. This mixture was naturally filtered, and the resulting filtrate was concentrated to obtain 3.0 g of light brown solid of the target product with a yield of 99%. The synthesis scheme for step 2 is shown below.

[Formula 56]

<Step 3: Synthesis of 10-iodobenzo[b]naphtho[2,1-d]furan>

In a 200 mL three-necked flask, 3.0 g (14 mmol) of benzo[b]naphtho[2,1-d]furan was added, the inside of the flask was replaced with nitrogen, and then 70 mL of tetrahydrofuran (THF) was added. did. After cooling this solution to -75°C, 8.5 mL (14 mmol) of n-butyllithium (1.64 mol/L n-hexane solution) was added dropwise to this solution. After dropwise addition, the obtained solution was stirred at room temperature for 1 hour. After stirring, the solution was cooled to -75°C, and then a solution of 3.6 g (14 mmol) of iodine dissolved in 10 mL of THF was added dropwise. After dropwise addition, the obtained solution was stirred for 17 hours while returning to room temperature. After stirring, an aqueous solution of sodium thiosulfate was added to the obtained solution, and after stirring for 1 hour, the organic layer of this mixture was washed with water, and the aqueous layer was subjected to extraction with ethyl acetate. The extract and the organic layer were combined, washed with saturated saline solution, and the obtained organic layer was dried over magnesium sulfate. After drying, this mixture was naturally filtered, and the obtained solution was concentrated, yielding the target white solid in the amount of 4.4 g, yield 93%. The synthesis scheme for Step 3 is shown below.

[Formula 57]

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

<Step 4: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviated name: BBAaBnf(10))>

In a 200 mL three-necked flask provided with a reflux tube, 2.0 g (6.0 mmol) of 10-iodobenzo[b]naphtho[2,1-d]furan and 1.9 g (6.0 mmol) of bis(4-biphenyl) were added. mono)amine, 42 mg (0.12 mmol) di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (cBRIDP (registered trademark)), 1.2 g (12 mmol) sodium tert-butoxide , and 70 mL of toluene were added, the mixture was degassed under reduced pressure, and the inside of the flask was replaced with nitrogen. After adding 34 mg (0.060 mmol) of bis(benzylideneacetone)palladium, the mixture was stirred at 110°C for 10 hours. After stirring, water was added to the resulting mixture, and extraction with toluene was performed on the aqueous layer. The organic layer and the resulting extract were combined, washed with water and saturated saline solution, and dried over magnesium sulfate. This mixture was naturally filtered, and the obtained filtrate was concentrated. The obtained crude product was purified by silica gel chromatography (mobile phase: hexane:toluene = 5:1), and 0.75 g of brown solid of the target product was obtained in a yield of 23%. The synthesis scheme for Step 4 is shown below.

[Formula 58]

¹ H NMR data of the obtained solid are shown below. As a result, it was found that in this synthesis example, BBAaBnf (10), which is a type of organic compound of the present invention, was obtained.

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

The obtained solid was purified by sublimation purification. Sublimation purification was performed by heating the solid to 270°C under the conditions of an argon flow rate of 15 mL/min and a pressure of 3.7 Pa. After purification by sublimation, the target compound was obtained as a free yellow solid with a yield of 0.44 g and a recovery rate of 58%.

(Example 4)

In this embodiment, light-emitting element 1 and light-emitting element 2 of one form of the present invention described in embodiment 2 will be described. The structural formulas of the organic compounds used in Light-emitting Element 1 and Light-emitting Element 2 are shown below.

[Formula 59]

(Method of manufacturing light emitting device 1)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated name: HAT-CN) represented by the above structural formula (i) by vapor deposition method. ) was deposited to a thickness of 5 nm to form the hole injection layer 111.

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

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv), and the structural formula (v) ) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine represented by ) (Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm to have a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, cgDBCzPA was deposited on the light emitting layer 113 to a film thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 represented by the structural formula (vi) was deposited on the light emitting layer 113. -Phenanthroline (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), the light emitting device 1 of this example was produced.

(Method of manufacturing light emitting device 2)

Light-emitting device 2 has an electron transport layer 114 of 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline represented by the structural formula (vii). (abbreviated name: 2mDBTBPDBq-II) was deposited to a thickness of 15 nm, and then NBPhen was deposited to a film thickness of 10 nm, and was manufactured in the same manner as light emitting device 1.

The device structures of light-emitting device 1 and light-emitting device 2 are summarized in the table below.

[Table 1]

The operation of sealing light-emitting element 1 and light-emitting element 2 with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting element is not exposed to the atmosphere (a sealant is applied around the element, UV treatment is applied at the time of sealing, 1 at 80°C) After performing time heat treatment, measurements were performed on the initial characteristics and reliability of these light emitting devices. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The luminance-current density characteristics of light-emitting device 1 and light-emitting device 2 are shown in Figure 22, the current efficiency-luminance characteristics are shown in Figure 23, the luminance-voltage characteristics are shown in Figure 24, the current-voltage characteristics are shown in Figure 25, and the external quantum efficiency- The luminance characteristics are shown in Figure 26 and the emission spectrum is shown in Figure 27. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 2.

[Table 2]

From Figures 22 to 27 and Table 2, it was found that Light-emitting Element 1 and Light-emitting Element 2, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

Additionally, a graph showing the change in luminance versus driving time at a current density of 50 mA/cm ² is shown in Figure 28. As shown in FIG. 28, it was found that Light-emitting Element 1 and Light-emitting Element 2, which are one type of light-emitting element of the present invention, have a small decrease in luminance due to accumulation of driving time and have a good lifespan.

(Example 5)

In this embodiment, light-emitting element 3 and light-emitting element 4 of one form of the present invention described in embodiment 2 will be described. The structural formulas of the organic compounds used in Light-emitting Element 3 and Light-emitting Element 4 are shown below.

[Formula 60]

(Method of manufacturing light-emitting device 3)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)(4)) represented by the above structural formula (iii) by vapor deposition method. ) and molybdenum (VI) oxide were co-deposited at 10 nm in a weight ratio of 4:2 (=BBABnf(II)(4):molybdenum oxide) to form the hole injection layer 111.

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

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv), and the structural formula (v) ) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine represented by ) (Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm to have a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, cgDBCzPA was deposited on the light emitting layer 113 to a film thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 represented by the structural formula (vi) was deposited on the light emitting layer 113. -Phenanthroline (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), the light emitting device 3 of this example was produced.

(Method of manufacturing light emitting element 4)

Light-emitting device 4 is an electron transport layer 114 of 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline represented by the structural formula (vii). (abbreviated name: 2mDBTBPDBq-II) was deposited to a thickness of 15 nm, and then NBPhen was deposited to a film thickness of 10 nm to form it in the same manner as light emitting device 3.

The device structures of light-emitting device 3 and light-emitting device 4 are summarized in the table below.

[Table 3]

The operation of sealing light-emitting element 3 and light-emitting element 4 with a glass substrate to prevent the light-emitting elements from being exposed to the atmosphere in a glove box in a nitrogen atmosphere (a sealant is applied around the elements, UV treatment is applied during sealing, and 1 at 80°C). After performing time heat treatment, measurements were performed on the initial characteristics and reliability of these light emitting devices. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The luminance-current density characteristics of Light-emitting Element 3 and Light-emitting Element 4 are shown in Figure 29, the current efficiency-luminance characteristics are shown in Figure 30, the luminance-voltage characteristics are shown in Figure 31, the current-voltage characteristics are shown in Figure 32, and the external quantum efficiency- The luminance characteristics are shown in Figure 33 and the emission spectrum is shown in Figure 34. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 4.

[Table 4]

From Figures 29 to 34 and Table 4, it was found that Light-emitting Element 3 and Light-emitting Element 4, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

Additionally, a graph showing the change in luminance versus driving time at a current density of 50 mA/cm ² is shown in Figure 35. As shown in FIG. 35, it was found that Light-emitting Element 3 and Light-emitting Element 4, which are one type of light-emitting element of the present invention, have a small decrease in luminance due to accumulation of driving time and have a good lifespan.

(Example 6)

In this embodiment, light-emitting element 5 and light-emitting element 6 of one form of the present invention described in embodiment 2 will be described. The structural formulas of the organic compounds used in Light-emitting Element 5 and Light-emitting Element 6 are shown below.

[Formula 61]

(Method of manufacturing light emitting element 5)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)(4)) represented by the above structural formula (iii) by vapor deposition method. ) and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated name: F6-TCNNQ) at a weight ratio of 1:0.5 (=BBABnf(II)(4):F6- The hole injection layer 111 was formed by co-depositing to a thickness of 10 nm (TCNNQ).

Next, on the hole injection layer 111, BBABnf(II) (4) is deposited to a film thickness of 10 nm to form a first hole transport layer 112-1, and on the first hole transport layer 112-1 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPPn) represented by the structural formula (ix) was deposited to a film thickness of 20 nm to form a second hole transport layer (112). By forming -2), the hole transport layer 112 was formed.

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv), and the structural formula (v) ) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine represented by ) (Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm to have a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: : After depositing 2mDBTBPDBq-II to a film thickness of 15 nm, 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline ( Abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), thereby producing light-emitting device 5 of this example.

(Method of manufacturing light emitting element 6)

Light-emitting device 6 was manufactured in the same manner as light-emitting device 5, except that PCPPn was deposited to a film thickness of 30 nm to form a hole transport layer 112.

The device structures of light-emitting device 5 and light-emitting device 6 are summarized in the table below.

[Table 5]

The operation of sealing light-emitting element 5 and light-emitting element 6 with a glass substrate in a nitrogen atmosphere glove box to prevent the light-emitting element from being exposed to the atmosphere (a sealant is applied around the element, UV treatment is applied at the time of sealing, 1 at 80°C) After performing time heat treatment, measurements were performed on the initial characteristics and reliability of these light emitting devices. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The luminance-current density characteristics of Light-emitting Element 5 and Light-emitting Element 6 are shown in Figure 36, the current efficiency-luminance characteristics are shown in Figure 37, the luminance-voltage characteristics are shown in Figure 38, the current-voltage characteristics are shown in Figure 39, and the external quantum efficiency- The luminance characteristics are shown in Figure 40 and the emission spectrum is shown in Figure 41. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 6.

[Table 6]

From Figures 36 to 41 and Table 6, it was found that light-emitting elements 5 and 6, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

Additionally, a graph showing the change in luminance versus driving time at a current density of 50 mA/cm ² is shown in Figure 42. As shown in Figure 42, it was found that Light-emitting Element 5 and Light-emitting Element 6, which are one type of light-emitting element of the present invention, have a small decrease in luminance due to accumulation of driving time and have a good lifespan.

(Example 7)

In this embodiment, light emitting element 7 of one form of the present invention described in Embodiment 2 will be described. The structural formula of the organic compound used in light-emitting device 7 is shown below.

[Formula 62]

(Method of manufacturing light emitting element 7)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated name: HAT-CN) represented by the above structural formula (i) by vapor deposition method. ) was deposited to a thickness of 5 nm to form the hole injection layer 111.

Next, on the hole injection layer 111, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the structural formula (ii) above was added to a thickness of 20 nm. The first hole transport layer 112-1 is formed by depositing to a film thickness, and N,N-bis(4-biphenyl)benzo[ b]Naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)(2)) was deposited to a film thickness of 10 nm to form the second hole transport layer 112-2.

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv), and the structural formula (v) ) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine represented by ) (Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm to have a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: : After depositing 2mDBTBPDBq-II) to a film thickness of 15 nm, 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline represented by the structural formula (vi) (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ) was formed to produce light emitting device 7 of this example.

The device structure of light emitting device 7 is summarized in the table below.

[Table 7]

The light-emitting element 7 is placed in a nitrogen atmosphere glove box, and the light-emitting element is sealed with a glass substrate to prevent it from being exposed to the atmosphere. The sealant is applied around the element, UV treated during sealing, and heat treated at 80°C for 1 hour. After performing the measurement, the initial characteristics and reliability of the light emitting device 7 were measured. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The brightness-current density characteristics of light emitting device 7 are shown in Figure 43, the current efficiency-brightness characteristics are shown in Figure 44, the brightness-voltage characteristics are shown in Figure 45, the current-voltage characteristics are shown in Figure 46, and the external quantum efficiency-brightness characteristics are shown in Figure 46. 47, the emission spectrum is shown in Figure 48. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 8.

[Table 8]

From Figures 43 to 48 and Table 8, it was found that light-emitting device 7, which is one embodiment of the present invention, is a blue light-emitting device with good characteristics such as driving voltage and luminous efficiency.

(Example 8)

In this embodiment, light emitting element 8 of one form of the present invention described in Embodiment 2 will be described. The structural formula of the organic compound used in light-emitting device 8 is shown below.

[Formula 63]

(Method of manufacturing light emitting element 8)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)(2)) represented by the above structural formula (x) by vapor deposition method. ) and molybdenum (VI) oxide were co-deposited at a thickness of 10 nm at a weight ratio of 4:2 (=BBABnf(II)(2):molybdenum oxide) to form the hole injection layer 111.

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

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv), and the structural formula (v) ) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine represented by ) (Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm to have a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: : After depositing 2mDBTBPDBq-II) to a film thickness of 15 nm, 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline represented by the structural formula (vi) (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), thereby producing light emitting device 8 of this example.

The device structure of light emitting device 8 is summarized in the table below.

[Table 9]

The light emitting element 8 is placed in a nitrogen atmosphere glove box, and the light emitting element is sealed with a glass substrate to prevent the light emitting element from being exposed to the atmosphere. The material is applied around the element, UV treated during sealing, and heat treated at 80°C for 1 hour. After performing the measurement, the initial characteristics and reliability of the light emitting device 8 were measured. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The brightness-current density characteristics of light emitting element 8 are shown in Figure 49, the current efficiency-brightness characteristics are shown in Figure 50, the brightness-voltage characteristics are shown in Figure 51, the current-voltage characteristics are shown in Figure 52, and the external quantum efficiency-brightness characteristics are shown in Figure 52. 53, the emission spectrum is shown in Figure 54. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 10.

[Table 10]

From Figures 49 to 54 and Table 10, it was found that Light-emitting Element 3 and Light-emitting Element 4, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

(Example 9)

In this embodiment, light-emitting element 9 and light-emitting element 10 of one form of the present invention described in Embodiment 2 will be described. The structural formulas of the organic compounds used in Light-emitting Element 9 and Light-emitting Element 10 are shown below.

[Formula 64]

(Method of manufacturing light emitting element 9)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated name: HAT-CN) represented by the above structural formula (i) by vapor deposition method. ) was deposited to a thickness of 5 nm to form the hole injection layer 111.

Next, on the hole injection layer 111, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the structural formula (ii) above was added to a thickness of 10 nm. The first hole transport layer 112-1 is formed by depositing to a film thickness, and N,N-bis(4-biphenyl)benzo[ b]naphtho[2,3-d]furan-4-amine (abbreviated name: BBABnf(II)(4)) is deposited to a film thickness of 10 nm to form a second hole transport layer 112-2, On the hole transport layer 112-2, 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviated name: PCzN2)) represented by the above structural formula (xi) was formed with a film thickness of 10 nm. was deposited to form a third hole transport layer (112-3).

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv) and the structural formula (v) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (represented by Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm at a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, cgDBCzPA was deposited on the light emitting layer 113 to a film thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 represented by the structural formula (vi) was deposited on the light emitting layer 113. -Phenanthroline (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), the light emitting device 1 of this example was produced.

(Method for manufacturing light emitting element 10)

The light emitting device 10 has an electron transport layer 114 of 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline represented by the structural formula (vii). (abbreviated name: 2mDBTBPDBq-II) was deposited to a thickness of 15 nm, and then NBPhen was deposited to a film thickness of 10 nm to form the same as light emitting device 9.

The device structures of light-emitting device 9 and light-emitting device 10 are summarized in the table below.

[Table 11]

The operation of sealing light-emitting element 9 and light-emitting element 10 with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting element is not exposed to the atmosphere (a sealant is applied around the element, UV treatment is applied at the time of sealing, 1 at 80°C) After performing time heat treatment), measurements were performed on the initial characteristics and reliability of these light emitting devices. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The luminance-current density characteristics of light-emitting element 9 and light-emitting element 10 are shown in Figure 55, the current efficiency-luminance characteristics are shown in Figure 56, the luminance-voltage characteristics are shown in Figure 57, the current-voltage characteristics are shown in Figure 58, and the external quantum efficiency- The luminance characteristics are shown in Figure 59 and the emission spectrum is shown in Figure 60. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 12.

[Table 12]

From Figures 55 to 60 and Table 12, it was found that light-emitting elements 9 and 10, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

Additionally, a graph showing the change in luminance versus driving time at a current density of 50 mA/cm ² is shown in Figure 61. As shown in FIG. 61, it was found that light-emitting elements 9 and 10, which are one type of light-emitting elements of the present invention, have a small decrease in luminance due to accumulation of driving time and have a good lifespan.

(Example 10)

In this embodiment, light-emitting elements 11 and 12 of one embodiment of the present invention described in Embodiment 2 will be described. The structural formulas of the organic compounds used in Light-emitting Element 11 and Light-emitting Element 12 are shown below.

[Formula 65]

(Method for manufacturing light emitting element 11)

First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. Additionally, the film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

Next, as a pre-treatment for forming a light emitting device on the substrate, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

After that, the substrate is introduced into a vacuum evaporation device whose internal pressure has been reduced to about 10 ^-4 Pa, vacuum baking is performed at 170°C for 30 minutes in a heating chamber within the vacuum evaporation device, and then the substrate is left to cool for about 30 minutes. did.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the side on which the first electrode 101 is formed is facing downward, and a process using resistance heating is placed on the first electrode 101. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated name: HAT-CN) represented by the above structural formula (i) by vapor deposition method. ) was deposited to a thickness of 5 nm to form the hole injection layer 111.

Next, on the hole injection layer 111, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) represented by the structural formula (ii) above was added to a thickness of 10 nm. The first hole transport layer 112-1 is formed by depositing to a film thickness, and N,N-bis(4-biphenyl)benzo[ b]naphtho[2,3-d]furan-2-amine (abbreviated name: BBABnf(II)(2)) is deposited to a film thickness of 10 nm to form a second hole transport layer 112-2, On the hole transport layer 112-2, 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviated name: PCzN2)) represented by the above structural formula (xi) was formed with a film thickness of 10 nm. was deposited to form a third hole transport layer (112-3).

Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated name: cgDBCzPA) represented by the structural formula (iv) and the structural formula (v) N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (represented by Abbreviated name: 1,6mMemFLPAPrn) was co-deposited at 25 nm at a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light emitting layer 113.

Thereafter, cgDBCzPA was deposited on the light emitting layer 113 to a film thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 represented by the structural formula (vi) was deposited on the light emitting layer 113. -Phenanthroline (abbreviated name: NBPhen) was deposited to a film thickness of 10 nm to form the electron transport layer 114.

After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a film thickness of 1 nm to form the electron injection layer 115, and then aluminum is deposited to a film thickness of 200 nm to form the second electrode 102. ), the light emitting device 11 of this example was produced.

(Method for manufacturing light emitting element 12)

The light-emitting device 12 has an electron transport layer 114 of 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline represented by the structural formula (vii). (abbreviated name: 2mDBTBPDBq-II) was deposited to a thickness of 15 nm, and then NBPhen was deposited to a film thickness of 10 nm, and was manufactured in the same manner as light emitting device 11.

The device structures of light-emitting device 11 and light-emitting device 12 are summarized in the table below.

[Table 13]

The operation of sealing the light emitting element 11 and the light emitting element 12 with a glass substrate in a nitrogen atmosphere glove box to prevent the light emitting element from being exposed to the atmosphere (a sealant is applied around the element, UV treatment is applied at the time of sealing, temperature 1 at 80°C) After performing time heat treatment, measurements were performed on the initial characteristics and reliability of these light emitting devices. Additionally, the measurements were performed at room temperature (an atmosphere maintained at 25°C).

The luminance-current density characteristics of light-emitting elements 11 and 12 are shown in Figure 62, the current efficiency-luminance characteristics are shown in Figure 63, the luminance-voltage characteristics are shown in Figure 64, the current-voltage characteristics are shown in Figure 65, and the external quantum efficiency- The luminance characteristics are shown in Figure 66 and the emission spectrum is shown in Figure 67. Additionally, the main characteristics of each light emitting device around 1000 cd/m ² are shown in Table 14.

[Table 14]

From Figures 62 to 67 and Table 14, it was found that light-emitting elements 11 and 12, which are one embodiment of the present invention, are blue light-emitting elements with good characteristics such as driving voltage and luminous efficiency.

Additionally, a graph showing the change in luminance versus driving time at a current density of 50 mA/cm ² is shown in Figure 68. As shown in FIG. 68, it was found that light-emitting elements 11 and 12, which are one type of light-emitting elements of the present invention, have a small decrease in luminance due to accumulation of driving time and have a good lifespan.

101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 112: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 112-3: Third hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer, 116: charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection buffer layer, 400: substrate, 401: third 1 electrode, 403: EL layer, 404: second electrode, 405: real, 406: real, 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: driving circuit portion (source line driving circuit), 602: pixel portion, 603: driving circuit portion (gate line driving circuit), 604: sealing substrate, 605: reality, 607: space, 608: wiring, 609: FPC (flexible printed circuit), 610: device substrate, 611: FET for switching, 612: FET for current control, 613: first electrode, 614: insulator, 616: EL layer, 617 : second electrode, 618: light emitting element, 951: substrate, 952: electrode, 953: insulating layer, 954: partition layer, 955: EL layer, 956: electrode, 1001: substrate, 1002: base insulating film, 1003: gate insulating film , 1006: gate electrode, 1007: gate electrode, 1008: gate electrode, 1020: first interlayer insulating film, 1021: second interlayer insulating film, 1022: electrode, 1024W: anode, 1024R: anode, 1024G: anode, 1024B: anode, 1025: partition, 1028: EL layer, 1029: second electrode, 1031: sealing substrate, 1032: material, 1033: transparent substrate, 1034R: red colored layer, 1034G: green colored layer, 1034B: blue colored layer, 1035: black Matrix, 1036: Overcoat layer, 1037: Third interlayer insulating film, 1040: Pixel part, 1041: Driving circuit part, 1042: Peripheral part, 2001: Housing, 2002: Light source, 2100: Robot, 2110: Operation unit, 2101: Illuminance sensor, 2102: microphone, 2103: upper camera, 2104: speaker, 2105: display, 2106: lower camera, 2107: obstacle sensor, 2108: moving mechanism, 3001: lighting device, 5000: housing, 5001: display unit, 5002: second display unit , 5003: speaker, 5004: LED lamp, 5005: operation key, 5006: connection terminal, 5007: sensor, 5008: microphone, 5012: support, 5013: earphone, 5100: cleaning robot, 5101: display, 5102: camera, 5103 : brush, 5104: operation button, 5150: mobile information terminal, 5151: housing, 5152: display area, 5153: bend, 5120: trash, 5200: display area, 5201: display area, 5202: display area, 5203: display area , 7101: housing, 7103: display unit, 7105: stand, 7107: display unit, 7109: operation keys, 7110: remote controller, 7201: main body, 7202: housing, 7203: display unit, 7204: keyboard, 7205: external connection port, 7206 : Pointing device, 7210: Second display unit, 7401: Housing, 7402: Display unit, 7403: Operation button, 7404: External connection port, 7405: Speaker, 7406: Microphone, 7400: Mobile phone, 9310: Mobile information terminal, 9311: Display panel, 9313: hinge, 9315: housing

Claims (34)

An organic compound represented by the following general formula (G1),

In the general formula (G1),
Among R ¹ to R ¹⁰ , R ¹ , R ⁸ or R ¹⁰ is a group represented by the general formula (g1) below, and the remainder are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, or a cyclic hydrocarbon with 3 to 6 carbon atoms. group, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,

In the general formula (g1),
Ar ³ and Ar ⁴ each independently represent any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4),
Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2, but Ar ³ has the following general formula (g4 ), n is 1 or 2, and when Ar ⁴ is a group represented by the following general formula (g4), m is 1 or 2,
When n is 2, the two Ar ^1s may be different or the same, and when m is 2, the two Ar ^2s may be different or the same,
When Ar ³ and Ar ⁴ are aromatic hydrocarbon groups with 6 to 10 carbon atoms and have a substituent, the substituents are aromatic hydrocarbon groups with 6 to 10 carbon atoms, hydrocarbon groups with 1 to 6 carbon atoms, and cyclic hydrocarbon groups with 3 to 6 carbon atoms. Any one or plural of the groups represented,
Configurations in which n and m are 0, Ar ³ and Ar ⁴ are phenyl groups, and the 2nd and 6th positions of the phenyl group are substituted with aromatic hydrocarbon groups are excluded,

In the general formula (g2),
One of R ³¹ to R ⁴⁰ represents a single bond, and the others each represent hydrogen,
In the general formula (g3),
One of R ⁴¹ to R ⁵⁰ represents a single bond, and the others each represent hydrogen,
In the general formula (g4),
An organic compound in which one of R ⁵¹ to R ⁶⁰ represents a single bond and the others each represent hydrogen. delete According to claim 1,
An organic compound in which the group represented by the general formula (g1) is bonded to R ¹⁰ in the organic compound represented by the general formula (G1). An organic compound represented by the following general formula (G2),

In the general formula (G2),
Among R ¹¹ to R ²⁰ , R ¹⁸ or R ²⁰ is a group represented by the following general formula (g1), and the remainder are each independently hydrogen, a hydrocarbon group with 1 to 6 carbon atoms, a cyclic hydrocarbon group with 3 to 6 carbon atoms, or a carbon number. Represents any one of an alkoxy group of 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group of 6 to 60 carbon atoms,

In the general formula (g1),
Ar ³ and Ar ⁴ each independently represent any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formulas (g2) to (g4),
Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and n and m each independently represent an integer of 0 to 2, but Ar ³ has the following general formula (g4 ), n is 1 or 2, and when Ar ⁴ is a group represented by the following general formula (g4), m is 1 or 2,
When n is 2, the two Ar ^1s may be different or the same, and when m is 2, the two Ar ^2s may be different or the same,
When Ar ³ and Ar ⁴ are aromatic hydrocarbon groups with 6 to 10 carbon atoms and have a substituent, the substituents are aromatic hydrocarbon groups with 6 to 10 carbon atoms, hydrocarbon groups with 1 to 6 carbon atoms, and cyclic hydrocarbon groups with 3 to 6 carbon atoms. Any one or plural of the groups represented,
Configurations in which n and m are 0, Ar ³ and Ar ⁴ are phenyl groups, and the 2nd and 6th positions of the phenyl group are substituted with aromatic hydrocarbon groups are excluded,

In the general formula (g2),
One of R ³¹ to R ⁴⁰ represents a single bond, and the others each represent hydrogen,
In the general formula (g3),
One of R ⁴¹ to R ⁵⁰ represents a single bond, and the others each represent hydrogen,
In the general formula (g4),
An organic compound in which one of R ⁵¹ to R ⁶⁰ represents a single bond and the others each represent hydrogen. delete According to claim 4,
An organic compound in which the group represented by the general formula (g1) is bonded to R ²⁰ in the organic compound represented by the general formula (G2). According to claim 1 or 4,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, and Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms. organic compounds. According to claim 1 or 4,
An organic compound in which Ar ³ and Ar ⁴ are each independently any one of a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. According to claim 1 or 4,
An organic compound wherein Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group. According to claim 1 or 4,
An organic compound wherein Ar ³ and Ar ⁴ are phenyl groups. According to claim 1 or 4,
An organic compound wherein Ar ¹ and Ar ² are phenylene groups. According to claim 11,
An organic compound wherein n and m are 2. According to claim 1 or 4,
An organic compound wherein both n and m are 1. As a light emitting device,
anode,
cathode, and
With an EL layer,
The EL layer is located between the anode and the cathode,
A light emitting device wherein the EL layer contains the organic compound according to claim 1 or 4. As a light emitting device,
anode,
cathode, and
With an EL layer,
The EL layer is located between the anode and the cathode,
The EL layer has a light emitting layer,
A light-emitting device comprising the organic compound according to claim 1 or 4 in the light-emitting layer. According to claim 15,
A light-emitting device wherein the light-emitting layer further includes a light-emitting material. According to claim 16,
A light emitting device wherein the light emitting layer further includes a material having electron transport properties. As a light emitting device,
anode,
cathode, and
With an EL layer,
The EL layer is located between the anode and the cathode,
The EL layer has a light emitting layer and a hole transport layer,
The light-emitting layer has a light-emitting material,
The hole transport layer is located between the light emitting layer and the anode,
A light emitting device comprising the organic compound according to claim 1 or 4 in the hole transport layer. According to claim 18,
The EL layer further has a hole injection layer,
The hole injection layer is provided in contact with the anode and the hole transport layer,
A light emitting device wherein the hole injection layer contains an organic compound having acceptor properties. According to claim 19,
A light emitting device wherein the compound having the acceptor property is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene. According to claim 19,
wherein the hole transport layer has a first layer, a second layer, and a third layer,
The first layer is located between the hole injection layer and the second layer,
The third layer is located between the second layer and the light emitting layer,
The first layer is in contact with the hole injection layer,
The third layer is in contact with the light emitting layer,
the first layer comprising a first hole transport material,
the second layer includes the organic compound,
the third layer comprising a third hole transport material,
The light-emitting layer includes a host material and a light-emitting material,
The HOMO level of the organic compound is deeper than the HOMO level of the first hole transport material,
The HOMO level of the host material is deeper than the HOMO level of the organic compound,
A light emitting device wherein the difference between the HOMO level of the organic compound and the HOMO level of the third hole transport material is 0.3 eV or less. According to claim 21,
A light emitting device wherein the HOMO level of the first hole transport material is -5.4 eV or higher. According to claim 21,
A light emitting device wherein the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound is 0.3 eV or less. According to claim 21,
A light emitting device wherein the difference between the HOMO level of the organic compound and the HOMO level of the third hole transport material is 0.2 eV or less. According to claim 21,
A light emitting device wherein the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound is 0.2 eV or less. According to claim 21,
A light-emitting device wherein the HOMO level of the light-emitting material is higher than the HOMO level of the host material. According to claim 21,
A light emitting device wherein the HOMO level of the third hole transport material is equal to or deeper than the HOMO level of the host material. According to claim 16,
A light-emitting device, wherein the light-emitting material is a fluorescent light-emitting material. According to claim 16,
A light-emitting device, wherein the light emitted by the light-emitting material is blue fluorescent light. According to claim 16,
The light-emitting material is a condensed aromatic diamine compound,
A light-emitting device wherein the amino group of the aromatic diamine compound includes a carbazolyl group. According to claim 16,
The light-emitting material is a diaminopyrene compound,
A light-emitting device wherein the amino group of the diaminopyrene compound includes a carbazolyl group. As a light emitting device,
A light emitting device according to claim 16, and
A light emitting device having a transistor or a substrate. As an electronic device,
A light emitting device according to claim 32, and
An electronic device that has sensors, operation buttons, speakers, or microphones. As a lighting device,
A light emitting device according to claim 32, and
A lighting device having a housing.