Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting apparatus

文档序号：231329 发布日期：2021-11-09 浏览：22次中文

阅读说明：本技术 有机化合物、发光器件、发光装置、电子设备及照明装置 (Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting apparatus ) 是由门间裕史濑尾哲史奥山拓梦桥本直明滝田悠介铃木恒德于 2020-03-11 设计创作，主要内容包括：提供一种新颖有机化合物的喹喔啉衍生物。通式(G1)所示的喹喔啉衍生物具有如下结构：喹喔啉骨架与蒽骨架的9位键合,该蒽骨架的10位与杂芳环键合,该杂芳环的3位含有氮。在上述通式(G1)中,a及b分别独立地表示取代或未取代的形成环的碳原子数为6至13的亚芳基。此外,m及n分别独立地为0、1或2。(Quinoxaline derivatives of novel organic compounds are provided. The quinoxaline derivative represented by the general formula (G1) has the following structure: the quinoxaline skeleton is bonded to the 9-position of the anthracene skeleton, the 10-position of the anthracene skeleton is bonded to a heteroaromatic ring, the 3-position of which contains nitrogen. In the above general formula (G1), a and b are each independentlyIndependently represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, m and n are each independently 0,1 or 2.)

1. An organic compound represented by the formula (G1):

wherein a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring,

m and n are each independently 0,1 or 2,

R¹to R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring,

a is represented by the formula (g1),

X¹to X⁴Each independently represents N orCR¹⁴，

And, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

2. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein the organic compound is represented by formula (G2):

3. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein the organic compound is represented by formula (G3):

4. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein m is a number of 2,

and a as the two arylene groups is the same.

5. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein n is a number of 2,

and b as the two arylene groups is the same.

6. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein a represents a substituted or unsubstituted phenylene group.

7. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein formula (g1) is represented by any one of formula (g1-1) to formula (g 1-3):

and R is²¹To R²⁴、R³¹To R³³、R⁴¹To R⁴³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

8. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein formula (g1) is represented by any one of formula (g1-4) to formula (g 1-6):

9. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein the organic compound is represented by any one of formulae (100), (101), (102), (135), (147), and (175):

10. a light-emitting device comprising the organic compound according to claim 1.

11. A light emitting device comprising:

a first electrode;

an EL layer over the first electrode, the EL layer comprising the organic compound according to claim 1; and

a second electrode on the EL layer.

12. A light emitting device comprising:

a first electrode;

a light emitting layer on the first electrode;

an electron transport layer on the light emitting layer, the electron transport layer comprising the organic compound according to claim 1; and

a second electrode on the electron transport layer.

13. A light emitting device comprising:

a first electrode;

a light emitting layer on the first electrode, the light emitting layer including a fluorescent material;

an electron transport layer on the light emitting layer, the electron transport layer comprising the organic compound according to claim 1; and

a second electrode on the electron transport layer.

14. A light emitting device comprising:

the light emitting device of claim 11; and

at least one of a transistor and a substrate.

15. An electronic device, comprising:

the light-emitting device according to claim 14; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

16. An illumination device, comprising:

the light emitting device of claim 11; and

at least one of a housing, a cover, and a bracket.

17. An organic compound represented by the formula (G4):

wherein a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring,

R¹to R¹³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring,

a is represented by the formula (g1),

X¹to X⁴Each independently represents N or CR¹⁴，

18. The organic compound according to claim 17, wherein the organic compound is selected from the group consisting of,

wherein a represents a substituted or unsubstituted phenylene group.

19. The organic compound according to claim 17, wherein the organic compound is selected from the group consisting of,

wherein formula (g1) is represented by any one of formula (g1-1) to formula (g 1-3):

20. The organic compound according to claim 17, wherein the organic compound is selected from the group consisting of,

wherein formula (g1) is represented by any one of formula (g1-4) to formula (g 1-6):

21. a light-emitting device comprising the organic compound according to claim 17.

22. A light emitting device comprising:

a first electrode;

a light emitting layer on the first electrode;

an electron transporting layer on the light-emitting layer, the electron transporting layer comprising the organic compound according to claim 17; and

a second electrode on the electron transport layer.

23. A light emitting device comprising:

the light emitting device of claim 21; and

at least one of a transistor and a substrate.

24. An electronic device, comprising:

the light emitting device of claim 23; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

Technical Field

One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, a display module, an illumination module, a display device, a light-emitting device, an electronic device, and an illumination device. Further, one embodiment of the present invention is not limited to the above-described technical field. The technical field of one embodiment of the invention disclosed in this specification and the like relates to an object, a method, or a method of manufacture. Further, an embodiment of the present invention relates to a process, machine, product, or composition. Thus, more specifically, as an example of the technical field of one embodiment of the present invention disclosed in the present specification, a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, an illumination device, a power storage device, a memory device, an imaging device, a method for driving these devices, or a method for manufacturing these devices can be given.

Background

Since a light-emitting device (also referred to as an organic EL device or a light-emitting element) including an EL layer between a pair of electrodes has characteristics such as thinness, lightness in weight, high-speed response to an input signal, and low power consumption, a display using the light-emitting device is expected to be used as a next-generation flat panel display.

The light-emitting device is configured such that electrons and holes injected from each electrode are recombined in an EL layer by applying a voltage between a pair of electrodes, so that a light-emitting substance (organic compound) contained in the EL layer becomes an excited state, and light is emitted when the excited state returns to a ground state. Further, as the kind of excited state, a singlet excited state (S) may be mentioned^*) And triplet excited state (T)^*) In this case, light emission from a singlet excited state is referred to as fluorescence, and light emission from a triplet excited state is referred to as phosphorescence. Further, in the light-emitting device, the statistical generation ratio of the singlet excited state and the triplet excited state is considered to be S^*：T^*1: 3. an emission spectrum obtained from a luminescent material is peculiar to the luminescent material, and by using different kinds of organic compounds as the luminescent material, light emitting devices of various emission colors can be obtained.

In order to improve the device characteristics of such a light-emitting device, improvement of the device structure, development of materials, and the like have been actively performed (for example, see patent document 1).

[ reference documents ]

[ patent document ]

[ patent document 1] Japanese patent application laid-open No. 2010-182699

Disclosure of Invention

In view of the above problems, an object of one embodiment of the present invention is to provide a novel organic compound. Further, it is another object of another embodiment of the present invention to provide a quinoxaline derivative as a novel organic compound. Further, another embodiment of the present invention aims to provide a novel light-emitting device, a light-emitting device with high light-emitting efficiency, a light-emitting device with a long lifetime, and a light-emitting device with low driving voltage.

Another object of another embodiment of the present invention is to provide a light-emitting device, an electronic device, and a display device each having high reliability. Another object of another embodiment of the present invention is to provide a light-emitting device, an electronic device, and a display device each having low power consumption.

One embodiment of the present invention may be implemented as long as any of the above objects is achieved.

One embodiment of the present invention is a quinoxaline derivative, that is, an organic compound represented by the following general formula (G1). The quinoxaline derivative represented by the following general formula (G1) has the following structure: the 2-position or 3-position of the quinoxaline skeleton is bonded to the 9-position of the anthracene skeleton, and the heteroaromatic ring bonded to the 10-position of the anthracene skeleton contains N (nitrogen) at the 3-position from the bonding to the anthracene skeleton. Further, in the following general formula (G1), the quinoxaline skeleton and the anthracene skeleton may be bonded through an arylene group, and the anthracene skeleton and the heteroaromatic ring may be bonded through an arylene group.

[ chemical formula 1]

In the general formula (G1), a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, m and n are each independently 0,1 or 2. Note that two a when m is 2 or two b when n is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Further, another embodiment of the present invention is a quinoxaline derivative, that is, an organic compound represented by the following general formula (G2).

[ chemical formula 2]

In the above general formula (G2), a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, m represents 0,1 or 2. Note that two a's in the case where m is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Further, another embodiment of the present invention is a quinoxaline derivative, that is, an organic compound represented by the following general formula (G3).

[ chemical formula 3]

In the general formula (G3), a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, n is 0,1 or 2. Note that two b in the case where n is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted ring having 3 to 7 carbon atomsAny one of an alkyl group and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Further, another embodiment of the present invention is a quinoxaline derivative, that is, an organic compound represented by the following general formula (G4).

[ chemical formula 4]

In the above general formula (G4), a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Further, another embodiment of the present invention is an organic compound, wherein a in the above general formula (G4) represents a substituted or unsubstituted phenylene group.

Further, another embodiment of the present invention is an organic compound, wherein the above general formula (g1) is represented by any one of the following general formula (g1-1) to general formula (g 1-3).

[ chemical formula 5]

In the above general formulae (g1-1) to (g1-3), R²¹To R²⁴、R³¹To R³³、R⁴¹To R⁴³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted carbon forming a ringAny of a cycloalkyl group having 3 to 7 atoms and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

[ chemical formula 6]

Further, another embodiment of the present invention is an organic compound represented by structural formula (100), structural formula (101), structural formula (102), structural formula (135), structural formula (147), or structural formula (175).

[ chemical formula 7]

Further, another embodiment of the present invention is a light-emitting device using the organic compound of one embodiment of the present invention described above. Further, a light-emitting device containing not only the above-described organic compound but also a guest material is also included in the scope of the present invention. Further, a light-emitting device containing not only the above-described organic compound but also a phosphorescent material is also included in the scope of the present invention. A light-emitting device including not only a light-emitting device but also a transistor, a substrate, and the like is also included in the scope of the invention. Further, an electronic device and a lighting device including a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support base, a speaker, and the like, in addition to the light-emitting device are also included in the scope of the invention.

The light-emitting device in this specification includes an image display device or a light source (including a lighting device) using a light-emitting device. In addition, the light-emitting device further includes the following modules: the light emitting device is mounted with a module of a connector such as FPC (flexible printed circuit) or TCP (tape carrier package); a module with a printed circuit board arranged at the end of the TCP; or a module in which an IC (integrated circuit) is directly mounted to a light emitting device by a COG (chip on glass) method

One embodiment of the present invention can provide a novel organic compound. Further, an embodiment of the present invention can provide a quinoxaline derivative as a novel organic compound. Further, an embodiment of the present invention can provide a novel light-emitting device, provide a light-emitting device with a long lifetime, and provide a light-emitting device with high light-emitting efficiency.

In addition, another embodiment of the present invention can provide a light-emitting device, an electronic device, and a display device each having high reliability. In addition, another embodiment of the present invention can provide a light-emitting device, an electronic device, and a display device each having low power consumption.

Note that the description of these effects does not hinder the existence of other effects. Note that one embodiment of the present invention is not required to achieve all of the above-described effects. Note that effects other than the above-described effects are obvious from the description of the specification, the drawings, the claims, and the like, and the effects can be derived from the description of the specification, the drawings, the claims, and the like.

Drawings

Fig. 1A and 1B are diagrams illustrating a structure of a light emitting device;

fig. 2A to 2C are diagrams illustrating a light emitting device;

fig. 3A is a plan view illustrating a light emitting device, and fig. 3B is a sectional view illustrating the light emitting device;

fig. 4A is a diagram illustrating a mobile computer, fig. 4B is a diagram illustrating a portable image reproduction device, fig. 4C is a diagram illustrating a digital camera, fig. 4D is a diagram illustrating a portable information terminal, fig. 4E is a diagram illustrating a portable information terminal, fig. 4F is a diagram illustrating a television device, and fig. 4G is a diagram illustrating a portable information terminal;

fig. 5A to 5C are diagrams illustrating an electronic apparatus;

fig. 6A and 6B are diagrams illustrating an automobile;

fig. 7A and 7B are diagrams illustrating an illumination device;

FIG. 8 shows a method for producing an organic compound represented by the structural formula (100)¹H-NMR spectrum;

fig. 9 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (100);

fig. 10 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (100);

fig. 11 is a diagram illustrating a light emitting device;

fig. 12 is a graph showing current density-luminance characteristics of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

fig. 13 is a graph showing voltage-luminance characteristics of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

fig. 14 is a graph showing luminance-current efficiency characteristics of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

fig. 15 is a graph showing voltage-current characteristics of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

fig. 16 is a graph showing emission spectra of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

fig. 17 is a graph showing the reliability of the light emitting device 1, the comparative light emitting device 2, and the comparative light emitting device 3;

FIG. 18 shows a method for producing an organic compound represented by the structural formula (200)¹H-NMR spectrum;

FIG. 19 shows a method for producing an organic compound represented by the structural formula (101)¹H-NMR spectrum;

fig. 20 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (101);

fig. 21 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (101);

FIG. 22 shows a method for producing an organic compound represented by the structural formula (102)¹H-NMR spectrum;

fig. 23 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (102);

fig. 24 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (102);

FIG. 25 shows an organic compound represented by structural formula (135)Of an object¹H-NMR spectrum;

fig. 26 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (135);

fig. 27 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (135);

FIG. 28 shows a method for producing an organic compound represented by the structural formula (147)¹H-NMR spectrum;

fig. 29 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (147);

fig. 30 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by structural formula (147);

FIG. 31 shows a method for producing an organic compound represented by the structural formula (175)¹H-NMR spectrum;

fig. 32 shows an ultraviolet-visible absorption spectrum and an emission spectrum of the organic compound represented by structural formula (175);

fig. 33 is a graph showing current density-luminance characteristics of the light emitting device 4 and the comparative light emitting device 5;

fig. 34 is a graph showing voltage-luminance characteristics of the light emitting device 4 and the comparative light emitting device 5;

fig. 35 is a graph showing luminance-current efficiency characteristics of the light emitting device 4 and the comparative light emitting device 5;

fig. 36 is a graph showing voltage-current characteristics of the light emitting device 4 and the comparative light emitting device 5;

fig. 37 is a graph showing emission spectra of the light-emitting device 4 and the comparative light-emitting device 5;

fig. 38 is a graph showing the reliability of the light emitting device 4 and the comparative light emitting device 5;

fig. 39 is a diagram illustrating the reliability of the light emitting devices 6,7, 8, and 9.

Detailed Description

Embodiments of the present invention will be described below in detail with reference to the accompanying drawings. Note that the present invention is not limited to the following description, and the mode and the details thereof may be changed into various forms without departing from the spirit and the scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments shown below.

(embodiment mode 1)

In this embodiment, an organic compound according to an embodiment of the present invention will be described.

The organic compound according to one embodiment of the present invention is a quinoxaline derivative represented by the following general formula (G1). An organic compound according to an embodiment of the present invention has a structure represented by the following general formula (G1): the 2-position or 3-position of the quinoxaline skeleton is bonded to the 9-position of the anthracene skeleton, and the heteroaromatic ring bonded to the 10-position of the anthracene skeleton contains N (nitrogen) at the 3-position from the bonding to the anthracene skeleton. Further, the 2-position or 3-position of the quinoxaline skeleton and the 9-position of the anthracene skeleton may be bonded via an arylene group, and the 10-position of the anthracene skeleton and the heteroaromatic ring may be bonded via an arylene group.

[ chemical formula 8]

In the above general formula (G1), the quinoxaline skeleton has a high electron-transporting property, and the anthracene skeleton has a high stability to a hole. Further, a heteroaromatic ring containing N (nitrogen) at the 3-position from the bonding to the anthracene skeleton can improve the electron injection property from the electrode.

Another embodiment of the present invention is an organic compound represented by the following general formula (G2). That is, the organic compound has a structure in which the heteroaromatic ring directly bonded to the 10-position of the anthracene skeleton contains N at the 3-position from the bonding to the anthracene skeleton.

[ chemical formula 9]

In the general formula (G2), since the heteroaromatic ring directly bonded to the 10-position of the anthracene skeleton has a structure in which N is contained at the 3-position from the bonding with the anthracene skeleton, electrons are easily transferred to the quinoxaline skeleton having a LUMO orbital in the same molecule, and thus the electron transporting property is improved, which is preferable.

Another embodiment of the present invention is an organic compound represented by the following general formula (G3). That is, the organic compound has the following structure: the 2-position or 3-position of the quinoxaline skeleton is bonded to the 9-position of the anthracene skeleton via an arylene group, and the heteroaromatic ring bonded to the 10-position of the anthracene skeleton contains N at the 3-position from the bonding to the anthracene skeleton.

[ chemical formula 10]

In the general formula (G3), a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, n is 0,1 or 2. Note that two b in the case where n is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Since the above general formula (G3) has a structure in which the 2-or 3-position of the quinoxaline skeleton and the 9-position of the anthracene skeleton are bonded through one arylene group, steric hindrance around the quinoxaline skeleton is relieved, so that electron transportability is improved, and thus it is preferable. Further, since steric hindrance in the molecule is relieved, electron transfer becomes smooth, whereby electron transportability is improved. Further, in view of intramolecular electron transfer, a distance that electrons having the same intramolecular molecule easily transfer to the quinoxaline skeleton having the LUMO orbital is preferable.

Another embodiment of the present invention is an organic compound represented by the following general formula (G4). That is, the organic compound has the following structure: the 2-position or 3-position of the quinoxaline skeleton is bonded to the 9-position of the anthracene skeleton via an arylene group, and the heteroaromatic ring directly bonded to the 10-position of the anthracene skeleton contains N at the 3-position from the bonding to the anthracene skeleton.

[ chemical formula 11]

Since the above general formula (G4) has a structure in which the 2-or 3-position of the quinoxaline skeleton and the 9-position of the anthracene skeleton are bonded through one arylene group, steric hindrance around the quinoxaline skeleton is relieved, and thus it is preferable. Further, since steric hindrance in the molecule is relieved, electron transfer becomes smooth, whereby electron transportability is improved. Further, in view of the intramolecular electron transfer, it is preferable that the hetero aromatic ring directly bonded to the 10-position of the anthracene skeleton contains N at the 3-position from the bonding with the anthracene skeleton in addition to the above structure, and therefore, electrons having the same intramolecular length are easily transferred to the quinoxaline skeleton having the LUMO orbital.

Further, another embodiment of the present invention is an organic compound, wherein a in the above general formula (G4) represents a substituted or unsubstituted phenylene group. Since a represents a substituted or unsubstituted phenylene group, steric hindrance around the quinoxaline skeleton is relieved, and thus this is preferable. Further, a distance that electrons having the same molecule easily migrate to the quinoxaline skeleton having a LUMO orbital is preferable.

[ chemical formula 12]

In the above general formulae (g1-1) to (g1-3), R²¹To R²⁴、R³¹To R³³、R⁴¹To R⁴³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

[ chemical formula 13]

Note that in the organic compounds represented by the above general formula (G1), the above general formula (G2), the above general formula (G3), and the above general formula (G4), the substitution is preferably a substitution with a substituent having 6 to 13 carbon atoms, such as an alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, or an n-hexyl group, a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 1-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a fluoren-2-yl group, or a fluoren-4-yl group. These substituents may be bonded to each other to form a ring. For example, when the aryl group is a fluoren-2-yl group having two phenyl groups as substituents at the 9-position, the two phenyl groups may be bonded to each other to form a spiro-9, 9' -bifluoren-2-yl group. More specifically, examples thereof include phenyl, tolyl, xylyl, biphenyl, indenyl, naphthyl and fluorenyl.

In the organic compounds represented by the general formula (G1), the general formula (G2), the general formula (G3) and the general formula (G4), specific examples of the arylene group having 6 to 13 carbon atoms forming a ring in the formula include a phenylene group, a naphthalenediyl group, a biphenyldiyl group and a fluorenediyl group.

In the organic compounds represented by the general formula (G1), the general formula (G2), the general formula (G3) and the general formula (G4), R is represented by¹To R¹³、R¹⁴、R²¹To R²⁴、R³¹To R³³、R⁴¹To R⁴³Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, sec-hexyl, tert-hexyl, neohexyl, 3-methylpentyl, 2-ethylbutyl, 1, 2-dimethylbutyl, and 2, 3-dimethylbutyl.

The following shows a specific structural formula of the organic compound according to one embodiment of the present invention.

[ chemical formula 14]

[ chemical formula 15]

[ chemical formula 16]

[ chemical formula 17]

[ chemical formula 18]

[ chemical formula 19]

[ chemical formula 20]

Note that the organic compounds represented by the structural formulae (100) to (175) described above are examples of the organic compound of one embodiment of the present invention represented by any one of the general formula (G1) described above, the general formula (G2) described above, the general formula (G3) described above, and the general formula (G4) described above. However, the organic compound according to one embodiment of the present invention is not limited thereto.

An example of a method for synthesizing an organic compound according to an embodiment of the present invention represented by general formula (G1) will be described below.

[ chemical formula 21]

First, as shown in the following synthetic scheme (a-1), an organic boron compound or boric acid of a quinoxaline derivative (compound 1) is coupled with a halide or triflate substituent of an anthracene derivative (compound 2) by a suzuki-miyaura reaction, thereby obtaining an organic compound represented by the general formula (G1).

[ chemical formula 22]

In the synthetic route (A-1), a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, m and n are each independently 0,1 or 2. Note that two a when m is 2 or two b when n is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Furthermore, in the synthetic route (A-1), R⁵⁰And R⁵¹May be bonded to each other to form a ring. Further, X¹¹Represents halogen or a triflate group.

Examples of the palladium catalyst which can be used in the synthetic route (A-1) include, but are not limited to, palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) dichloride, and the like.

Examples of the ligand of the palladium catalyst which can be used in the synthetic route (A-1) include tri (o-tolyl) phosphine, triphenylphosphine, tricyclohexylphosphine, and the like. However, the ligand of the palladium catalyst which can be used is not limited thereto.

As the base which can be used in the synthetic route (A-1), there may be mentioned: organic bases such as sodium tert-butoxide; or inorganic bases such as potassium carbonate and sodium carbonate, but bases that can be used are not limited thereto.

As the solvent which can be used in the synthetic route (A-1), there can be mentioned the following solvents: a mixed solvent of toluene and water; mixed solvents of water and alcohols such as toluene and ethanol; a mixed solvent of xylene and water; mixed solvents of water and alcohols such as xylene and ethanol; a mixed solvent of benzene and water; mixed solvents of water and alcohols such as benzene and ethanol; and mixed solvents of water and ethers such as ethylene glycol dimethyl ether. However, the solvent that can be used is not limited thereto. Further, it is more preferable to use a mixed solvent of toluene and water; a mixed solvent of toluene, ethanol and water; or a mixed solvent of water and ethers such as ethylene glycol dimethyl ether.

In the suzuki-miyaura coupling reaction shown in the synthetic route (a-1), a cross-coupling reaction using an organoaluminum compound, an organozirconium compound, an organozinc compound, an organotin compound, or the like, in addition to the organoboron compound or boric acid shown in the compound 1, may also be employed. However, it is not limited thereto.

In addition, in the suzuki-miyaura coupling reaction, an organoboron compound or boric acid of an anthracene derivative may be coupled to a halide or trifluoromethanesulfonate substituent of a quinoxaline derivative by the suzuki-miyaura coupling reaction. Specifically, as shown in the following synthetic scheme (a-2), an organic compound represented by the general formula (G1) is obtained by coupling an organoboron compound or boric acid (compound 3) of an anthracene derivative with a halide or triflate substituent (compound 4) of a heterocyclic compound derivative by the suzuki-miyaura reaction.

[ chemical formula 23]

In the synthetic route (A-2), a and b each independently represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a ring. Further, m and n are each independently 0,1 or 2. Note that two a when m is 2 or two b when n is 2 may be the same or different. R¹To R¹³Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A is represented by the general formula (g 1). Further, X¹To X⁴Each independently represents N or CR¹⁴. Furthermore, R¹⁴Represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms forming a ring, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Furthermore, in the synthetic route (A-2), R⁵²And R⁵³May be bonded to each other to form a ring. Further, X¹²Represents halogen or a triflate group.

Examples of the palladium catalyst that can be used in the synthetic route (A-2) include, but are not limited to, palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) dichloride, and the like. Examples of the ligand of the palladium catalyst which can be used in the synthesis route (A-2) include tri (o-tolyl) phosphine, triphenylphosphine, tricyclohexylphosphine, and the like. However, the ligand of the palladium catalyst which can be used is not limited thereto.

As the base which can be used in the synthetic route (A-2), there may be mentioned: organic bases such as sodium tert-butoxide; or inorganic bases such as potassium carbonate and sodium carbonate, but bases that can be used are not limited thereto.

As the solvent which can be used in the synthetic route (A-2), there can be mentioned the following solvents: a mixed solvent of toluene and water; mixed solvents of water and alcohols such as toluene and ethanol; a mixed solvent of xylene and water; mixed solvents of water and alcohols such as xylene and ethanol; a mixed solvent of benzene and water; mixed solvents of water and alcohols such as benzene and ethanol; and mixed solvents of water and ethers such as ethylene glycol dimethyl ether. However, the solvent that can be used is not limited thereto. Further, it is more preferable to use a mixed solvent of toluene and water; a mixed solvent of toluene, ethanol and water; or a mixed solvent of water and ethers such as ethylene glycol dimethyl ether.

In the suzuki-miyaura coupling reaction shown in the synthetic route (A-2), a cross-coupling reaction using an organoaluminum compound, an organozirconium compound, an organozinc compound, an organotin compound, or the like, in addition to the organoboron compound or boric acid shown in the compound 3, may be employed. However, it is not limited thereto.

(embodiment mode 2)

In this embodiment mode, a light-emitting device according to one embodiment of the present invention is described.

< example of Structure of light emitting device >

Fig. 1A shows an example of a light-emitting device including an EL layer having a light-emitting layer between a pair of electrodes. Specifically, the EL layer 103 is interposed between the first electrode 101 and the second electrode 102. For example, when the first electrode 101 is used as an anode, the EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked as functional layers.

As other structures of the light-emitting device, a light-emitting device which can be driven at a low voltage by having a structure including a plurality of EL layers formed so as to sandwich a charge generation layer between a pair of electrodes (a series structure), a light-emitting device which improves optical characteristics by forming an optical microcavity resonator (microcavity) structure between a pair of electrodes, and the like are also included in one embodiment of the present invention. The charge generation layer has the following functions: a function of injecting electrons into one of the adjacent EL layers and injecting holes into the other EL layer when a voltage is applied to the first electrode 101 and the second electrode 102.

At least one of the first electrode 101 and the second electrode 102 of the light-emitting device is an electrode having light-transmitting properties (e.g., a transparent electrode, a semi-transmissive and semi-reflective electrode). When the electrode having light transmittance is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In the case where the electrode is a semi-transmissive and semi-reflective electrode, the visible light reflectance of the semi-transmissive and semi-reflective electrode is 20% or more and 80% or less, and preferably 40% or more and 70% or less. Further, the resistivity of these electrodes is preferably 1 × 10^-2Omega cm or less.

In the light-emitting device according to the above-described embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the visible light reflectance of the reflective electrode is 40% or more and 100% or less, and preferably 70% or more and 100% or less. Further, the resistivity of the electrode is preferably 1 × 10^-2Omega cm or less.

< first electrode and second electrode >

As materials for forming the first electrode 101 and the second electrode 102, the following materials may be appropriately combined if the functions of the two electrodes can be satisfied. For example, metals, alloys, conductive compounds, mixtures thereof, and the like can be suitably used. Specific examples thereof include an In-Sn oxide (also referred to as ITO), an In-Si-Sn oxide (also referred to as ITSO), an In-Zn oxide, and an In-W-Zn oxide. In addition to the above, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), and alloys appropriately combining these metals may be mentioned. In addition to the above, elements belonging to group 1 or group 2 of the periodic table (for example, rare earth metals such as lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium (Yb), etc., alloys in which these are appropriately combined, graphene, and the like can be used.

Note that these electrodes can be formed by a sputtering method or a vacuum evaporation method.

< hole injection layer >

The hole injection layer 111 is a layer containing an organic acceptor material and a hole-transporting material, and preferably a hole-transporting material having a deep HOMO. The organic acceptor material is a substance that exhibits an electron accepting property with respect to a hole transporting material having a relatively deep HOMO. Further, the hole-transporting material having a deep HOMO is a substance having a deep HOMO level with a HOMO level of-5.7 eV or more and-5.4 eV or less. In this manner, since the HOMO level of the hole-transporting material is deep, holes are easily injected into the hole-transporting layer 112.

As the organic acceptor material, an organic compound having an electron-withdrawing group (particularly, a halogen group such as a fluorine group or a cyano group) or the like can be used, and a substance having an electron-accepting property with respect to the hole-transporting material can be appropriately selected from such substances. Examples of such organic compounds include 7,7,8, 8-tetracyano-2, 3,5, 6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10, 11-hexacyan-1, 4,5,8,9, 12-hexaazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7, 8-hexafluorotetracyano (hexafluoro) -naphthoquinodimethane (abbreviated as F6-TCNNQ), and 2- (7-dicyanomethylene-1, 3,4,5, 6, 8,9, 10-octafluoro-7H-pyrene-2-ylidene) malononitrile. In particular, a compound in which an electron-withdrawing group is bonded to a fused aromatic ring having a plurality of hetero atoms, such as HAT-CN, is thermally stable, and is therefore preferable. Further, the [3] axis ene derivative including an electron-withdrawing group (particularly, a halogen group such as a fluoro group, a cyano group) is particularly preferable because it has a very high electron-accepting property, and specifically, there may be mentioned: a, a ', a "-1, 2, 3-cyclopropanetriylidenetris [ 4-cyano-2, 3,5, 6-tetrafluorophenylacetonitrile ], a ', a" -1,2, 3-cyclopropanetriylidenetris [2, 6-dichloro-3, 5-difluoro-4- (trifluoromethyl) phenylacetonitrile ], a ', a "-1, 2, 3-cyclopropanetriylidenetris [2,3, 4,5, 6-pentafluorophenylacetonitrile ], and the like.

The hole-transporting material having a deep HOMO is preferably a hole-transporting material having a hole-transporting property, and preferably has any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, an aromatic amine having a substituent including a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine including a naphthalene ring, or an aromatic monoamine in which 9-fluorenyl group is bonded to nitrogen of the amine through arylene group may be used.

As the hole transporting material having a deep HOMO, it is preferable to use an electric field strength [ V/cm ]]Has a hole mobility of 1X 10 when the square root of (A) is 600^-6cm²A substance having a ratio of Vs to V or more. In addition, any substance other than the above may be used as long as it has a hole-transporting property higher than an electron-transporting property. Note that these materials are preferably substances containing N, N-bis (4-biphenyl) amino groups, whereby a long-life light-emitting device can be manufactured.

Specific examples of the hole-transporting material having a deep HOMO include N- (4-biphenyl) -6, N-diphenylbenzo [ b ] naphtho [1,2-d ] furan-8-amine (abbreviated as BnfABP), N-bis (4-biphenyl) -6-phenylbenzo [ b ] naphtho [1,2-d ] furan-8-amine (abbreviated as BBABnf), 4 '-bis (6-phenylbenzo [ b ] naphtho [1,2-d ] furan-8-yl) -4' -phenyltriphenylamine (abbreviated as BnfBB1BP), N-bis (4-biphenyl) benzo [ b ] naphtho [1,2-d ] furan-6-amine (abbreviated as BBABnf (6)), N-bis (4-biphenyl) benzo [ b ] naphtho [1,2-d ] furan-8-amine (abbreviated as BBABnf (8)), N-bis (4-biphenyl) benzo [ b ] naphtho [2, 3-d ] furan-4-amine (abbreviated as BBABnf (II) (4)), N-bis [4- (dibenzofuran-4-yl) phenyl ] -4-amino-p-terphenyl (abbreviated as DBfBB1TP), N- [4- (dibenzothiophene-4-yl) phenyl ] -N-phenyl-4-benzidine (abbreviated as ThBA1BP), 4- (2-naphthyl) -4', 4' -diphenyltriphenylamine (abbreviated as BBA beta NB), 4- [4- (2-naphthyl) phenyl ] -4', 4' -diphenyltriphenylamine (abbreviated as BBA beta NBi), 4- (2; 1 '-binaphthyl-6-yl) -4', 4 '-diphenyltriphenylamine (abbreviated as BBA. alpha. Nbeta. NB), 4' -diphenyl-4 '- (7; 1' -binaphthyl-2-yl) triphenylamine (abbreviated as BBA. alpha. Nbeta. NB-03), 4 '-diphenyl-4' - (7-phenyl) naphthyl-2-yltriphenylamine (abbreviated as BBAP. beta. NB-03), 4- (6; 2 '-binaphthyl-2-yl) -4', 4 '-diphenyltriphenylamine (abbreviated as BBA (. beta. N2) B), 4- (2; 2' -binaphthyl-7-yl) -4', 4' -diphenyltriphenylamine (abbreviated as BBA (. beta. N2) B-03), 4- (1; 2 '-binaphthyl-4-yl) -4', 4 '-diphenyltriphenylamine (abbreviated as BBA. beta. Nalpha NB), 4- (1; 2' -binaphthyl-5-yl) -4', 4' -diphenyltriphenylamine (abbreviated as BBA. beta. Nalpha NB-02), 4- (4-biphenyl) -4'- (2-naphthyl) -4' -phenyltriphenylamine (abbreviated as TPBiA. beta. NB), 4- (3-biphenyl) -4'- [4- (2-naphthyl) phenyl ] -4' -phenyltriphenylamine (abbreviated as mTPBiA. beta. NBi), 4- (4-biphenyl) -4'- [4- (2-naphthyl) phenyl ] -4' -phenyltriphenylamine (abbreviated as TPBiA. beta. NBi), 4- (1-naphthyl) -4 '-phenyltriphenylamine (abbreviation: α NBA1BP), 4' -bis (1-naphthyl) triphenylamine (abbreviation: α NBB1BP), 4 '-diphenyl-4 "- [4' - (carbazol-9-yl) biphenyl-4-yl ] triphenylamine (abbreviation: YGTBi1BP), 4'- [4- (3-phenyl-9H-carbazol-9-yl) phenyl ] tris (1, 1' -biphenyl-4-yl) amine (abbreviation: YGTBi1BP-02), 4- [4'- (carbazol-9-yl) biphenyl-4-yl ] -4' - (2-naphthyl) -4" -phenyltriphenylamine (abbreviation: YGTBi β NB), N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -N- [4- (1-naphthyl) phenyl ] -9,9 '-spirobi [ 9H-fluorene ] -2-amine (short for PCBNBSF), N-bis ([1,1' -biphenyl ] -4-yl) -9,9 '-spirobi [ 9H-fluorene ] -2-amine (short for BBASF), N-bis ([1,1' -biphenyl ] -4-yl) -9,9 '-spirobi [ 9H-fluorene ] -4-amine (short for BBASF (4)), N- (1, 1' -biphenyl-2-yl) -N- (9, 9-dimethyl-9H-fluoren-2-yl) -9,9' -spirobi [ 9H-fluoren ] -4-amine (abbreviation: oFBiSF), N- (4-biphenyl) -N- (9, 9-dimethyl-9H-fluoren-2-yl) dibenzofuran-4-amine (abbreviation: FrBiF), N- [4- (1-naphthyl) phenyl ] -N- [3- (6-phenyldibenzofuran-4-yl) phenyl ] -1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4' - (9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3' - (9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4' - [4- (9-phenylfluoren-9-yl) phenyl ] triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP), 4' -diphenyl-4 "- (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBANB), 4' -bis (1-naphthyl) -4 "- (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBNBB), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -9,9' -spirobi [ 9H-fluorene ] -2-amine (abbreviation: PCBASF), N- (1, 1' -biphenyl-4-yl) -9, 9-dimethyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -9H-fluoren-2-amine (abbreviation: PCBBiF), and the like.

Note that the hole injection layer 111 can be formed by a known film formation method, for example, by a vacuum evaporation method.

< hole transport layer >

The hole transport layer 112 is a layer that transports holes injected from the first electrode 101 through the hole injection layer 111 into the light emitting layer 113.

The hole transport layer 112 may use the above-described hole transport material. In addition, the hole transport layer 112 may also have a stacked-layer structure. In addition, in the case where the hole transport layer 112 has a stacked-layer structure, a layer on the light-emitting layer side may also serve as an electron-blocking layer.

In addition, when comparing the HOMO level of the hole transport material used for the hole injection layer 111 and the HOMO level of the hole transport material used for the hole transport layer 112, it is preferable to select the respective materials so that the HOMO level of the hole transport material used for the hole transport layer 112 is deeper and the difference is 0.2eV or less. Further, it is more preferable that both are the same substance to smoothly inject holes.

In addition, in the case where the hole transport layer 112 has a stacked-layer structure, when comparing the HOMO level of the hole transport material for forming the hole transport layer on the electron injection layer 111 side with the HOMO level of the hole transport material for forming the hole transport layer on the light emitting layer 113 side, the HOMO level of the latter material is preferably deeper. It is preferable to select the respective materials so that the difference is 0.2eV or less. By having the above-described relationship between the HOMO levels of the hole transport materials used for the hole injection layer 111 and the hole transport layer 112 having a stacked structure, holes can be smoothly injected into each layer, and thus, an increase in driving voltage and an excessively small number of holes in the light emitting layer 113 can be prevented.

The hole-transporting materials used for the hole-injecting layer 111 and the hole-transporting layer 112 having a stacked structure preferably each have a hole-transporting skeleton. As the hole-transporting skeleton, a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton, which do not make the HOMO level of the hole-transporting material too shallow, are preferably used. It is preferable that the materials of the adjacent layers share the hole-transporting skeleton of the hole-transporting material used for the hole-injecting layer 111 and the hole-transporting layer 112 having a stacked structure, since hole injection can be smoothly performed. The hole-transporting skeleton is particularly preferably a dibenzofuran skeleton.

Further, when the hole transport materials for the hole injection layer 111 and the hole transport layer 112 having a stacked structure are the same between adjacent layers, holes can be smoothly injected into the adjacent layers in the cathode direction, and thus this is a preferable structure.

< light-emitting layer >

In the light-emitting device of one embodiment of the present invention, the light-emitting layer 113 may have either a single-layer structure or a stacked-layer structure of a plurality of light-emitting layers. When a plurality of light-emitting layers are stacked, the light-emitting layers are preferably formed so that the light-emitting layers have different functions.

The light-emitting layer 113 contains a light-emitting substance (guest material) and a host material in which the light-emitting substance is dispersed.

As the light-emitting substance (guest material), a substance which emits fluorescence (fluorescent light-emitting material), a substance which emits phosphorescence (phosphorescent light-emitting material), a Thermally Activated Delayed Fluorescence (TADF) material which exhibits Thermally activated delayed fluorescence, and other light-emitting substances can be used. As the organic compound (host material), various carrier transport materials such as the above TADF material can be used in addition to the electron transport material and the hole transport material. In addition, as the host material, a hole transporting material, an electron transporting material, or the like can be used. Further, as a specific example of the hole transporting material, the electron transporting material, or the like, one or more of suitable materials described in this specification or known materials can be used.

Examples of the fluorescent substance that can be used as a guest material in the light-emitting layer 113 include the following substances. Note that other fluorescent substances may be used in addition to these.

For example, 5, 6-bis [4- (10-phenyl-9-anthryl) phenyl group]-2, 2 '-bipyridine (PAP 2BPy for short), 5, 6-bis [4' - (10-phenyl-9-anthryl) biphenyl-4-yl]-2, 2' -bipyridine (PAPP 2BPy), N ' -diphenyl-N, N ' -bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl]Pyrene-1, 6-diamine (1, 6FLPAPRn for short), N '-bis (3-methylphenyl) -N, N' -bis [3- (9-phenyl-9H-fluoren-9-yl) phenyl]Pyrene-1, 6-diamine (1, 6mM FLPAPPrn for short), N' -bis [4- (9H-carbazol-9-yl) phenyl]-N, N '-diphenylstilbene-4, 4' -diamine (abbreviation: YGA2S), 4- (9H-carbazol-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (9H-carbazol-9-yl) -4' - (9, 10-diphenyl-2-anthracenyl) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthracenyl) phenyl]-9H-carbazole-3-amine (PCAPA), perylene, 2, 5,8, 11-tetra (tert-butyl) perylene (TBP), 4- (10-phenyl-9-anthryl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (PCBAPA), N' - (2-tert-butylanthracene-9, 10-diylbis-4, 1-phenylene) bis [ N, N ', N' -triphenyl-1, 4-phenylenediamine](abbr.: DPABPA), N, 9-diphenyl-N- [4- (9, 10-diphenyl-2-anthryl) phenyl]-9H-carbazole-3-amine (2 PCAPPA for short), N- [4- (9, 10-diphenyl-2-anthryl) phenyl]-N, N ', N ' -triphenyl-1, 4-phenylenediamine (abbreviated as 2DPAPPA), N, N, N ', N ', N ' -octaphenyldibenzo [ g, p ]](chrysene) -2, 7,10, 15-tetramine (abbreviation: DBC1), coumarin 30, N- (9, 10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N- [9, 10-bis (1, 1' -biphenyl-2-yl) -2-anthryl]-N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9, 10-diphenyl-2-anthracenyl) -N, N ', N ' -triphenyl-1, 4-phenylenediamine (abbreviation: 2DPAPA), N- [9, 10-bis (1, 1' -biphenyl-2-yl) -2-anthraceneBase of]-N, N ', N ' -triphenyl-1, 4-phenylenediamine (2 DPABPhA for short), 9, 10-bis (1, 1' -biphenyl-2-yl) -N- [4- (9H-carbazol-9-yl) phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N, 9-triphenylanthracene-9-amine (abbreviation: DPhAPHA), coumarin 545T, N, N '-diphenylquinacridone (abbreviation: DPQd), rubrene, 5, 12-bis (1, 1' -biphenyl-4-yl) -6, 11-diphenyltetracene (abbreviation: BPT), 2- (2- {2- [4- (dimethylamino) phenyl ] tetraphenyl]Vinyl } -6-methyl-4H-pyran-4-ylidene) malononitrile (abbreviation: DCM1), 2- { 2-methyl-6- [2- (2,3, 6, 7-tetrahydro-1H, 5H-benzo [ ij ]]Quinolizin-9-yl) ethenyl]-4H-pyran-4-ylidene malononitrile (abbreviation: DCM2), N, N, N ', N' -tetrakis (4-methylphenyl) naphthacene-5, 11-diamine (abbreviation: p-mPTHTD), 7, 14-diphenyl-N, N, N ', N' -tetrakis (4-methylphenyl) acenaphtho [1, 2-a ]]Fluoranthene-3, 10-diamine (p-mPHAFD for short), 2- { 2-isopropyl-6- [2- (1, 1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H-benzo [ ij ]]Quinolizin-9-yl) ethenyl]-4H-pyran-4-ylidene malononitrile (abbreviated as 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 malononitrile (abbreviated as DCJTB), 2- (2, 6-bis {2- [4- (dimethylamino) phenyl group)]Vinyl } -4H-pyran-4-ylidene) malononitrile (abbreviation: BisDCM), 2- {2, 6-bis [2- (8-methoxy-1, 1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H-benzo [ ij ]]Quinolizin-9-yl) ethenyl]-4H-pyran-4-ylidene malononitrile (BisDCJTM for short), N' - (pyrene-1, 6-diyl) bis [ (6, N-diphenylbenzo [ b ]]Naphtho [1,2-d ]]Furan) -8-amines](abbreviation: 1, 6BnfAPrn-03), 3, 10-bis [ N- (9-phenyl-9H-carbazol-2-yl) -N-phenylamino]Naphtho [2, 3-b; 6, 7-b']Bis-benzofurans (abbreviation: 3,10PCA2Nbf (IV) -02), 3, 10-bis [ N- (dibenzofuran-3-yl) -N-phenylamino]Naphtho [2, 3-b; 6, 7-b']Bis-benzofurans (abbreviated as 3,10 FrA2Nbf (IV) -02), and the like. In particular, fused aromatic diamine compounds represented by pyrene diamine compounds such as 1, 6FLPAPrn, 1, 6mMemFLPAPrn, 1,6 bnfparn-03 and the like are preferable because they have suitable hole trapping properties and good light-emitting efficiency and reliability.

Examples of the phosphorescent substance which can be used as a guest material in the light-emitting layer 113 include the following substances.

For example, a material such as tris {2- [5- (2-methylphenyl) -4- (2, 6-dimethylphenyl) -4H-1,2, 4-triazol-3-yl-. kappa.N 2]Phenyl-kappa C iridium (III) (abbreviation: [ Ir (mpptz-dmp) ]₃]) Tris (5-methyl-3, 4-diphenyl-4H-1, 2, 4-triazole) iridium (III) (abbreviation: [ Ir (Mptz)₃]) Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1, 2, 4-triazole]Iridium (III) (abbreviation:

[Ir(iPrptz-3b)₃]) And the like organometallic iridium complexes having a 4H-triazole skeleton; tris [ 3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1, 2, 4-triazole]Iridium (III) (abbreviation: [ Ir (Mptz1-mp)₃]) Tris (1-methyl-5-phenyl-3-propyl-1H-1, 2, 4-triazole) iridium (III) (abbreviation: [ Ir (Prptz1-Me)₃]) And the like organometallic iridium complexes having a 1H-triazole skeleton; fac-tris [1- (2, 6-diisopropylphenyl) -2-phenyl-1H-imidazole]Iridium (III) (abbreviation: [ Ir (iPrpmi)₃]) Tris [3- (2, 6-dimethylphenyl) -7-methylimidazo [1,2-f ]]Phenanthridino (phenanthrinato)]Iridium (III) (abbreviation: [ Ir (dmpimpt-Me)₃]) And the like organometallic iridium complexes having an imidazole skeleton; and bis [2- (4',6' -difluorophenyl) pyridinato-N, C²']Iridium (III) tetrakis (1-pyrazolyl) borate (FIr 6 for short), bis [2- (4',6' -difluorophenyl) pyridinato-N, C²']Iridium (III) picolinate (FIrpic), bis {2- [3',5' -bis (trifluoromethyl) phenyl]pyridinato-N, C²' } Iridium (III) picolinate (abbreviation: [ Ir (CF)₃ppy)₂(pic)]) Bis [2- (4',6' -difluorophenyl) pyridinato-N, C²']Organometallic iridium complexes having a phenylpyridine derivative having an electron-withdrawing group as a ligand, such as iridium (III) acetylacetonate (FIr (acac)). The above substance is a compound emitting blue phosphorescence, and is a compound having a light emission peak at 440nm to 520 nm.

Further, there may be mentioned: tris (4-methyl-6-phenylpyrimidino) iridium (III) (abbreviation: [ Ir (mppm))₃]) Tris (4-tert-butyl-6-phenylpyrimidinate) iridium (III) (abbreviation: [ Ir (tBuppm)₃]) And (acetylacetonate) bis (6-methyl-4-phenylpyrimidinate) iridium (III) (abbreviation: [ Ir (mppm)₂(acac)]) And (acetylacetonate) bis (6-tert-butyl-4-phenylpyrimidinate) iridium (III) (abbreviation: [ Ir (tBuppm)₂(acac)]) And (acetylacetonate) bis [6- (2-norbornyl) -4-phenylpyrimidine]Iridium (III) (abbreviation: [ Ir (nbppm)₂(acac)]) And (acetylacetonate) bis [ 5-methyl-6- (2-methylphenyl) -4-phenylpyrimidine]Iridium (III) (simply: Ir (mppm))₂(acac)), (acetylacetonate) bis (4, 6-diphenylpyrimidinate) iridium (III) (abbreviation: [ Ir (dppm)₂(acac)]) And the like organometallic iridium complexes having a pyrimidine skeleton; (Acetylacetonato) bis (3, 5-dimethyl-2-phenylpyrazinato) iridium (III) (abbreviation: [ Ir (mppr-Me)₂(acac)]) And (acetylacetonate) bis (5-isopropyl-3-methyl-2-phenylpyrazinato) iridium (III) (abbreviation: [ Ir (mppr-iPr)₂(acac)]) And the like organometallic iridium complexes having a pyrazine skeleton; tris (2-phenylpyridinato-N, C)²') Iridium (III) (abbreviation: [ Ir (ppy)₃]) Bis (2-phenylpyridinato-N, C)²') Iridium (III) acetylacetone (abbreviation: [ Ir (ppy)₂(acac)]) Bis (benzo [ h ]]Quinoline) iridium (III) acetylacetone (abbreviation: [ Ir (bzq)₂(acac)]) Tris (benzo [ h ]) or a salt thereof]Quinoline) iridium (III) (abbreviation: [ Ir (bzq)₃]) Tris (2-phenylquinoline-N, C)²']Iridium (III) (abbreviation: [ Ir (pq))₃]) Bis (2-phenylquinoline-N, C)²') Iridium (III) acetylacetone (abbreviation: [ Ir (pq)₂(acac)]) And the like organometallic iridium complexes having a pyridine skeleton; and tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: [ Tb (acac))₃(Phen)]) And the like. The above substances are mainly green phosphorescent emitting compounds and have a light emission peak at 500nm to 600 nm. Further, an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because of its particularly excellent reliability and light emission efficiency.

Further, there may be mentioned: (diisobutyl methanolate) bis [4, 6-bis (3-methylphenyl) pyrimidinyl]Iridium (III) (abbreviation: [ Ir (5mdppm)₂(dibm)]) Bis [4, 6-bis (3-methylphenyl) pyrimidino) (dipivaloylmethanato) iridium (III) (abbreviation: [ Ir (5 mddppm)₂(dpm)]) Bis [4, 6-di (naphthalen-1-yl) pyrimidinium radical](Dipivaloylmethanato) iridium (III) (abbreviation: [ Ir (d1npm)₂(dpm)]) And the like organometallic iridium complexes having a pyrimidine skeleton; (Acetylacetonato) bis (2,3, 5-triphenylpyrazinato) iridium (III) (Jane)Weighing: [ Ir (tppr)₂(acac)]) Bis (2,3, 5-triphenylpyrazinyl) (dipivaloylmethanyl) iridium (III) (abbreviation: [ Ir (tppr)₂(dpm)]) (acetylacetonate) bis [2, 3-bis (4-fluorophenyl) quinoxalinyl]Iridium (III) (abbreviation: [ Ir (Fdpq)₂(acac)]) And the like organometallic iridium complexes having a pyrazine skeleton; tris (1-phenylisoquinoline-N, C)^2’) Iridium (III) (abbreviation: [ Ir (piq)₃]) Bis (1-phenylisoquinoline-N, C)^2’) Iridium (III) acetylacetone (abbreviation: [ Ir (piq)₂(acac)]) And the like organometallic iridium complexes having a pyridine skeleton; platinum complexes such as 2,3,7,8,12,13,17, 18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviated as PtOEP); and tris (1, 3-diphenyl-1, 3-propanedione (panediatoo)) (monophenanthroline) europium (III) (abbreviation: [ Eu (DBM))₃(Phen)]) Tris [1- (2-thenoyl) -3,3, 3-trifluoroacetone](Monophenanthroline) europium (III) (abbreviation: [ Eu (TTA))₃(Phen)]) And the like. The above substance is a compound emitting red phosphorescence, and has a light emission peak at 600nm to 700 nm. In addition, the organometallic iridium complex having a pyrazine skeleton can obtain red light emission with good chromaticity.

In addition, a known phosphorescent substance may be used in addition to the above.

As TADF materials that can be used as guest materials for the light-emitting layer 113, the following materials can be mentioned, for example.

As the TADF material, fullerene and its derivative, acridine and its derivative, eosin derivative, and the like can be used. Examples of the metal-containing porphyrin include magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like. Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complexes (SnF) represented by the following structural formula₂(Proto IX)), mesoporphyrin-tin fluoride complex (SnF)₂(Meso IX)), hematoporphyrin-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)), protoporphyrin-tin fluoride complex (SnF)₂(Etio I)) and octaethylporphyrin-platinum chloride complex (PtCl)₂OEP), and the like.

[ chemical formula 24]

Further, 2- (biphenyl-4-yl) -4, 6-bis (12-phenylindole [2, 3-a ] carbazol-11-yl) -1,3, 5-triazine (abbreviated as PIC-TRZ), 9- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -9 ' -phenyl-9H, 9' H-3, 3' -bicarbazole (abbreviated as PCCZTzn), 2- {4- [3- (N-phenyl-9H-carbazol-3-yl) -9H-carbazol-9-yl ] phenyl } -4, 6-diphenyl-1, 3, 5-triazine (abbreviated as PCCZPTzn) represented by the following structural formula, 2- [4- (10H-phenoxazin-10-yl) phenyl ] -4, 6-diphenyl-1, 3, 5-triazine (abbreviation: PXZ-TRZ), 3- [4- (5-phenyl-5, 10-dihydrophenazine-10-yl) phenyl ] -4, 5-diphenyl-1, 2, 4-triazole (abbreviation: PPZ-3TPT), 3- (9, 9-dimethyl-9H-acridin-10-yl) -9H-xanthen-9-one (abbreviation: ACRXTN), bis [4- (9, 9-dimethyl-9, 10-dihydroacridin) phenyl ] sulfolane (abbreviation: DMAC-DPS), 10-phenyl-10H, 10 ' H-spiro [ acridine-9, 9' -anthracene ] -10 ' -one (ACRSA), 4- (9 ' -phenyl-3, 3' -bi-9H-carbazol-9-yl) benzofuro [3, 2-d ] pyrimidine (4 PCCzBfpm), 4- [4- (9 ' -phenyl-3, 3' -bi-9H-carbazol-9-yl) phenyl ] benzofuro [3, 2-d ] pyrimidine (4 PCCzPBfpm), 9- [3- (4, 6-diphenyl-1, 3, 5-triazine-2-yl) phenyl ] -9 ' -phenyl-2, 3' -bi-9H-carbazole (mPCzPTzn-02), and other heterocyclic compounds having an electron-rich heteroaromatic ring and an electron-deficient heteroaromatic ring .

[ chemical formula 25]

The heterocyclic compound has a pi-electron-rich heteroaromatic ring and a pi-electron-deficient heteroaromatic ring, and is preferably high in both electron-transporting property and hole-transporting property. In particular, among the skeletons having a pi-electron deficient heteroaromatic ring, a pyridine skeleton, a diazine skeleton (a pyrimidine skeleton, a pyrazine skeleton, a pyridazine skeleton) and a triazine skeleton are preferable because they are stable and have good reliability. In particular, a benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, or benzothienopyrazine skeleton is preferable because it has high electron-accepting properties and good reliability.

In addition, in the skeleton having a pi-electron-rich heteroaromatic ring, an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton are stable and have good reliability, and therefore, it is preferable to have at least one of the above-described skeletons. Further, a dibenzofuran skeleton is preferably used as the furan skeleton, and a dibenzothiophene skeleton is preferably used as the thiophene skeleton. As the pyrrole skeleton, an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarbazole skeleton, or a 3- (9-phenyl-9H-carbazol-3-yl) -9H-carbazole skeleton is particularly preferably used.

In addition, in the case where a pi-electron-rich aromatic heterocycle and a pi-electron-deficient aromatic heterocycle are directly bonded to each other, it is particularly preferable that the electron donating property and the electron accepting property of the pi-electron-rich aromatic heterocycle are both high and the energy difference between the S1 level and the T1 level is small, so that the thermally activated delayed fluorescence can be efficiently obtained. Note that instead of the pi-electron deficient aromatic heterocycle, an aromatic ring to which an electron withdrawing group such as a cyano group is bonded may be used. Further, as the pi-electron-rich skeleton, an aromatic amine skeleton, a phenazine skeleton, or the like can be used. As the pi-deficient electron skeleton, a xanthene skeleton, a thioxanthene dioxide (thioxanthene dioxide) skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, and the like can be used.

Thus, a pi-electron deficient backbone and a pi-electron rich backbone can be used in place of at least one of the pi-electron deficient heteroaromatic ring and the pi-electron rich heteroaromatic ring.

The TADF material is a material having a small difference between the S1 energy level and the T1 energy level and having a function of converting triplet excitation energy into singlet excitation energy by intersystem crossing. Therefore, it is possible to up-convert (up-convert) triplet excitation energy into singlet excitation energy (inter-inversion cross over) by a minute thermal energy and to efficiently generate a singlet excited state. Further, triplet excitation energy can be converted into light emission.

An Exciplex (exiplex) in which two species form an excited state has a function as a TADF material that converts triplet excitation energy into singlet excitation energy because the difference between the S1 energy level and the T1 energy level is extremely small.

Note that as an index of the T1 level, a phosphorescence spectrum observed at a low temperature (for example, 77K to 10K) may be used. With regard to the TADF material, it is preferable that, when the wavelength energy of the extrapolated line obtained by drawing a tangent at the tail on the short wavelength side of the fluorescence spectrum is the S1 level and the wavelength energy of the extrapolated line obtained by drawing a tangent at the tail on the short wavelength side of the phosphorescence spectrum is the T1 level, the difference between S1 and T1 is 0.3eV or less, more preferably 0.2eV or less.

Further, when a TADF material is used as the guest material of the light-emitting layer 113, the S1 level of the host material is preferably higher than the S1 level of the TADF material. Further, the T1 level of the host material is preferably higher than the T1 level of the TADF material.

As the hole transporting material which can be used as the host material of the light-emitting layer 113, it is preferable to use a hole transporting material having an electric field strength [ V/cm ]]Has a hole mobility of 1X 10 when the square root of (A) is 600^-6cm²Examples of the material having a value of Vs or more include the following.

There may be mentioned: 4,4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (abbreviated to NPB), N' -bis (3-methylphenyl) -N, N '-diphenyl- [1,1' -biphenyl ] -4,4 '-diamine (abbreviated to TPD), 4' -bis [ N- (spiro-9, 9 '-bifluoren-2-yl) -N-phenylamino ] biphenyl (abbreviated to BSPB), 4-phenyl-4' - (9-phenylfluoren-9-yl) triphenylamine (abbreviated to BPAFLP), 4-phenyl-3 '- (9-phenylfluoren-9-yl) triphenylamine (abbreviated to mBPAFLP), 4-phenyl-4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated to mBPAFLP) For short: PCBA1BP), 4' -diphenyl-4 "- (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBANB), 4' -bis (1-naphthyl) -4 "- (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBNBB), 9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -9,9' -spirobi [ 9H-fluorene ] -2-amine (abbreviation: PCBASF), and the like having an aromatic amine skeleton; compounds having a carbazole skeleton such as 1, 3-bis (N-carbazolyl) benzene (abbreviated as mCP), 4 '-bis (N-carbazolyl) biphenyl (abbreviated as CBP), 3, 6-bis (3, 5-diphenylphenyl) -9-phenylcarbazole (abbreviated as CzTP), 3' -bis (9-phenyl-9H-carbazole) (abbreviated as PCCP); compounds having a thiophene skeleton such as 4,4',4 "- (benzene-1, 3, 5-triyl) tris (dibenzothiophene) (abbreviated as DBT3P-II), 2, 8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl ] dibenzothiophene (abbreviated as DBTFLP-III), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl ] -6-phenyldibenzothiophene (abbreviated as DBTFLP-IV); and compounds having a furan skeleton such as 4,4' - (benzene-1, 3, 5-triyl) tris (dibenzofuran) (abbreviated as DBF3P-II) and 4- {3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl ] phenyl } dibenzofuran (abbreviated as mmDBFFLBi-II). Among them, a compound having an aromatic amine skeleton and a compound having a carbazole skeleton are preferable because they have good reliability and high hole-transporting property and contribute to reduction of driving voltage. In addition, organic compounds exemplified as the above organic compounds may also be used.

Further, as an electron transporting material which can be used as a host material of the light emitting layer 113, it is preferable to use a material having an electric field strength [ V/cm ]]Has an electron mobility of 1X 10 at a square root of 600^-6cm²Examples of the substance having an electron mobility equal to or higher than Vs include the following substances. In addition, an electron transporting material which can be used for the electron transporting layer 114 described later can be used.

Examples thereof include: bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (II) (abbreviation: BeBq₂) Bis (2-methyl-8-quinolinol) (4-phenylphenol) aluminum (III) (abbreviation: BAlq), bis (8-hydroxyquinoline) zinc (II) (abbreviation: znq), bis [2- (2-benzoxazolyl) phenol]Zinc (II) (ZnPBO for short), bis [2- (2-benzothiazolyl) phenol]Metal complexes such as zinc (II) (ZnBTZ for short); 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (abbreviated as PBD), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2, 4-triazole (abbreviated as TAZ), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl]Benzene (abbreviated as OXD-7), 9-[4- (5-phenyl-1, 3, 4-oxadiazol-2-yl) phenyl]-9H-carbazole (abbreviation: CO11), 2' - (1,3, 5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophen-4-yl) phenyl]Heterocyclic compounds having a polyazole skeleton such as-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II); 2- [3- (dibenzothiophen-4-yl) phenyl]Dibenzo [ f, h ]]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2- [3' - (dibenzothiophen-4-yl) biphenyl-3-yl]Dibenzo [ f, h ]]Quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3' - (9H-carbazol-9-yl) biphenyl-3-yl]Dibenzo [ f, h ]]Quinoxaline (abbreviation: 2mCZBPDBq), 4, 6-bis [3- (phenanthrene-9-yl) phenyl]Pyrimidine (abbreviation: 4,6mPnP2Pm), 4, 6-bis [3- (4-dibenzothienyl) phenyl]Heterocyclic compounds having a diazine skeleton such as pyrimidine (4, 6mDBTP2 Pm-II); and 3, 5-bis [3- (9H-carbazol-9-yl) phenyl]Pyridine (35 DCzPPy for short), 1,3, 5-tri [3- (3-pyridyl) -phenyl]And heterocyclic compounds having a pyridine skeleton such as benzene (abbreviated as TmPyPB). Among them, a heterocyclic compound having a diazine skeleton or a heterocyclic compound having a pyridine skeleton is preferable because it has good reliability. In particular, a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has a high electron-transporting property and also contributes to a reduction in driving voltage.

In the case where a TADF material is used as the host material of the light-emitting layer 113, the same materials as described above can be used. When the TADF material is used as the host material, triplet excitation energy generated from the TADF material is converted into singlet excitation energy through intersystem crossing and further energy is transferred to the luminescence center substance, whereby the light emission efficiency of the light-emitting device can be improved. At this time, the TADF material is used as an energy donor, and the luminescence center substance is used as an energy acceptor. Thus, in the case of using a fluorescent substance as a guest material, it is very effective to use a TADF material as a host material. In this case, in order to obtain high luminous efficiency, the TADF material preferably has a higher S1 level than the fluorescent luminescent material has a higher S1 level. Further, the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent substance. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent substance.

Further, a TADF material that exhibits luminescence overlapping with the wavelength of the absorption band on the lowest energy side of the fluorescent substance is preferably used. This is preferable because excitation energy is smoothly transferred from the TADF material to the fluorescent substance, and light emission can be efficiently obtained.

In order to efficiently generate singlet excitation energy from triplet excitation energy by intersystem crossing, it is preferable to generate carrier recombination in the TADF material. Further, it is preferable that the triplet excitation energy generated in the TADF material is not transferred to the fluorescent substance. Therefore, the fluorescent substance preferably has a protective group around a light emitter (skeleton that causes light emission) included in the fluorescent substance. The protecting group is preferably a substituent having no pi bond, preferably a saturated hydrocarbon, specifically, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a trialkylsilyl group having 3 to 10 carbon atoms, and more preferably, a plurality of protecting groups. The substituent having no pi bond has almost no function of transporting carriers, and therefore has almost no influence on carrier transport or carrier recombination, and can separate the TADF material and the light-emitting body of the fluorescent substance from each other. Here, the light-emitting substance refers to an atomic group (skeleton) that causes light emission in the fluorescent substance. The light emitter preferably has a backbone with pi bonds, preferably comprises aromatic rings, and preferably has a fused aromatic ring or a fused heteroaromatic ring. Examples of the fused aromatic ring or fused heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, and the like. In particular, a compound having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton,The fluorescent substance having a skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, naphtho-dibenzofuran skeleton is preferable because it has a high fluorescence quantum yield.

In the case where a fluorescent light-emitting substance is used as a guest material of the light-emitting layer 113, a material having an anthracene skeleton is preferably used as a host material. By using a substance having an anthracene skeleton, a light-emitting layer having excellent light-emitting efficiency and durability can be realized. A substance having a diphenylanthracene skeleton (particularly, a 9, 10-diphenylanthracene skeleton) is preferable because it is chemically stable.

In addition, in the case where the host material has a carbazole skeleton, injection/transport properties of holes are improved, and therefore, the host material is preferable, and in particular, in the case where the host material includes a benzocarbazole skeleton in which a benzene ring is fused to the carbazole skeleton, the HOMO level is shallower by about 0.1eV than the carbazole skeleton, and holes are easily injected, which is more preferable. In particular, when the host material has a dibenzocarbazole skeleton, the HOMO level is shallower by about 0.1eV than carbazole, and not only holes are easily injected, but also the hole-transporting property and heat resistance are improved, which is preferable.

Therefore, a substance having both a 9, 10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton) is more preferably used as the host material. Note that, from the viewpoint of improving the hole injection/transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Examples of such a substance include 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazole (abbreviated as PCzPA), 3- [4- (1-naphthyl) -phenyl ] -9-phenyl-9H-carbazole (abbreviated as PCPN), 9- [4- (10-phenylanthracen-9-yl) phenyl ] -9H-carbazole (abbreviated as CzPA), 7- [4- (10-phenyl-9-anthryl) phenyl ] -7H-dibenzo [ c, g ] carbazole (abbreviated as cgDBCzPA), 6- [3- (9, 10-diphenyl-2-anthryl) phenyl ] -benzo [ b ] naphtho [1,2-d ] furan (abbreviated as 2mBnfPPA), 9-phenyl-10- {4- (9-phenyl-9H-fluoren-9-yl) -biphenyl-4' -yl } -anthracene (abbreviated as FLPPA), 9- (1-naphthyl) -10- [4- (2-naphthyl) phenyl ] anthracene (abbreviated as. alpha.N-. beta.NPAnth), and the like. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferable because they exhibit very good characteristics.

The host material may be a mixture of a plurality of substances, and when a mixed host material is used, it is preferable to mix an electron-transporting material and a hole-transporting material. By mixing the electron-transporting material and the hole-transporting material, the transport property of the light-emitting layer 113 can be adjusted more easily, and the recombination region can be controlled more easily. The content ratio by weight of the hole-transporting material and the electron-transporting material may be 1:19 to 19: 1.

As described above, when the host material is a material in which a plurality of substances are mixed, a phosphorescent substance may be used as part of the mixed material. The phosphorescent substance may be used as an energy donor for supplying excitation energy to the fluorescent substance when the fluorescent substance is used as a luminescence center material.

In addition, an exciplex can be formed using a mixture of these materials. It is preferable to select a mixed material so as to form an exciplex that emits light with a wavelength overlapping with the wavelength of the absorption band on the lowest energy side of the light-emitting material, because energy transfer can be smoothly performed and light emission can be efficiently obtained. Further, this structure is preferable because the driving voltage can be reduced.

Note that at least one of the materials forming the exciplex may be a phosphorescent substance. This enables efficient conversion of triplet excitation energy into singlet excitation energy through intersystem crossing.

Regarding the combination of the materials forming the exciplex, the HOMO level of the hole-transporting material is preferably equal to or higher than the HOMO level of the electron-transporting material. The LUMO level of the hole-transporting material is preferably equal to or higher than the LUMO level of the electron-transporting material. Note that the LUMO level and the HOMO level of a material can be obtained from the electrochemical characteristics (reduction potential and oxidation potential) of the material measured by Cyclic Voltammetry (CV) measurement.

Note that the formation of the exciplex can be confirmed, for example, by the following method: when the emission spectra of the hole-transporting material, the electron-transporting material, and the mixed film formed by mixing these materials are compared, the formation of the exciplex is described when the phenomenon that the emission spectrum of the mixed film shifts to the longer wavelength side than the emission spectra of the respective materials (or has a new peak value on the longer wavelength side) is observed. Alternatively, when transient responses such as a transient Photoluminescence (PL) of a hole-transporting material, a transient PL of an electron-transporting material, and a mixed film formed by mixing these materials are different from each other, the formation of an exciplex is indicated when transient responses such as a transient PL lifetime of the mixed film having a longer lifetime component or a larger ratio of retardation components than the transient PL lifetime of each material are observed. Further, the above transient PL may be referred to as transient Electroluminescence (EL). In other words, the formation of the exciplex was confirmed by observing the difference in transient response as compared with the transient EL of the hole-transporting material, the transient EL of the electron-transporting material, and the transient EL of the mixed film of these materials.

< Electron transport layer >

The electron transport layer 114 is a layer that transports electrons injected from the second electrode 102 to the light emitting layer 113, and is in contact with the light emitting layer 113. The electron transport layer 114 contains an electron transport material having a HOMO level of-6.0 eV or more and an organic complex of an alkali metal or an alkaline earth metal. Further, as an electron transport material having a HOMO energy level of-6.0 eV or more, electric field intensity [ V/cm ]]The square root of (2) is preferably 1X 10^-7cm²1 × 10 at a ratio of Vs or more^-5cm²Less than Vs, more preferably 1X 10^-7cm²5 × 10 at a rate of more than Vs^-5cm²Vs or less.

The electron-transporting material having a HOMO level of-6.0 eV or more preferably has an anthracene skeleton, and more preferably has an anthracene skeleton or a heterocyclic skeleton. Therefore, the quinoxaline derivative according to one embodiment of the present invention is preferably used as an electron transporting material. In addition, a part of an electron-transporting material which can be used for the above-described host material and a substance exemplified as a material which can be used for the host material in combination with the above-described fluorescent substance can be used for the electron-transporting layer 114.

Furthermore, as the organic complex of an alkali metal or an alkaline earth metal, an organometallic complex of lithium is preferably used, and lithium 8-quinolinolato (abbreviated as Liq) is particularly preferred.

Further, it is preferable that the electron mobility of the electron transporting material having the HOMO level of-6.0 eV or more for the electron transporting layer 114 (the electron mobility when the square root of the electric field strength [ V/cm ] is 600) is lower than the electron mobility of the host material for the light emitting layer 113. The injection amount of electrons into the light-emitting layer can be controlled by reducing the electron transport property in the electron transport layer, and thereby the light-emitting layer can be prevented from being in an electron-rich state.

< Electron injection layer >

The electron injection layer 115 is a layer for improving the efficiency of electron injection from the second electrode 102 of the cathode, and it is preferable to use a material in which the difference between the value of the work function of the material of the second electrode 102 and the value of the LUMO level of the material for the electron injection layer 115 is small (0.5eV or less). Therefore, as the electron injection layer 115, lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF) can be used₂) And 8- (hydroxyquinoxaline) lithium (abbreviation: liq), lithium 2- (2-pyridyl) phenoxide (abbreviation: LiPP), 2- (2-pyridyl) -3-hydroxypyridinium (abbreviation: LiPPy), lithium 4-phenyl-2- (2-pyridyl) phenoxide (abbreviation: LiPPP), lithium oxide (LiO)_x) And alkali metals, alkaline earth metals, or compounds thereof such as cesium carbonate. In addition, erbium fluoride (ErF) may be used₃) And the like.

Further, as in the light-emitting device shown in fig. 1B, by providing the charge generation layer 104 between the two EL layers (103a and 103B), a structure in which a plurality of EL layers are stacked between a pair of electrodes (also referred to as a series structure) can be provided. Note that in this embodiment mode, the functions and materials of the hole injection layer (111), the hole transport layer (112), the light-emitting layer (113), the electron transport layer (114), and the electron injection layer (115) described in fig. 1A are the same as those of the hole injection layer (111A, 111B), the hole transport layer (112a, 112B), the light-emitting layer (113a, 113B), the electron transport layer (114a, 114B), and the electron injection layer (115a, 115B) described in fig. 1B.

< Charge generation layer >

In the light-emitting device shown in fig. 1B, the charge generation layer 104 has the following functions: when a voltage is applied between the first electrode 101 (anode) and the second electrode 102 (cathode), electrons are injected into the EL layer 103a and holes are injected into the EL layer 103 b. The charge generation layer 104 may have a structure in which an electron acceptor (acceptor) is added to a hole-transporting material (P-type layer) or a structure in which an electron donor (donor) is added to an electron-transporting material (N-type layer). Alternatively, these two structures may be stacked. In addition, the P-type layer may be combined with one or both of an electron relay layer and an electron buffer layer, which will be described later. Further, by forming the charge generation layer 104 using the above-described material, an increase in driving voltage at the time of stacking the EL layers can be suppressed.

When the charge generation layer 104 has a structure in which an electron acceptor is added to a hole-transporting material (P-type layer), the materials described in this embodiment mode can be used as the hole-transporting material. Further, as the electron acceptor, 7,8, 8-tetracyano-2, 3,5, 6-tetrafluoroquinodimethane (abbreviated as F)₄-TCNQ), chloranil, and the like. Further, oxides of metals belonging to groups 4 to 8 of the periodic table may be mentioned. Specific examples thereof include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.

In the case where the charge generation layer 104 has a structure in which an electron donor is added to an electron transporting material (N-type layer), the materials described in this embodiment mode can be used as the electron transporting material. Further, as the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to group 2 or group 13 of the periodic table of the elements, and an oxide or a carbonate thereof can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, and the like are preferably used. Further, an organic compound such as tetrathianaphtalene (tetrathianaphtalene) may also be used as the electron donor.

The above-described electron relay layer, preferably in combination with the P-type layer, is provided between the electron injection buffer layer and the P-type layer, thereby serving to prevent the interaction of the electron injection buffer layer and the P-type layer and to smoothly transfer electrons. Further, the electron relay layer preferably contains an electron transporting material, and the LUMO level of the electron transporting material contained in the electron relay layer is preferably set between the LUMO level of the electron accepting substance in the P-type layer and the LUMO level of the substance contained in the electron buffer layer. Specifically, the LUMO level of the electron transporting material in the electron relay layer is preferably-5.0 eV or more, and more preferably-5.0 eV or more and-3.0 eV or less. Further, as the electron transporting material in the electron relay layer, a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand is preferably used.

The electron injection buffer layer can be formed using a substance having a high electron injection property, such as an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a halide, a carbonate such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide, or a carbonate), or a compound of a rare earth metal (including an oxide, a halide, or a carbonate)).

In addition, when the electron injection buffer layer contains an electron transporting material and an electron donor substance, an organic compound such as tetrathianaphthacene (TTN), nickelocene, decamethylnickelocene, or the like can be used as the electron donor substance in addition to an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a carbonate such as lithium carbonate, cesium carbonate, or the like), an alkaline earth metal compound (including an oxide, a halide, a carbonate, or a compound of a rare earth metal (including an oxide, a halide, and a carbonate)). Further, as the electron transporting material, the same material as that for the electron transporting layer 114 described above can be used.

Although fig. 1B shows a structure in which two EL layers 103 are stacked, it is possible to make a stacked structure of three or more by providing a charge generation layer between different EL layers.

In addition, the above-described charge generation layer may be used instead of the above-described electron injection layer. In this case, it is preferable that the electron injection buffer layer, the electron relay layer, and the P-type layer are stacked in this order from the anode side.

< substrate >

The light-emitting device shown in this embodiment mode can be formed over various substrates. Note that there is no particular limitation on the kind of the substrate. Examples of the substrate include a semiconductor substrate (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate including a stainless steel foil, a tungsten substrate, a substrate including a tungsten foil, a flexible substrate, a bonding film, a paper film including a fibrous material, a base film, and the like.

Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, and soda lime glass. Examples of the flexible substrate, the adhesive film, and the base film include plastics typified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyether sulfone (PES), synthetic resins such as acrylic resins, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid resins, epoxy resins, inorganic vapor-deposited films, and paper.

In the case of manufacturing the light-emitting device described in this embodiment mode, a vacuum process such as a vapor deposition method or a solution process such as a spin coating method or an ink jet method can be used. As the vapor deposition method, a physical vapor deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam vapor deposition method, a molecular beam vapor deposition method, or a vacuum vapor deposition method, a chemical vapor deposition method (CVD method), or the like can be used. In particular, the functional layer (the hole injection layer (111, 111a, 111b), the hole transport layer (112, 112a, 112b), the light emitting layer (113, 113a, 113b, 113c), the electron transport layer (114, 114a, 114b), the electron injection layer (115, 115a, 115b), and the charge generation layer (104, 104a, 104b)) included in the EL layer of the light emitting device can be formed by a method such as a vapor deposition method (vacuum vapor deposition method), a coating method (dip coating method, dye coating method, bar coating method, spin coating method, spray coating method), a printing method (an ink jet method, screen printing (stencil printing) method, offset printing (lithography printing) method, flexography (relief printing) method, gravure printing method, microcontact printing method, nanoimprint method), or the like.

The materials of the functional layers (the hole injection layers (111, 111a, 111b), the hole transport layers (112, 112a, 112b), the light emitting layers (113, 113a, 113b, 113c), the electron transport layers (114, 114a, 114b), the electron injection layers (115, 115a, 115b), and the charge generation layers (104, 104a, 104b)) constituting the EL layers (103, 103a, 103b) of the light emitting device shown in this embodiment mode are not limited to these materials, and any materials may be used in combination as long as they can satisfy the functions of the respective layers. As an example, a high molecular compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (compound between low and high molecules: molecular weight 400 to 4000), an inorganic compound (quantum dot material, etc.), or the like can be used. As the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core-shell type quantum dot material, a core type quantum dot material, or the like can be used.

The light-emitting device used for the light-emitting apparatus of one embodiment of the present invention having the structure as described above may be a long-life light-emitting device.

The structure described in this embodiment can be used in combination with the structures described in the other embodiments as appropriate.

(embodiment mode 3)

In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light-emitting device shown in fig. 2A is an active matrix light-emitting device in which a transistor (FET)202 and light-emitting devices (203R, 203G, 203B, and 203W) are electrically connected to each other over a first substrate 201, and has a microcavity structure in which an EL layer 204 is used in common for a plurality of light-emitting devices (203R, 203G, 203B, and 203W) and an optical distance between electrodes of each light-emitting device is adjusted in accordance with a light emission color of each light-emitting device. Further, a top emission type light-emitting device is employed in which light obtained from the EL layer 204 is emitted through color filters (206R, 206G, 206B) formed on the second substrate 205.

In the light-emitting device shown in fig. 2A, the first electrode 207 is used as a reflective electrode, and the second electrode 208 is used as a transflective electrode having both transparency and reflectivity to light (visible light or near-infrared light). As an electrode material for forming the first electrode 207 and the second electrode 208, any electrode material can be used as appropriate with reference to other embodiments.

Further, in fig. 2A, for example, in the case where the light emitting devices 203R, 203G, 203B, 203W are respectively a red light emitting device, a green light emitting device, a blue light emitting device, a white light emitting device, as shown in fig. 2B, the distance between the first electrode 207 and the second electrode 208 in the light emitting device 203R is adjusted to the optical distance 200R, the distance between the first electrode 207 and the second electrode 208 in the light emitting device 203G is adjusted to the optical distance 200G, and the distance between the first electrode 207 and the second electrode 208 in the light emitting device 203B is adjusted to the optical distance 200B. Further, as shown in fig. 2B, optical adjustment can be performed by laminating the conductive layer 210R on the first electrode 207 in the light emitting device 203R and the conductive layer 210G on the first electrode 207 in the light emitting device 203G.

Color filters (206R, 206G, 206B) are formed on the second substrate 205. The color filter transmits visible light in a specific wavelength range and blocks visible light in the specific wavelength range. Therefore, as shown in fig. 2A, by providing a color filter 206R that transmits only light in the red wavelength range at a position overlapping with the light-emitting device 203R, red light can be obtained from the light-emitting device 203R. Further, by providing the color filter 206G which transmits only light in the green wavelength range at a position overlapping with the light emitting device 203G, green light can be obtained from the light emitting device 203G. Further, by providing the color filter 206B which transmits only light in the blue wavelength range at a position overlapping with the light-emitting device 203B, blue light can be obtained from the light-emitting device 203B. However, white light can be obtained from the light emitting device 203W without providing a filter. Further, a black layer (black matrix) 209 may be provided at an end portion of each color filter. The color filters (206R, 206G, 206B) or the black layer 209 may be covered with a protective layer made of a transparent material.

Although the light-emitting device of the structure (top emission type) in which light is extracted on the second substrate 205 side is shown in fig. 2A, a light-emitting device of the structure (bottom emission type) in which light is extracted on the first substrate 201 side where the FET202 is formed as shown in fig. 2C may be employed. In the bottom emission type light emitting device, the first electrode 207 is used as a semi-transmissive-semi-reflective electrode, and the second electrode 208 is used as a reflective electrode. As the first substrate 201, at least a substrate having a light-transmitting property is used. As shown in fig. 2C, the color filters (206R ', 206G ', 206B ') may be provided on the side closer to the first substrate 201 than the light-emitting devices (203R, 203G, 203B).

In fig. 2A, the light-emitting device is illustrated as a red light-emitting device, a green light-emitting device, a blue light-emitting device, or a white light-emitting device, but the light-emitting device according to one embodiment of the present invention is not limited to this structure, and a yellow light-emitting device or an orange light-emitting device may be used. As a material for manufacturing an EL layer (a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a charge generation layer, or the like) of these light-emitting devices, it can be used as appropriate with reference to other embodiments. In this case, it is necessary to appropriately select the color filter according to the emission color of the light emitting device.

By adopting the above configuration, a light-emitting device including a light-emitting device that emits light of a plurality of colors can be obtained.

The structure described in this embodiment can be used in combination with the structures described in the other embodiments as appropriate.

(embodiment mode 4)

In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

By using the light-emitting device according to one embodiment of the present invention, an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured. In addition, the active matrix light-emitting device has a structure in which a light-emitting device and a transistor (FET) are combined. Thus, both the passive matrix light-emitting device and the active matrix light-emitting device are included in one embodiment of the present invention. Further, the light-emitting device shown in other embodiments can be applied to the light-emitting apparatus shown in this embodiment.

In this embodiment, an active matrix light-emitting device will be described with reference to fig. 3A and 3B.

Fig. 3A is a plan view of the light emitting device, and fig. 3B is a sectional view cut along a chain line a-a' in fig. 3A. An active matrix light-emitting device includes a pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate line driver circuit) (304a and 304b) provided over a first substrate 301. The pixel portion 302 and the driver circuit portions (303, 304a, 304b) are sealed between the first substrate 301 and the second substrate 306 with a sealant 305.

A lead 307 is provided over the first substrate 301. The lead wire 307 is electrically connected to an FPC308 as an external input terminal. The FPC308 is used to transmit signals (for example, video signals, clock signals, start signals, reset signals, or the like) or potentials from the outside to the driver circuit portions (303, 304a, 304 b). In addition, the FPC308 may be mounted with a Printed Wiring Board (PWB). The state in which these FPC and PWB are mounted may be included in the category of the light-emitting device.

Fig. 3B shows a cross-sectional structure.

The pixel portion 302 is configured by a plurality of pixels each having an FET (switching FET)311, an FET (current control FET)312, and a first electrode 313 electrically connected to the FET 312. The number of FETs provided in each pixel is not particularly limited, and may be appropriately set as necessary.

The FETs 309, 310, 311, and 312 are not particularly limited, and for example, staggered transistors or inversely staggered transistors may be used. Further, a transistor structure of a top gate type, a bottom gate type, or the like may be employed.

Further, the crystallinity of a semiconductor which can be used for the FETs 309, 310, 311, and 312 is not particularly limited, and any of an amorphous semiconductor and a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor a part of which has a crystalline region) can be used. The use of a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed.

As the semiconductor, for example, a group 14 element, a compound semiconductor, an oxide semiconductor, an organic semiconductor, or the like can be used. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, or the like can be used.

The driver circuit portion 303 includes FETs 309 and 310. The driver circuit portion 303 may be formed of a circuit including a transistor having a single polarity (either of N-type and P-type), or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. Further, a configuration having a driving circuit outside may be employed.

The end of the first electrode 313 is covered with an insulator 314. As the insulator 314, an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin) or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride can be used. The upper or lower end of the insulator 314 preferably has a curved surface with curvature. This makes it possible to provide a film formed on the insulator 314 with good coverage.

An EL layer 315 and a second electrode 316 are stacked over the first electrode 313. The EL layer 315 includes a light-emitting layer, a hole-injecting layer, a hole-transporting layer, an electron-injecting layer, a charge-generating layer, and the like.

As the structure of the light-emitting device 317 described in this embodiment mode, structures or materials described in other embodiment modes can be applied. Although not shown here, the second electrode 316 is electrically connected to the FPC308 serving as an external input terminal.

Although only one light emitting device 317 is illustrated in the cross-sectional view illustrated in fig. 3B, a plurality of light emitting devices are arranged in a matrix in the pixel portion 302. By selectively forming light-emitting devices capable of emitting light of three (R, G, B) colors in the pixel portion 302, a light-emitting device capable of full-color display can be formed. In addition to the light-emitting device capable of obtaining light emission of three colors (R, G, B), for example, a light-emitting device capable of obtaining light emission of colors such as white (W), yellow (Y), magenta (M), and cyan (C) may be formed. For example, by adding a light-emitting device capable of obtaining the above-described plurality of types of light emission to a light-emitting device capable of obtaining light emission of three (R, G, B) colors, effects such as improvement in color purity and reduction in power consumption can be obtained. Further, a light-emitting device capable of full-color display may be realized by combining with a color filter. As the type of the color filter, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), or the like can be used.

By attaching the second substrate 306 to the first substrate 301 using the sealant 305, the FETs (309, 310, 311, 312) and the light emitting device 317 over the first substrate 301 are located in a space 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305. In addition, the space 318 may be filled with an inert gas (e.g., nitrogen, argon, or the like) or may be filled with an organic substance (including the sealant 305).

Epoxy or glass frit may be used as the sealant 305. As the sealing agent 305, a material which does not transmit moisture or oxygen as much as possible is preferably used. In addition, the same material as that of the first substrate 301 can be used for the second substrate 306. Thus, various substrates shown in other embodiments can be used. As the substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, or the like can be used in addition to a glass substrate and a quartz substrate. In the case where glass frit is used as a sealant, a glass substrate is preferably used for the first substrate 301 and the second substrate 306 in view of adhesiveness.

As described above, an active matrix light-emitting device can be obtained.

In the case of forming an active matrix light-emitting device over a flexible substrate, the FET and the light-emitting device may be formed directly over the flexible substrate, or the FET and the light-emitting device may be formed over another substrate having a release layer, and then the FET and the light-emitting device may be separated from each other by applying heat, force, laser irradiation, or the like to the release layer and then transferred to the flexible substrate. The release layer may be, for example, a laminate of an inorganic film such as a tungsten film and a silicon oxide film, or an organic resin film such as polyimide. In addition to a substrate in which a transistor can be formed, examples of the flexible substrate include a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a cloth substrate (including natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester), regenerated fibers (acetate fibers, cuprammonium fibers, rayon, regenerated polyester), and the like), a leather substrate, a rubber substrate, and the like. By using such a substrate, it is possible to realize excellent resistance and heat resistance, and to reduce the weight and thickness of the substrate.

In driving a light-emitting device included in an active matrix light-emitting device, the light-emitting device can emit light in a pulse form (for example, using a frequency such as kHz or MHz) and use the light for display. The light emitting device formed using the above organic compound has excellent frequency characteristics, and can reduce the driving time of the light emitting device to reduce power consumption. Further, heat generation due to the shortening of the driving time is suppressed, whereby deterioration of the light emitting device can be reduced.

The structure described in this embodiment can be used in combination with the structures described in the other embodiments as appropriate.

(embodiment 5)

In this embodiment, examples of various electronic devices and automobiles each using the light-emitting device according to one embodiment of the present invention or the light-emitting device including the light-emitting device according to one embodiment of the present invention will be described. Note that the light-emitting device can be mainly used for the display portion in the electronic apparatus described in this embodiment mode.

The electronic apparatus shown in fig. 4A to 4E may include a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), connection terminals 7006, a sensor 7007 (having a function of measuring a force, a displacement, a position, a velocity, an acceleration, an angular velocity, a rotational speed, a distance, light, liquid, magnetism, a temperature, a chemical substance, sound, time, hardness, an electric field, current, voltage, electric power, radiation, a flow rate, humidity, inclination, vibration, odor, or infrared ray), a microphone 7008, and the like.

Fig. 4A shows a mobile computer which may include a switch 7009, an infrared port 7010, and the like, in addition to those described above.

Fig. 4B shows a portable image reproducing apparatus (for example, a DVD reproducing apparatus) provided with a recording medium, which can include the second display portion 7002, the recording medium reading portion 7011, and the like in addition to the above.

Fig. 4C shows a digital camera having a television receiving function, which can include an antenna 7014, a shutter button 7015, an image receiving portion 7016, and the like in addition to the above.

Fig. 4D shows a portable information terminal. The portable information terminal has a function of displaying information on three or more surfaces of the display portion 7001. Here, an example is shown in which the information 7052, the information 7053, and the information 7054 are displayed on different surfaces. For example, in a state where the portable information terminal is placed in a jacket pocket, the user can confirm the information 7053 displayed at a position viewed from above the portable information terminal. The user can confirm the display without taking out the portable information terminal from the pocket and can judge whether to answer the call.

Fig. 4E shows a portable information terminal (including a smartphone), which can include a display portion 7001, operation keys 7005, and the like in a housing 7000. The portable information terminal may be provided with a speaker 7003, a connection terminal 7006, a sensor 7007, and the like. Further, the portable information terminal can display text or image information on a plurality of faces thereof. Here, an example in which three icons 7050 are displayed is shown. Further, information 7051 indicated by a dotted rectangle may be displayed on the other surface of the display portion 7001. Examples of the information 7051 include information for prompting reception of an email, SNS (Social Networking Services), a telephone, or the like; titles of e-mails or SNS, etc.; a sender name of an email, SNS, or the like; a date; time; the remaining amount of the battery; and antenna received signal strength, etc. Alternatively, an icon 7050 or the like may be displayed at a position where the information 7051 is displayed.

Fig. 4F is a large-sized television device (also referred to as a television or a television receiver), and may include a housing 7000, a display portion 7001, and the like. Further, the structure of the housing 7000 supported by the stand 7018 is shown here. Further, the television apparatus can be operated by using a remote controller 7111 or the like which is separately provided. The display portion 7001 may be provided with a touch sensor, and the display portion 7001 may be touched with a finger or the like to be operated. The remote controller 7111 may include a display unit for displaying data output from the remote controller 7111. By using an operation key or a touch panel provided in the remote controller 7111, a channel and a volume can be operated, and an image displayed on the display portion 7001 can be operated.

The electronic devices shown in fig. 4A to 4F may have various functions. For example, the following functions may be provided: a function of displaying various information (still image, moving image, character image, and the like) on the display unit; a touch panel function; a function of displaying a calendar, date, time, or the like; a function of controlling processing by using various software (programs); a wireless communication function; a function of connecting to various computer networks by using a wireless communication function; a function of transmitting or receiving various data by using a wireless communication function; a function of reading out a program or data stored in a recording medium and displaying the program or data on a display unit. Further, an electronic apparatus including a plurality of display portions may have a function of mainly displaying image information on one display portion and mainly displaying text information on another display portion, a function of displaying a three-dimensional image by displaying an image in consideration of parallax on a plurality of display portions, or the like. Further, the electronic device having the image receiving unit may have the following functions: a function of shooting a still image; a function of shooting a moving image; a function of automatically or manually correcting the captured image; a function of storing a captured image in a recording medium (external or built-in camera); a function of displaying the captured image on a display unit, and the like. Note that the functions that the electronic apparatuses shown in fig. 4A to 4F may have are not limited to the above-described functions, but may have various functions.

Fig. 4G is a wristwatch-type portable information terminal that can be used as a smart watch, for example. The wristwatch-type portable information terminal includes a housing 7000, a display portion 7001, operation buttons 7022, 7023, a connection terminal 7024, a band 7025, a microphone 7026, a sensor 7029, a speaker 7030, and the like. Since the display surface of the display portion 7001 is curved, display can be performed along the curved display surface. Further, the wristwatch-type portable information terminal can perform a handsfree call by communicating with a headset that can perform wireless communication, for example. In addition, data transmission or charging with another information terminal can be performed by using the connection terminal 7024. Charging may also be by wireless power.

The display portion 7001 mounted in the housing 7000 also serving as a frame (bezel) portion has a display region having a non-rectangular shape. The display unit 7001 can display an icon indicating time, other icons, and the like. The display portion 7001 may be a touch panel (input/output device) to which a touch sensor (input device) is attached.

The smart watch shown in fig. 4G may have various functions. For example, the following functions may be provided: a function of displaying various information (still image, moving image, character image, and the like) on the display unit; a touch panel function; a function of displaying a calendar, date, time, or the like; a function of controlling processing by using various software (programs); a wireless communication function; a function of connecting to various computer networks by using a wireless communication function; a function of transmitting or receiving various data by using a wireless communication function; a function of reading out a program or data stored in a recording medium and displaying the program or data on a display unit.

The interior of the housing 7000 may be provided with a speaker, a sensor (having a function of measuring a force, a displacement, a position, a velocity, an acceleration, an angular velocity, a rotational speed, a distance, light, liquid, magnetism, temperature, a chemical substance, sound, time, hardness, an electric field, current, voltage, electric power, radiation, flow, humidity, inclination, vibration, smell, or infrared ray), a microphone, or the like.

The light-emitting device according to one embodiment of the present invention can be used for each display portion of the electronic device described in this embodiment, whereby a long-life electronic device can be realized.

As an electronic device using a light-emitting device, a foldable portable information terminal shown in fig. 5A to 5C can be given. Fig. 5A shows the portable information terminal 9310 in an expanded state. Fig. 5B shows the portable information terminal 9310 in the middle of changing from one state to the other state of the expanded state and the folded state. Fig. 5C shows a portable information terminal 9310 in a folded state. The portable information terminal 9310 has good portability in the folded state and has a large display area seamlessly connected in the unfolded state, so that it has a high display list.

The display portion 9311 is supported by three housings 9315 connected by hinge portions 9313. The display portion 9311 may be a touch panel (input/output device) to which a touch sensor (input device) is attached. Further, the display portion 9311 can be reversibly changed from the folded state to the unfolded state of the portable information terminal 9310 by folding the two housings 9315 with the hinge portions 9313. A light-emitting device according to one embodiment of the present invention can be used for the display portion 9311. Further, a long-life electronic apparatus can be realized. The display region 9312 in the display portion 9311 is a display region located on the side of the portable information terminal 9310 in a folded state. An information icon, a shortcut of an application or program that is frequently used, or the like can be displayed in the display region 9312, and information can be confirmed or the application can be started smoothly.

Fig. 6A and 6B show an automobile using a light-emitting device. That is, the light emitting device may be formed integrally with the automobile. Specifically, the present invention can be applied to a lamp 5101 (including a rear body portion) on the outer side of the automobile shown in fig. 6A, a hub 5102 of a tire, a part or the whole of a door 5103, and the like. The present invention can be applied to a display portion 5104, a steering wheel 5105, a shift lever 5106, a seat 5107, an interior mirror 5108, a windshield 5109, and the like on the inside of the automobile shown in fig. 6B. In addition to this, it can also be used for a part of a glazing.

As described above, an electronic device or an automobile using the light-emitting device of one embodiment of the present invention can be obtained. In this case, a long-life electronic apparatus can be realized. The electronic device or the automobile that can be used is not limited to the electronic device or the automobile described in this embodiment, and can be applied to various fields.

Note that the structure described in this embodiment can be used in appropriate combination with the structures described in other embodiments.

(embodiment mode 6)

In this embodiment, a structure of an illumination device manufactured by applying a light-emitting device according to one embodiment of the present invention or a part of a light-emitting device thereof will be described with reference to fig. 7A and 7B.

Fig. 7A and 7B show examples of cross-sectional views of the illumination device. Fig. 7A is a bottom emission type lighting device extracting light on the substrate side, and fig. 7B is a top emission type lighting device extracting light on the sealing substrate side.

The lighting apparatus 4000 illustrated in fig. 7A includes a light-emitting device 4002 over a substrate 4001. Further, the lighting device 4000 includes a substrate 4003 having irregularities on the outer side of the substrate 4001. The light-emitting device 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. Further, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. Further, an insulating layer 4010 is formed over the auxiliary wiring 4009.

The substrate 4001 and the sealing substrate 4011 are bonded by a sealant 4012. Further, a drying agent 4013 is preferably provided between the sealing substrate 4011 and the light-emitting device 4002. Since the substrate 4003 has irregularities as shown in fig. 7A, the extraction efficiency of light generated in the light-emitting device 4002 can be improved.

The lighting device 4200 illustrated in fig. 7B includes a light emitting device 4202 on a substrate 4201. The light emitting device 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.

The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. In addition, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided under the auxiliary wiring 4209.

The substrate 4201 and the sealing substrate 4211 having the concave and convex are bonded by a sealant 4212. Further, a barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light-emitting device 4202. Since the sealing substrate 4211 has irregularities as shown in fig. 7B, the extraction efficiency of light generated in the light emitting device 4202 can be improved.

An example of an application of the lighting device is a ceiling lamp for indoor lighting. As the ceiling spotlight, there are a ceiling-mounted type lamp, a ceiling-embedded type lamp, and the like. Such lighting means may be constituted by a combination of light emitting means and a housing or cover.

In addition, the present invention can be applied to a footlight that can illuminate the ground to improve safety. For example, the footlight can be effectively used in bedrooms, stairs, passageways, and the like. In this case, the size or shape of the room may be appropriately changed according to the size or structure thereof. Further, the light emitting device and the support base may be combined to constitute a mounting type lighting device.

Further, the present invention can also be applied to a film-like lighting device (sheet lighting). Since the sheet lighting is used by being attached to a wall, it can be applied to various uses in a space-saving manner. In addition, a large area can be easily realized. In addition, it can also be attached to a wall or housing having a curved surface.

By using the light-emitting device according to one embodiment of the present invention or a part of the light-emitting device thereof in a part of indoor furniture other than the above, a lighting device having a function of furniture can be provided.

As described above, various lighting devices using the light-emitting device can be obtained. Further, such a lighting device is included in one embodiment of the present invention.

The structure described in this embodiment can be implemented in appropriate combination with the structures described in the other embodiments.

[ example 1]

< Synthesis example 1>

In this example, a method for synthesizing 2-phenyl-3- {4- [10- (3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviated as PyA1PQ), which is an organic compound according to one embodiment of the present invention represented by the structural formula (100) of embodiment 1, will be described. The structure of PyA1PQ is shown below.

[ chemical formula 26]

In a 50mL three-necked flask, 0.74g (2.2mmol) of 3- (10-bromo-9-anthryl) pyridine, 0.26g (0.85mmol) of tri (o-tolyl) phosphine, 0.73g (2.3mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 1.3g (9.0mmol) of an aqueous potassium carbonate solution, 40mL of ethylene glycol dimethyl ether (DME), and 4.4mL of water were placed. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen.

To the mixture in the flask was added 65mg (0.29mmol) of palladium (II) acetate, and the mixture was stirred at 80 ℃ for 11 hours under a nitrogen stream. After stirring, water was added to the mixture in the flask, and extraction was performed using toluene. The obtained extract solution was washed with saturated brine and dried over magnesium sulfate. It was gravity filtered and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography using chloroform and toluene: purify twice with 5:1 and recrystallize from toluene/hexanes. 0.43g of the objective product was obtained as a yellow solid in a yield of 36%. The following shows the synthetic route (a-1).

[ chemical formula 27]

The obtained yellow solid 0.44g was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, the reaction mixture was heated at 260 ℃ for 18 hours under a pressure of 10Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.35g of the objective yellow solid was obtained in a recovery rate of 79%.

The nuclear magnetic resonance spectroscopy of the yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 8 shows¹H-NMR spectrum. From the results, in this example, PyA1PQ, which is an organic compound according to one embodiment of the present invention represented by the structural formula (100), was obtained.

¹H NMR(CDCl3，300MHz)：δ＝7.37-7.50(m，9H)、7.56-7.78(m，9H)、7.82-7.86(m，3H)、8.24-8.30(m，2H)、8.75(dd，J＝1.8Hz，0.9Hz，1H)、8.84(dd，J＝4.8Hz，1.8Hz，1H)。

< physical Properties of PyA1PQ >)

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PyA1PQ were measured.

The absorption spectrum of the PyA1PQ toluene solution was measured using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the toluene solution of PyA1PQ was measured by a fluorescence spectrometer (FS 920, manufactured by hamamatsu photonics corporation). Note that the absorption spectrum of the toluene solution of PyA1PQ was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish. Fig. 9 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution of PyA1 PQ. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 9, the toluene solution of PyA1PQ showed absorption peaks at around 397nm, 376nm and 358nm, and a peak of luminescence wavelength at around 446nm (excitation wavelength 397 nm).

Further, a solid thin film of PyA1PQ was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum of the PyA1PQ solid film was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the solid thin film of PyA1PQ was measured using a fluorescence spectrometer (FS 920, manufactured by hamamatsu photonics corporation). Note that the absorption spectrum of the solid thin film of PyA1PQ was calculated by subtracting the absorption spectrum of the quartz substrate. Fig. 10 shows the measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film of PyA1 PQ. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 10, the solid thin film of PyA1PQ exhibited absorption peaks at around 404nm, 382nm, and 363nm and an emission peak at around 457nm (excitation wavelength of 394 nm).

Further, it was confirmed that PyA1PQ emits blue light. An organic compound according to one embodiment of the present invention, PyA1PQ, can be used as a host for a luminescent substance or a fluorescent luminescent substance in a visible region.

The HOMO level and LUMO level of PyA1PQ can then be calculated by Cyclic Voltammetry (CV). The calculation method is explained below. As the measuring device, an electrochemical analyzer (ALS model 600A or 600C manufactured by BAS corporation) was used. The solution for CV measurement was prepared as follows: as a solvent, dehydrated Dimethylformamide (DMF) (99.8% manufactured by Aldrich, Ltd., catalog number: 22705-6) was used, and tetra-n-butylammonium perchlorate (n-Bu) as a supporting electrolyte was used₄NClO₄) (manufactured by Tokyo Chemical Industry co., Ltd.) catalog No.: t0836) was dissolved at a concentration of 100mmol/L, and the measurement object was dissolved at a concentration of 2mmol/L to prepare a solution.

A platinum electrode (manufactured by BAS Inc., PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Inc., VC-3 Pt counter electrode (5cm)) was used as the auxiliary electrode, and Ag/Ag was used as the reference electrode⁺An electrode (RE 7 non-aqueous solution type reference electrode manufactured by BAS corporation). Note that the measurement was performed at room temperature (20 ℃ or higher and 25 ℃ or lower).

At this time, the scanning speed during CV measurement was set to 0.1V/sec, and the oxidation potential Ea [ V ] and the reduction potential Ec [ V ] were measured with respect to the reference electrode, respectively. Furthermore, Ea is the intermediate potential between the oxidation-reduction waves, and Ec is the intermediate potential between the reduction-oxidation waves. Since the potential of the reference electrode used in this example was-4.94 [ eV ] with respect to the vacuum level, the HOMO level [ eV ] (-4.94-Ea) and the LUMO level [ eV ] (-4.94-Ec) were calculated.

As a result, the HOMO level and LUMO level of PyA1PQ were-5.91 eV and-3.00 eV, respectively.

[ example 2]

In this embodiment, an element structure, a manufacturing method, and characteristics of a light emitting device are described as follows: as a light-emitting device of one embodiment of the present invention, 2-phenyl-3- {4- [10- (3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviation: PyA1PQ) (structural formula (100)) shown in example 1 was used for the light-emitting device 1 of the electron transporting layer; as a light emitting device for comparison, a comparative light emitting device 2 using 2, 3-bis [4- (10-phenyl-9-anthryl ] phenyl ] quinoxaline (abbreviated as PAPQ) for an electron transporting layer, and a comparative light emitting device 3 using 2-phenyl-3- [4- (10-phenyl-9-anthryl ] phenyl ] quinoxaline (abbreviated as PA1PQ) for an electron transporting layer as a light emitting device for comparison fig. 11 shows an element structure of a light emitting device used in this example, and table 1 shows a specific structure, and further, chemical formulae of materials used in this example are shown below.

[ Table 1]

*CzPA:PCBAPA(1:0.1 30nm)

[ chemical formula 28]

< production of light-emitting device >

As shown in fig. 11, the light emitting device shown in this embodiment has the following structure: a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and an electron injection layer 915 which constitute an EL layer 902 are sequentially stacked over a first electrode 901 formed over a substrate 900, and a second electrode 903 is stacked over the electron injection layer 915.

First, a first electrode 901 is formed over a substrate 900. The electrode area is 4mm²(2 mm. times.2 mm). The substrate 900 uses a glass substrate. As for the first electrode 901, an indium tin oxide (ITSO) film containing silicon oxide was formed to a thickness of 110nm by a sputtering method.

Here, as the pretreatment, the surface of the substrate was washed with water, baked at a temperature of 200 ℃ for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was put into the inside thereof and depressurized to 1 × 10^-4In a vacuum deposition apparatus of about Pa, vacuum baking was performed at a temperature of 170 ℃ for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was cooled for about 30 minutes.

Next, a hole injection layer 911 is formed on the first electrode 901. The pressure in the vacuum evaporation equipment is reduced to 1 x 10^- ⁴After Pa, 4' -bis [ N- (1-naphthyl) -N-phenylamino]Biphenyl (NPB) and molybdenum oxide are mixed according to the mass ratio of NPB: molybdenum oxide ═ 4: 1 and 50nm thick, to form a hole injection layer 911.

Next, a hole transporting layer 912 is formed on the hole injecting layer 911. The hole transport layer 912 was formed by vapor deposition of NPB to a thickness of 10 nm.

Next, a light-emitting layer 913 is formed over the hole-transporting layer 912.

As the light-emitting layer 913, 9- [4- (10-phenyl-9-anthracenyl) phenyl ] -9H-carbazole (abbreviated as: CzPA) and 4- (10-phenyl-9-anthracenyl) -4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as: PCBAPA) were added in a weight ratio of CzPA: PCBAPA ═ 1: co-evaporation method 0.1. Further, the thickness of the light-emitting layer 913 is 30 nm.

Next, an electron transporting layer 914 is formed over the light-emitting layer 913. The electron transit layer 914 is formed by an evaporation method using resistance heating.

In the light-emitting device 1, tris (8-hydroxyquinoline) aluminum (iii) (Alq for short) and PyA1PQ were sequentially vapor-deposited to have thicknesses of 10nm and 20nm, respectively, to form the electron transporting layer 914. In the comparative light-emitting device 2, the electron transport layer 914 was formed by sequentially depositing Alq and PAPQ to a thickness of 10nm and 20nm, respectively. In the comparative light-emitting device 3, Alq and PA1PQ were sequentially vapor-deposited to have thicknesses of 10nm and 20nm, respectively, to form the electron transport layer 914.

Next, an electron injection layer 915 is formed on the electron transit layer 914. The electron injection layer 915 is formed by evaporating lithium fluoride (LiF) so as to have a thickness of 1 nm.

Next, a second electrode 903 is formed over the electron injection layer 915. The second electrode 903 is formed by vapor deposition of aluminum to a thickness of 200 nm. In the present embodiment, the second electrode 903 is used as a cathode.

Through the above steps, a light-emitting device in which an EL layer is interposed between a pair of electrodes is formed over the substrate 900. The hole injection layer 911, the hole transport layer 912, the light-emitting layer 913, the electron transport layer 914, and the electron injection layer 915, which are described in the above steps, are functional layers constituting the EL layer in one embodiment of the present invention. In the vapor deposition process of the above-described manufacturing method, a vapor deposition method using a resistance heating method is used.

Further, the light emitting device manufactured as described above is sealed with another substrate (not shown). When sealing is performed using another substrate (not shown), another substrate (not shown) to which a sealant hardened by ultraviolet light is applied is fixed to the substrate 900 in a glove box in a nitrogen atmosphere, and the two substrates are bonded to each other so that the sealant adheres to the periphery of the light-emitting device formed over the substrate 900. At 6J/cm when sealing²Irradiating 365nm ultraviolet light to harden the sealant, and heating at 80 deg.CThe sealant was stabilized by heat treatment for 1 hour.

< operating characteristics of light emitting device >)

The operating characteristics of each of the fabricated light-emitting devices were measured. Note that the measurement was performed at room temperature (atmosphere maintained at 25 ℃). Fig. 12 to 15 show a current density-luminance characteristic, a voltage-luminance characteristic, a luminance-current efficiency characteristic, and a voltage-current characteristic, respectively, as a result of the operation characteristics of the respective light emitting devices.

Furthermore, Table 2 below shows 1000cd/m²Main initial characteristic values of the respective light emitting devices on the left and right sides.

[ Table 2]

Further, FIG. 16 shows the signal at 25mA/cm²The current density of (a) is such that the emission spectrum when a current flows through each light emitting device. As shown in fig. 16, the emission spectrum of each light-emitting device had a peak around 470nm, which was derived from the emission of PCBAPA contained in the light-emitting layer 913.

As is clear from the results shown in fig. 12 to 15 and table 2, the light-emitting device 1 using PyA1PQ, which is one embodiment of the present invention, is superior in current-voltage characteristics, power efficiency, and light-emitting efficiency to the comparative light-emitting device 2 and the comparative light-emitting device 3.

Further, FIG. 17 shows luminance 1000cd/m²Luminance change with respect to driving time. As is clear from fig. 17, the light-emitting device 1 according to the embodiment of the present invention has a small decrease in luminance with the accumulation of driving time and a good life.

(reference synthesis example)

In the reference synthesis example, a synthesis example of an organic compound represented by the following structural formula, namely 2-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl } quinoxaline (abbreviated as: PA1PQ) (structural formula (200)), used in comparative light-emitting device 3 of example 2 is specifically described.

[ chemical formula 29]

In a 100mL eggplant type flask, 1.0g (3.0mmol) of 9-bromo-10-phenylanthracene, 0.21g (0.70mmol) of tri (o-tolyl) phosphine, 1.0g (3.0mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 0.85g (6.2mmol) of potassium carbonate, 30mL of ethylene glycol dimethyl ether (DME), and 3.0mL of water were placed.

After the pressure in the flask was reduced and the mixture was stirred, the flask was purged with nitrogen. To the mixture was added 62mg (0.27mmol) of palladium (II) acetate, and the mixture was refluxed at 100 ℃ for 14 hours under a nitrogen stream. After refluxing, water was added to the mixture in the flask, followed by extraction with toluene. The obtained extract solution was washed with saturated brine and dried over magnesium sulfate. It was gravity filtered and the filtrate was concentrated to give a solid. Toluene was added to the obtained solid, followed by suction filtration through celite, magnesium silicate and alumina, and the filtrate was concentrated. Purification by silica gel column chromatography (toluene), recrystallization from toluene/hexane, and the like gave 0.91g of the objective pale yellow solid in a yield of 56%. The synthetic route (x-1) is shown below.

[ chemical formula 30]

The obtained pale yellow solid (0.79 g) was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, the reaction mixture was heated at 240 ℃ for 16 hours under a pressure of 10Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.79g of the objective pale yellow solid was obtained in a recovery rate of 88%.

The nuclear magnetic resonance spectroscopy of a pale yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 18 shows¹H-NMR spectrum. From the results, it was found that PA1PQ represented by the structural formula (200) was obtained in the present reference synthesis example.

¹H NMR(CDCl3，300MHz)：δ＝7.31-7.40(m，4H)、7.43-7.77(m，18H)、7.81-7.87(m，2H)、8.24-8.30(m，2H)。

[ example 3]

< Synthesis example 2>

In this example, a method for synthesizing 2-phenyl-3- {4- [10- (pyrimidin-5-yl) -9-anthryl ] phenyl } quinoxaline (abbreviated as 1PQPMA), which is an organic compound according to one embodiment of the present invention represented by the structural formula (101) of embodiment 1, will be described. The structure of 1PQPMA is shown below.

[ chemical formula 31]

1.1g (3.4mmol) of 5- (10-bromo-9-anthryl) pyrimidine, 0.23g (0.76mmol) of tri (o-tolyl) phosphine, 1.3g (3.9mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 1.1g (7.7mmol) of potassium carbonate, 35mL of toluene, 4mL of ethanol, and 4mL of water were placed in a 50mL three-necked flask. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen.

79mg (0.35mmol) of palladium (II) acetate was added to the mixture, and the mixture was stirred at 80 ℃ for 9 hours under a nitrogen stream. After stirring, water was added to the mixture, and the organic matter was extracted from the aqueous layer using toluene. The obtained extract solution and organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography (toluene: ethyl acetate 9:1) to obtain a solid. The obtained solid was purified by high performance liquid chromatography (chloroform) to obtain a solid. The obtained solid was subjected to ultrasonic irradiation with methanol to recover the solid, and 0.95g of the objective pale yellow solid was obtained in a yield of 53%. The following shows the synthetic route (b-1).

[ chemical formula 32]

The obtained pale yellow solid (0.93 g) was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, under reduced pressure, the mixture was heated at 235 ℃ for 15 hours under an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.86g of the objective pale yellow solid was obtained in a recovery rate of 92%.

The nuclear magnetic resonance spectroscopy of a pale yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 19 shows¹H-NMR spectrum. As a result, in this example, 1PQPmA, which is an organic compound according to one embodiment of the present invention represented by the structural formula (101) above, was obtained.

¹H NMR(CDCl3，300MHz)：δ＝7.39-7.48(m，9H)、7.55-7.61(m，2H)、7.68-7.71(m，2H)、7.74-7.79(m，4H)、7.83-7.88(m，2H)、8.24-8.30(m，2H)、8.91(s，2H)、9.46(s，1H)。

< physical Properties of 1PQPmA >

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the 1PQPmA in toluene solution and the solid thin film were measured.

The absorption spectrum of the 1PQPMA toluene solution was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the 1PQPMA toluene solution was measured by a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the toluene solution of 1PQPmA was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz cell. Fig. 20 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution of 1 PQPmA. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 20, the toluene solution of 1PQPMA showed absorption peaks at 359nm, 377nm and 398nm, and a peak of emission wavelength at 434nm (excitation wavelength 377 nm).

Further, a solid thin film of 1PQPmA was formed on a quartz substrate by a vacuum deposition method. The absorption spectrum of the solid thin film of 1PQPMA was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the solid thin film of 1PQPMA was measured by a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the solid thin film of 1PQPmA was calculated by subtracting the absorption spectrum of the quartz substrate. Fig. 21 shows the results of measurement of the absorption spectrum and emission spectrum of the obtained 1PQPmA solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 21, the solid film of 1PQPMA has absorption peaks at about 362nm, 382nm, and 403nm, and a peak of emission wavelength at about 456nm (excitation wavelength 380 nm).

The results showed that 1PQPMA emitted blue light. The organic compound of one embodiment of the present invention, i.e., 1PQPmA, can be used as a host for a luminescent material or a fluorescent luminescent material in a visible region.

[ example 4]

< Synthesis example 3>

In this example, a method for synthesizing 2-phenyl-3- [10- (pyrazin-2-yl) -9-anthryl ] quinoxaline (abbreviated as: 1PQPrA), which is an organic compound according to one embodiment of the present invention represented by the structural formula (102) of embodiment 1, will be described. The structure of 1PQPrA is shown below.

[ chemical formula 33]

0.58g (1.7mmol) of 2- (10-bromo-9-anthryl) pyrazine, 0.62g (1.9mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 0.47g (3.4mmol) of potassium carbonate, 20mL of toluene, 4mL of ethanol and 2mL of water were placed in a 200mL three-necked flask. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen.

To the mixture in the flask were added 0.10g (0.34mmol) of tri (o-tolyl) phosphine and 15mg (68. mu. mol) of palladium (II) acetate, and the mixture was stirred at 80 ℃ for 19 hours. After stirring, water was added to the mixture, and the organic matter was extracted from the aqueous layer using toluene. The obtained extract solution and organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography (ethyl acetate: hexane ═ 1:2), and then recrystallized from toluene/hexane to obtain 0.47g of a yellow solid of the desired product in a yield of 52%. The following shows the synthetic route (c-1).

[ chemical formula 34]

The obtained yellow solid 0.46g was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, heating was carried out at 250 ℃ for 18 hours under a pressure of 3.1Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.37g of the objective yellow solid was obtained in a recovery rate of 80%.

The nuclear magnetic resonance spectroscopy of the yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 22 shows¹H-NMR spectrum. As a result, in this example, 1PQPrA, which is an organic compound according to one embodiment of the present invention represented by the structural formula (102), was obtained.

¹H NMR(CDCl3，300MHz)：δ＝7.38-7.56(m，11H)、7.67-7.86(m，8H)、8.24-8.30(m，2H)、8.79(d，1H)、8.87(d，1H)、8.94-8.96(m，1H)。

< physical Properties of 1PQPrA >

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the 1PQPrA in toluene solution and the solid film were measured.

The absorption spectrum of the 1PQPrA in toluene was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the 1PQPrA in toluene was measured by using a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the toluene solution of 1PQPrA was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz cell. Fig. 23 shows the results of measurement of the absorption spectrum and emission spectrum of the obtained toluene solution of 1 PQPrA. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 23, the toluene solution of 1PQPrA showed absorption peaks at about 358nm, 375nm and 396nm and a peak at about 455nm (excitation wavelength 375nm) in the emission wavelength.

Further, a solid thin film of 1PQPrA was formed on the quartz substrate by a vacuum deposition method. The absorption spectrum of the solid film of 1PQPrA was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the solid thin film of 1PQPrA was measured by a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the solid thin film of 1PQPrA was calculated by subtracting the absorption spectrum of the quartz substrate. Fig. 24 shows the results of measurement of the absorption spectrum and emission spectrum of the obtained 1PQPrA solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 24, the solid film of 1PQPrA showed absorption peaks at wavelengths around 362nm, 380nm, and 401nm, and a peak at an emission wavelength at 468nm (excitation wavelength 360 nm).

The results showed that 1PQPrA emits blue light. The organic compound of one embodiment of the present invention, i.e., 1PQPrA, can be used as a host for a luminescent material or a fluorescent luminescent material in the visible region.

[ example 5]

< Synthesis example 4>

In this example, a method for synthesizing 2-phenyl-3- (4- {10- [4- (3-pyridyl) phenyl ] -9-anthryl } phenyl) quinoxaline (abbreviated as 1PQPyPA), which is an organic compound of one embodiment of the present invention represented by the structural formula (135) of embodiment 1, will be described. The structure of 1PQPyPA is shown below.

[ chemical formula 35]

1.8g (4.4mmol) of 3- [4- (10-bromo-9-anthryl) phenyl ] pyridine, 1.6g (4.8mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 1.2g (8.8mmol) of potassium carbonate, 50mL of toluene, 10mL of ethanol, and 5mL of water were placed in a 200mL three-necked flask. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen.

To the mixture in the flask were added 0.13g (0.44mmol) of tri (o-tolyl) phosphine and 20mg (88. mu. mmol) of palladium (II) acetate, and the mixture was stirred at 80 ℃ for 20 hours under a nitrogen atmosphere. After stirring, the precipitated solid was filtered, and the recovered solid and the filtrate were purified, respectively. First, the obtained solid was dissolved in chloroform, and insoluble matter was removed by filtration, and the filtrate was concentrated and purified by silica gel column chromatography (toluene: ethyl acetate 1: 1).

Next, the organic substance was extracted with toluene, and the obtained extract solution and the organic layer were combined and dried over magnesium sulfate. The mixture was gravity-filtered and the filtrate was concentrated, followed by purification using silica gel column chromatography (hexane: ethyl acetate ═ 2: 1). The solid obtained by each purification step was recrystallized using toluene/hexane to obtain 2.1g of a pale yellow solid of the objective compound in a yield of 78%. The following shows the synthetic route (d-1).

[ chemical formula 36]

The resulting pale yellow solid (2.1 g) was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, heating was carried out at 260 ℃ for 19 hours under a pressure of 6.2Pa and an argon flow rate of 10 mL/min. After purification by sublimation, 1.8g of the objective pale yellow solid was obtained in a recovery rate of 88%.

The nuclear magnetic resonance spectroscopy of a pale yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 25 shows¹H-NMR spectrum. As a result, in this example, 1PQPyPA, which is an organic compound according to one embodiment of the present invention represented by the structural formula (135), was obtained.

¹H NMR(CDCl3，300MHz)：δ＝7.36-7.50(m，10H)、7.60(d，2H)、7.68-7.78(m，8H)、7.83-7.86(m，4H)、8.06(d，1H)、8.24-8.30(m，2H)、8.67(d，1H)、9.05(d，1H)。

< physical Properties of 1PQPyPA >

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the 1PQPyPA toluene solution and the solid thin film were measured.

The absorption spectrum of the 1PQPyPA in toluene was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the 1PQPyPA in toluene was measured by using a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the toluene solution of 1PQPyPA was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish. Fig. 26 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution of 1 PQPyPA. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 26, the toluene solution of 1PQPyPA showed absorption peaks at about 358nm, 376nm and 397nm and a peak of emission wavelength at about 442nm (excitation wavelength 375 nm).

Further, a solid thin film of 1PQPyPA was formed on the quartz substrate by vacuum deposition. The absorption spectrum of the solid thin film of 1PQPyPA was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the solid thin film of 1PQPyPA was measured by a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the solid thin film of 1PQPyPA was calculated by subtracting the absorption spectrum of the quartz substrate. Fig. 27 shows the measurement results of the absorption spectrum and emission spectrum of the obtained 1PQPyPA solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 27, the solid thin film of 1PQPyPA showed absorption peaks at wavelengths around 362nm, 382nm and 402nm and a peak at an emission wavelength around 464nm (excitation wavelength: 360 nm).

The results showed that 1PQPyPA emitted blue light. The organic compound according to one embodiment of the present invention, i.e., 1PQPyPA, can be used as a host for a luminescent material or a fluorescent luminescent material in a visible region.

[ example 6]

< Synthesis example 5>

In this example, a method for synthesizing 2-phenyl-3- {4- [10- (5-phenyl-3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviated as: 1 PQmPyA), which is an organic compound according to one embodiment of the present invention represented by the structural formula (147) of embodiment 1, will be described. The structure of 1PQmPPyA is shown below.

[ chemical formula 37]

< step 1: synthesis of 3- (9-anthracenyl) -5-phenylpyridine >

1.0g (4.3mmol) of 3-bromo-5-phenylpyridine, 2.0g (9.2mmol) of 9-anthraceneboronic acid and 2.4g (17mmol) of potassium carbonate were placed in a 200mL three-necked flask, and the inside of the flask was replaced with nitrogen. To the mixture were added 40mL of tetrahydrofuran and 8mL of water, and the mixture was stirred under reduced pressure to conduct degassing. To the mixture were added 0.10g (0.35mmol) of tri-tert-butylphosphine tetrafluoroborate and 98mg (0.11mmol) of tris (dibenzylideneacetone) dipalladium (0), followed by stirring at 80 ℃ for 14 hours under a nitrogen stream.

After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract solution and organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a solid. Purification by silica gel column chromatography (toluene: ethyl acetate ═ 9:1) and recrystallization using methanol gave 1.4g of the desired product as a white solid in 98% yield. The following shows the synthetic route (e-1).

[ chemical formula 38]

< step 2: synthesis of 3- (10-bromo-9-anthracenyl) -5-phenylpyridine >

In a 200mL round bottom flask, 1.4g (4.2mmol) of 3- (9-anthryl) -5-phenylpyridine, 40mL (4.6mmol) of dimethylformamide and 0.82g (4.6mmol) of bromosuccinimide were placed, and the mixture was stirred at room temperature for 45 hours.

After stirring, water was added to the mixture, suction filtration was performed through celite, and the aqueous layer was extracted with toluene. The resulting extract solution and organic layer were combined, washed with an aqueous sodium thiosulfate solution, an aqueous sodium hydrogencarbonate solution and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography (toluene: ethyl acetate 19:1) to obtain 1.1g of the desired product as a solid in 65% yield. The following shows the synthetic route (e-2).

[ chemical formula 39]

< step 3: synthesis of 1 PQmPyA >

1.1g (2.7mmol) of 3- (10-bromo-9-anthryl) -5-phenylpyridine, 0.98g (3.0mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 83mg (0.27mmol) of tri (o-tolyl) phosphine, and 0.76g (5.5mmol) of potassium carbonate were placed in a 100mL three-necked flask, and the inside of the flask was subjected to nitrogen substitution. To the mixture were added 25mL of toluene, 5.0mL of ethanol, and 2.5mL of water, and the mixture was stirred under reduced pressure to conduct degassing. After 12mg (55. mu. mol) of palladium (II) acetate was added to the mixture, the mixture was stirred at 80 ℃ for 25 hours under a nitrogen stream.

After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract solution and organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate ═ 19:1), and recrystallized from ethyl acetate/hexane to obtain 0.85g of the objective product as a pale yellow solid in a yield of 51%. The synthetic route (e-3) is shown below.

[ chemical formula 40]

The obtained pale yellow solid (0.87 g) was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, the mixture was heated at 310 ℃ for 16 hours under a pressure of 4.5Pa and an argon flow rate of 15.0 mL/min. After purification by sublimation, 0.50g of the objective pale yellow solid was obtained in a recovery rate of 57%.

The nuclear magnetic resonance spectroscopy of a pale yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 28 shows¹H-NMR spectrum. As a result, in this example, 1PQmPPyA, which is an organic compound according to one embodiment of the present invention represented by the structural formula (147) was obtained.

¹H NMR(CDCl3，300MHz)：δ＝7.38-7.57(m，12H)、7.67-7.82(m，10H)、7.83-7.90(m，2H)、8.07(t，J＝2.1Hz，1H)、8.24-8.34(m，2H)、8.74(d，J＝1.8Hz，1H)、9.10(d，J＝2.1Hz，1H)。

< physical Properties of 1 PQmPyA >

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the 1PQmPPyA in toluene solution and the solid film were measured.

The absorption spectrum of the 1 PQmPyA toluene solution was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the 1 PQmPyA toluene solution was measured by a fluorescence spectrometer (FP-8600, manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the toluene solution of 1PQmPPyA was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz cell. Fig. 29 shows the results of measurement of the absorption spectrum and emission spectrum of the obtained 1PQmPPyA toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 29, the toluene solution of 1 PQmPyA showed absorption peaks at wavelengths of 358nm, 377nm and 398nm, and a peak at an emission wavelength of 437nm (398 nm excitation wavelength).

Further, a solid thin film of 1PQmPPyA was formed on the quartz substrate by vacuum evaporation. The absorption spectrum of the solid thin film of 1 PQmPyA was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the solid thin film of 1 PQmPyA was measured by a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the solid thin film of 1PQmPPyA was calculated by subtracting the absorption spectrum of the quartz substrate. Fig. 30 shows the measurement results of the absorption spectrum and emission spectrum of the obtained 1PQmPPyA solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 30, the solid thin film of 1 PQmPyA showed absorption peaks at around 363nm, 381nm, and 402nm, and a peak of luminescence wavelength at around 460nm (excitation wavelength of 360 nm).

The results showed that 1PQmPPyA emitted blue light. An organic compound according to one embodiment of the present invention, i.e., 1PQmPPyA, can be used as a host for a luminescent material or a fluorescent luminescent material in a visible region.

[ example 7]

< Synthesis example 6>

In this example, a method for synthesizing 2-phenyl-3- {4- [10- (2, 6-dimethyl-3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviated as 1PQDMePyA), which is an organic compound of one embodiment of the present invention represented by the structural formula (175) of embodiment 1, will be described. The structure of 1PQDMePyA is shown below.

[ chemical formula 41]

< step 1: synthesis of 3- (9-anthracenyl) -2, 6-dimethylpyridine >

2.4g (13mmol) of 2, 6-dimethyl-3-bromopyridine, 3.2g (14mmol) of 9-anthraceneboronic acid and 7.2g (52mmol) of potassium carbonate were placed in a 300mL three-necked flask, and the inside of the flask was replaced with nitrogen. THF130mL, 26mL of water, was added to the mixture, and the mixture was stirred under reduced pressure to conduct degassing. To the mixture were added 0.11g (0.39mmol) of tri-tert-butylphosphine tetrafluoroborate and 0.12g (0.13mmol) of tris (dibenzylideneacetone) dipalladium (0), followed by stirring at 80 ℃ for 11 hours under a nitrogen stream.

After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract solution and organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate ═ 9:1), and 3.4g of the desired product was obtained as a solid in 92% yield. The following shows the synthetic route (f-1).

[ chemical formula 42]

< step 2: synthesis of 3- (10-bromo-9-anthracenyl) -2, 6-dimethylpyridine >

2.7g (9.4mmol) of 3- (9-anthryl) -2, 6-dimethylpyridine and DMF100mL were put in a 300mL round bottom flask and stirred at 0 ℃. To the mixture was added bromosuccinimide (1.8 g, 10mmol), and the mixture was warmed to room temperature and stirred for 66 hours. After stirring, water was added to the mixture, suction filtration was performed through celite, and the aqueous layer was extracted with toluene. The resulting extract solution and organic layer were combined, washed with an aqueous sodium thiosulfate solution, an aqueous sodium hydrogencarbonate solution and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate ═ 19:1), and 3.3g of the desired product was obtained as a solid in 99% yield. The following shows the synthetic route (f-2).

[ chemical formula 43]

< step 3: synthesis of 1PQDMePyA >

In a 100mL three-necked flask, 1.2g (3.3mmol) of 3- (10-bromo-9-anthryl) -2, 6-dimethylpyridine, 1.2g (3.7mmol) of 4- (3-phenylquinoxalin-2-yl) phenylboronic acid, 98mg (0.32mmol) of tri (o-tolyl) phosphine and 0.92g (6.6mmol) of potassium carbonate were placed, and the inside of the flask was subjected to nitrogen substitution. To the mixture were added 30mL of toluene, 6.0mL of ethanol, and 3.0mL of water, and the mixture was stirred under reduced pressure to conduct degassing. After 14.9mg (66. mu. mol) of palladium (II) acetate was added to the mixture, it was stirred at 80 ℃ for 21 hours under a nitrogen stream. After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract solution and organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate ═ 19:1), and recrystallized using toluene/methanol to obtain 1.4g (2.5mmol) of the objective pale yellow solid in a yield of 75%. The following shows the synthetic route (f-3).

[ chemical formula 44]

1.4g of the obtained pale yellow solid was purified by sublimation using a gradient sublimation method. As sublimation purification conditions, heating was carried out at 250 ℃ for 16 hours under a pressure of 6.7Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 1.3g of the objective pale yellow solid was obtained in a recovery rate of 92%.

The nuclear magnetic resonance spectroscopy of a pale yellow solid obtained by the above reaction is shown below (¹H-NMR). FIG. 31 shows¹H-NMR spectrum. As a result, in this example, 1PQDMePyA, which is an organic compound according to one embodiment of the present invention represented by the structural formula (175), was obtained.

¹H NMR(CD2Cl2，300MHz)：δ＝2.10(s，3H)、2.69(s，3H)、7.26(d，J＝7，8Hz，1H)、7.34-7.56(m，12H)、7.66-7.80(m，6H)、7.82-7.89(m，2H)、8.18-8.27(m，2H)。

< physical Properties of PQDMePyA >

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the 1PQDMePyA in toluene solution and the solid thin film were measured.

The absorption spectrum of the 1PQDMePyA toluene solution was measured by using an ultraviolet-visible spectrometer (V-550 manufactured by Nippon spectral Co., Ltd.). The emission spectrum of the 1PQDMePyA in toluene was measured by using a fluorescence spectrometer (FP-8600 manufactured by Nippon spectral Co., Ltd.). Note that the absorption spectrum of the toluene solution of 1PQDMePyA was calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz cell. Fig. 32 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution of 1 PQDMePyA. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 32, the toluene solution of 1PQDMePyA showed absorption peaks at around 397nm, 376nm and 358nm and a peak of luminescence wavelength at around 446nm (excitation wavelength 397 nm).

The results showed that 1PQDMePyA emitted blue light. The organic compound of one embodiment of the present invention, i.e., 1PQDMePyA, can be used as a host for a luminescent material or a fluorescent luminescent material in a visible region.

[ example 8]

In this embodiment, an element structure, a manufacturing method, and characteristics of a light emitting device are described as follows: as a light-emitting device of one embodiment of the present invention, 2-phenyl-3- {4- [10- (3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviation: PyA1PQ) (structural formula (100)) shown in example 1 was used for the light-emitting device 4 of the electron transporting layer; as a comparative light-emitting device for comparison, 2-phenyl-3- [4' - (3-pyridyl) biphenyl-4-yl ] quinoxaline (abbreviated as PPy1PQ) was used for comparative light-emitting device 5 of the electron transport layer. Further, PyA1PQ used for the light emitting device 4 and PPy1PQ used for the comparative light emitting device 5 were each a quinoxaline derivative in which PyA1PQ had a heteroaromatic ring bonded to an anthracene skeleton bonded to a quinoxaline skeleton, and PPy1PQ had a heteroaromatic ring bonded to a phenylene skeleton bonded to a quinoxaline skeleton. Table 3 shows an element structure of the light emitting device used in the present embodiment. Further, the chemical formula of the material used in this example is shown below.

[ Table 3]

*αN-βNPAnth:3,10PCA2Nbf(IV)-02(1:0.15 25nm)

[ chemical formula 45]

< production of light-emitting device >

As with the light emitting device described in embodiment 2 with reference to fig. 11, the light emitting device shown in this embodiment has the following structure: a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and an electron injection layer 915 are sequentially stacked over the first electrode 901 formed over the substrate 900, and a second electrode 903 is stacked over the electron injection layer 915.

In addition, the hole injection layer 911 was formed by mixing N, N-bis (4-biphenyl) -6-phenylbenzo [ b ] naphtho [1,2-d ] furan-8-amine (abbreviation: BBABnf) and ALD-MP001Q (analysis house co., serial No. 1S20180314) in a weight ratio of BBABnf: ALD-MP001Q ═ 1: 0.1 and 10nm thick. The hole-transporting layer 912 was formed by vapor deposition of BBABnf to a thickness of 20nm and then 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) to a thickness of 10 nm.

In addition, the light-emitting layer 913 is formed by mixing 9- (1-naphthyl) -10- [4- (2-naphthyl) phenyl ] anthracene (abbreviated as α N- β npanthh) with 3, 10-bis [ N- (9-phenyl-9H-carbazol-2-yl) -N-phenylamino ] naphtho [2, 3-b; 6, 7-b' ] bis-benzofurans (abbreviation: 3,10PCA2Nbf (IV) -02) in a weight ratio of 1: 0.015(═ α N- β npath: 3,10PCA2Nbf (IV) -02) and a thickness of 25nm were formed by co-evaporation.

In the light-emitting device 4, a light-emitting element was manufactured by mixing PyA1PQ and 8-hydroxyquinoline lithium (abbreviated as: Liq) in a weight ratio of 1: 1(═ PyA1 PQ: Liq) and a thickness of 25nm were co-evaporated to form the electron transporting layer 914. Further, in comparative light-emitting device 5, by mixing PPy1PQ and 8-hydroxyquinoline lithium (abbreviation: Liq) in a weight ratio of 1: 1(═ PPy1 PQ: Liq) and a thickness of 25nm were co-evaporated to form the electron transporting layer 914.

< operating characteristics of light emitting device >)

The operating characteristics of each of the fabricated light-emitting devices were measured. Note that the measurement was performed at room temperature (atmosphere maintained at 25 ℃). Fig. 33 to 36 show a current density-luminance characteristic, a voltage-luminance characteristic, a luminance-current efficiency characteristic, and a voltage-current characteristic, respectively, as a result of the operation characteristics of the respective light emitting devices.

Furthermore, Table 4 below shows 1000cd/m²Main initial characteristic values of the respective light emitting devices on the left and right sides.

[ Table 4]

Further, the luminance of each light emitting device was measured at 1000cd/m²The nearby emission spectrum. That is, fig. 37 shows an emission spectrum when a voltage of 4.4V is applied to the light emitting device 4 and an emission spectrum when a voltage of 4.6V is applied to the comparative light emitting device 5. As shown in fig. 37, the emission spectrum of each light-emitting device has a peak around 458nm, which is derived from the light emission of 3,10PCA2Nbf (IV) -02 contained in the light-emitting layer 913.

From the results shown in fig. 33 to fig. 36 and table 4, it is understood that the light-emitting device 4 using PyA1PQ as one embodiment of the present invention is superior in current-voltage characteristics, power efficiency, and light-emitting efficiency to the comparative light-emitting device 5. This is because: the PyA1PQ used for the light-emitting device 4 has a heteroaromatic ring bonded to a quinoxaline skeleton via an anthracene skeleton, and thereby has an effect of easily extracting electrons from the electron injection layer 915 and injecting the electrons into the electron transport layer 914, and in addition, has a high electron transport property due to the anthracene skeleton.

Further, FIG. 38 shows a current density of 50mA/cm²Luminance change with respect to driving time. As shown in fig. 38, the luminance drop of the light emitting device 4 of one embodiment of the present invention accumulated with the driving time is equivalent to the comparative light emitting device 5. The light emitting device 4 of one embodiment of the present invention has higher current efficiency than the comparative light emitting device 5, and therefore even if the luminance of the light emitting device 4 is high at the same current density, the luminance drop with respect to the driving time is equivalent.

[ example 9]

In this embodiment, an element structure, a manufacturing method, and characteristics of a light emitting device are described as follows: as a light-emitting device of one embodiment of the present invention, 2-phenyl-3- {4- [10- (pyrimidin-5-yl) -9-anthryl ] phenyl } quinoxaline (abbreviated as 1PQPmA) (structural formula (101)) shown in example 3 was used for the light-emitting device 6 of the electron transporting layer; 2-phenyl-3- [10- (pyrazin-2-yl) -9-anthryl ] quinoxaline (abbreviated as: 1PQPrA) (structural formula (102)) shown in example 4 was used for the light-emitting device 7 of the electron transporting layer; 2-phenyl-3- (4- {10- [4- (3-pyridyl) phenyl ] -9-anthryl } phenyl) quinoxaline (abbreviated as 1PQPyPA) (structural formula (135)) shown in example 5 was used for the light-emitting device 8 of the electron transport layer; 2-phenyl-3- {4- [10- (5-phenyl-3-pyridyl) -9-anthryl ] phenyl } quinoxaline (abbreviated as: 1 PQmPyA) (structural formula (147)) shown in example 6 was used for the light-emitting device 9 of the electron transporting layer. Table 5 shows an element structure of the light emitting device used in this embodiment. Further, the chemical formula of the material used in this example is shown below.

[ Table 5]

*αN-βNPAnth:3,10PCA2Nbf(IV)-02(1:0.15 25nm)

[ chemical formula 46]

< production of light-emitting device >

In the light emitting device 6, by mixing 1PQPmA and Liq in a weight ratio of 1:2 (1 PQPmA: Liq) and a thickness of 25nm were co-evaporated to form the electron transport layer 914. In the light-emitting device 7, by mixing 1PQPrA and Liq in a weight ratio of 1:2 (1 PQPrA: Liq) and a thickness of 25nm were co-evaporated to form the electron transit layer 914. In the light-emitting device 8, the light-emitting element was manufactured by mixing 1PQPyPA and Liq in a weight ratio of 1:2 (1 PQPyPA: Liq) and a thickness of 25nm were co-evaporated to form the electron transporting layer 914. In the light-emitting device 9, the light-emitting element was manufactured by mixing 1PQmPPyA and Liq in a weight ratio of 1: the electron transport layer 914 was formed by co-evaporation of 1 (1 PQmPPyA: Liq) to a thickness of 25 nm.

< operating characteristics of light emitting device >)

The operating characteristics of each of the fabricated light-emitting devices were measured. Note that the measurement was performed at room temperature (atmosphere maintained at 25 ℃). Further, Table 6 below shows 1000cd/m²Main initial characteristic values of the respective light emitting devices on the left and right sides.

[ Table 6]

As is clear from the results shown in table 6, the light-emitting devices 6 to 9 according to the embodiment of the present invention are excellent in the operating characteristics such as the current-voltage characteristics, the power efficiency, and the light-emitting efficiency.

Further, FIG. 39 shows that each light-emitting device was operated at a current density of 50mA/cm²Luminance change with respect to driving time. As shown in fig. 39, the light-emitting devices 6 to 9 according to one embodiment of the present invention have a small decrease in luminance with the accumulation of driving time and have a good life.

Description of the symbols

101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 112: hole transport layer, 113: light-emitting layer, 114: electron transport layer, 115: electron injection layer, 103a, 103 b: EL layer, 104: charge generation layer, 111a, 111 b: hole injection layer, 112a, 112 b: hole transport layer, 113a, 113 b: light-emitting layers, 114a, 114 b: electron transport layer, 115a, 115 b: electron injection layer, 200R, 200G, 200B: optical distance, 201: first substrate, 202: transistor (FET), 203R, 203G, 203B, 203W: light-emitting device, 204: EL layer, 205: second substrate, 206R, 206G, 206B: color filters, 206R ', 206G ', 206B ': color filter, 207: first electrode, 208: second electrode, 209: black layer (black matrix), 210R, 210G: conductive layer, 301: first substrate, 302: pixel portion, 303: driver circuit portion (source line driver circuit), 304a, 304 b: driver circuit portion (gate line driver circuit), 305: sealant, 306: second substrate, 307: lead, 308: FPC, 309: FET, 310: FET, 311: FET, 312: FET, 313: first electrode, 314: insulator, 315: EL layer, 316: second electrode, 317: light emitting device, 318: space, 901: first electrode, 902: EL layer, 903: second electrode, 911: hole injection layer, 912: hole-transport layer, 913: light-emitting layer, 914: electron transport layer, 915: electron injection layer, 4000: lighting device, 4001: substrate, 4002: light-emitting device, 4003: substrate, 4004: first electrode, 4005: EL layer, 4006: second electrode, 4007: electrode, 4008: electrode, 4009: auxiliary wiring, 4010: insulating layer, 4011: sealing substrate, 4012: sealant, 4013: drying agent, 4200: lighting device, 4201: substrate, 4202: light-emitting device, 4204: first electrode, 4205: EL layer, 4206: second electrode, 4207: electrode, 4208: electrode, 4209: auxiliary wiring, 4210: insulating layer, 4211: sealing substrate, 4212: sealant, 4213: barrier film, 4214: planarizing film, 5101: lamp, 5102: hub, 5103: vehicle door, 5104: display unit, 5105: steering wheel, 5106: gear lever, 5107: seat, 5108: interior rearview mirror, 5109: windshield, 7000: case, 7001: display unit, 7002: second display portion, 7003: speaker, 7004: LED lamp, 7005: operation keys, 7006: connection terminal, 7007: sensor, 7008: microphone, 7009: switch, 7010: infrared port, 7011: recording medium reading unit, 7014: antenna, 7015: shutter button, 7016: image receiving unit, 7018: stents, 7022, 7023: operation buttons, 7024: connection terminal, 7025: watchband, 7026: microphone, 7029: sensor, 7030: speakers, 7052, 7053, 7054: information, 9310: portable information terminal, 9311: display portion, 9312: display region, 9313: hinge portion, 9315: outer casing

The present application is based on japanese patent application No.2019-055331, filed on day 22/3/2019, the entire contents of which are incorporated herein by reference.

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Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting apparatus

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